Cefpimizole

Title: Cefpimizole
CAS Registry Number: 84880-03-5
CAS Name: 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
Additional Names: 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-b-[D-(-)-a-(4-carboxyimidazole-5-carboxamido)phenylacetamido]-3-(4-b-sulfoethylpyridinium)methyl-3-cephem-4-carboxylic acid
Manufacturers' Codes: U-63196; AC-1370
Molecular Formula: C28H26N6O10S2
Molecular Weight: 670.67
Percent Composition: C 50.14%, H 3.91%, N 12.53%, O 23.86%, S 9.56%
Literature 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 b-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.
Derivative Type: Monosodium salt
CAS Registry Number: 85287-61-2
Manufacturers' Codes: U-63196E
Trademarks: Ajicef (Ajinomoto); Renilan (Mochida)
Molecular Formula: C28H25N6NaO10S2
Molecular Weight: 692.65
Percent Composition: C 48.55%, H 3.64%, N 12.13%, Na 3.32%, O 23.10%, S 9.26%
Properties: [a]D20 -28.2° (c = 0.5 in water). uv max (water): 257 nm (e 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).
Optical Rotation: [a]D20 -28.2° (c = 0.5 in water)
Absorption maximum: uv max (water): 257 nm (e 22400)
Toxicity data: 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)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefpiramide Cefpirome Cefpodoxime Proxetil Cefprozil Cefquinome

Cefpimizole
Cefpimizole.png
Systematic (IUPAC) name
2-[1-([(6R,7R)-2-carboxy-7-([(2R)-2-[(5-carboxy1H-imidazole-4-carbonyl)amino]-2-phenylacetyl]amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl)pyridin-1-ium-4-yl]ethanesulfonate
Clinical data
Legal status Prescription only
Identifiers
CAS number 84880-03-5 YesY
ATC code None
PubChem CID 11765031
ChemSpider 61863 N
UNII 24S58UHU7N YesY
KEGG D03427 YesY
Chemical data
Formula C28H26N6O10S2 
Mol. mass 670.67 g/mol
 N (what is this?)  (verify)

Cefpimizole (INN) is a third-generation cephalosporin antibiotic.