1933. Cefotaxime

Nomenclature

CAS number: 63527-52-6
(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (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.
C16H17N5O7S2; mol wt 455.47.
C 42.19%, H 3.76%, N 15.38%, O 24.59%, S 14.08%.

Description and 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). Review of antibacterial activity, pharmacokinetics, and clinical efficacy: R. N. Brogden, C. M. Spencer, Drugs 53, 483-510 (1997).

Chemical structure

Derivative

Sodium salt (syn-isomer).

Nomenclature

CAS number: 64485-93-4
HR-756; RU-24756; Cefotax (Sanofi-Aventis); Claforan (Sanofi-Aventis).
C16H16N5NaO7S2; mol wt 477.45.
C 40.25%, H 3.38%, N 14.67%, Na 4.82%, O 23.46%, S 13.43%.

Properties

[α]D20 +55±2° (c = 0.8 in water).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins