1941. Cefpodoxime Proxetil

Nomenclature

CAS number: 87239-81-4
(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-[[(1-methylethoxy)carbonyl]oxy]ethyl ester; 1-(isopropoxycarbonyloxy)ethyl (6R,7R)-7-[2-(2-amino-4-thiazolyl)-(Z)-2-(methoxyimino)acetamido]-3-methoxymethyl-3-cephem-4-carboxylate; CS-807; U-76252; Cefodox (Scharper); Orelox (Sanofi-Aventis); Otreon (Sankyo); Simplicef (Pharmacia & Upjohn); Vantin (Pharmacia & Upjohn).
C21H27N5O9S2; mol wt 557.60.
C 45.23%, H 4.88%, N 12.56%, O 25.82%, S 11.50%.

Description and references

Broad spectrum, orally absorbed third generation cephalosporin, ester prodrug of the active free acid metabolite, cefpodoxime. Prepn: H. Nakao et al., EP 49118; eidem, US 4486425 (1982, 1984 both to Sankyo). Prepn, pharmacokinetics and NMR analysis: K. Fujimoto et al., J. Antibiot. 40, 370 (1987). In vitro and in vivo antibacterial activity: Y. Utsui et al., Antimicrob. Agents Chemother. 31, 1085 (1987). In vitro antibacterial spectrum and susceptibility testing of free acid: R. N. Jones, A. L. Barry, ibid. 32, 443 (1988). Isomer-specific HPLC determn in biological fluids: V. K. Kakumanu et al., J. Chromatogr. B 835, 16 (2006). Characterization of isomers: eidem, Eur. J. Pharm. Biopharm. 64, 255 (2006). Series of articles on antibacterial spectrum, pharmacokinetics, toxicology and clinical studies: Chemotherapy (Tokyo) 36, Suppl. 1, 1-1126 (1988). Symposium on pharmacokinetics and clinical efficacy: J. Antimicrob. Chemother. 26, Suppl. E, 1-101 (1990). Review of chemistry, antibacterial activity, toxicity and clinical studies: H. Nakao et al., Sankyo Kenkyusho Nempo 39, 1-44 (1987), C.A. 109, 27503x (1988). Comprehensive review: W. M. Todd, Int. J. Antimicrob. Agents 4, 37-62 (1994).

Chemical structure

Properties

White to slightly brownish white powder; bitter taste and no odor or slight unique smell. No defined mp. Very sol in acetonitrile, methanol; freely sol in dehydrated ethanol; slightly sol in ether; very slightly sol in water. pKa 3.20±0.13. Partition coefficient (octanol/water): 0.08 (pH 1.2); 1.53 (pH 5); 1.50 (pH 9). Partition coefficient (chloroform/water): 1.60 (pH 1.2); 3.08 (pH 5); 3.18 (pH 9). LD50 in male, female mice, male, female rats (mg/kg): >10000, >10000, >2000, >2000 s.c., 3502, 2535, >4000, >4000 i.p.; >8000, >8000, >4000, >4000 orally (Nakao, 1988).

Derivative

Free acid.

Nomenclature

CAS number: 80210-62-4
Cefpodoxime; R-3763; U-76253.
C15H17N5O6S2; mol wt 427.46.
C 42.15%, H 4.01%, N 16.38%, O 22.46%, S 15.00%.

Derivative

Free acid sodium salt.

Nomenclature

CAS number: 82619-04-3
U-76253A; R-3746.
C15H16N5NaO6S2; mol wt 449.44.
C 40.09%, H 3.59%, N 15.58%, Na 5.12%, O 21.36%, S 14.27%.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); β-Lactams; Cephalosporins