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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30N3O5.Na
Molecular Weight 427.4698
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of (R)-Lisinopril Sodium Salt

SMILES

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

InChI

InChIKey=MIRTZIYIUNFNIM-RXQQAGQTSA-M
InChI=1S/C21H31N3O5.Na/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);/q;+1/p-1/t16-,17+,18-;/m0./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H30N3O5
Molecular Weight 404.48
Charge -1
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.
2010-01
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 Wed Apr 02 20:18:24 GMT 2025
Edited
by admin
on Wed Apr 02 20:18:24 GMT 2025
Record UNII
FGL9YNW4JT
Record Status Validated (UNII)
Record Version
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Name Type Language
(R)-Lisinopril Sodium Salt
Preferred Name English
Code System Code Type Description
PUBCHEM
131667857
Created by admin on Wed Apr 02 20:18:24 GMT 2025 , Edited by admin on Wed Apr 02 20:18:24 GMT 2025
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FDA UNII
FGL9YNW4JT
Created by admin on Wed Apr 02 20:18:24 GMT 2025 , Edited by admin on Wed Apr 02 20:18:24 GMT 2025
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CAS
1356019-70-9
Created by admin on Wed Apr 02 20:18:24 GMT 2025 , Edited by admin on Wed Apr 02 20:18:24 GMT 2025
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Related Record Type Details
PARENT -> SALT/SOLVATE