Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H16N4O8S |
Molecular Weight | 424.385 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C3=CC=CO3)C(O)=O
InChI
InChIKey=JFPVXVDWJQMJEE-IZRZKJBUSA-N
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
Molecular Formula | C16H16N4O8S |
Molecular Weight | 424.385 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Cefuroxime is a semisynthetic, broad-spectrum, cephalosporin antibiotic. Cefuroxime is a bactericidal agent that acts by inhibition of bacterial cell wall synthesis. Cefuroxime has activity in the presence of some beta-lactamases, both penicillinases and cephalosporinases, of Gram-negative and Gram-positive bacteria. Cefuroxime has been shown to be active against most isolates of the following bacteria, both in vitro and in clinical infection: Enterobacter spp., Escherichia coli, Klebsiella spp., Haemophilus influenzae, Neisseria meningitidis, Neisseria gonorrhoeae, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Cefuroxime is indicated for the treatment of patients with septicemia, meningitis, gonorrhea, lower respiratory tract, urinary tract, skin and skin-structure, bone and joint infections caused by susceptible strains of the designated organisms.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7968655 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | ZINACEF Approved UseZINACEF is indicated for the treatment of patients with infections caused by susceptible strains of the designated organisms in the following diseases:
1. Lower Respiratory Tract Infections, including pneumonia, caused by Streptococcus pneumoniae, Haemophilus influenzae (including ampicillin-resistant strains), Klebsiella spp., Staphylococcus aureus (penicillinase- and non–penicillinase-producing strains), Streptococcus pyogenes, and Escherichia coli.
2. Urinary Tract Infections caused by Escherichia coli and Klebsiella spp.
3. Skin and Skin-Structure Infections caused by Staphylococcus aureus (penicillinaseand non–penicillinase-producing strains), Streptococcus pyogenes, Escherichia coli, Klebsiella spp., and Enterobacter spp.
4. Septicemia caused by Staphylococcus aureus (penicillinase- and non– penicillinase-producing strains), Streptococcus pneumoniae, Escherichia coli, Haemophilus influenzae (including ampicillin-resistant strains), and Klebsiella spp.
5. Meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (including ampicillin-resistant strains), Neisseria meningitidis, and Staphylococcus aureus (penicillinase- and non–penicillinase-producing strains).
6. Gonorrhea: Uncomplicated and disseminated gonococcal infections due to Neisseria gonorrhoeae (penicillinase- and non–penicillinase-producing strains) in both males and females.
7. Bone and Joint Infections caused by Staphylococcus aureus (penicillinase- and nonpenicillinase-producing strains). Launch Date1983 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
32.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/949172/ |
750 mg single, intramuscular dose: 750 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFUROXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
27 μg/mL |
750 mg single, intramuscular dose: 750 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFUROXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
88.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/949172/ |
750 mg single, intramuscular dose: 750 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFUROXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
82.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/949172/ |
750 mg single, intramuscular dose: 750 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFUROXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
80 min |
750 mg single, intramuscular dose: 750 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFUROXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50% |
750 mg single, intramuscular dose: 750 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFUROXIME plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3000 mg 3 times / day multiple, intravenous|intramuscular Recommended Dose: 3000 mg, 3 times / day Route: intravenous|intramuscular Route: multiple Dose: 3000 mg, 3 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: Page: p.9 |
Disc. AE: Allergy, Pseudomembranous colitis... AEs leading to discontinuation/dose reduction: Allergy Sources: Page: p.9Pseudomembranous colitis |
500 mg 2 times / day multiple, oral (max) Recommended Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: Page: p.1 |
Disc. AE: Hypersensitivity reaction, Diarrhea, Clostridium difficile... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction (serious) Sources: Page: p.1Diarrhea, Clostridium difficile |
500 mg 2 times / day multiple, oral (max) Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.11 |
unhealthy n = 912 Health Status: unhealthy Condition: Bacterial infections Population Size: 912 Sources: Page: p.11 |
Disc. AE: Diarrhea, Nausea... AEs leading to discontinuation/dose reduction: Diarrhea Sources: Page: p.11Nausea Vomiting Abdominal pain |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Allergy | Disc. AE | 3000 mg 3 times / day multiple, intravenous|intramuscular Recommended Dose: 3000 mg, 3 times / day Route: intravenous|intramuscular Route: multiple Dose: 3000 mg, 3 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: Page: p.9 |
Pseudomembranous colitis | Disc. AE | 3000 mg 3 times / day multiple, intravenous|intramuscular Recommended Dose: 3000 mg, 3 times / day Route: intravenous|intramuscular Route: multiple Dose: 3000 mg, 3 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: Page: p.9 |
Diarrhea, Clostridium difficile | Disc. AE | 500 mg 2 times / day multiple, oral (max) Recommended Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: Page: p.1 |
Hypersensitivity reaction | serious Disc. AE |
500 mg 2 times / day multiple, oral (max) Recommended Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Bacterial infections Sources: Page: p.1 |
Abdominal pain | Disc. AE | 500 mg 2 times / day multiple, oral (max) Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.11 |
unhealthy n = 912 Health Status: unhealthy Condition: Bacterial infections Population Size: 912 Sources: Page: p.11 |
Diarrhea | Disc. AE | 500 mg 2 times / day multiple, oral (max) Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.11 |
unhealthy n = 912 Health Status: unhealthy Condition: Bacterial infections Population Size: 912 Sources: Page: p.11 |
Nausea | Disc. AE | 500 mg 2 times / day multiple, oral (max) Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.11 |
unhealthy n = 912 Health Status: unhealthy Condition: Bacterial infections Population Size: 912 Sources: Page: p.11 |
Vomiting | Disc. AE | 500 mg 2 times / day multiple, oral (max) Studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: Page: p.11 |
unhealthy n = 912 Health Status: unhealthy Condition: Bacterial infections Population Size: 912 Sources: Page: p.11 |
PubMed
Title | Date | PubMed |
---|---|---|
Local and Gastrointestinal reactions to intravenously administered cefoxitin and cefuroxime. | 1979 |
|
[Fosfomycin: animal experiments on nephrotoxicity, pharmacokinetics and therapeutic efficacy (author's transl)]. | 1980 |
|
Treatment of gentamicin-resistant Klebsiella urinary tract infections with cephradine, augmentin, cefuroxime and amikacin. | 1981 Sep |
|
Renal function in patients treated with tobramycin-cefuroxime or tobramycin-penicillin G. | 1983 Dec |
|
Psychotic reaction to cefuroxime. | 1984 Apr 28 |
|
Comparative efficacy of ceftriaxone and cefuroxime for treatment of bacterial meningitis. | 1989 Jun |
|
Cimetidine in the treatment of refractory anaphylaxis. | 1989 Sep |
|
Cefuroxime-induced acute renal failure. | 1994 Jul-Aug |
|
Drug-related Henoch-Schönlein Purpura. | 1996 Jan-Feb |
|
Cefuroxime axetil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. | 1996 Jul |
|
Sequential therapy with cefuroxime followed by cefuroxime axetil in acute exacerbations of chronic bronchitis. | 1997 Dec |
|
Cefuroxime-induced encephalopathy. | 1998 Jun |
|
Cefuroxime-induced acute renal failure. | 2000 Feb |
|
Clinical efficacy of intravenous followed by oral azithromycin monotherapy in hospitalized patients with community-acquired pneumonia. The Azithromycin Intravenous Clinical Trials Group. | 2000 Jul |
|
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study. | 2001 |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Antibiotic-induced recurring interstitial nephritis. | 2002 Jan |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/cefuroxime.html
Adult
Note: Cefuroxime axetil film-coated tablets and oral suspension are not bioequivalent and are not substitutable on a mg/mg basis. All oral doses listed are for tablet formulation:
Acute bacterial maxillary sinusitis: Oral: 250 mg twice daily for 10 days
Bone and joint infections: IM, IV: 1.5 g every 8 hours (adjunctive surgical intervention may be necessary); upon completion of parenteral therapy follow with oral antibiotic therapy if indicated.
Acute bacterial exacerbations of chronic bronchitis:
Oral: 250 to 500 mg every 12 hours for 10 days
IV: 500 to 750 mg every 8 hours (complete therapy with oral dosing)
Cholecystitis, mild to moderate (off-label): IV: 1.5 g every 8 hours for 4 to 7 days (provided source controlled) (IDSA [Solomkin 2010])
Intra-abdominal infection, complicated, community-acquired, mild to moderate (in combination with metronidazole): (off-label): IV: 1.5 g every 8 hours for 4 to 7 days (provided source controlled) (IDSA [Solomkin 2010])
Lyme disease (early): Oral: 500 mg twice daily for 20 days
Pharyngitis/tonsillitis: Oral: 250 mg twice daily for 10 days
Pneumonia, community-acquired:
Note: Cefuroxime is considered an alternate therapy for CAP in adults caused by Streptococcus pneumoniae (with MICs <2 mcg/mL for penicillin); may also be used as outpatient empiric therapy in combination with a macrolide (preferred) or doxycycline (IDSA [Mandell 2007]).
