Ceftin for sinus infection

Contents

Ceftin

SIDE EFFECTS

The following serious and otherwise important adverse reaction is described in greater detail in the Warnings and Precautions section of the label:

Anaphylactic Reactions

Clinical Trials Experience

Because clinical trials are conducted under widely varying conditions, adverse reaction rates observed in the clinical trials of a drug cannot be directly compared with rates in the clinical trials of another drug and may not reflect the rates observed in practice.

Tablets

Multiple-Dose Dosing Regimens With 7 To 10 Days’ Duration

In multiple-dose clinical trials, 912 subjects were treated with CEFTIN (125 to 500 mg twice daily). It is noted that 125 mg twice daily is not an approved dosage. Twenty (2.2%) subjects discontinued medication due to adverse reactions. Seventeen (85%) of the 20 subjects who discontinued therapy did so because of gastrointestinal disturbances, including diarrhea, nausea, vomiting, and abdominal pain. The percentage of subjects treated with CEFTIN who discontinued study drug because of adverse reactions was similar at daily doses of 1,000, 500, and 250 mg (2.3%, 2.1%, and 2.2%, respectively). However, the incidence of gastrointestinal adverse reactions increased with the higher recommended doses.

The adverse reactions in Table 5 are for subjects (n = 912) treated with CEFTIN in multiple-dose clinical trials.

Table 5: Adverse Reactions (≥1%) after Multiple-Dose Regimens with CEFTIN Tablets

Adverse Reaction CEFTIN
(n = 912)
Blood and lymphatic system disorders
Eosinophilia 1%
Gastrointestinal disorders
Diarrhea 4%
Nausea/Vomiting 3%
Investigations
Transient elevation in AST 2%
Transient elevation in ALT 2%
Transient elevation in LDH 1%

The following adverse reactions occurred in less than 1% but greater than 0.1% of subjects (n = 912) treated with CEFTIN in multiple-dose clinical trials.

Immune System Disorders: Hives, swollen tongue.

Metabolism and Nutrition Disorders: Anorexia.

Nervous System Disorders: Headache.

Cardiac Disorders: Chest pain.

Respiratory Disorders: Shortness of breath.

Gastrointestinal Disorders: Abdominal pain, abdominal cramps, flatulence, indigestion, mouth ulcers.

Skin and Subcutaneous Tissue Disorders: Rash, itch.

Renal and Urinary Disorders: Dysuria.

Reproductive System and Breast Disorders: Vaginitis, vulvar itch.

General Disorders and Administration Site Conditions: Chills, sleepiness, thirst.

Investigations: Positive Coombs’ test.

Early Lyme Disease With 20-Day Regimen

Two multicenter trials assessed CEFTIN 500 mg twice daily for 20 days. The most common drug-related adverse experiences were diarrhea (10.6%), Jarisch-Herxheimer reaction (5.6%), and vaginitis (5.4%). Other adverse experiences occurred with frequencies comparable to those reported with 7 to 10 days’ dosing.

Single-Dose Regimen For Uncomplicated Gonorrhea

In clinical trials using a single 1,000-mg dose of CEFTIN, 1,061 subjects were treated for uncomplicated gonorrhea. The adverse reactions in Table 6 were for subjects treated with a single dose of 1,000 mg CEFTIN in U.S. clinical trials.

Table 6: Adverse Reactions (≥1%) after Single-Dose Regimen with 1,000-mg CEFTIN Tablets for Uncomplicated Gonorrhea

Adverse Reaction CEFTIN
(n = 1,061)
Gastrointestinal disorders
Nausea/Vomiting 7%
Diarrhea 4%

The following adverse reactions occurred in less than 1% but greater than 0.1% of subjects (n = 1,061) treated with a single dose of CEFTIN 1,000 mg for uncomplicated gonorrhea in U.S. clinical trials.

Infections and Infestations: Vaginal candidiasis.

Nervous System Disorders: Headache, dizziness, somnolence.

Cardiac Disorders: Tightness/pain in chest, tachycardia.

Gastrointestinal Disorders: Abdominal pain, dyspepsia.

Skin and Subcutaneous Tissue Disorders: Erythema, rash, pruritus.

Musculoskeletal and Connective Tissue Disorders: Muscle cramps, muscle stiffness, muscle spasm of neck, lockjaw-type reaction.

Renal and Urinary Disorders: Bleeding/pain in urethra, kidney pain.

Reproductive System and Breast Disorders: Vaginal itch, vaginal discharge.

Oral Suspension

In clinical trials using multiple doses of CEFTIN, pediatric subjects (96.7% were younger than 12 years) were treated with CEFTIN (20 to 30 mg/kg/day divided twice daily up to a maximum dose of 500 or 1,000 mg/day, respectively). Eleven (1.2%) U.S. subjects discontinued medication due to adverse reactions. The discontinuations were primarily for gastrointestinal disturbances, usually diarrhea or vomiting. Thirteen (1.4%) U.S. pediatric subjects discontinued therapy due to the taste and/or problems with drug administration.

The adverse reactions in Table 7 are for U.S. subjects (n = 931) treated with CEFTIN in multiple-dose clinical trials.

Table 7: Adverse Reactions (>1%) after Multiple-Dose Regimens with CEFTIN for Oral Suspension

Adverse Reaction CEFTIN
(n = 931)
Gastrointestinal disorders
Diarrhea 9%
Dislike of taste 5%
Nausea/vomiting 3%
Skin and subcutaneous tissue disorders
Diaper rash 3%

The following adverse reactions occurred in less than 1% but greater than 0.1% of U.S. subjects (n = 931) treated with CEFTIN for oral suspension in multiple-dose clinical trials.

Infections and Infestations: Gastrointestinal infection, candidiasis, viral illness, upper respiratory infection, sinusitis, urinary tract infection.

Blood and Lymphatic System Disorders: Eosinophilia.

Psychiatric Disorders: Hyperactivity, irritable behavior.

Gastrointestinal Disorders: Abdominal pain, flatulence, ptyalism.

Skin and Subcutaneous Tissue Disorders: Rash.

Musculoskeletal and Connective Tissue Disorders: Joint swelling, arthralgia.

Reproductive System and Breast Disorders: Vaginal irritation.

General Disorders and Administration Site Conditions: Cough, fever.

Investigations: Elevated liver enzymes, positive Coombs’ test.

Postmarketing Experience

The following adverse reactions have been identified during post-approval use of CEFTIN. Because these reactions are reported voluntarily from a population of uncertain size, it is not always possible to reliably estimate their frequency or establish a causal relationship to drug exposure.

Blood and Lymphatic System Disorders

Hemolytic anemia, leukopenia, pancytopenia, thrombocytopenia.

Gastrointestinal Disorders

Pseudomembranous colitis .

Hepatobiliary Disorders

Hepatic impairment including hepatitis and cholestasis, jaundice.

Immune System Disorders

Anaphylaxis, serum sickness-like reaction.

Investigations

Increased prothrombin time.

Nervous System Disorders

Seizure, encephalopathy.

Renal and Urinary Disorders

Renal dysfunction.

Skin and Subcutaneous Tissue Disorders

Angioedema, erythema multiforme, Stevens-Johnson syndrome, toxic epidermal necrolysis, urticaria.

Read the entire FDA prescribing information for Ceftin (Cefuroxime Axetil)

Generic Name: cefuroxime (SEF ue ROX eem)
Brand Name: Ceftin, Kefurox, Zinacef, Zinacef ADD-Vantage, Zinacef TwistVial

Medically reviewed by Drugs.com on May 17, 2019 – Written by Cerner Multum

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What is cefuroxime?

Cefuroxime is a cephalosporin (SEF a low spor in) antibiotic. It works by fighting bacteria in your body.

Cefuroxime is used to treat many kinds of bacterial infections, including severe or life-threatening forms.

Cefuroxime may also be used for purposes not listed in this medication guide.

Important Information

You should not use cefuroxime if you are allergic to cefuroxime or to similar antibiotics, such as cefdinir (Omnicef), cefprozil (Cefzil), cephalexin (Keflex), and others.

Before taking this medicine

Do not take this medicine if you are allergic to cefuroxime, or to other cephalosporin antibiotics, such as:

To make sure cefuroxime is safe for you, tell your doctor if you have:

  • an allergy to penicillin;

  • kidney disease;

  • liver disease;

  • a history of intestinal problems, such as colitis;

  • diabetes; or

  • if you are malnourished.

The liquid form may contain phenylalanine. Talk to your doctor before using this form of cefuroxime if you have phenylketonuria (PKU).

This medicine is not expected to harm an unborn baby. Tell your doctor if you are pregnant or plan to become pregnant.

Cefuroxime can make birth control pills less effective. Ask your doctor about using a non hormonal birth control (condom, diaphragm with spermicide) to prevent pregnancy.

Cefuroxime can pass into breast milk and may harm a nursing baby. Tell your doctor if you are breast-feeding a baby.

Cefuroxime is not approved for use by anyone younger than 3 months old.

How should I take cefuroxime?

Follow all directions on your prescription label. Do not take cefuroxime in larger or smaller amounts or for longer than recommended.

You may take cefuroxime tablets with or without meals. Do not crush the tablet or it could have an unpleasant bitter taste.

Cefuroxime oral suspension (liquid) must be taken with food.

Shake the liquid well just before you measure a dose. Measure liquid medicine with the dosing syringe provided, or with a special dose-measuring spoon or medicine cup. If you do not have a dose-measuring device, ask your pharmacist for one.

If you switch from using the tablet form to using the liquid form of cefuroxime, you may not need to use the same exact dosage in number of milligrams. This medicine may not be as effective unless you use the exact form and strength your doctor has prescribed.

Use this medicine for the full prescribed length of time. Your symptoms may improve before the infection is completely cleared. Skipping doses may also increase your risk of further infection that is resistant to antibiotics. Cefuroxime will not treat a viral infection such as the flu or a common cold.

This medicine can cause unusual results with certain lab tests for glucose (sugar) in the urine. Tell any doctor who treats you that you are using cefuroxime.

Store cefuroxime tablets at room temperature away from moisture and heat. Keep the bottle tightly closed when not in use.

Store cefuroxime liquid in the refrigerator. Do not allow it to freeze. Throw away any unused cefuroxime liquid that is older than 10 days.

What happens if I miss a dose?

Take the missed dose as soon as you remember. Skip the missed dose if it is almost time for your next scheduled dose. Do not take extra medicine to make up the missed dose.

What happens if I overdose?

Seek emergency medical attention or call the Poison Help line at 1-800-222-1222.

Overdose symptoms may include seizure (black-out or convulsions).

What should I avoid while taking cefuroxime?

Antibiotic medicines can cause diarrhea, which may be a sign of a new infection. If you have diarrhea that is watery or bloody, call your doctor. Do not use anti-diarrhea medicine unless your doctor tells you to.

Cefuroxime side effects

Get emergency medical help if you have signs of an allergic reaction: hives; difficulty breathing; swelling of your face, lips, tongue, or throat.

Call your doctor at once if you have:

  • severe stomach pain, diarrhea that is watery or bloody;

  • jaundice (yellowing of the skin or eyes);

  • skin rash, bruising, severe tingling, or numbness;

  • seizure (black-out or convulsions);

  • kidney problems–little or no urination, painful or difficult urination, swelling in your feet or ankles, feeling tired or short of breath; or

  • severe skin reaction–fever, sore throat, swelling in your face or tongue, burning in your eyes, skin pain followed by a red or purple skin rash that spreads (especially in the face or upper body) and causes blistering and peeling.

Common side effects may include:

  • diarrhea;

  • nausea, vomiting;

  • unusual or unpleasant taste in your mouth; or

  • diaper rash in an infant taking liquid cefuroxime.

This is not a complete list of side effects and others may occur. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

What other drugs will affect cefuroxime?

Tell your doctor about all your current medicines and any you start or stop using, especially:

  • probenecid (Benemid);

  • a blood thinner such as warfarin (Coumadin, Jantoven); or

  • a diuretic or “water pill.”

This list is not complete. Other drugs may interact with cefuroxime, including prescription and over-the-counter medicines, vitamins, and herbal products. Not all possible interactions are listed in this medication guide.

Further information

Remember, keep this and all other medicines out of the reach of children, never share your medicines with others, and use this medication only for the indication prescribed.

Always consult your healthcare provider to ensure the information displayed on this page applies to your personal circumstances.

Copyright 1996-2018 Cerner Multum, Inc. Version: 7.01.

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More about cefuroxime

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  • Drug class: second generation cephalosporins

Consumer resources

  • Cefuroxime Injection
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  • Cefuroxime Tablets
  • Cefuroxime (Advanced Reading)
  • Cefuroxime Injection, Intravenous (Advanced Reading)

Other brands: Ceftin, Zinacef

Professional resources

  • Cefuroxime Axetil (AHFS Monograph)
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Related treatment guides

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  • Bronchitis
  • Bladder Infection
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PMC

Discussion

Cefuroxime is a second-generation semi-synthetic cephalosporin that, despite its use for a wide variety of pediatric infections, has been reported to cause anaphylaxis only in a few cases. Furthermore, it is exceedingly rare for children to develop anaphylaxis from cephalosporins.4

Regarding near-fatal cephalosporin anaphylaxis, although the possibility of developing anaphylaxis is very low, deaths following cephalosporin have been reported.1

Cephalosporins can cause a range of hypersensitivity reactions, from mild, delayed-onset cutaneous reactions to life-threatening anaphylaxis in patients with immunoglobulin E (IgE)-mediated allergy.5,6

The most important risk factor for allergy to cephalosporins is a history of allergy reactions to penicillin or cephalosporins which increases the risk by eight times.1

Unlike penicillin tests, attempts to develop a skin test for allergy to cephalosporins have been unsuccessful, and skin testing with the native drug alone has little predictive value.7

Skin testing for cephalosporin allergy is sometimes performed, but is not standardized because the antigenic determinants of a serious allergic reaction have not been established.1

Skin testing for penicillin allergy can be useful in patients with an allergy history of cephalosporin who require penicillin. If penicillin skin tests are negative, penicillin can be administered safely; if positive, patients should either receive an alternative medication or undergo desensitization to penicillin.1 Also, the detection of IgE antibody to penicillin or cephalosporins or of cross-reactive IgE antibody does not predict a definite clinical reaction.9

A negative skin test to cephalosporin does not rule out the presence of drug-specific IgE antibodies.8 Furthermore, the presence of IgE antibodies to penicillin and cephalosporin is predictive of possible subsequent immediate, IgE-mediated allergic hypersensitivity reactions, but many patients with detectable IgE antibodies may not display a clinical allergic reaction.8

Hence, the role of both testing for IgE antibody to cephalosporin or penicillin and skin testing prior to administration are still uncertain. Test dosing with titrated doses could be considered as an alternative approach; but, it is still far from a flawless method.1

Due to uncertainties in predicting anaphylaxis to cephalosporin, medical histories regarding previous antibiotic allergies should then include a comprehensive description of the symptoms such as: urticaria; pruritus; angioedema or respiratory difficulties; severity and timing of reaction after drug therapy.9 This could facilitate a quick response in case of a moderate anaphylactic reaction (hypotension, tachycardia, bronchial hyperreactivity).

In summary, we present a case report of cefuroxima-induced anaphylaxis in which IgE-mediated responses appear to be involved in the pathogenic mechanism and, thus, avoidance of the cephalosporin or induction of drug tolerance would be recommended if no alternative drugs were available.

Physicians should be aware of this potentially life-threatening complication which can occur even after first dose and should be vigilant of recognizing anaphylaxis and provide prompt treatment accordingly.

Cefuroxime (also called Ceftin®) is used to prevent or treat infections. It is available as a 250 mg tablet and as a liquid suspension. Both are taken by mouth. It is also available as a clear liquid that is given by vein (IV).

How to take and store cefuroxime

  • You should take cefuroxime with food.
  • Store the tablet form at room temperature in dry place.
  • Shake the liquid well before you take it. Use an oral syringe or medicine cup to be sure you are taking the correct amount.
  • Store the liquid medicine in the refrigerator.
  • Discard the liquid medicine after 10 days or on the expiration date printed on the label.

Possible side effects of cefuroxime

  • Nausea, vomiting
  • Diarrhea
  • Rash
  • Loss of appetite
  • Headache
  • Stomach pain
  • Allergic reaction with the following symptoms: rash, hives, itching, chills, fever, swelling in the facial area, and joint pain

These are the most common side effects, but there may be others. Please report all side effects to the doctor or nurse.

In case of a severe side effect or reaction, call the doctor, nurse, or pharmacist at 901-595-3300. If you are outside the Memphis area, dial toll-free 1-866-2STJUDE (1-866-278-5833), and press 0 once the call is connected.

Special instructions for cefuroxime

  • Before taking cefuroxime, tell your doctor if you have had an allergic reaction to any other cephalosporin or penicillin antibiotics. If you have allergy symptoms (listed above) or you have severe or watery diarrhea, tell your doctor right away.
  • Finish all doses of this medicine as instructed by your doctor, even if you think your condition is better. Do not stop taking this medicine unless your doctor tells you to do so.
  • Do not take cefuroxime while you are taking probenecid without telling your doctor. Probenecid may increase the levels of cefuroxime in your body.
  • Cefuroxime may cause a false-positive urine test result when checking your urine for sugar (glucose) levels.
  • If you are an outpatient taking cefuroxime through a portable pump (such as an Eclipse® device):
    • Finish all doses of cefuroxime as instructed by your doctor, even if you think your condition has improved.
    • Store cefuroxime in the refrigerator or on ice.
    • Place one (1) dose of cefuroxime at room temperature about 30 minutes before the dose is received.
    • See “Do You Know…Using the Eclipse® medicine device” for details.

How does this medication work? What will it do for me?

Cefuroxime is an antibiotic that belongs to the family of medications known as cephalosporins. It is used to treat infections caused by bacteria. It is most often used to treat infections of the ear, throat, sinus, lung, and skin.

