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85955-59-5Lisinopril EP Impurity E

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Catalogue No.:	VL600001
CAS No.:	85955-59-5
Mol. Formula:	C21H31N3O5
Mol. Weight:	405.49 g/mol

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Additional information on CAS 85955-59-5

Parent drug

Lisinopril

IUPAC Name

(2S)-1-[(2S)-6-Amino-2-[[(1R)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid

Pharmacopeial Synonyms

Lisinopril (R,S,S)-Isomer; Lisinopril (1R)-Epimer

Other Synonyms

(S)-1-((S)-6-Amino-2-(((R)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic acid; L-Proline, N2-((1R)-1-carboxy-3-phenylpropyl)-L-lysyl-

Smiles

C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O

InChI

InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17+,18-/m0/s1

Description

Lisinopril EP Impurity E, also designated Lisinopril (R,S,S)-Isomer or Lisinopril (1R)-Epimer, CAS 85955-59-5, is a stereoisomeric process-related impurity of the ACE inhibitor lisinopril rather than a distinct degradant class. Its molecular formula, C21H31N3O5, and molecular weight, 405.49 g/mol, correspond to an epimeric inversion at the 1-position of the proline-derived moiety, typically arising from stereochemical drift during synthesis or racemization under acidic or thermal stress. Because it is structurally close to the active pharmaceutical ingredient, chromatographic separation with chiral or highly selective reversed-phase LC is commonly required, often coupled to LC-MS/MS for definitive identification and trace quantification.