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Details

Stereochemistry MIXED
Molecular Formula C20H22N4O10S
Molecular Weight 510.474
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFUROXIME AXETIL

SMILES

[H][C@]12SCC(COC(N)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C3=CC=CO3)C(=O)OC(C)OC(C)=O

InChI

InChIKey=KEJCWVGMRLCZQQ-YJBYXUATSA-N
InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H22N4O10S
Molecular Weight 510.474
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 3
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZINACEF

Approved Use

ZINACEF 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 Date

4.35369607E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
32.8 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: 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

AUC

ValueDoseCo-administeredAnalytePopulation
88.6 μg × h/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: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
82.3 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Pseudomembranous colitis
Sources: Page: p.9
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)
Diarrhea, Clostridium difficile
Sources: Page: p.1
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
Nausea
Vomiting
Abdominal pain
Sources: Page: p.11
AEs

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Renal tolerance of ceftazidime in animals.
1981 Sep
Renal function in patients treated with tobramycin-cefuroxime or tobramycin-penicillin G.
1983 Dec
Psychotic reaction to cefuroxime.
1984 Apr 28
Cimetidine in the treatment of refractory anaphylaxis.
1989 Sep
Randomised single blind trial to compare the toxicity of subconjunctival gentamicin and cefuroxime in cataract surgery.
1990 Dec
A comparison of ceftriaxone and cefuroxime for the treatment of bacterial meningitis in children.
1990 Jan 18
Treatment of meningitis and other infections due to ampicillin-resistant Haemophilus influenzae type b in children.
1991 Mar-Apr
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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Antibiotic-induced recurring interstitial nephritis.
2002 Jan
Acute renal failure and cystic fibrosis.
2003 Jul
Hyperammonemic encephalopathy induced by a combination of valproate and pivmecillinam.
2004 Apr
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Drug-induced granulomatous interstitial nephritis in a pediatric patient.
2007 Feb
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
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
Cefuroxime is active against gram-negative and gram-positive organisms with minimum inhibitory concentrations (MICs) values of 0.25-125 ug/ml
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:37:19 UTC 2023
Edited
by admin
on Fri Dec 15 15:37:19 UTC 2023
Record UNII
Z49QDT0J8Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFUROXIME AXETIL
EP   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
CUROCEF
Brand Name English
CEFUROXIME AXETIL [USP-RS]
Common Name English
CETOXIL
Brand Name English
CCI-15641
Code English
NOVADOR
Brand Name English
CEFTIN
Brand Name English
CEFUROXIME AXETIL [MART.]
Common Name English
Cefuroxime axetil [WHO-DD]
Common Name English
NSC-758677
Code English
CEPAZINE
Brand Name English
NOVOCEF
Brand Name English
CEFUROXIME AXETIL [ORANGE BOOK]
Common Name English
ORAXIM
Brand Name English
CEFURAX
Brand Name English
CEFUROXIME 1-ACETOXYETHYL ESTER [MI]
Common Name English
ELOBACT
Brand Name English
CEFUROXIME AXETIL [USP MONOGRAPH]
Common Name English
CEFUROXIME AXETIL [EP MONOGRAPH]
Common Name English
CEFUROXIME AXETIL [VANDF]
Common Name English
ZINNAT
Brand Name English
CEFUROXIME AXETIL [USAN]
Common Name English
CEFUROXIME (AS AXETIL)
Common Name English
CCI 15641
Code English
CEFUROXIME AXETIL [JAN]
Common Name English
ZINAT
Brand Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-(((AMINOCARBONYL)OXY)METHYL)-7-((2-FURANYL(METHOXYIMINO)ACETYL)AMINO)-8-OXO-, 1-(ACETYLOXY)ETHYL ESTER, (6R-(6.ALPHA.,7.BETA.(Z)))-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
Code System Code Type Description
USAN
U-49
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
PUBCHEM
6321416
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
EVMPD
SUB01139MIG
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
HSDB
8150
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID0022775
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
RS_ITEM_NUM
1098220
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
SMS_ID
100000093039
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
RXCUI
20493
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
566
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
CAS
64544-07-6
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
MERCK INDEX
m3226
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1095930
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
MESH
C040738
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
NSC
758677
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
DAILYMED
Z49QDT0J8Z
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
WIKIPEDIA
Cefuroxime axetil
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
FDA UNII
Z49QDT0J8Z
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
NCI_THESAURUS
C28918
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
EVMPD
SUB127268
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
DRUG BANK
DBSALT001355
Created by admin on Fri Dec 15 15:37:19 UTC 2023 , Edited by admin on Fri Dec 15 15:37:19 UTC 2023
PRIMARY
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