APAFANT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H22ClN5O2S
Molecular Weight	455.96
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NN=C2CN=C(C3=C(SC(CCC(=O)N4CCOCC4)=C3)N12)C5=CC=CC=C5Cl

InChI

InChIKey=JGPJQFOROWSRRS-UHFFFAOYSA-N

InChI=1S/C22H22ClN5O2S/c1-14-25-26-19-13-24-21(16-4-2-3-5-18(16)23)17-12-15(31-22(17)28(14)19)6-7-20(29)27-8-10-30-11-9-27/h2-5,12H,6-11,13H2,1H3

HIDE SMILES / InChI

Molecular Formula	C22H22ClN5O2S
Molecular Weight	455.96
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9395010
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25053619 | https://www.ncbi.nlm.nih.gov/pubmed/1671420 | https://www.ncbi.nlm.nih.gov/pubmed/12784066 | https://www.ncbi.nlm.nih.gov/pubmed/9131176

APAFANT is a platelet activating factor receptor (PAF-R) antagonist shown to have anticancer and cell differentiation effects. APAFANT has been found to be a specific PAF-R antagonist in pulmonary vasculature and when administered intratracheally in rats. APAFANT was observed to decrease lung nuclear factor-κB (NF-κB) activation, myeloperoxidase activity, and lavage neutrophil numbers. It has been shown to be a cytodifferentiating agent in murine erythroleukemia cells in vitro.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1671420	Inhibitor 8504		40.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatitis 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12784066	Primary		Not Provided 511	Unknown Approved Use Unknown
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9131176	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Specific PAF antagonist WEB-2086 induces terminal differentiation of murine and human leukemia cells.	2002-05	11923217
Role of platelet-activating factor in phosphatidylcholine secretion in primary cultures of rat type II pneumocytes.	2002-04	12013527
Single nucleotide polymorphism of human platelet-activating factor receptor impairs G-protein activation.	2001-11-16	11560941
Oxidized low-density lipoprotein downregulates endothelial basic fibroblast growth factor through a pertussis toxin-sensitive G-protein pathway: mediator role of platelet-activating factor-like phospholipids.	2001-07-31	11479258
Identification of transmembrane domain residues determinant in the structure-function relationship of the human platelet-activating factor receptor by site-directed mutagenesis.	1996-09-20	8798529
Mechanisms of platelet-activating factor-induced lipid body formation: requisite roles for 5-lipoxygenase and de novo protein synthesis in the compartmentalization of neutrophil lipids.	1996-04-01	8666909
A radioreceptor binding assay for platelet-activating factor (PAF) using membranes from CHO cells expressing human PAF receptor.	1995-10-26	7594622
Regulation of prostaglandin H synthase 2 expression in human monocytes by the marine natural products manoalide and scalaradial. Novel effects independent of inhibition of lipid mediator production.	1995-09-28	7575673
Mechanisms for lipoxin A4-induced neutrophil-dependent cytotoxicity for human endothelial cells.	1995-07	7602232
In vitro modulation of interleukin-1 beta secretion by cultured rat doxorubicin-stimulated whole glomeruli and dissociated mesangial glomerular cells.	1994-01	8132220
Evidence for the presence of specific high affinity cytosolic binding sites for platelet-activating factor in human neutrophils.	1993-01-15	8380690
Molecular cloning and expression of platelet-activating factor receptor from human leukocytes.	1991-10-25	1657923
Effects of YM264, a novel PAF antagonist, on puromycin aminonucleoside-induced nephropathy in the rat.	1991-04-30	2025290

Patents

Sample Use Guides

In Vivo Use Guide

40 or 80 mg during 8 wk-treatment period

Route of Administration: Oral

In Vitro Use Guide

The ATRA-sensitive APL cell line NB4 and ATRA-resistant NB4 subclones NB4-007-6 and NB4-MR4 (gift of C Gambacorti-Passerini and WH Miller, respectively) were used for activity evaluation. Cells (1x105/ml) were incubated for 5 days without and with 1mkM WEB-2086 (APAFANT) or 1mM ATRA. Cell densities were evaluated daily.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:00 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:00 GMT 2025`
Record UNII	J613NI05SV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APAFANT

Official Name

English

WEB 2086 BS

Preferred Name

English

APAFANT [USAN]

Common Name

English

APAFANT [JAN]

Common Name

English

apafant [INN]

Common Name

English

APAFANT [MI]

Common Name

English

APAFANT [MART.]

Common Name

English

WEB-2086-BS

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1327