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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 of APAFANT

SMILES

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

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
40.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

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
Record UNII
J613NI05SV
Record Status Validated (UNII)
Record Version