ADIBENDAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H14N4O
Molecular Weight	278.3086
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)C(=O)NC2=C1C=C3NC(=NC3=C2)C4=CC=NC=C4

InChI

InChIKey=TVLQBBHUNDMTEC-UHFFFAOYSA-N

InChI=1S/C16H14N4O/c1-16(2)10-7-12-13(8-11(10)20-15(16)21)19-14(18-12)9-3-5-17-6-4-9/h3-8H,1-2H3,(H,18,19)(H,20,21)

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Description
Sources: https://adisinsight.springer.com/drugs/800000332 | https://www.ncbi.nlm.nih.gov/pubmed/2457816 | https://www.ncbi.nlm.nih.gov/pubmed/2049889

Adibendan [BM 14478] is a phosphodiesterase inhibitor that increases the calcium sensitivity of the myocardium. Adibendan selectively inhibited phosphodiesterase III (PDE III) activity concentration-dependently (IC50 = 2.0 umol/l). The IC50 values for the inhibition of PDE I or II were more than 60-fold higher. Adibendan has both vasodilator and positive inotropic properties. Adibendan was investigated as the potential treatment of heart failure and ischaemic heart disorders. However, research has been discontinued at phase II of development.

Originator

Approval Year

PubMed

Title	Date	PubMed
In vitro investigations on a new positive inotropic and vasodilating agent (BM 14.478) that increases myocardial cyclic AMP content and myofibrillar calcium sensitivity.	1988 Jan	2450261
Hemodynamic profile of BM 14.478: a new positive inotropic and vasodilating agent.	1988 Jan	2450246

Patents

Sample Use Guides

In Vivo Use Guide

Hemodynamic parameters and plasma hormone levels of 8 patients (1 female, 7 male) with chronic congestive heart failure NYHA Classes II-IV (1 patient with coronary artery disease, 7 patients with primary dilated cardiomyopathy) were assessed before and until 6 h after the intravenous application of 1.0 mg Adibendan.

Route of Administration: Intravenous

In Vitro Use Guide

Adibendan exerted a concentration-dependent (0.03-300 umol/l) positive inotropic effect in guinea-pig papillary muscles (EC50 = 1.3 umol/l) which was only partially reversible. Adibendan selectively inhibited phosphodiesterase III (PDE III) activity concentration-dependently (IC50 = 2.0 umol/l). The IC50 values for the inhibition of PDE I or II were more than 60-fold higher.

Name

Type

Language

ADIBENDAN

Official Name

English

5,7-DIHYDRO-7,7-DIMETHYL-2-(4-PYRIDYL)PYRROLO(2,3-F)BENZIMIDAZOL-6(3H)-ONE

Systematic Name

English

ADIBENDAN [MART.]

Common Name

English

adibendan [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744