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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(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

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
5W66M58H0T
Record Status Validated (UNII)
Record Version