Oral (off-label route in US): 500 mg twice daily for a minimum of 5 days (patients should be afebrile for ≥48 hours and clinically stable before discontinuing therapy) (IDSA [Mandell 2007])
IM, IV:
Manufacturer's labeling: IM, IV: 750 mg every 8 hours
Alternate dosing: IV: 1.5 g every 8 hours. Note: This higher dose should be considered in hospitalized patients, especially if bacteremic (Caballero-Granado 1996)
Severe or complicated infections: IV: 1.5 g every 8 hours (up to 1.5 g every 6 hours in life-threatening infections)
Skin/skin structure infection, uncomplicated:
Oral: 250 to 500 mg every 12 hours for 10 days
IM, IV: 750 mg every 8 hours
Surgical (perioperative) prophylaxis: IV:
Manufacturer's labeling: 1.5 g 30 minutes to 1 hour prior to procedure (if procedure is prolonged can give 750 mg every 8 hours IV or IM)
Open heart: IV: 1.5 g every 12 hours for a total of 4 doses starting at anesthesia induction
Alternative recommendation: 1.5 g within 60 minutes prior to surgical incision. Doses may be repeated in 4 hours if procedure is lengthy or if there is excessive blood loss (Bratzler 2013).
Urinary tract infection, uncomplicated:
Oral: 250 mg twice daily for 7 to 10 days
IV, IM: 750 mg every 8 hours
Bite wounds (animal) (off-label use) (IDSA [Stevens 2014]): Oral: 500 mg twice daily in combination with clindamycin or metronidazole for anaerobic coverage
Dosing: Geriatric
Refer to adult dosing.
Dosing: Pediatric
Note: Cefuroxime axetil film-coated tablets and oral suspension are not bioequivalent and are not substitutable on a mg/mg basis.
Children ≥1 year:
Surgical (perioperative) prophylaxis: IV: 50 mg/kg within 60 minutes prior to surgical incision (maximum dose: 1,500 mg). Doses may be repeated in 4 hours if procedure is lengthy or if there is excessive blood loss (Bratzler 2013).
Infants ≥3 months and Children:
Acute bacterial maxillary sinusitis, acute otitis media:
Oral: Suspension: 30 mg/kg/day in 2 divided doses for 10 days (maximum dose: 1,000 mg/day); tablet: 250 mg twice daily for 10 days
IM, IV: 75 to 150 mg/kg/day divided every 8 hours (maximum dose: 6 g/day)
Bone and joint infection: IM, IV: 50 mg/kg/dose every 8 hours; maximum single dose: 1,500 mg. Upon completion of parenteral therapy follow with oral antibiotic therapy if indicated.
Pharyngitis/tonsillitis:
Oral: Suspension: 20 mg/kg/day (maximum: 500 mg/day) in 2 divided doses for 10 days
IM, IV: 75 to 150 mg/kg day divided every 8 hours (maximum: 6 g/day)
Skin and skin structure infection (impetigo): Oral: Suspension: 30 mg/kg/day in 2 divided doses for 10 days (maximum dose: 1,000 mg/day)
Urinary tract infection, uncomplicated (off-label dosing):
Infants and Children ≥2 months to 2 years: Oral: 20 to 30 mg/kg/day divided twice daily for 7 to 14 days (AAP 2011)
Children ≥2 years: Moderate to severe disease (possible pyelonephritis): Oral: 20 to 30 mg/kg/day divided twice daily (maximum dose: 1,000 mg/day) (Bradley 2012; Red Book [AAP 2012])
Adolescents:
Acute bacterial exacerbations of chronic bronchitis: Oral: 250 to 500 mg every 12 hours for 10 days.
Acute bacterial maxillary sinusitis: Oral: 250 mg twice daily for 10 days.
Bone and joint infection: IM, IV: Refer to adult dosing.
Lyme disease (early): Oral: 500 mg twice daily for 20 days.
Pharyngitis/tonsillitis: Oral: 250 mg every 12 hours for 10 days.
Skin/skin structure infection, uncomplicated: Oral: 250 to 500 mg every 12 hours for 10 days.
Urinary tract infection, uncomplicated: Oral: 250 mg twice daily for 7 to 10 days.
Route of Administration:
Other
Substance Class |
Chemical
Created
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on
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Record UNII |
O1R9FJ93ED
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C357
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
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EXCRETED UNCHANGED |
Metabolically stable
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PRODRUG -> METABOLITE ACTIVE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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