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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
Structure of CEFUROXIME

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

HIDE SMILES / InChI

Molecular Formula C16H16N4O8S
Molecular Weight 424.385
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ZINACEF

Cmax

ValueDoseCo-administeredAnalytePopulation
32.8 μg/mL
750 mg single, intramuscular
CEFUROXIME plasma
Homo sapiens
27 μg/mL
750 mg single, intramuscular
CEFUROXIME plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
88.6 μg × h/mL
750 mg single, intramuscular
CEFUROXIME plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
82.3 h
750 mg single, intramuscular
CEFUROXIME plasma
Homo sapiens
80 min
750 mg single, intramuscular
CEFUROXIME plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
750 mg single, intramuscular
CEFUROXIME plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Tox targets

PubMed

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
In Vitro Use Guide
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
Record UNII
O1R9FJ93ED
Record Status Validated (UNII)
Record Version