LIBENZAPRIL

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 Search

SMILES

NCCCC[C@H](N[C@H]1CCC2=CC=CC=C2N(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

Description
Sources: https://www.chemarc.com/content/chemicals/libenzapril/12398 | https://adisinsight.springer.com/drugs/800000333 | https://www.ncbi.nlm.nih.gov/pubmed/1553348

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.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
Inhibition of angiotensin-converting enzyme with libenzapril in normotensive males.	1994-12	7738213
Absorption of ACE inhibitors from small intestine and colon.	1994-09	7830254
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).	1993-12	8263802
Increased blood-brain barrier permeability of amino acids in chronic hypertension.	1993	7902950
Time-dependent effect of the angiotensin converting enzyme inhibitor, abutapril, on voluntary alcohol intake in the rat.	1992-05	1449562
Effect of chronic hypertension on the blood-brain barrier permeability of libenzapril.	1992-02	1553348
Patterns of renal function in hypertension due to unilateral renal artery occlusion.	1992	1358485
Inhibition of thromboxane synthetase potentiates the antihypertensive action of an angiotensin-converting enzyme inhibitor by a prostaglandin-dependent but kinin-independent mechanism.	1991-10	1920118
Determination of CGS 16617 and stable isotope-labeled CGS 16617, an angiotensin-converting enzyme inhibitor, in human plasma by gas chromatography/mass spectrometry.	1991-01	1883857
Additive beneficial effects of two inhibitors of vasoconstrictor mediators in acute myocardial ischemia.	1987-07	3037554
Potentiation of the protective effects of a converting enzyme inhibitor and a thromboxane synthetase inhibitor in hemorrhagic shock.	1987-07	3039116
Direct determination of angiotensin-converting enzyme inhibitors in plasma by radioenzymatic assay.	1987-04	3030582

Sample Use Guides

In Vivo Use Guide

Single dose of 100 mg

Route of Administration: Oral

Name

Type

Language

CGS 16617

Preferred Name

English

LIBENZAPRIL

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

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