FOROPAFANT FUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H40N4S.C4H4O4
Molecular Weight	580.781
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CC(C)C1=CC(C(C)C)=C(C2=CSC(=N2)N(CCN(C)C)CC3=CN=CC=C3)C(=C1)C(C)C

InChI

InChIKey=VVMIAYBAROQMMT-WLHGVMLRSA-N

InChI=1S/C28H40N4S.C4H4O4/c1-19(2)23-14-24(20(3)4)27(25(15-23)21(5)6)26-18-33-28(30-26)32(13-12-31(7)8)17-22-10-9-11-29-16-22;5-3(6)1-2-4(7)8/h9-11,14-16,18-21H,12-13,17H2,1-8H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Description
Sources: http://adisinsight.springer.com/drugs/800002078 | https://www.ncbi.nlm.nih.gov/pubmed/10543285 | https://www.ncbi.nlm.nih.gov/pubmed/9834260

Foropafant is a platelet-activating factor (PAF) antagonist which was developed by Sanofi. It was in clinical development for the treatment of asthma, thrombosis and ulcerative colitis. The development of the drug was discontinued due to lack of efficacy.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Platelet-activating factor receptor 3 Target ID: P25105 Gene ID: 5724.0 Gene Symbol: PTAFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1656029	Antagonist 2778		57.0 pM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ulcerative colitis 123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9834260	Primary	Not Provided 504	Unknown Approved Use Unknown
Acute asthma 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10543285	Primary	Not Provided 504	Unknown Approved Use Unknown
Thrombosis 22 Sources: http://adisinsight.springer.com/drugs/800002078	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of SR 27417 on the binding of [3H]PAF to rabbit and human platelets and human polymorphonuclear leukocytes.	1993 May	8395255
Role of tachykinins in castor oil diarrhoea in rats.	1997 Jun	9179376
Platelet-leukocyte cross talk in whole blood.	2000 Dec	11116075

Patents

Sample Use Guides

In Vivo Use Guide

In acute asthma study, foropafant was administered orally at 20 mg dosage

Route of Administration: Oral

In Vitro Use Guide

Foropafant displayed marked in vitro inhibition of PAF-induced oxidative burst in guinea pig macrophages (IC50 = 32 nM). Foropafant potently inhibited PAF-induced aggregation of rabbit and human platelets in vitro (IC50 = 0.10 and 0.50 nM, respectively).

Name

Type

Language

FOROPAFANT FUMARATE

Common Name

English

SR-27417A

Code

English

1,2-ETHANEDIAMINE, N1,N1-DIMETHYL-N2-(3-PYRIDINYLMETHYL)-N2-(4-(2,4,6-TRIS(1-METHYLETHYL)PHENYL)-2-THIAZOLYL)-, (2E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

9938199

Created by admin on Fri Dec 15 15:57:19 GMT 2023 , Edited by admin on Fri Dec 15 15:57:19 GMT 2023

PRIMARY

FDA UNII

77229931IM

Created by admin on Fri Dec 15 15:57:19 GMT 2023 , Edited by admin on Fri Dec 15 15:57:19 GMT 2023

PRIMARY

CAS

136470-45-6

Created by admin on Fri Dec 15 15:57:19 GMT 2023 , Edited by admin on Fri Dec 15 15:57:19 GMT 2023

PRIMARY

ACTIVE MOIETY


					VWJ2QVH41J

FOROPAFANT

PARENT (SALT/SOLVATE)


					88XHZ13131

Fumaric acid

SUBSTANCE RECORD


					77229931IM

FOROPAFANT FUMARATE

Details

SMILES

InChI

DescriptionSources: http://adisinsight.springer.com/drugs/800002078 | https://www.ncbi.nlm.nih.gov/pubmed/10543285 | https://www.ncbi.nlm.nih.gov/pubmed/9834260

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: http://adisinsight.springer.com/drugs/800002078 | https://www.ncbi.nlm.nih.gov/pubmed/10543285 | https://www.ncbi.nlm.nih.gov/pubmed/9834260