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328385-86-0Lisinopril EP Impurity C (Free Base)

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Catalogue No.:	VL600004
CAS No.:	328385-86-0
Mol. Formula:	C21H29N3O4
Mol. Weight:	387.47 g/mol

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Additional information on CAS 328385-86-0

Parent drug

Lisinopril

Pharmacopeial Synonyms

Lisinopril Related Compound A

IUPAC Name

(2S)-2-[(3S,8aS)-3-(4-Aminobutyl)-1,4-dioxohexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-4-phenylbutanoic acid

Synonyms

Lisinopril S, S, S-Diketopiperazine

Smiles

O=C(O)[C@@H](N([C@H]1CCCCN)C([C@@](CCC2)([H])N2C1=O)=O)CCC3=CC=CC=C3

InChI

InChI=1S/C21H29N3O4/c22-13-5-4-9-17-19(25)23-14-6-10-16(23)20(26)24(17)18(21(27)28)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18H,4-6,9-14,22H2,(H,27,28)/t16-,17-,18-/m0/s1

Description

Lisinopril EP Impurity C, also designated Lisinopril Related Compound A and Lisinopril (S,S,S)-diketopiperazine, is the cyclized degradation product of the ACE inhibitor lisinopril. The diketopiperazine ring arises through intramolecular condensation of the lysine and proline-derived amino acid functions, typically under thermal or acidic stress during synthesis or storage. CAS 328385-86-0, molecular formula C21H29N3O4, molecular weight 387.47 g/mol. Because this impurity reflects structural rearrangement rather than nitrosative chemistry, its toxicological concern is primarily impurity profiling rather than ICH M7 genotoxic classification. Quantification commonly relies on stability-indicating LC-MS/MS, LC-UV, and, where needed, high-resolution MS for confirmation.