This medication may be available under multiple brand names and/or in several different forms. Any specific brand name of this medication may not be available in all of the forms or approved for all of the conditions discussed here. As well, some forms of this medication may not be used for all of the conditions discussed here.

Your doctor may have suggested this medication for conditions other than those listed in these drug information articles. If you have not discussed this with your doctor or are not sure why you are taking this medication, speak to your doctor. Do not stop taking this medication without consulting your doctor.

Do not give this medication to anyone else, even if they have the same symptoms as you do. It can be harmful for people to take this medication if their doctor has not prescribed it.

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What form(s) does this medication come in?

Suspension

Dry, white-to-pale-yellow, tutti-frutti-flavoured granules. After reconstitution, each 5 mL contains 125 mg of cefuroxime (as cefuroxime axetil). Nonmedicinal ingredients: acesulfame potassium, aspartame, polyvinyl pyrrolidone, stearic acid, sucrose (about 3 g/5 mL), tutti-frutti flavouring, and xanthan gum.

Tablet

250 mg
Each white-to-off-white, film-coated, capsule-shaped, biconvex tablet, engraved with “GXES7” on one side, contains 250 mg of cefuroxime (as cefuroxime axetil). Nonmedicinal ingredients: colloidal silicon dioxide, croscarmellose sodium, hydrogenated vegetable oil, hydroxypropyl methylcellulose, methylparaben, microcrystalline cellulose, propylene glycol, propylparaben, sodium benzoate, sodium lauryl sulfate, and titanium dioxide.

500 mg
Each white-to-off-white, film-coated, capsule-shaped, biconvex tablet, engraved with “GXEG2” on one side, contains 500 mg of cefuroxime (as cefuroxime axetil). Nonmedicinal ingredients: colloidal silicon dioxide, croscarmellose sodium, hydrogenated vegetable oil, hydroxypropyl methylcellulose, methylparaben, microcrystalline cellulose, propylene glycol, propylparaben, sodium benzoate, sodium lauryl sulfate, and titanium dioxide.

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How should I use this medication?

Adults and children 12 years of age and older: The recommended dose of cefuroxime ranges from 250 mg twice daily to 500 mg twice daily for 7 to 10 days. Taking cefuroxime with food helps the medication to be better absorbed into the bloodstream. Swallow the medication whole with a glass of water; do not chew, divide, or crush the tablets.

Children less than 12 years of age: The recommended children’s dose of cefuroxime ranges from 10 mg to 15 mg per kg of body weight twice daily for 7 to 10 days. The medication should be taken with food. The exact dose depends on the condition being treated. Children less than 12 years of age should take the oral suspension (not the tablets). Use an oral syringe to measure each dose of the liquid, as it gives a more accurate measurement than household teaspoons.

Many things can affect the dose of medication that a person needs, such as body weight, other medical conditions, and other medications. If your doctor has recommended a dose different from the ones listed here, do not change the way that you are taking the medication without consulting your doctor.

It is important to take this medication exactly as prescribed by your doctor. Finish all of this medication, even if you start to feel better. If you miss a dose, take it as soon as possible and continue with your regular schedule. If it is almost time for your next dose, skip the missed dose and continue with your regular dosing schedule. Do not take a double dose to make up for a missed one. If you are not sure what to do after missing a dose, contact your doctor or pharmacist for advice.

Store the tablets at room temperature, protect them from light and moisture, and keep out of the reach of children.

Store the oral suspension in the refrigerator, and keep it out of the reach of children. Discard any medication that remains after 10 days.

Do not dispose of medications in wastewater (e.g. down the sink or in the toilet) or in household garbage. Ask your pharmacist how to dispose of medications that are no longer needed or have expired.

Who should NOT take this medication?

Do not take this medication if you:

  • are allergic to cefuroxime or any ingredients of this medication
  • are allergic to any of the cephalosporin antibiotics

What side effects are possible with this medication?

Many medications can cause side effects. A side effect is an unwanted response to a medication when it is taken in normal doses. Side effects can be mild or severe, temporary or permanent.

The side effects listed below are not experienced by everyone who takes this medication. If you are concerned about side effects, discuss the risks and benefits of this medication with your doctor.

The following side effects have been reported by at least 1% of people taking this medication. Many of these side effects can be managed, and some may go away on their own over time.

Contact your doctor if you experience these side effects and they are severe or bothersome. Your pharmacist may be able to advise you on managing side effects.

  • abdominal pain (mild)
  • diarrhea (mild)
  • dizziness
  • drowsiness
  • headache
  • nausea
  • vomiting

Although most of the side effects listed below don’t happen very often, they could lead to serious problems if you do not seek medical attention.

Check with your doctor as soon as possible if any of the following side effects occur:

  • diaper rash
  • diarrhea (watery and severe; may also be bloody)
  • fever
  • severe abdominal pain or stomach cramps and pain
  • signs of clotting problems (e.g., unusual nosebleeds, bruising, blood in urine, coughing blood, bleeding gums, cuts that don’t stop bleeding)
  • signs of liver problems (e.g., nausea, vomiting, diarrhea, loss of appetite, weight loss, yellowing of the skin or whites of the eyes, dark urine, pale stools)
  • skin rash, itching, or hives
  • vaginal itching or discharge
  • white patches in the mouth (thrush; yeast infection in the mouth)

Stop taking the medication and seek immediate medical attention if any of the following occur:

  • seizures
  • signs of a severe skin reaction such as blistering, peeling, a rash covering a large area of the body, a rash that spreads quickly, or a rash combined with fever or discomfort
  • symptoms of an allergic reaction, (e.g., swelling of the hands, feet, ankles, face, lips, mouth, or throat; difficulty breathing or swallowing)

Some people may experience side effects other than those listed. Check with your doctor if you notice any symptom that worries you while you are taking this medication.

Are there any other precautions or warnings for this medication?

Before you begin using a medication, be sure to inform your doctor of any medical conditions or allergies you may have, any medications you are taking, whether you are pregnant or breast-feeding, and any other significant facts about your health. These factors may affect how you should use this medication.

Allergy: Before taking cefuroxime, inform your doctor about any adverse reactions you have had to medications, especially cefuroxime, cephalosporins, and penicillins. Some people who are allergic to penicillin may also be allergic to cephalosporins such as cefuroxime. If you have an allergic reaction, contact a doctor immediately.

Bacterial resistance: Misuse of an antibiotic such as cefuroxime may lead to the growth of resistant bacteria that will not be killed by the antibiotic. If this happens, the antibiotic may not work for you in the future. Although you may begin to feel better early in your course of treatment with cefuroxime, you need to take the full course exactly as directed to finish ridding your body of the infection and to prevent resistant bacteria from growing. Do not take cefuroxime or other antibiotics to treat a viral infection such as the common cold; antibiotics do not kill viruses, and using them to treat viral infections can lead to the growth of resistant bacteria.

Blood cells: Rarely, cefuroxime may cause a faster breakdown of red blood cells, leading to a form of anemia (hemolytic anemia). If you experience symptoms of anemia such as fatigue or lack of energy, pale skin, dizziness, or weakness, contact your doctor as soon as possible. If you are taking a blood test, let your doctor know that you are taking cefuroxime. This medication may affect the result of blood tests.

If you have a history of anemia caused by cephalosporin antibiotics, this anemia can be much more severe. Discuss with your doctor how this medication may affect your medical condition, how your medical condition may affect the dosing and effectiveness of this medication, and whether any special monitoring is needed.

Diabetes: The suspension form of this medication contains approximately 3 grams of sugar in each teaspoonful. If you have diabetes, it may affect your blood sugar control. If you have diabetes, discuss with your doctor how this medication may affect your medical condition, how your medical condition may affect the dosing and effectiveness of this medication, and whether any special monitoring is needed.

Diarrhea: People taking this medication may develop diarrhea caused by an infection with the bacteria C. difficile. If you have loose, watery, and bloody bowel movements, with or without fever, or stomach cramps after taking cefuroxime, get medical attention as soon as possible. Diarrhea caused by C. difficile infection can lead to serious health problems if it is not properly treated.

Kidney function: Kidney disease or reduced kidney function may cause this medication to build up in the body, causing side effects. If you have reduced kidney function or kidney disease, discuss with your doctor how this medication may affect your medical condition, how your medical condition may affect the dosing and effectiveness of this medication, and whether any special monitoring is needed.

Other infections: Use of cefuroxime for a long time may result in the overgrowth of organisms not affected by the medication, such as yeast, which can lead to other infections.

Phenylketonuria: People with phenylketonuria are not able to break down the amino acid phenylalanine, allowing it to build up in the body, causing harmful effects. The suspension form of this medication contains aspartame, a sweetener that is a source of phenylalanine, and should not be used by people with phenylketonuria.

Stomach and bowel problems: If you have had stomach or bowel problems (especially colitis), discuss with your doctor how this medication may affect your medical condition, how your medical condition may affect the dosing and effectiveness of this medication, and whether any special monitoring is needed.

Pregnancy: This medication should not be used during pregnancy unless the benefits outweigh the risks. If you become pregnant while taking this medication, contact your doctor immediately.

Breast-feeding: This medication passes into breast milk. If you are a breast-feeding mother and are taking cefuroxime, it may affect your baby. Talk to your doctor about whether you should continue breast-feeding.

What other drugs could interact with this medication?

There may be an interaction between cefuroxime axetil and any of the following:

  • aminoglycoside antibiotics (e.g., amikacin, gentamicin, tobramycin)
  • antacids (e.g., aluminum hydroxide, calcium carbonate, magnesium hydroxide)
  • H2 antagonists (e.g., famotidine, ranitidine)
  • BCG
  • BCG vaccine
  • cholera vaccine
  • birth control pills
  • disulfiram
  • sodium picosulfate
  • typhoid vaccine
  • warfarin

If you are taking any of these medications, speak with your doctor or pharmacist. Depending on your specific circumstances, your doctor may want you to:

  • stop taking one of the medications,
  • change one of the medications to another,
  • change how you are taking one or both of the medications, or
  • leave everything as is.

An interaction between two medications does not always mean that you must stop taking one of them. Speak to your doctor about how any drug interactions are being managed or should be managed.

Medications other than those listed above may interact with this medication. Tell your doctor or prescriber about all prescription, over-the-counter (non-prescription), and herbal medications you are taking. Also tell them about any supplements you take. Since caffeine, alcohol, the nicotine from cigarettes, or street drugs can affect the action of many medications, you should let your prescriber know if you use them.

All material copyright MediResource Inc. 1996 – 2020. Terms and conditions of use. The contents herein are for informational purposes only. Always seek the advice of your physician or other qualified health provider with any questions you may have regarding a medical condition. Source: www.medbroadcast.com/drug/getdrug/Ceftin

Cefuroxime Side Effects

Medically reviewed by Drugs.com. Last updated on Nov 20, 2018.

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In Summary

Commonly reported side effects of cefuroxime include: diarrhea. See below for a comprehensive list of adverse effects.

For the Consumer

Applies to cefuroxime: oral powder for suspension, oral tablet

Other dosage forms:

  • powder for solution

Along with its needed effects, cefuroxime may cause some unwanted effects. Although not all of these side effects may occur, if they do occur they may need medical attention.

Check with your doctor immediately if any of the following side effects occur while taking cefuroxime:

More common

  • Chills
  • diarrhea
  • fever
  • general feeling of illness or discomfort
  • headache
  • itching of the vagina or genital area
  • pain during sexual intercourse
  • rigidity
  • sweating
  • thick, white vaginal discharge with no odor or with a mild odor

Less common

  • Black, tarry stools
  • chest pain
  • cough
  • loose stools
  • painful or difficult urination
  • shortness of breath
  • sore throat
  • sores, ulcers, or white spots on the lips or in the mouth
  • swollen glands
  • unusual bleeding or bruising
  • unusual tiredness or weakness

Rare

  • Back, leg, or stomach pains
  • bladder pain
  • bleeding gums
  • bloody or cloudy urine
  • body aches or pain
  • burning while urinating
  • dark urine
  • difficulty with breathing
  • ear congestion
  • fast, pounding, or irregular heartbeat or pulse
  • frequent urge to urinate
  • general body swelling
  • loss of appetite
  • loss of voice
  • lower back or side pain
  • nasal congestion
  • nausea or vomiting
  • nosebleeds
  • pain or tenderness around the eyes and cheekbones
  • pale skin
  • pink or red urine
  • sneezing
  • stuffy or runny nose
  • swelling of the joints
  • swollen glands
  • tightness of chest or wheezing
  • white or brownish vaginal discharge
  • white patches in the mouth or throat or on the tongue
  • white patches with diaper rash
  • yellowing of the eyes or skin

Incidence not known

  • Blistering, peeling, or loosening of the skin
  • bloody, black, or tarry stools
  • clay-colored stools
  • cough or hoarseness
  • coughing up blood
  • decrease in urine output or decrease in urine-concentrating ability
  • feeling of discomfort
  • fever with or without chills
  • general feeling of tiredness or weakness
  • high fever
  • hives
  • increased menstrual flow or vaginal bleeding
  • joint or muscle pain
  • large, hive-like swelling on the face, eyelids, lips, tongue, throat, hands, legs, feet, or sex organs
  • light-colored stools
  • paralysis
  • prolonged bleeding from cuts
  • puffiness or swelling of the eyelids or around the eyes, face, lips, or tongue
  • red or black, tarry stools
  • red or dark brown urine
  • red skin lesions, often with a purple center
  • red, irritated eyes
  • seizures
  • swollen lymph glands
  • swollen or painful glands
  • unpleasant breath odor
  • upper right abdominal or stomach pain
  • vomiting of blood

Some side effects of cefuroxime may occur that usually do not need medical attention. These side effects may go away during treatment as your body adjusts to the medicine. Also, your health care professional may be able to tell you about ways to prevent or reduce some of these side effects. Check with your health care professional if any of the following side effects continue or are bothersome or if you have any questions about them:

Less common

  • Bad, unusual, or unpleasant (after) taste
  • change in taste
  • diaper rash

Rare

  • Abdominal or stomach cramps
  • acid or sour stomach
  • belching
  • bloated
  • difficulty with moving
  • excess air or gas in the stomach or intestines
  • flushing or redness of the skin
  • full feeling
  • gas in the stomach
  • heartburn
  • indigestion
  • irritability
  • irritation or soreness of the mouth
  • itching skin
  • muscle pain or stiffness
  • muscle spasm of the neck
  • passing gas
  • restlessness
  • sleepiness or unusual drowsiness
  • stomach discomfort, upset, or pain
  • swelling of the tongue
  • thirst
  • trouble sitting still
  • unusually warm skin
  • watering of the mouth and drooling
  • weight loss

Incidence not known

  • Hives or welts
  • redness of the skin

For Healthcare Professionals

Applies to cefuroxime: injectable powder for injection, intravenous solution, oral powder for reconstitution, oral tablet

General

Cefuroxime was generally well tolerated. The side effects most commonly reported with the parenteral formulation have included neutropenia, eosinophilia, transient liver enzyme/bilirubin elevations, and injection site reactions. The side effects most commonly reported with the oral formulations have included Candida overgrowth, eosinophilia, headache, dizziness, gastrointestinal disturbances, and transient liver enzyme elevations.

Side effects may be more likely and more severe in patients with liver disease and/or renal dysfunction.

Gastrointestinal

Common (1% to 10%): Diarrhea/loose stools, nausea/vomiting, abdominal pain, nausea

Frequency not reported: Abdominal discomfort, dry mouth, Clostridium difficile-associated diarrhea

Postmarketing reports: GI disturbances (including diarrhea, nausea, vomiting, abdominal pain), pseudomembranous colitis

Cephalosporin-class:

-Frequency not reported: Vomiting, abdominal pain, colitis

The onset of pseudomembranous colitis symptoms has been reported during or after antibacterial therapy.

Hepatic

Common (1% to 10%): Transient increase in AST, transient increase in ALT, transient increase in liver enzyme levels

Uncommon (0.1% to 1%): Transient increase in bilirubin

Postmarketing reports: Hepatic dysfunction, hepatitis, cholestasis, jaundice (mainly cholestatic)

Cephalosporin-class:

-Frequency not reported: Hepatic dysfunction (including cholestasis)

Nervous system

Common (1% to 10%): Headache, dizziness

Uncommon (0.1% to 1%): Sleepiness, somnolence, hyperactivity

Postmarketing reports: Seizures, encephalopathy

Cephalosporin-class antibiotics (including this drug) have been associated with seizures, especially in patients with renal dysfunction when the dose was not reduced.

Hypersensitivity

Delayed hypersensitivity reaction to this drug has been reported in 2.9% of patients with history of delayed hypersensitivity to penicillin (but not a cephalosporin).

Rare cases of severe hypersensitivity reactions (including erythema multiforme, toxic epidermal necrolysis , drug fever, serum sickness-like reaction, anaphylaxis, Stevens-Johnson syndrome) have been reported.

Common (1% to 10%): Delayed hypersensitivity reaction

Uncommon (0.1% to 1%): Hypersensitivity reactions (including rash, pruritus, urticaria)

Rare (0.01% to 0.1%): Severe hypersensitivity reactions

Frequency not reported: Serum sickness

Postmarketing reports: Anaphylaxis, serum sickness-like reaction

Hematologic

Profound leukopenia has sometimes been profound with oral therapy.

Common (1% to 10%): Eosinophilia, decreased hemoglobin and hematocrit, neutropenia, decreased hemoglobin concentration

Uncommon (0.1% to 1%): Positive Coombs test, leukopenia, thrombocytopenia

Frequency not reported: Autoimmune granulocytopenia, increased coagulation time

Postmarketing reports: Hemolytic anemia, pancytopenia, increased prothrombin time

Cephalosporin-class:

-Frequency not reported: Aplastic anemia, hemolytic anemia, hemorrhage, prolonged prothrombin time, pancytopenia, agranulocytosis

Renal

Acute renal failure has been reported. Renal function improved after this drug was stopped, and deteriorated upon rechallenge.

