BEPAFANT

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H22ClN5O2S
Molecular Weight	467.971
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NN=C2CN=C(C3=C(SC4=C3CC(C4)C(=O)N5CCOCC5)N12)C6=CC=CC=C6Cl

InChI

InChIKey=FWYVRZOREBYLCY-UHFFFAOYSA-N

InChI=1S/C23H22ClN5O2S/c1-13-26-27-19-12-25-21(15-4-2-3-5-17(15)24)20-16-10-14(11-18(16)32-23(20)29(13)19)22(30)28-6-8-31-9-7-28/h2-5,14H,6-12H2,1H3

HIDE SMILES / InChI

Molecular Formula	C23H22ClN5O2S
Molecular Weight	467.971
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8572529 | https://www.ncbi.nlm.nih.gov/pubmed/1793067 | https://adisinsight.springer.com/drugs/800000108 | https://www.ncbi.nlm.nih.gov/pubmed/19615424

Bepafant (also known as WEB-2170), an inverse agonist of platelet-activating factor receptor that has been preclinical studied in asthma, Ischemic heart disorder and in reperfusion injury after orthotopic liver transplantation. However, these studies were discontinued. Besides, several experiments have shown that bepafant induced apoptosis in human acute myelogenous leukemia and thus could be the powerful antileukemic agent.

Originator

Approval Year

PubMed

Title	Date	PubMed
Lipopolysaccharide and platelet-activating factor stimulate expression of platelet-activating factor acetylhydrolase via distinct signaling pathways.	2011-08	21432021
PAR-2 activating peptide-induced stimulation of pregnant rat myometrium contractile activity partly involves the other membrane receptors.	2007-01	16386349
PAF is involved in the Mycoplasma arthritidis superantigen-triggering pathway for iNOS and COX-2 expression in murine peritoneal cells.	2004-08-01	15242784
Regulation of platelet-activating factor receptor gene expression in vivo by endotoxin, platelet-activating factor and endogenous tumour necrosis factor.	1997-03-01	9065783
Effect of BN 52256 and other mediator antagonists on ouabain-induced ventricular fibrillation in sensitized guinea-pigs and on ischemia-induced fibrillation in rats.	1992	1632298
Pharmacologic activity of bepafant (WEB 2170), a new and selective hetrazepinoic antagonist of platelet activating factor.	1990-12	2262914
Pharmacological actions of PCA 4248, a new platelet-activating factor receptor antagonist: in vivo studies.	1990-10	2170626

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:15 GMT 2025`
Record UNII	CKS724B66O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BEPAFANT

Official Name

English

WEB-2170

Preferred Name

English

BEPAFANT [MART.]

Common Name

English

bepafant [INN]

Common Name

English

4-((6-(O-CHLOROPHENYL)-8,9-DIHYDRO-1-METHYL-4H,7H-CYCLOPENTA(4,5)THIENO(3,2-F)-S-TRIAZOLO(4,3-A)(1,4)DIAZEPIN-8-YL)CARBONYL)MORPHOLINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1327