1364932-19-3

Basic information

• Product Name: OseltaMivir IMpurity A
• Synonyms: OseltaMivir IMpurity A;(3R,4R,5S)-5-Acetamido-4-amino-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylic acid;(3R,4R,5S)-5-acetamido-4-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylic acid
• CAS NO: 1364932-19-3
• Molecular Formula: C14H24N2O4
• Molecular Weight: 284.35136
• Mol File: 1364932-19-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 508.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• PKA: 3.51±0.60(Predicted)
• CAS DataBase Reference: OseltaMivir IMpurity A(CAS DataBase Reference)
• NIST Chemistry Reference: OseltaMivir IMpurity A(1364932-19-3)
• EPA Substance Registry System: OseltaMivir IMpurity A(1364932-19-3)

Safety Data

• Hazardous Substances Data: 1364932-19-3(Hazardous Substances Data)

Usage

Uses

Desethyl Oseitamivir is an impurity of the antiviral drug oseltamivir.

Upstream product

• 1163128-59-3 ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate 
• 204255-04-9 ethyl-(3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 204255-02-7 ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate 
• 204254-98-8 ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate 
• 204254-96-6 (1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester 
• 196618-13-0 oseltamivir 

Relevant articles and documents

Biexponential decomposition of a neuraminidase inhibitor prodrug (GS- 4104) in aqueous solution

Purpose. To examine the degradation kinetics and identify the degradation products of a neuraminidase inhibitor prodrug, GS-4104. Methods. Degradation was studied as a function of pH and temperature using a stability-indicating RP-HPLC assay. Degradation products were isolated by RP- HPLC and identified by NMR. Specific rate constants were calculated based on a scheme defined by product(s) analysis. Results. Three distinct degradation products were observed in the pH region studied (pH 2-8): Isomer I, GS-4071, and isomer II. Isomer I resulted from the N, N-migration of the acetyl group. GS-4071 was formed by the hydrolysis of the ethyl ester. Both GS-4071 and isomer I degraded further to isomer [I by N, N-acyl migration and ester hydrolysis, respectively. The N, N-acyl migration reaction was characterized using two dimensional heteronuclear multiple bond correlation (HMBC) NMR. The decomposition kinetics of GS-4104 follow a biexponential decay at pH 2-7. The degradation kinetics of GS-4104 at pH 4.0, 70°C were independent of the initial GS-4104 concentration. Conclusions. The degradation profile indicates that development of solution or solid dosage form of GS-4104 with adequate shelf-life stability at room temperature is feasible.