Frequency not reported: Increased BUN, increased creatinine, decreased CrCl, acute renal failure

Postmarketing reports: Renal dysfunction, interstitial nephritis (including reversible fever, azotemia, pyuria, eosinophilia)

Cephalosporin-class:

-Frequency not reported: Toxic nephropathy

Genitourinary

Common (1% to 10%): Vaginitis

Cephalosporin-class:

-Frequency not reported: Vaginitis (including vaginal candidiasis)

Dermatologic

A case of occupational contact dermatitis due to cephalosporin allergy has been reported in a nurse who prepared cephalosporin solutions for administration to patients. The dermatitis resolved after the nurse stopped preparing the solutions.

Common (1% to 10%): Diaper/nappy rash

Uncommon (0.1% to 1%): Rash, urticaria/hives, pruritus, erythema

Rare (0.01% to 0.1%): Erythema multiforme, toxic epidermal necrolysis (exanthematic necrolysis), Stevens-Johnson syndrome

Frequency not reported: Acute generalized exanthematous pustulosis

Postmarketing reports: Angioedema, urticaria, toxic epidermal necrolysis, Stevens-Johnson syndrome, erythema multiforme, cutaneous vasculitis

Metabolic

Uncommon (0.1% to 1%): Anorexia

Cephalosporin-class:

-Frequency not reported: Urine glucose false positive

Other

Common (1% to 10%): Transient increase in LDH, transient increase in alkaline phosphatase, Candida overgrowth, dislike of taste

Uncommon (0.1% to 1%): Chest pain/tightness, chills, thirst, viral illness, candidiasis, fever

Rare (0.01% to 0.1%): Drug fever

Frequency not reported: Clostridium difficile overgrowth, disulfiram reaction

Respiratory

Uncommon (0.1% to 1%): Shortness of breath, sinusitis, cough, upper respiratory infection

Musculoskeletal

Cardiovascular

A 90-year-old man, with no history of coronary artery disease, diabetes mellitus, hypertension, or hyperlipidemia, was administered 750 mg cefuroxime axetil IM for urinary tract infection. About 10 minutes after the injection, the patient developed chest pain and pruritic skin rashes. Kounis syndrome type I variant was diagnosed secondary to the drug. Five days after stopping the drug, the patient’s symptoms had resolved.

Uncommon (0.1% to 1%): Tachycardia

Frequency not reported: Kounis syndrome type I variant

Local

Common (1% to 10%): Injection site reactions (including pain, thrombophlebitis), thrombophlebitis with IV administration

Frequency not reported: Pain at IM injection site

Immunologic

Common (1% to 10%): Jarisch-Herxheimer reaction

Psychiatric

Uncommon (0.1% to 1%): Irritable behavior

1. Cerner Multum, Inc. “Australian Product Information.” O 0

2. Bulpitt D, Potter CE, Jaderberg M “A large scale, general practice based investigation into the clinical efficacy and tolerability of cefuroxime axetil in women with uncomplicated urinary tract infect.” Curr Med Res Opin 12 (1991): 318-24

3. Yangco BG, Lowe J, Nolen TM, et al “A multicenter trial comparing the efficacy and safety of cefuroxime axetil and cefaclor in pneumonia of adults.” Clin Ther 12 (1990): 440-6

4. Henry D, Ruoff GE, Rhudy J, Puopolo A, Drehobl M, Schoenberger J, Giguere G, Collins JJ “Clinical comparison of cefuroxime axetil and amoxicillin/clavulanate in the treatment of patients with secondary bacterial infections of acute bronchitis.” Clin Ther 17 (1995): 861-74

5. “Product Information. Ceftin (cefuroxime).” Glaxo Wellcome, Research Triangle Park, NC.

6. Henry D, Ruoff GE, Rhudy J, Puopolo A, Drehobl M, Schoenberger J, Giguere G, Collins JJ “Effectiveness of short-course therapy (5 days) with cefuroxime axetil in treatment of secondary bacterial infections of acute bronchitis.” Antimicrob Agents Chemother 39 (1995): 2528-34

7. Pines A, Raafat H, Kennedy MR, Mullinger BM “Experience with cefuroxime in 190 patients with severe respiratory infections.” Chemotherapy 26 (1980): 212-7

8. Cannon SR, Dyson PH, Sanderson PJ “Pseudomembranous colitis associated with antibiotic prophylaxis in orthopaedic surgery.” J Bone Joint Surg Br 70 (1988): 600-2

9. Sommers D, Van Wyk M, Williams PE, Harding SM “Pharmacokinetics and tolerance of cefuroxime axetil in volunteers during repeated dosing.” Antimicrob Agents Chemother 25 (1984): 344-7

10. Hebblethwaite EM, Brown GW, Cox DM “A comparison of the efficacy and safety of cefuroxime axetil and augmentin in the treatment of upper respiratory tract infections.” Drugs Exp Clin Res 13 (1987): 91-4

11. Holloway KL, Smith KW, Wilberger JE, Jemsek JG, Giguere GC, Collins JJ “Antibiotic prophylaxis during clean neurosurgery: a large, multicenter study using cefuroxime.” Clin Ther 18 (1996): 84-94

12. Wormser GP “Clinical practice. Early Lyme disease.” N Engl J Med 354 (2006): 2794-801

13. Griffiths GK, Vandenburg MJ, Wight LJ, et al “Efficacy and tolerability of cefuroxime axetil in patients with upper respiratory tract infections.” Curr Med Res Opin 10 (1987): 555-61

14. “Product Information. Zinacef (cefuroxime).” Glaxo Wellcome, Research Triangle Park, NC.

15. Abramowicz M, Aaron H “Cefuroxime axetil.” Med Lett Drugs Ther 30 (1988): 57-9

16. Higuera F, Hidalgo H, Feris J, Giguere G, Collins JJ “Comparison of oral cefuroxime axetil and oral amoxycillin/clavulanate in the treatment of community-acquired pneumonia.” J Antimicrob Chemother 37 (1996): 555-64

17. Baniasadi S, Fahimi F, Mansouri D “Serum sickness-like reaction associated with cefuroxime and ceftriaxone.” Ann Pharmacother 41 (2007):

20. Filipe P, Almeida RSLS, Rodrigo FG “Occupational allergic contact dermatitis from cephalosporins.” Contact Dermatitis 34 (1996): 226

21. Viken R, Van Arsdel PP “Allergy to cephalosporins.” JAMA 265 (1991): 2254

23. Murphy MF, Metcalfe P, Grint PC, et al “Cephalosporin-induced immune neutropenia.” Br J Haematol 59 (1985): 9-14

24. Malloy CA, Kiss JE, Challapalli M “Cefuroxime-induced immune hemolysis.” J Pediatr 143 (2003): 130-2

25. Goddard JK, Janning SW, Gass JS, Wilson RF “Cefuroxime-induced acute renal failure.” Pharmacotherapy 14 (1994): 488-91

26. Leong CL, Thiruventhiran T “Cefuroxime-induced acute renal failure.” Nephron 84 (2000): 185

27. Manley HJ, Bailie GR, Eisele G “Bilateral renal cortical necrosis associated with cefuroxime axetil.” Clin Nephrol 49 (1998): 268-70

28. Cohen AD, Cagnano E, Halevy S “Acute generalized exanthematous pustulosis mimicking toxic epidermal necrolysis.” Int J Dermatol 40 (2001): 458-61

29. Cerner Multum, Inc. “UK Summary of Product Characteristics.” O 0

30. Mattes JA “Antabuse reaction with ceftin.” Am J Psychiatry 163 (2006): 2019-20

Always consult your healthcare provider to ensure the information displayed on this page applies to your personal circumstances.

Some side effects may not be reported. You may report them to the FDA.

Medical Disclaimer

About cefuroxime

Type of medicine A cephalosporin antibiotic
Used for Treatment (or prevention) of infection
Also called Britacef®; Zinacef®; Zinnat®
Available as Tablets, oral liquid medicine and injection

Cefuroxime is a broad-spectrum antibiotic, which means that it is active against a wide variety of bacteria. It is used to treat bacterial infections such as urinary tract infections, skin infections, chest infections, ear infections and sinusitis. It is also given before some surgical operations, to prevent an infection from occurring. Cefuroxime treats an infection by killing the bacteria that are causing it.

Cefuroxime is suitable for adults and children, and can be taken during pregnancy. Some people who are allergic to penicillin antibiotics may not be able to take cefuroxime, so make sure your doctor knows if you have ever had an allergic reaction to any other antibiotic.

Before taking cefuroxime

Some medicines are not suitable for people with certain conditions, and sometimes a medicine may only be used if extra care is taken. For these reasons, before you start taking cefuroxime it is important that your doctor knows:

  • If you have ever had an allergic reaction to a medicine. It is particularly important that you tell your doctor if you have had a bad reaction to a penicillin or cephalosporin antibiotic.
  • If you have any problems with the way your kidneys work.
  • If you are pregnant, trying for a baby or breast-feeding. (Although cefuroxime is not known to be harmful to babies, it is still important that you tell your doctor if you are expecting or breast-feeding a baby.)
  • If you are taking or using any other medicines. This includes any medicines you are taking which are available to buy without a prescription, as well as herbal and complementary medicines.

