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
Pharmacologic activity of bepafant (WEB 2170), a new and selective hetrazepinoic antagonist of platelet activating factor.	1990 Dec	2262914
Pharmacological actions of PCA 4248, a new platelet-activating factor receptor antagonist: in vivo studies.	1990 Oct	2170626
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
Regulation of platelet-activating factor receptor gene expression in vivo by endotoxin, platelet-activating factor and endogenous tumour necrosis factor.	1997 Mar 1	9065783
PAF is involved in the Mycoplasma arthritidis superantigen-triggering pathway for iNOS and COX-2 expression in murine peritoneal cells.	2004 Aug 1	15242784
PAR-2 activating peptide-induced stimulation of pregnant rat myometrium contractile activity partly involves the other membrane receptors.	2007 Jan	16386349
Lipopolysaccharide and platelet-activating factor stimulate expression of platelet-activating factor acetylhydrolase via distinct signaling pathways.	2011 Aug	21432021

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:06:38 UTC 2023` Edited by `admin` on `Fri Dec 15 16:06:38 UTC 2023`
Record UNII	CKS724B66O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BEPAFANT

Official Name

English

BEPAFANT [MART.]

Common Name

English

bepafant [INN]

Common Name

English

WEB-2170

Code

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