149709-63-7Sacubitril (2S,4S)-Isomer

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Catalogue No.:	VE005967
CAS No.:	149709-63-7
Mol. Formula:	C24H29NO5
Mol. Weight:	411.49 g/mol

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Additional information on CAS 149709-63-7

Parent drug

Sacubitril

IUPAC Name

(2S,4S)-5-(Biphenyl-4-yl)-4-[(3-carboxypropionyl)amino]-2-methylpentanoic acid ethyl ester

Pharmacopoeial Synonyms

N/A

Other synonyms

Sacubitril 2-Epimer

Smiles

O=C(OCC)[C@@H](C)C[C@H](NC(CCC(O)=O)=O)CC1=CC=C(C2=CC=CC=C2)C=C1

InChI

InChI=1S/C24H29NO5/c1-3-30-24(29)17(2)15-21(25-22(26)13-14-23(27)28)16-18-9-11-20(12-10-18)19-7-5-4-6-8-19/h4-12,17,21H,3,13-16H2,1-2H3,(H,25,26)(H,27,28)/t17-,21-/m0/s1

Description

Sacubitril (2S,4S)-Isomer, also designated Sacubitril 2-Epimer, CAS 149709-63-7, is a stereoisomeric process-related impurity of the neprilysin inhibitor sacubitril rather than a distinct structural degradant. The C24H29NO5 composition and molecular weight of 411.49 g/mol correspond to the epimerized stereochemical variant generated by incomplete stereochemical control during synthesis or resolution. Because the impurity is closely related to the active pharmaceutical ingredient, its trace-level discrimination typically requires chiral HPLC with orthogonal confirmation by LC-MS/MS and, where necessary, NMR. Regulatory assessment focuses on impurity specification, stereochemical purity, and control of epimer formation under ICH Q3A and Q3B principles.