How to take cefuroxime

  • Before you start taking cefuroxime, read the manufacturer’s printed information leaflet from inside your pack. The manufacturer’s leaflet will give you more information about the antibiotic and a full list of side-effects which you may experience from taking it.
  • You should take cefuroxime exactly as your doctor tells you to. There are two strengths of cefuroxime tablets available: 125 mg and 250 mg. It is usual to be prescribed either 125 mg or 250 mg to be taken twice a day, although doses can be higher than this for severe infections. Your doctor will tell you what dose is right for you (or your child), and this information will be printed on the label of the pack to remind you. If you have been given liquid medicine, read the directions carefully to make sure you measure out the correct amount of medicine. Your doctor will also tell you how long your course of treatment will last – this is commonly about 5-7 days.
  • Take your doses with a snack, or just after eating a meal. Swallow the tablets whole with a drink of water. Do not chew or break the tablets.
  • Space your doses out evenly throughout the day. Keep taking the antibiotic until the course is finished unless you are told to stop. Taking the full course is important (even if you feel your infection has cleared up) in order to prevent the infection from coming back.
  • If you forget to take a dose, take one as soon as you remember. Try to take the correct number of doses each day, but do not take two doses at the same time to make up.

Getting the most from your treatment

  • Some people develop thrush (redness and itching in the mouth or vagina) after taking a course of antibiotics. If you think you have thrush speak with your doctor or pharmacist for advice.
  • If you are using oral combined hormonal contraception (the ‘pill’), additional contraceptive precautions such as condoms are recommended for a time if you have vomiting or diarrhoea which lasts for more than 24 hours. If you need further advice about this, speak with your doctor or pharmacist.
  • If you are having an operation or any other medical treatment, tell the person carrying out the treatment that you are taking an antibiotic. This is because cefuroxime may interfere with the results of some tests to check for sugar in your urine.
  • Cefuroxime may stop the oral typhoid vaccine from working. If you are having any vaccinations, make sure the person treating you knows that you are taking this antibiotic.

Can cefuroxime cause problems?

Along with their useful effects, most medicines can cause unwanted side-effects although not everyone experiences them. The table below contains some of the most common ones associated with cefuroxime. You will find a full list in the manufacturer’s information leaflet supplied with your medicine. The unwanted effects often improve as your body adjusts to the new medicine, but speak with your doctor or pharmacist if any of the following continue or become troublesome.

Common cefuroxime side-effects – these affect less than 1 in 10 people who take this medicine What can I do if I experience this?
Diarrhoea Drink plenty of water to replace any lost fluids. If the diarrhoea continues for longer than 24 hours, or becomes severe or contains blood, let your doctor know straightaway
Feeling sick (nausea), tummy (abdominal) discomfort Stick to simple foods. Make sure you take your doses after meals
Headache Ask your pharmacist to recommend a suitable painkiller
Feeling dizzy Do not drive and do not use tools or machines until you feel better
Changes to some blood tests (these are temporary) Speak with your doctor if you have concerns about this
Skin rash, and other allergic-type reactions Let your doctor know as soon as possible, as your treatment may need to be changed

Important: if you develop an itchy rash, or a swollen face or mouth, or have difficulty breathing, these can be signs that you are allergic to the antibiotic. Do not take any more cefuroxime and speak with your doctor or go to your local accident and emergency department straightaway.

If you experience any other symptoms which you think may be due to this medicine, speak with your doctor or pharmacist for further advice.

How to store cefuroxime

  • Keep all medicines out of the reach and sight of children.
  • Store in a cool, dry place, away from direct heat and light.
  • If you have been given liquid medicine, store it in a refrigerator. It will have been made up by the pharmacy and lasts for 10 days, so remember to check the expiry date on the bottle and do not use it after this date.

Important information about all medicines

Never take more than the prescribed dose. If you suspect that you or someone else might have taken an overdose of this medicine, go to the accident and emergency department of your local hospital. Take the container with you, even if it is empty.

This medicine is for you. Never give it to other people even if their condition appears to be the same as yours.

If you buy any medicines, check with a pharmacist that they are safe to take with your other medicines.

If you are having an operation or any dental treatment, tell the person carrying out the treatment which medicines you are taking.

Do not keep out-of-date or unwanted medicines. Take them to your local pharmacy which will dispose of them for you.

If you have any questions about this medicine ask your pharmacist.

Identification

Are you a new drug developer? Contact us to learn more about our customized products and solutions. Stay in the know! As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages. #DrugBankUpdates Name Cefuroxime Accession Number DB01112 (APRD00285) Type Small Molecule Groups Approved Description

Broad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus.

Structure 3D Download Similar Structures

Structure for Cefuroxime (DB01112)

× Close Synonyms Product Ingredients

Ingredient UNII CAS InChI Key
Cefuroxime axetil Z49QDT0J8Z 64544-07-6 KEJCWVGMRLCZQQ-YJBYXUATSA-N
Cefuroxime sodium R8A7M9MY61 56238-63-2 URDOHUPGIOGTKV-JTBFTWTJSA-M

Product Images Prescription Products

Name Dosage Strength Route Labeller Marketing Start Marketing End
Unlock Additional Data
Ceftin Powder, for suspension 250 mg/5mL Oral Glaxosmithkline Inc 2004-06-02 2018-09-30 US
Ceftin Tablet, film coated 250 mg/1 Oral Glaxosmithkline Inc 1989-10-01 2018-04-30 US
Ceftin Powder, for suspension 250 mg/5mL Oral A S Medication Solutions 2004-06-02 Not applicable US
Ceftin Tablet 500 mg/1 Oral GlaxoSmithKline 2006-03-10 2006-09-28 US
Ceftin Powder, for suspension 125 mg/5mL Oral Glaxosmithkline Inc 2004-06-02 2018-09-30 US
Ceftin Tablet, film coated 250 mg/1 Oral Physicians Total Care, Inc. 1989-10-01 2012-06-30 US
Ceftin – Pwr 250mg/sachet Powder Oral Glaxosmithkline Inc 1999-11-10 2003-02-07 Canada
Ceftin – Pws 125mg/5ml Powder, for solution Oral Glaxosmithkline Inc 1999-09-13 Not applicable Canada
Ceftin – Tab 250mg Tablet Oral Glaxosmithkline Inc 1998-12-31 Not applicable Canada
Ceftin – Tab 500mg Tablet Oral Glaxosmithkline Inc 1998-10-27 Not applicable Canada

Additional Data Available

  • Application Number Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name Dosage Strength Route Labeller Marketing Start Marketing End
Unlock Additional Data
Apo-cefuroxime Tablet Oral Apotex Corporation 2001-08-29 Not applicable Canada
Apo-cefuroxime Tablet Oral Apotex Corporation 2001-08-29 Not applicable Canada
Auro-cefuroxime Tablet Oral Aurobindo Pharma Limited (Unit Vi) 2012-01-13 Not applicable Canada
Auro-cefuroxime Tablet Oral Aurobindo Pharma Limited (Unit Vi) 2012-01-13 Not applicable Canada
Cefuroxime Injection, powder, for solution 95 mg/1mL Intravenous Hospira, Inc. 2009-04-27 2013-02-28 US
Cefuroxime Injection, powder, for solution 750 mg/1 Intramuscular; Intravenous WG Critical Care, LLC 2012-10-04 Not applicable US
Cefuroxime Injection, powder, for solution 1.5 g/1 Intravenous APP Pharmaceuticals, Inc. 2011-05-24 2018-09-07 US
Cefuroxime Injection, powder, for solution 750 mg/1 Intramuscular; Intravenous West-Ward Pharmaceuticals Corp 2004-01-09 Not applicable US
Cefuroxime Injection, powder, for solution 750 mg/1 Intramuscular; Intravenous APP Pharmaceuticals, Inc. 2011-05-24 2018-09-07 US
Cefuroxime Injection, powder, for solution 1.5 g/1 Intravenous West-Ward Pharmaceuticals Corp 2004-01-09 Not applicable US

Additional Data Available

  • Application Number Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more

  • Product Code Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands Cefurax (Lindopharm) / Elobact (GlaxoSmithKline) / Oraxim (Malesci) / Sharox (Fahrenheit) / Supacef (GlaxoSmithKline) / Zinacef danmark / Zinnat (GlaxoSmithKline) Categories UNII O1R9FJ93ED CAS number 55268-75-2 Weight Average: 424.385
Monoisotopic: 424.068884198 Chemical Formula C16H16N4O8S InChI Key JFPVXVDWJQMJEE-IZRZKJBUSA-N InChI InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1 IUPAC Name (6R,7R)-3–7–8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid SMILES 12SCC(COC(N)=O)=C(N1C(=O)2NC(=O)C(=N/OC)\C1=CC=CO1)C(O)=O

Pharmacology

Indication

For the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.

