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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H25N3O5
Molecular Weight 363.4082
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIBENZAPRIL

SMILES

NCCCC[C@H](N[C@H]1CCC2=C(C=CC=C2)N(CC(O)=O)C1=O)C(O)=O

InChI

InChIKey=AXTCRUUITQKBAV-KBPBESRZSA-N
InChI=1S/C18H25N3O5/c19-10-4-3-6-14(18(25)26)20-13-9-8-12-5-1-2-7-15(12)21(17(13)24)11-16(22)23/h1-2,5,7,13-14,20H,3-4,6,8-11,19H2,(H,22,23)(H,25,26)/t13-,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H25N3O5
Molecular Weight 363.4082
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Libenzapril is a long-acting, small polar angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Libenzapril competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Libenzapril also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow. Both libenzapril and water transport was found to be significantly higher (about two- to five-fold) in six of the seven different brain regions in hypertensive rats as compared to the normotensive controls.

Approval Year

PubMed

PubMed

TitleDatePubMed
Direct determination of angiotensin-converting enzyme inhibitors in plasma by radioenzymatic assay.
1987 Apr
Additive beneficial effects of two inhibitors of vasoconstrictor mediators in acute myocardial ischemia.
1987 Jul
Potentiation of the protective effects of a converting enzyme inhibitor and a thromboxane synthetase inhibitor in hemorrhagic shock.
1987 Jul
Determination of CGS 16617 and stable isotope-labeled CGS 16617, an angiotensin-converting enzyme inhibitor, in human plasma by gas chromatography/mass spectrometry.
1991 Jan
Inhibition of thromboxane synthetase potentiates the antihypertensive action of an angiotensin-converting enzyme inhibitor by a prostaglandin-dependent but kinin-independent mechanism.
1991 Oct
Patterns of renal function in hypertension due to unilateral renal artery occlusion.
1992
Effect of chronic hypertension on the blood-brain barrier permeability of libenzapril.
1992 Feb
Time-dependent effect of the angiotensin converting enzyme inhibitor, abutapril, on voluntary alcohol intake in the rat.
1992 May
Increased blood-brain barrier permeability of amino acids in chronic hypertension.
1993
Rapid reversal of angiotensin I-induced contractions in rat carotid arteries after acute and chronic treatment with the angiotensin-converting enzyme inhibitor, 3-[(5-amino-1-carboxy-1S-pentyl)amino]2,3,4,5-tetrahydro-2-oxo- 3S-1H-1-benzazepena-1-acetic acid (CGS 16617).
1993 Dec
Inhibition of angiotensin-converting enzyme with libenzapril in normotensive males.
1994 Dec
Absorption of ACE inhibitors from small intestine and colon.
1994 Sep

Sample Use Guides

Single dose of 100 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:50:16 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:16 GMT 2023
Record UNII
QD8496WWYK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIBENZAPRIL
INN   MART.   USAN   WHO-DD  
USAN   INN  
Official Name English
CGS-16617
Code English
1H-1-BENZAZEPINE-1-ACETIC ACID, 3-(((1S)-5-AMINO-1-CARBOXYPENTYL)AMINO)-2,3,4,5-TETRAHYDRO-2-OXO-, (3S)-
Common Name English
ABUTAPRIL
Common Name English
Libenzapril [WHO-DD]
Common Name English
N-((3S)-1-(CARBOXYMETHYL)-2,3,4,5-TETRAHYDRO-2-OXO-1H-1-BENZAZEPIN-3-YL)-L-LYSINE
Systematic Name English
CGS 16617
Code English
LIBENZAPRIL [USAN]
Common Name English
1H-1-BENZAZEPINE-1-ACETIC ACID, 3-((5-AMINO-1-CARBOXYPENTYL)AMINO)-2,3,4,5-TETRAHYDRO-2-OXO-, (S-(R*,R*))
Common Name English
libenzapril [INN]
Common Name English
LIBENZAPRIL [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
Code System Code Type Description
SMS_ID
100000082308
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
INN
6110
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL430554
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID50911031
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
EVMPD
SUB08502MIG
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
FDA UNII
QD8496WWYK
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
CAS
109214-55-3
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
USAN
Y-73
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
NCI_THESAURUS
C81335
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
PUBCHEM
71320
Created by admin on Fri Dec 15 15:50:16 GMT 2023 , Edited by admin on Fri Dec 15 15:50:16 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY