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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 of FOROPAFANT FUMARATE

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
Molecular Formula C28H40N4S
Molecular Weight 464.709
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Platelet-activating factor receptor
3
Target ID: P25105
Gene ID: 5724.0
Gene Symbol: PTAFR
Target Organism: Homo sapiens (Human)
Antagonist
2778
 57.0 pM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of SR 27417 on the binding of [3H]PAF to rabbit and human platelets and human polymorphonuclear leukocytes.
1993 May
Role of tachykinins in castor oil diarrhoea in rats.
1997 Jun
Platelet-leukocyte cross talk in whole blood.
2000 Dec
Activation of PAF receptor by oxidised LDL in human monocytes stimulates chemokine releases but not urokinase-type plasminogen activator expression.
2004 Jun
Patents

Patents

US-5780468-A
2

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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:57:19 GMT 2023
Edited
by admin
on Fri Dec 15 15:57:19 GMT 2023
Record UNII
77229931IM
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
Structure of FOROPAFANT
PARENT -> SALT/SOLVATE
Structure of Fumaric acid
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of FOROPAFANT
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