Associated Conditions

  • Acute Bacterial Exacerbation of Chronic Bronchitis (ABECB)
  • Animal bite
  • Bacterial Infections
  • Bloodstream Infections
  • Bone and Joint Infections
  • Gonorrhea
  • Impetigo
  • Lower Respiratory Tract Infection (LRTI)
  • Lyme Disease
  • Maxillary Sinusitis
  • Meningitis
  • Otitis media bacterial
  • Skin and Subcutaneous Tissue Bacterial Infections
  • Urinary Tract Infection
  • Mild Streptococcal pharyngitis
  • Mild Streptococcal tonsillitis
  • Moderate Streptococcal pharyngitis
  • Moderate Streptococcal tonsillitis

Pharmacodynamics

Cefuroxime is a β-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Aerobic Gram-negative Microorganisms: Escherichia coli, Haemophilus influenzae (including beta-lactamase-producing strains), Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis (including beta-lactamase-producing strains), Neisseria gonorrhoeae (including beta-lactamase-producing strains). Spirochetes: Borrelia burgdorferi. Cefuroxime axetil is the prodrug

Mechanism of action

Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor.

Target Actions Organism
APenicillin-binding protein 1A inhibitor Clostridium perfringens (strain 13 / Type A)

Unlock Additional Data Additional Data Available Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more Absorption

Absorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).

Volume of distribution Not Available Protein binding

50% to serum protein

Metabolism

The axetil moiety is metabolized to acetaldehyde and acetic acid.

  • Cefuroxime Acetic acid
  • Cefuroxime acetaldehyde

Route of elimination Not Available Half life

Approximately 80 minutes following intramuscular or intravenous injection.

Clearance Not Available Toxicity

Allergic reactions might be expected, including rash, nasal congestion, cough, dry throat, eye irritation, or anaphylactic shock. Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.

Affected organisms

  • Enteric bacteria and other eubacteria

Pathways Not Available Pharmacogenomic Effects/ADRs Not Available

Interactions

Drug Interactions This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

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  • Vet approved
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Drug Interaction
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(R)-warfarin The risk or severity of bleeding can be increased when Cefuroxime is combined with (R)-warfarin.
(S)-Warfarin The risk or severity of bleeding can be increased when Cefuroxime is combined with (S)-Warfarin.
4-hydroxycoumarin The risk or severity of bleeding can be increased when Cefuroxime is combined with 4-hydroxycoumarin.
Abacavir Cefuroxime may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefuroxime.
Acarbose Cefuroxime may decrease the excretion rate of Acarbose which could result in a higher serum level.
Aceclofenac Cefuroxime may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
Acemetacin The risk or severity of nephrotoxicity can be increased when Cefuroxime is combined with Acemetacin.
Acenocoumarol The risk or severity of bleeding can be increased when Cefuroxime is combined with Acenocoumarol.
Acetaminophen Cefuroxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level.

Additional Data Available

  • Extended Description Extended Description

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  • Severity Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level Evidence Level

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  • Action Action

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Food Interactions

  • Take with food to increase absorption.

Synthesis Reference

Vijay Kumar Handa, Ramesh Dandala, Jag Mohan Khanna, “Process for the preparation of cefuroxime.” U.S. Patent US6235896, issued February, 1976.

US6235896 General References External Links Human Metabolome Database HMDB0015244 KEGG Drug D00262 KEGG Compound C06894 PubChem Compound 5479529 PubChem Substance 46506681 ChemSpider 4586393 BindingDB 50422689 ChEBI 3515 ChEMBL CHEMBL1436 Therapeutic Targets Database DAP000445 PharmGKB PA448868 HET KOV RxList RxList Drug Page Drugs.com Drugs.com Drug Page PDRhealth PDRhealth Drug Page Wikipedia Cefuroxime ATC Codes S01AA27 — Cefuroxime

  • S01AA — Antibiotics
  • S01A — ANTIINFECTIVES
  • S01 — OPHTHALMOLOGICALS
  • S — SENSORY ORGANS

J01DC02 — Cefuroxime

  • J01DC — Second-generation cephalosporins
  • J01D — OTHER BETA-LACTAM ANTIBACTERIALS
  • J01 — ANTIBACTERIALS FOR SYSTEMIC USE
  • J — ANTIINFECTIVES FOR SYSTEMIC USE

J01RA03 — Cefuroxime and metronidazole

  • J01RA — Combinations of antibacterials
  • J01R — COMBINATIONS OF ANTIBACTERIALS
  • J01 — ANTIBACTERIALS FOR SYSTEMIC USE
  • J — ANTIINFECTIVES FOR SYSTEMIC USE

AHFS Codes

  • 08:12.06.08 — Second Generation Cephalosporins

PDB Entries 4kov FDA label (809 KB) MSDS (52.7 KB)

Clinical Trials

Clinical Trials

Phase Status Purpose Conditions Count
0 Recruiting Prevention Complications of Surgical Procedures 1
0 Recruiting Treatment Osteomyelitis 1
1, 2 Recruiting Prevention Endophthalmitis Postoperative 1
2 Completed Prevention 1
2 Withdrawn Treatment Human Immunodeficiency Virus (HIV) Infections / Sinusitis 1
2, 3 Recruiting Prevention Emergency Cesarean Section / Infection Wound 1
3 Completed Prevention Appendicitis Acute / Perforated Gastroduodenal Ulcer / Small intestinal obstruction 1
3 Completed Treatment Pneumonia 1
3 Recruiting Treatment Enterobacteriaceae Infections 1
4 Completed Prevention Infection 1
4 Completed Prevention Infection Prophylaxis in Colo Rectal Surgery 1
4 Completed Prevention Obesity; Drug 1
4 Completed Prevention Postoperative Infections 1
4 Completed Prevention Postoperative Wound Infection 2
4 Completed Prevention 1
4 Completed Treatment Community Acquired Pneumonia (CAP) 1
4 Completed Treatment Complications; Cesarean Section / Infection; Cesarean Section / Postoperative Wound Infection 1
4 Completed Treatment Erythema Chronicum Migrans / Post-Lyme Disease Symptoms 1
4 Completed Treatment Infection 1
4 Completed Treatment Knee Osteoarthritis (Knee OA) 1
4 Completed Treatment Wound Infections 1
4 Recruiting Health Services Research Antibiotic Resistant Infection / Uncomplicated Urinary Tract Infections 1
4 Recruiting Prevention Premature Rupture of Membranes 1
4 Terminated Treatment Streptococcal Infections 1
4 Withdrawn Treatment Postoperative Infections 1
Not Available Completed Not Available Drug-Induced Liver Injury 1
Not Available Completed Prevention Endophthalmitis 1
Not Available Completed Supportive Care Osteoarthritis (OA) / Post-traumatic; Arthrosis 1
Not Available Completed Treatment Cataracts / Endophthalmitis 1
Not Available Completed Treatment Complications, Pregnancy 1
Not Available Completed Treatment Post Operative Nausea and Vomiting (PONV) 1
Not Available Completed Treatment Ulcerative Colitis 1
Not Available Completed Treatment Postoperative paralytic ileus 1
Not Available Not Yet Recruiting Not Available Infectious Diseases 1
Not Available Recruiting Treatment Appendicitis 1
Not Available Unknown Status Prevention Cystocele / Enterocele / Rectocele / Uterine Prolapse 1
Not Available Unknown Status Prevention Infection 1
Not Available Unknown Status Prevention Peristomal Wound Infection After the Operation of PEG / Prophylactic Antibiotics Before PEG / The Patients Who Receive Percutaneous Endoscopic Gastrostomy 1
Not Available Withdrawn Not Available Cardiovascular Events 1

Pharmacoeconomics

Manufacturers Not Available Packagers

  • Aidarex Pharmacuticals LLC
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • B. Braun Melsungen AG
  • Baxter International Inc.
  • BMH Ltd.
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Cura Pharmaceutical Co. Inc.
  • DAVA Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Dorx LLC
  • Elan Pharmaceuticals Inc.
  • Eli Lilly & Co.
  • F Hoffmann-La Roche Ltd.
  • Forum Products Inc.
  • GC Hanford Manufacturing Co.
  • GlaxoSmithKline Inc.
  • Greenstone LLC
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Liberty Pharmaceuticals
  • Lupin Pharmaceuticals Inc.
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Orchid Healthcare
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Sagent Pharmaceuticals
  • Samson Medical Technologies
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wockhardt Ltd.
  • World Gen LLC
  • Zyber Pharmaceuticals

Dosage forms

Form Route Strength
Powder, for suspension Oral 125 mg/5mL
Powder, for suspension Oral 250 mg/5mL
Powder Oral
Powder, for solution Oral
Tablet Oral
Injection, powder, for solution Intramuscular; Intravenous 750 mg/1
Injection, powder, for solution Intravenous 1.5 g/16mL
Injection, powder, for solution Intravenous 1.5 g/1
Injection, powder, for solution Intravenous 1.5 g/100mL
Injection, powder, for solution Intravenous 7.5 g/82.5mL
Injection, powder, for solution Intravenous 7.5 g/80mL
Injection, powder, for solution Intravenous 7.5 g/1
Injection, powder, for solution Intravenous 750 mg/8mL
Injection, powder, for solution Intravenous 750 mg/100mL
Injection, powder, for solution Intravenous 90 mg/1mL
Injection, powder, for solution Intravenous 95 mg/1mL
Tablet Oral 125 mg/1
Tablet Oral 250 mg/1
Tablet Oral 500 mg/1
Tablet, film coated Oral 125 mg/1
Tablet, film coated Oral 250 mg/1
Tablet, film coated Oral 500 mg/1
Suspension Oral 125 mg/5mL
Suspension Oral 250 mg/1mL
Powder, for solution Intravenous
Injection, powder, for solution Intravenous 225 g/1
Injection, powder, for solution Intravenous 75 g/1
Injection, powder, for solution Intramuscular; Intravenous 750 mg/8.3mL
Injection, powder, for solution Intramuscular; Intravenous 90 mg/1mL
Injection, powder, for solution Intravenous 7.5 g/77mL
Injection, powder, for solution Intravenous 750 mg/8.3mL
Injection, powder, lyophilized, for solution Intravenous 1.5 g/1
Injection, powder, lyophilized, for solution Intravenous 750 mg/1
Injection, solution Intravenous 1.5 g/50mL
Injection, solution Intravenous 750 mg/50mL
Powder, for solution Intramuscular; Intravenous

Prices

Unit description Cost Unit
Rocephin 10 gm vial 478.32USD vial
Ceftin 20 500 mg tablet Bottle 436.36USD bottle
Cefuroxime Axetil 250 mg/5ml Suspension 100ml Bottle 121.27USD bottle
Rocephin 2 gm vial 97.5USD vial
Cefzil 250 mg/5ml Suspension 100ml Bottle 87.62USD bottle
Zinacef 7.5 gm vial 65.94USD vial
Rocephin 1 gm Solution Vial 65.53USD vial
Rocephin 1 gm vial 62.02USD vial
Duricef 500 mg/5ml Suspension 100ml Bottle 59.36USD bottle
Cefzil 125 mg/5ml Suspension 100ml Bottle 48.36USD bottle
Duricef 500 mg/5ml Suspension 75ml Bottle 46.93USD bottle
Maxipime 2 gram vial 43.04USD vial
Velosef 250 mg/5ml Suspension 100ml Bottle 23.99USD bottle
Maxipime 1 gm piggyback vial 23.24USD vial
Duricef 250 mg/5ml Suspension 50ml Bottle 22.99USD bottle
Maxipime 1 gram vial 21.7USD vial
Ceftin 500 mg tablet 20.98USD tablet
Cefuroxime 1.5 g/50 ml bag 16.8USD each
Cedax 400 mg capsule 16.13USD each
Zinacef 1.5 gm add-vant vial 13.94USD vial
Zinacef 1.5 gm vial 13.45USD vial
Cefuroxime sod 1.5 gm vial 13.44USD vial
Ceftin 250 mg tablet 11.74USD tablet
Cefzil 500 mg tablet 9.77USD tablet
Cefuroxime axetil 500 mg tablet 8.11USD tablet
Duricef 1 gm tablet 7.35USD tablet
Cefzil 250 mg tablet 4.76USD tablet
Ceftin 500 mg Tablet 3.61USD tablet
Cefuroxime axetil 250 mg tablet 2.82USD tablet
Velosef 500 mg capsule 2.02USD capsule
Apo-Cefuroxime 500 mg Tablet 2.02USD tablet
Ratio-Cefuroxime 500 mg Tablet 2.02USD tablet
Ceftin 250 mg Tablet 1.82USD tablet
Velosef 250 mg capsule 1.03USD capsule
Apo-Cefuroxime 250 mg Tablet 1.02USD tablet
Ratio-Cefuroxime 250 mg Tablet 1.02USD tablet
Zinacef-water 1.5 gm/50 ml 0.32USD ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. Patents

Patent Number Pediatric Extension Approved Expires (estimated)
Unlock Additional Data
CA2408198 No 2004-03-09 2022-11-21 Canada
CA1328405 No 1994-04-12 2011-04-12 Canada

Additional Data Available

  • Filed On Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State Solid Experimental Properties

Property Value Source
melting point (°C) 218-225 °C Not Available
water solubility Freely soluble as sodium salt (145 mg/L) Not Available
logP -0.16 SANGSTER (1993)

Predicted Properties

Property Value Source
Water Solubility 0.284 mg/mL ALOGPS
logP -0.24 ALOGPS
logP -0.9 ChemAxon
logS -3.2 ALOGPS
pKa (Strongest Acidic) 3.15 ChemAxon
pKa (Strongest Basic) -1.1 ChemAxon
Physiological Charge -1 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 173.76 Å2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 97.17 m3·mol-1 ChemAxon
Polarizability 38.75 Å3 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five Yes ChemAxon
Ghose Filter No ChemAxon
Veber’s Rule No ChemAxon
MDDR-like Rule Yes ChemAxon

Predicted ADMET features

Property Value Probability
Human Intestinal Absorption + 0.6504
Blood Brain Barrier 0.9863
Caco-2 permeable 0.7051
P-glycoprotein substrate Substrate 0.7253
P-glycoprotein inhibitor I Non-inhibitor 0.8621
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Non-inhibitor 0.8688
CYP450 2C9 substrate Non-substrate 0.8686
CYP450 2D6 substrate Non-substrate 0.8196
CYP450 3A4 substrate Substrate 0.5051
CYP450 1A2 substrate Non-inhibitor 0.6957
CYP450 2C9 inhibitor Non-inhibitor 0.7771
CYP450 2D6 inhibitor Non-inhibitor 0.8707
CYP450 2C19 inhibitor Non-inhibitor 0.7064
CYP450 3A4 inhibitor Non-inhibitor 0.8308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8916
Ames test Non AMES toxic 0.7525
Carcinogenicity Non-carcinogens 0.8816
Biodegradation Not ready biodegradable 0.9759
Rat acute toxicity 1.6593 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9724
hERG inhibition (predictor II) Non-inhibitor 0.8292

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST) Not Available Spectra

Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum – GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum – 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum – 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum – 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum – 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum – 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum – 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Taxonomy

Description This compound belongs to the class of organic compounds known as cephalosporin 3′-carbamates. These are cephalosporins that are substituted at the 3′-position by a carbamate group. Kingdom Organic compounds Super Class Organoheterocyclic compounds Class Lactams Sub Class Beta lactams Direct Parent Cephalosporin 3′-carbamates Alternative Parents N-acyl-alpha amino acids and derivatives / 1,3-thiazines / Tertiary carboxylic acid amides / Carbamate esters / Furans / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Organic carbonic acids and derivatives / Thiohemiaminal derivativesAzacyclic compounds / Oxacyclic compounds / Carboxylic acids / Dialkylthioethers / Monocarboxylic acids and derivatives / Carbonyl compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Organopnictogen compounds show 10 more Substituents Cephalosporin 3′-carbamate / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Meta-thiazine / Furan / Heteroaromatic compound / Carbamic acid ester / Tertiary carboxylic acid amide / Azetidine / Carboxamide groupCarbonic acid derivative / Secondary carboxylic acid amide / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Oxacycle / Azacycle / Dialkylthioether / Hemithioaminal / Thioether / Hydrocarbon derivative / Organopnictogen compound / Carbonyl group / Organonitrogen compound / Organooxygen compound / Organic oxide / Organic nitrogen compound / Organic oxygen compound / Aromatic heteropolycyclic compound show 19 more Molecular Framework Aromatic heteropolycyclic compounds External Descriptors oxime O-ether, furans, 3-(carbamoyloxymethyl)cephalosporin (CHEBI:3515)

Targets

Kind Protein Organism Clostridium perfringens (strain 13 / Type A) Pharmacological action Yes Actions Inhibitor General Function Transferase activity, transferring glycosyl groups Specific Function Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str… Gene Name pbpA Uniprot ID Q8XJ01 Uniprot Name Penicillin-binding protein 1A Molecular Weight 75176.35 Da

Transporters

Binding Properties

×

Property Measurement pH Temperature (°C)
Ki (nM) >5000000 N/A N/A 15567297
Ki (nM) 26000000 N/A N/A 15567297 / 15974593

Details Binding Properties1. Solute carrier family 15 member 1 Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Proton-dependent oligopeptide secondary active transmembrane transporter activity Specific Function Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products. Gene Name SLC15A1 Uniprot ID P46059 Uniprot Name Solute carrier family 15 member 1 Molecular Weight 78805.265 Da

  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24.

×

Property Measurement pH Temperature (°C)
Ki (nM) 12589254 N/A N/A 21741846
Ki (nM) 12600000 N/A N/A 21741846

Details Binding Properties2. Solute carrier family 15 member 2 Kind Protein Organism Humans Pharmacological action Unknown Actions Inhibitor General Function Peptide:proton symporter activity Specific Function Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Gene Name SLC15A2 Uniprot ID Q16348 Uniprot Name Solute carrier family 15 member 2 Molecular Weight 81782.77 Da

  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24.

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Drug created on June 13, 2005 07:24 / Updated on February 02, 2020 04:18

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