NUPAFANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H32N4O3S
Molecular Weight	444.59
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC[C@H](CC(C)C)N(C)S(=O)(=O)C1=CC=C(CN2C(C)=NC3=CN=CC=C23)C=C1

InChI

InChIKey=GFUNPHNHBVCVHW-FQEVSTJZSA-N

InChI=1S/C23H32N4O3S/c1-6-30-16-20(13-17(2)3)26(5)31(28,29)21-9-7-19(8-10-21)15-27-18(4)25-22-14-24-12-11-23(22)27/h7-12,14,17,20H,6,13,15-16H2,1-5H3/t20-/m0/s1

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Description
Sources: https://adisinsight.springer.com/drugs/800003680 | https://www.ncbi.nlm.nih.gov/pubmed/16921398

Nupafant (BB-960) is a potent platelet activating factor antagonist that is active both orally and intravenously. Nupafant was in phase I clinical trials in the UK for the treatment of ischemia-reperfusion injury, however this compound has since been suspended.

Originator

Approval Year

PubMed

Title	Date	PubMed
Nupafant, a PAF-antagonist prototype for suppression of ventricular fibrillation without liability for QT prolongation?	2006-10	16921398

Sample Use Guides

In Vitro Use Guide

Global (whole-heart) delivery of 10 uM nupafant, reduced the incidence of ischaemia-induced VF and widened QT interval without affecting coronary flow. Importantly, lower concentrations (0.1 and 1 uM) had no effect on VF, yet widened QT almost identically to 10 uM nupafant.

Name

Type

Language

NUPAFANT

Official Name

English

BB-960

Preferred Name

English

N-((S)-1-(ETHOXYMETHYL)-3-METHYLBUTYL)-N-METHYL-.ALPHA.-(2-METHYL-1H-IMIDAZO(4,5-C)PYRIDIN-1-YL)-P-TOLUENESULFONAMIDE

Common Name

English

BENZENESULFONAMIDE, N-((1S)-1-(ETHOXYMETHYL)-3-METHYLBUTYL)-N-METHYL-4-((2-METHYL-1H-IMIDAZO(4,5-C)PYRIDIN-1-YL)METHYL)-

Systematic Name

English

nupafant [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1327