1938. Cefpimizole

Nomenclature

CAS number: 84880-03-5
1-[[(6R,7R)-2-Carboxy-7-[[(2R)-[[(5-carboxy-1H-imidazol-4-yl)carbonyl]amino]phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-4-(2-sulfoethyl)pyridinium inner salt; 1-[(6R,7R)-2-carboxy-7-[(R)-2-(5-carboxy-4-imidazolylcarboxamido)-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-ylmethyl]pyridino-4-ethylsulfonate; 7-β-[d-(-)-α-(4-carboxyimidazole-5-carboxamido)phenylacetamido]-3-(4-β-sulfoethylpyridinium)methyl-3-cephem-4-carboxylic acid; U-63196; AC-1370.
C28H26N6O10S2; mol wt 670.67.
C 50.14%, H 3.91%, N 12.53%, O 23.86%, S 9.56%.

Description and references

Third generation injectable cephalosporin antibiotic. Prepn: N. Yasuda et al., DE 2826546; eidem, US 4217450 (1979, 1980 both to Ajinomoto); N. Yasuda et al., J. Antibiot. 36, 242 (1983). In vitro antibacterial activity and β-lactamase stability: H. C. Neu, P. Labthavikul, Antimicrob. Agents Chemother. 24, 375 (1983). Potentiating effect on phagocyte functions: H. Ohnishi et al., ibid. 23, 874 (1983). Toxicity study: S. Hashimoto et al., Toxicol. Lett. 23, 135 (1984). Therapeutic efficacy in mice: Y. Obana et al., J. Antimicrob. Chemother. 16, 727 (1985). HPLC determn in human plasma and urine: D. B. Lakings, J. M. Wozniak, J. Chromatogr. 308, 261 (1984). Pharmacokinetics in humans: D. B. Lakings et al., Antimicrob. Agents Chemother. 29, 271 (1986). Efficacy and tolerance in gonorrhea in men: E. T. Sandberg et al., ibid. 849.

Chemical structure

Derivative

Monosodium salt.

Nomenclature

CAS number: 85287-61-2
U-63196E; Ajicef (Ajinomoto); Renilan (Mochida).
C28H25N6NaO10S2; mol wt 692.65.
C 48.55%, H 3.64%, N 12.13%, Na 3.32%, O 23.10%, S 9.26%.

Properties

[α]D20 -28.2° (c = 0.5 in water). uv max (water): 257 nm (ε 22400). Sol in water. LD50 in male, female mice, male, female rats (g/kg): 2.7, 2.9, 4.2, 3.5 i.v.; 8.2, 6.8, 12.2, 11.5 s.c.; all >15.0 orally (Hashimoto).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins