Cefpodoxime Proxetil

Title: Cefpodoxime Proxetil
CAS Registry Number: 87239-81-4
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(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
Additional Names: 1-(isopropoxycarbonyloxy)ethyl (6R,7R)-7-[2-(2-amino-4-thiazolyl)-(Z)-2-(methoxyimino)acetamido]-3-methoxymethyl-3-cephem-4-carboxylate
Manufacturers' Codes: CS-807; U-76252
Trademarks: Cefodox (Scharper); Orelox (Sanofi-Aventis); Otreon (Sankyo); Vantin (Pharmacia & Upjohn)
Molecular Formula: C21H27N5O9S2
Molecular Weight: 557.60
Percent Composition: C 45.23%, H 4.88%, N 12.56%, O 25.82%, S 11.50%
Literature 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). 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).
Properties: 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).
Toxicity data: 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 Type: Free acid
Additional Names: Cefpodoxime
Manufacturers' Codes: R-3763; U-76253
Molecular Formula: C15H17N5O6S2
Molecular Weight: 427.46
Percent Composition: C 42.15%, H 4.01%, N 16.38%, O 22.46%, S 15.00%
Derivative Type: Free acid sodium salt
Manufacturers' Codes: U-76253A; R-3746
Molecular Formula: C15H16N5NaO6S2
Molecular Weight: 449.44
Percent Composition: C 40.09%, H 3.59%, N 15.58%, Na 5.12%, O 21.36%, S 14.27%
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
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