1925. Cefmenoxime

Nomenclature

CAS number: 65085-01-0
(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-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-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime); SCE-1365.
C16H17N9O5S3; mol wt 511.56.
C 37.57%, H 3.35%, N 24.64%, O 15.64%, S 18.80%.

Description and references

Third generation cephalosporin antibiotic; related structurally to cefotaxime and ceftizoxime, q.q.v. The name cefmenoxime 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 2713272; eidem, US 4476122 (1983, 1984 both to Roussel-Uclaf). Series of articles on antibacterial activity, absorption, excretion, metabolism, mechanism of action, clinical studies: Chemotherapy (Tokyo) 29, Suppl. 1, 1-998 (1979). In vitro and in vivo study: K. Tsuchiya et al., Antimicrob. Agents Chemother. 19, 56 (1981). β-Lactamase stability: K. Okonogi et al., ibid. 20, 171 (1981). Clinical pharmacokinetics study: D. H"offler, P. Koeppe, Arzneim.-Forsch. 33, 269 (1983). Symposium: Am. J. Med. 77(6A), 1-59 (1984).

Chemical structure

Derivative

Hydrochloride (syn-isomer).

Nomenclature

CAS number: 75738-58-8
Abbott 50192; Bestcall (Takeda); Cefmax (TAP); Cemix (Takeda); Tacef (Grünenthal).
(C16H17N9O5S3)2.HCl; mol wt 1059.58.
C 36.27%, H 3.33%, N 23.79%, O 15.10%, S 18.16%, Cl 3.35%.

Derivative

Sodium salt (syn-isomer).

Nomenclature

CAS number: 65085-02-1
C16H16N9NaO5S3; mol wt 533.54.
C 36.02%, H 3.02%, N 23.63%, Na 4.31%, O 14.99%, S 18.03%.

Properties

[α]D20 -13.5 ±1° (c = 1 in water).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins