1926. Cefmetazole

Nomenclature

CAS number: 56796-20-4
(6R,7S)-7-[[[(Cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; CS-1170; SKF-83088.
C15H17N7O5S3; mol wt 471.53.
C 38.21%, H 3.63%, N 20.79%, O 16.97%, S 20.40%.

Description and references

Semi-synthetic antibiotic derived from cephamycin C, q.v. Prepn: H. Nakao et al., DE 2455884 (1975 to Sankyo), C.A. 83, 97330g (1975); eidem, J. Antibiot. 29, 554 (1976). See also: J. E. Dolfini, US 3920639 (1975 to Squibb). In vitro study: J. V. Uri et al., ibid. 31, 82 (1978). Immunological study: M. Iwata, T. Matuhasi, Jpn. J. Exp. Med. 48, 401 (1978). Absorption, distribution, excretion, metabolism in various species: H. Shindo et al., Chemotherapy (Tokyo) 27, Suppl. 1, 64 (1979). Pharmacology: S. Kobayashi et al., ibid. 26, Suppl. 5, 115 (1978). Toxicological studies: H. Masuda et al., Sankyo Kenkyusho Nempo 30, 112 (1978), C.A. 90, 180268h (1979). Comparative clinical study: M. Nishida et al., J. Antibiot. 32, 1319 (1979).

Chemical structure

Derivative

Sodium salt.

Nomenclature

CAS number: 56796-39-5
Cefmetazon (Sankyo); Metafar (Lafare); Zefazone (Pharmacia & Upjohn).
C15H16N7NaO5S3; mol wt 493.52.
C 36.51%, H 3.27%, N 19.87%, Na 4.66%, O 16.21%, S 19.49%.

Properties

White solid. Very sol in water, methanol, sol in acetone. Practically insol in chloroform. LD50 i.v. in rats: >5000 mg/kg (Masuda).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephamycins