Cefuroxime

Title: Cefuroxime
CAS Registry Number: 55268-75-2
CAS Name: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: (6R,7R)-3-carbamoyloxymethyl-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-carbamoyloxymethyl-7-[2-(2-furyl)-2-(methoxyimino)acetamido]ceph-3-em-4-carboxylic acid
Molecular Formula: C16H16N4O8S
Molecular Weight: 424.39
Percent Composition: C 45.28%, H 3.80%, N 13.20%, O 30.16%, S 7.56%
Literature References: Prepn: M. C. Cook et al., DE 2439880; eidem, US 3974153 (1973, 1976 both to Glaxo). Prepn of the 1-acetoxyethyl ester: M. Gregson, B. Sykes, DE 2706413; eidem, US 4267320 (1977, 1981 both to Glaxo). In vitro studies: C. H. O'Callaghan et al., Antimicrob. Agents Chemother. 9, 511 (1976); R. N. Jones et al., ibid. 12, 47 (1977). In vitro antibacterial activity, human pharmacokinetics: C. H. O'Callaghan et al., J. Antibiot. 29, 29 (1976). Pharmacology: H. Freiesleben et al., Proc. 10th Int. Congr. Chemother., Zürich, 1977 (Am. Soc. for Microbiol., Washington, 1978) II, pp 873-874. Pharmacokinetics: P. E. Gower, ibid. 877-878; J. Kosmidis et al., ibid. 875-876. Clinical studies: P. F. Wood et al., ibid. 1042-1044; R. Norrby et al., J. Antimicrob. Chemother. 3, 355 (1977). Review of antibacterial activity, pharmacology and therapeutic efficacy: R. N. Brogden et al., Drugs 17, 233-266 (1979). Comprehensive description: T. J. Wozniak, J. R. Hicks, Anal. Profiles Drug Subs. 20, 209-236 (1991).
Properties: White crystalline solid. [a]D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer). uv max (pH 6 phosphate buffer): 274 nm (e 17600).
Optical Rotation: [a]D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer)
Absorption maximum: uv max (pH 6 phosphate buffer): 274 nm (e 17600)
Derivative Type: Sodium salt
CAS Registry Number: 56238-63-2
Trademarks: Anaptivan (Help); Biociclin (Del Saz & Filippini); Biofurex (Lenza); Bioxima (Ital. Suisse); Cefamar (Firma); Cefoprim (Esseti); Cefumax (Locatelli); Cefurex (Sarm); Cefurin (Magis); Curocef (GSK); Curoxim (Elan); Duxima (Dukron); Gibicef (Metapharma); Ipacef (IPA); Kefurox (Lilly); Kesint (Proter); Lampsporin (Von Boch); Medoxim (Medici); Novocef (Pliva); Spectrazole (Mallinckrodt); Ultroxim (Duncan Flockhart); Zinacef (GSK)
Molecular Formula: C16H15N4NaO8S
Molecular Weight: 446.37
Percent Composition: C 43.05%, H 3.39%, N 12.55%, Na 5.15%, O 28.67%, S 7.18%
Properties: White solid. [a]D20 +60° (c = 0.91 in water). uv max (water): 274 nm (e 17400). Freely sol in water and buffered solutions; sol in methanol; very slightly sol in ethyl acetate, diethyl ether, octanol, benzene and chloroform. Soly in water: 500 mg/2.5 ml. pKa (water): 2.5; (DMF): 5.1. Solns are stable at room temp for 13 hrs; <10% decompn in 48 hrs at 25° (O'Callaghan, J. Antibiot.).
pKa: pKa (water): 2.5; (DMF): 5.1
Optical Rotation: [a]D20 +60° (c = 0.91 in water)
Absorption maximum: uv max (water): 274 nm (e 17400)
Derivative Type: 1-Acetoxyethyl ester
Additional Names: Cefuroxime axetil
Manufacturers' Codes: CCI-15641
Trademarks: Ceftin (GSK); Cefurax (Betapharm); Cepazine (Sanofi-Synthelabo); Elobact (Cascan); Oraxim (Menarini); Zinat (GSK); Zinnat (GSK)
Molecular Formula: C20H22N4O10S
Molecular Weight: 510.47
Percent Composition: C 47.06%, H 4.34%, N 10.98%, O 31.34%, S 6.28%
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefuzonam Celery Seed Celesticetin Celestin Blue Cellobiose

Cefuroxime
Cefuroxime.svg
Cefuroxime ball-and-stick.png
Systematic (IUPAC) name
(6R,7R)-3-{[(aminocarbonyl)oxy]methyl}-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino) acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names Zinacef,TURBOCEF
MedlinePlus a601206
Pregnancy cat. B
Legal status RX only
Routes intramuscular, intravenous, oral
Pharmacokinetic data
Bioavailability 37 percent on empty stomach, up to 52 percent if taken after food
Half-life 80 minutes
Excretion Urine 66–100 percent unchanged
Identifiers
CAS number 55268-75-2 YesY
ATC code J01DC02 S01AA27 QJ51DC02
PubChem CID 5361202
DrugBank DB01112
ChemSpider 4514699 YesY
UNII O1R9FJ93ED YesY
KEGG D00262 YesY
ChEMBL CHEMBL466 YesY
Chemical data
Formula C16H16N4O8S 
Mol. mass 424.386 g/mol
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Cefuroxime is a parenteral or oral second-generation cephalosporin antibiotic. This antibiotic was discovered by the Glaxo company, now GlaxoSmithKline, and it was first marketed in 1978 as Zinacef. Zinacef was approved by the U.S. Food and Drug Administration on Oct 19, 1983.[1] The generic form of cefuroxime is also called "Ceftin". The 17-year patent for this antibiotic has now expired in the United States, hence the patent "rights" to produce this medication are now irrelevant.

In the United States this antibiotic is also sold as "Zinacef" by Covis Pharmaceuticals.[2] In India, this antibiotic is sold as Supacef by GSK.[3]

Cefuroxime axetil is an acetoxyetyl-ester-prodrug of cefuroxime which is effective orally.[4] In Bangladesh, this drug is available as Xorimax by Sandoz, Turbocef by Beximco Pharmaceuticals Limited.