EFIPLADIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C40H35Cl3N2O4S
Molecular Weight	746.141
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=C(CCCC2=C(CCNS(=O)(=O)CC3=CC=C(Cl)C(Cl)=C3)N(C(C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=C(Cl)C=C26)C=C1

InChI

InChIKey=HIZOPJQOPKRKFM-UHFFFAOYSA-N

InChI=1S/C40H35Cl3N2O4S/c41-32-19-21-37-34(25-32)33(13-7-8-27-14-17-31(18-15-27)40(46)47)38(22-23-44-50(48,49)26-28-16-20-35(42)36(43)24-28)45(37)39(29-9-3-1-4-10-29)30-11-5-2-6-12-30/h1-6,9-12,14-21,24-25,39,44H,7-8,13,22-23,26H2,(H,46,47)

HIDE SMILES / InChI

Molecular Formula	C40H35Cl3N2O4S
Molecular Weight	746.141
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/18498150 | https://www.ncbi.nlm.nih.gov/pubmed/21146550 | https://adisinsight.springer.com/drugs/800020059 | https://www.ncbi.nlm.nih.gov/pubmed/26416244 | https://www.ncbi.nlm.nih.gov/pubmed/25365190

Efipladib is an inhibitor of cytosolic phospholipase A2 alpha both in vitro and in vivo. It is able to relieve inflammatory pain in animal model. Additionally, efipladib exerts antitumor potential. Efipladib was in clinical trials for the treatment of asthma and arthritis however its development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
UniProtKB - Q6IRF5 (Q6IRF5_RAT) 1 Target ID: UniProtKB - Q6IRF5 (Q6IRF5_RAT) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18498150	Inhibitor 8297		0.07 µM [IC50]

PubMed

Title	Date	PubMed
Indole cytosolic phospholipase A2 alpha inhibitors: discovery and in vitro and in vivo characterization of 4-{3-[5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoic acid, efipladib.	2008 Jun 26	18498150
In vitro allergen challenge of peripheral blood induces differential gene expression in mononuclear cells of asthmatic patients: inhibition of cytosolic phospholipase A2alpha overcomes the asthma-associated response.	2008 Oct	18665843
The cPLA2α inhibitor efipladib decreases nociceptive responses without affecting PGE2 levels in the cerebral spinal fluid.	2011 Mar	21146550

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:42:46 GMT 2023` Edited by `admin` on `Sat Dec 16 17:42:46 GMT 2023`
Record UNII	S97YUG2A91
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EFIPLADIB

Official Name

English

4-[3-[5-Chloro-2-[2-[[(3,4-dichlorobenzyl)sulfonyl]amino]ethyl]-1-(diphenylmethyl)-1H-indol-3-yl]propyl]benzoic acid

Common Name

English

PLA-902

Code

English

EFIPLADIB [USAN]

Common Name

English

efipladib [INN]

Common Name

English

BENZOIC ACID, 4-(3-(5-CHLORO-2-(2-((((3,4-DICHLOROPHENYL)METHYL)SULFONYL)AMINO)ETHYL)-1-(DIPHENYLMETHYL)-1H-INDOL-3-YL)PROPYL)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257