1939. Cefpiramide

Nomenclature

CAS number: 70797-11-4
(6R,7R)-7-[[(2R)-[[(4-Hydroxy-6-methyl-3-pyridinyl)carbonyl]amino](4-hydroxyphenyl)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; 7-[(R)-2-(4-hydroxy-6-methylnicotinamido)-2-(p-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; d-7-[(4-hydroxy-6-methylnicotinamido)-4-hydroxyphenylacetamido]-3-(1-methyltetrazol-5-yl)thiomethylcephem-4-carboxylic acid.
C25H24N8O7S2; mol wt 612.64.
C 49.01%, H 3.95%, N 18.29%, O 18.28%, S 10.47%.

Description and references

Broad spectrum semi-synthetic cephalosporin antibiotic. Prepn: H. Yamada et al., BE 833063; eidem, US 4156724; US 4160087 (1975, 1979, 1979 all to Sumitomo); eidem, JP Kokai 79 119497 (1979 to Sumitomo), C.A. 92, 11042j (1980); I. Isaka et al., JP Kokai 79 30197 (1979 to Yamanouchi), C.A. 91, 57037a (1979); JP Kokai 84 65094 (1984 to Sumitomo), C.A. 101, 110641w (1984). Prepn, NMR data, antibacterial activity: H. Yamada et al., J. Antibiot. 36, 522, 543 (1983). Pharmacokinetics: H. Matsui et al., Antimicrob. Agents Chemother. 22, 213 (1982); K. Sata et al., ibid. 26, 578 (1984). Metabolism: H. Imasaki et al., ibid. 24, 42 (1983). In vitro activity: H. Wexler et al., ibid. 25, 162 (1984); M. A. Pfaller et al., ibid. 368. Comparison with other cephalosporins: N. J. Khan et al., ibid. 26, 585 (1984). Series of articles on in vitro, in vivo activity, determn in body fluids, pharmacokinetics, clinical studies: Chemotherapy (Tokyo) 31, Suppl. 1, 1-842 (1983).

Chemical structure

Properties

Yellow crystals, mp 213-215° (dec).

Derivative

Sodium salt.

Nomenclature

CAS number: 74849-93-7
SM-1652; Wy-44635; Cefpiran (Sumitomo); Suncefal (Yamanouchi); Sepatren (Sumitomo).
C25H23N8NaO7S2; mol wt 634.62.
C 47.31%, H 3.65%, N 17.66%, Na 3.62%, O 17.65%, S 10.11%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins