BENAFENTRINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H27N3O3
Molecular Weight	393.4788
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CCN(C)C[C@@]1([H])C3=C(C=C(OC)C(OC)=C3)C(=N2)C4=CC=C(NC(C)=O)C=C4

InChI

InChIKey=DCDXHGMCXGHXBM-PMACEKPBSA-N

InChI=1S/C23H27N3O3/c1-14(27)24-16-7-5-15(6-8-16)23-18-12-22(29-4)21(28-3)11-17(18)19-13-26(2)10-9-20(19)25-23/h5-8,11-12,19-20H,9-10,13H2,1-4H3,(H,24,27)/t19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H27N3O3
Molecular Weight	393.4788
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19508401 | https://adisinsight.springer.com/drugs/800000110

Benafentrine (also known as AH 21-132), an inhibitor of the phosphodiesterase (PDE) III and IV isoenzymes, had an anti-allergic effect and was studied for the treatment of allergic bronchial asthma. However, the development of the drug was discontinued at phase I.

Originator

Approval Year

PubMed

Title	Date	PubMed
Role of cAMP for regulation of impulse-evoked noradrenaline release from the rabbit pulmonary artery and its possible relationship to presynaptic ACTH receptors.	1984 Dec	6098833
Studies on anti-allergic action of AH 21-132, a novel isozyme-selective phosphodiesterase inhibitor in airways.	1995 Feb	7542355
Suppression of lipopolysaccharide-induced tumor necrosis factor-alpha generation from human peripheral blood monocytes by inhibitors of phosphodiesterase 4: interaction with stimulants of adenylyl cyclase.	1995 Oct	7476903
Phosphodiesterase 4 in macrophages: relationship between cAMP accumulation, suppression of cAMP hydrolysis and inhibition of [3H]R-(-)-rolipram binding by selective inhibitors.	1996 Sep 1	8809029
Effects of cAMP-phosphodiesterase isozyme inhibitor on cytokine production by lipopolysaccharide-stimulated human peripheral blood mononuclear cells.	1997 Oct	9352314

Patents

Sample Use Guides

In Vivo Use Guide

Each subject received cumulative intravenous doses of 5, 5, 10, 20 and 40 mg of AH 21-132 (Benafentrine) over 15 min incrementing every 30 min or similar volumes of a saline placebo in a random order. Dose-effect study In this study a similar protocol was followed except that doses of AH 21-132 of 2, 6 and 24 mg were inhaled at 30 min intervals. These doses were administered over 2, 11 and 21 min respectively. Similar volumes of saline were used as a placebo and a minimum of 72 h was allowed between each limb of the trial.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:44:53 GMT 2023` Edited by `admin` on `Sat Dec 16 16:44:53 GMT 2023`
Record UNII	3DXB7KMD1F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENAFENTRINE

Official Name

English

benafentrine [INN]

Common Name

English

AH-21-132

Code

English

CIS-4'-(1,2,3,4,4A,10B-HEXAHYDRO-8,9-DIMETHOXY-2-METHYLBENZO(C)(1,6)NAPHTHYRIDIN-6-YL)ACETANILIDE

Common Name

English

(±)-CIS-6-(P-ACETAMIDOPHENYL)-1,2,3,4,4A,10B-HEXAHYDRO-8,9-DIMETHOXY-2-METHYLBENZO-(C)(1,6)NAPHTYRIDINE

Systematic Name

English

ACETAMIDE, N-(4-((4AR,10BS)-1,2,3,4,4A,10B-HEXAHYDRO-8,9-DIMETHOXY-2-METHYLBENZO(C)(1,6)NAPHTHYRIDIN-6-YL)PHENYL)-, REL-

Systematic Name

English

BENZAFENTRINE

Common Name

English

AH21-132

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C744