1954. Cefuroxime

Nomenclature

CAS number: 55268-75-2
(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; (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.
C16H16N4O8S; mol wt 424.39.
C 45.28%, H 3.80%, N 13.20%, O 30.16%, S 7.56%.

Description and 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).

Chemical structure

Properties

White crystalline solid. [α]D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer). uv max (pH 6 phosphate buffer): 274 nm (ε 17600).

Derivative

Sodium salt.

Nomenclature

CAS number: 56238-63-2
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).
C16H15N4NaO8S; mol wt 446.37.
C 43.05%, H 3.39%, N 12.55%, Na 5.15%, O 28.67%, S 7.18%.

Properties

White solid. [α]D20 +60° (c = 0.91 in water). uv max (water): 274 nm (ε 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.).

Derivative

1-Acetoxyethyl ester.

Nomenclature

Cefuroxime axetil; CCI-15641; Ceftin (GSK); Cefurax (Betapharm); Cepazine (Sanofi-Synthelabo); Elobact (Cascan); Oraxim (Menarini); Zinat (GSK); Zinnat (GSK).
C20H22N4O10S; mol wt 510.47.
C 47.06%, H 4.34%, N 10.98%, O 31.34%, S 6.28%.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins