Structural Formula Vector Image
Title: Cefotaxime
CAS Registry Number: 63527-52-6
CAS Name: (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: (6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 72-(Z)-(O-methyloxime) acetate; 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]cephalosporanic acid
Molecular Formula: C16H17N5O7S2
Molecular Weight: 455.47
Percent Composition: C 42.19%, H 3.76%, N 15.38%, O 24.59%, S 14.08%
Literature References: Broad spectrum third generation cephalosporin antibiotic. The name cefotaxime applies to the isomer having a syn-methoxyimino group. Prepn (unspecified stereochemistry): M. Ochiai et al., DE 2556736; eidem, US 4098888 (1976, 1978 both to Takeda); syn-isomer: R. Heymes, A. Lutz, DE 2702501; eidem, US 4152432 (1977, 1979 both to Roussel-UCLAF). Antibacterial activity: R. Wise, Antimicrob. Agents Chemother. 14, 807 (1978); H. W. Van handuyt, M. Pyckavet, ibid. 16, 109 (1979). Human pharmacology: R. Lüthy et al., ibid. 127. Symposia: Drug Ther. Suppl., 1-108 (Jan. 1981); Rev. Infect. Dis. 4, Suppl., S281-S488 (1982); Diagn. Microbiol. Infect. Dis. 2(3), Suppl., 1S-92S (1984); Infection 13, Suppl. 1, S1-S162 (1985). Comprehensive description: F. J. Muhtadi, M. M. A. Hassan, Anal. Profiles Drug Subs. 11, 139-168 (1982). Series of articles on clinical efficacy: J. Antimicrob. Chemother. 26, Suppl. A, 1-83 (1990).
Derivative Type: Sodium salt (syn-isomer)
CAS Registry Number: 64485-93-4
Manufacturers' Codes: HR-756; RU-24756
Trademarks: Cefotax (Chugai); Chemcef (Chemil); Claforan (Aventis); Pretor (Aventis); Tolycar (Jugoremedija)
Molecular Formula: C16H16N5NaO7S2
Molecular Weight: 477.45
Percent Composition: C 40.25%, H 3.38%, N 14.67%, Na 4.82%, O 23.46%, S 13.43%
Properties: [a]D20 +55±2° (c = 0.8 in water).
Optical Rotation: [a]D20 +55±2° (c = 0.8 in water)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.

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