339528-86-8

Basic information

• Product Name: Cefpodoxime Proxetil EP Impurity C
• Synonyms: Cefpodoxime Proxetil EP Impurity C;a2-Cefpodoxime Proxetil
• CAS NO: 339528-86-8
• Molecular Formula: C21H27N5O9S2
• Molecular Weight: 557.59718
• Mol File: 339528-86-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.58±0.1 g/cm3(Predicted)
• PKA: 8.16±0.60(Predicted)
• CAS DataBase Reference: Cefpodoxime Proxetil EP Impurity C(CAS DataBase Reference)
• NIST Chemistry Reference: Cefpodoxime Proxetil EP Impurity C(339528-86-8)
• EPA Substance Registry System: Cefpodoxime Proxetil EP Impurity C(339528-86-8)

Safety Data

• Hazardous Substances Data: 339528-86-8(Hazardous Substances Data)

Usage

Uses

2-Cefpodoxime Proxetil (Cefpodoxime Proxetil EP Impurity C) is a structural isomer of Cefpodoxime Proxetil (C243860); an antibacterial and broad spectrum, orally absorbed third generation cephalosporin.

Upstream product

• 84089-73-6 1-iodoethyl isopropyl carbonate 
• 80210-62-4 cefpodoxime 
• 87239-81-4 cefpodoxime proxetil 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF CEPHEM ESTERS

The present invention relates to a process for the preparation of cephem esters.

Stability of cephalosporin prodrug esters in human intestinal juice: Implications for oral bioavailability

The levels of degradation of cefetamet pivoxil (CAT), cefuroxime axetil (CAE), and cefpodoxime proxetil (CPD) in 0.6 M phosphate buffer (pH 7.4) and human intestinal juice (pH 7.4) at 37°C over 24 h were compared. Significant differences in the time courses of degradation and in the patterns of degradation products were observed. (i) The relative proportions of the Δ2- and Δ3-cephalosporins were roughly reversed in the two incubation media. In phosphate buffer, the major degradation product was the Δ2-cephalosporin (CAT = 61%; CAE = 74%; CPD = 85%), while in intestinal juice it was the Δ3- cephalosporin (CAT = 86%; CAE = 75%; CPD = 87%). (ii) Generally, the degradation of the prodrug esters progressed faster in intestinal juice than in phosphate buffer (e.g., for CAT the half-lives [t(1/2)s] were 0.78 and 4.3 h, respectively). (iii) The two diastereoisomers of CAE and CPD were degraded at different rates in intestinal juice (for the CAE diastereoisomers, t(1/2)s = 0.37 and 0.93 h; for the CPD diastereoisomers, t(1/2)s = 0.18 and 0.98 h) but were degraded at similar rates in phosphate buffer (for the CAE diastereoisomers, t(1/2) = 1.6 h; for the CPD t(1/2) diastereoisomers, = 2.2 h). It is concluded that (i) the Δ2 isomerization does not significantly affect the bioavailability of prodrug esters since enzymatic hydrolysis in the intestinal fluid proceeds mainly to the active Δ3-cephalosporin and (ii) the high degree of stereoselectivity of the enzymatic ester hydrolysis should make it possible to increase the bioavailabilities of certain prodrug esters (CAE, CPD) by using the more stable diasterioisomer.