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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H31N3O5
Molecular Weight 405.4879
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LISINOPRIL R,S,S-ISOMER

SMILES

NCCCC[C@H](N[C@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O

InChI

InChIKey=RLAWWYSOJDYHDC-KSZLIROESA-N
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

HIDE SMILES / InChI

Molecular Formula C21H31N3O5
Molecular Weight 405.4879
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

(R)-Lisinopril Sodium Salt is the R,S,S-Isomer of Lisinopril. Lisinopril is a potent inhibitor of angiotensin-converting enzyme (ACE). Lisinopril prevents the conversion of angiotensin I to angiotensin II, which acts as a potent vasoconstrictor and also signals the release of aldosterone, which modulates sodium absorption. ACE inhibition has the net result of vasodilation and increased sodium and water excretion. Lisinopril, (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino] hexanoyl]pyrrole-2-carboxylic acid is an angiotensin-converting enzyme (ACE) inhibitor, used for the treatment of hypertension, heartfailure andacutemyocardial infarction. The RSS isomer of lisinopril ((2S)-1-[(2S)-6-amino-2-[[(1R)-1-carboxy- 3-phenylpropyl]amino]hexanoyl]pyrrole-2-carboxylic acid) is an impurity (impurity E) resulting from the synthesis of lisinopril. The impurity profile of a drug substance is critical to its safety assessment and is important for monitoring the manufacturing process.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Differentiation of lisinopril and its RSS diastereomer by liquid chromatography combined with collision-induced dissociation mass spectrometry.
2010 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:44:06 GMT 2023
Edited
by admin
on Sat Dec 16 09:44:06 GMT 2023
Record UNII
5W66M58H0T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LISINOPRIL R,S,S-ISOMER
Common Name English
L-PROLINE, 1-(N2-(1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL)-, (R)-
Systematic Name English
L-PROLINE, N2-((1R)-1-CARBOXY-3-PHENYLPROPYL)-L-LYSYL-
Systematic Name English
(2S)-1-((2S)-6-AMINO-2-(((1R)-1-CARBOXY-3-PHENYLPROPYL)AMINO)HEXANOYL)PYRROLIDINE-2-CARBOXYLIC ACID
Systematic Name English
LISINOPRIL EPIMER [USP IMPURITY]
Common Name English
LISINOPRIL IMPURITY E [EP IMPURITY]
Common Name English
Code System Code Type Description
CAS
85955-59-5
Created by admin on Sat Dec 16 09:44:07 GMT 2023 , Edited by admin on Sat Dec 16 09:44:07 GMT 2023
PRIMARY
FDA UNII
5W66M58H0T
Created by admin on Sat Dec 16 09:44:07 GMT 2023 , Edited by admin on Sat Dec 16 09:44:07 GMT 2023
PRIMARY
PUBCHEM
55187
Created by admin on Sat Dec 16 09:44:07 GMT 2023 , Edited by admin on Sat Dec 16 09:44:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID10235285
Created by admin on Sat Dec 16 09:44:07 GMT 2023 , Edited by admin on Sat Dec 16 09:44:07 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP