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Substance Name: Cefuroxime [USAN:INN:BAN]
RN: 55268-75-2
UNII: O1R9FJ93ED
InChIKey: JFPVXVDWJQMJEE-IZRZKJBUSA-N

Note

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

Molecular Formula

  • C16-H16-N4-O8-S

Molecular Weight

  • 424.3884
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Cefuroxime
  • Cefuroxime [USAN:INN:BAN]

MeSH Heading

  • Cefuroxime

Synonyms

  • (6R,7R)-7-(2-(2-Furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 7(sup 2)-(Z)-(O-methyloxime) carbamate (ester)
  • 640/359
  • Biofuroksym
  • BRN 5783190
  • Cefuril
  • Cefuroxim
  • Cefuroxime
  • Cefuroximo
  • Cefuroximo [INN-Spanish]
  • Cefuroximum
  • Cefuroximum [INN-Latin]
  • Cephuroxime
  • EINECS 259-560-1
  • Sharox
  • UNII-O1R9FJ93ED
  • Zinacef Danmark

Systematic Names

  • 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-, (6R-(6alpha,7beta(Z)))-
  • Cefuroxime

Registry Numbers

CAS Registry Number

  • 55268-75-2

FDA UNII

  • O1R9FJ93ED

Other Registry Number

  • 153012-39-6

System Generated Number

  • 0055268752

Structure Descriptors

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

InChIKey

JFPVXVDWJQMJEE-IZRZKJBUSA-N

Smiles

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)COC(=O)N)\c3occc3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 64mg/kg/16H-I (64mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Lancet. Vol. 1, Pg. 965, 1984.
mouse LD50 intramuscular > 2gm/kg (2000mg/kg) BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Chemotherapy Vol. 27(Suppl,
mouse LD50 intraperitoneal > 10gm/kg (10000mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Chemotherapy Vol. 27(Suppl,
mouse LD50 intravenous 10400mg/kg (10400mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 17, Pg. 233, 1979.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Chemotherapy Vol. 27(Suppl,
mouse LD50 oral > 10gm/kg (10000mg/kg) BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Chemotherapy Vol. 27(Suppl,
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: ATAXIA
Chemotherapy Vol. 27(Suppl,
rabbit LD50 intramuscular > 300mg/kg (300mg/kg)   Chemotherapy Vol. 27(Suppl,
rabbit LD50 intravenous > 1500mg/kg (1500mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Chemotherapy Vol. 27(Suppl,
rat LD50 intramuscular > 2gm/kg (2000mg/kg)   Chemotherapy Vol. 27(Suppl,
rat LD50 intraperitoneal > 10gm/kg (10000mg/kg)   Chemotherapy Vol. 27(Suppl,
rat LD50 intravenous > 8gm/kg (8000mg/kg)   Chemotherapy Vol. 27(Suppl,
rat LD50 oral 10gm/kg (10000mg/kg)   Chemotherapy Vol. 27(Suppl,
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Chemotherapy Vol. 27(Suppl,

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.16 (none)   EXP
Water Solubility 145 mg/L 25 EST
Vapor Pressure 1.72E-15 mm Hg 25 EST
Henry's Law Constant 2.77E-21 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.10E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.