1922. Cefepime

Nomenclature

CAS number: 88040-23-7
1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium inner salt; 1-[[(6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium hydroxide inner salt 72-(Z)-2-(O-methyloxime); 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate; BMY-28142.
C19H24N6O5S2; mol wt 480.56.
C 47.49%, H 5.03%, N 17.49%, O 16.65%, S 13.34%.

Description and references

Semisynthetic, fourth generation cephalosporin antibiotic. Prepn: S. Aburaki et al., DE 3307550; eidem, US 4406899 (both 1983 to Bristol-Myers); and antibacterial activity: T. Naito et al., J. Antibiot. 39, 1092 (1986). In vitro comparative antimicrobial spectrum: N. J. Khan et al., Antimicrob. Agents Chemother. 26, 585 (1984); and β-lactamase stability: H. C. Neu et al., J. Antimicrob. Chemother. 17, 441 (1986). HPLC determn in plasma and urine: R. H. Barbhaiya et al., Antimicrob. Agents Chemother. 31, 55 (1987). Clinical evaluations in infection: N. Clynes et al., Diagn. Microbiol. Infect. Dis. 12, 257 (1989); S. Oster et al., Antimicrob. Agents Chemother. 34, 954 (1990). Review of clinical pharmacokinetics: M. P. Okamoto et al., Clin. Pharmacokinet. 25, 88-102 (1993).

Chemical structure

Properties

Colorless powder, mp 150° (dec). uv max (pH 7 phosphate buffer): 235, 257 nm (ε 16700, 16100).

Derivative

Sulfate.
C19H24N6O5S2.H2SO4; mol wt 578.64.
C 39.44%, H 4.53%, N 14.52%, O 24.89%, S 16.62%.

Properties

mp 210° (dec). uv max (pH 7 phosphate buffer): 236, 258 nm (ε 17200, 16900).

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 123171-59-5
1-[[(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpyrrolidinium chloride monohydrochloride monohydrate; cefepime hydrochloride; Axepim (BMS); Cepimex (Mead Johnson); Maxipime (BMS).
C19H25ClN6O5S2.HCl.H2O; mol wt 571.50.
C 39.93%, H 4.94%, Cl 12.41%, N 14.71%, O 16.80%, S 11.22%.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins