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Details

Stereochemistry ACHIRAL
Molecular Formula C27H32O4
Molecular Weight 420.5406
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of 13-CIS-12-(3'-CARBOXYPHENYL)RETINOIC ACID

SMILES

CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C(/C(C)=C\C(O)=O)C2=CC=CC(=C2)C(O)=O

InChI

InChIKey=XKKDQOHDTASHCE-PAZAWXFKSA-N
InChI=1S/C27H32O4/c1-18(12-14-24-19(2)8-7-15-27(24,4)5)11-13-23(20(3)16-25(28)29)21-9-6-10-22(17-21)26(30)31/h6,9-14,16-17H,7-8,15H2,1-5H3,(H,28,29)(H,30,31)/b14-12+,18-11+,20-16-,23-13-

HIDE SMILES / InChI

Molecular Formula C27H32O4
Molecular Weight 420.5406
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

BMS-181162, a retinoid derivative, is a phospholipase A2 inhibitor. It was in clinical trials in the treatment of inflammatory diseases, atopic dermatitis, and psoriasis.

Approval Year

PubMed

PubMed

TitleDatePubMed
Mechanism of inhibition of human nonpancreatic secreted phospholipase A2 by the anti-inflammatory agent BMS-181162.
1995-01-06
Inhibitor of phospholipase A2 blocks eicosanoid and platelet activating factor biosynthesis and has topical anti-inflammatory activity.
1994-11
Novel inhibitor of phospholipase A2 with topical anti-inflammatory activity.
1992-11-30

Sample Use Guides

In Vitro Use Guide
BMS-181162 reversibly inhibited phospholipase A2 purified from human synovial fluid with an IC50 of 8 microns. In A23187-stimulated human polymorphonuclear leukocytes, BMS-181162 blocked arachidonic acid release with an IC50 of 10 microns. Leukotriene B4 biosynthesis in these cells was also inhibited.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:11:04 GMT 2025
Edited
by admin
on Mon Mar 31 18:11:04 GMT 2025
Record UNII
Y8U3B6ZM8D
Record Status Validated (UNII)
Record Version
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Name Type Language
BMS-181162
Preferred Name English
13-CIS-12-(3'-CARBOXYPHENYL)RETINOIC ACID
Common Name English
Code System Code Type Description
PUBCHEM
6438744
Created by admin on Mon Mar 31 18:11:04 GMT 2025 , Edited by admin on Mon Mar 31 18:11:04 GMT 2025
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CAS
141948-79-0
Created by admin on Mon Mar 31 18:11:04 GMT 2025 , Edited by admin on Mon Mar 31 18:11:04 GMT 2025
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FDA UNII
Y8U3B6ZM8D
Created by admin on Mon Mar 31 18:11:04 GMT 2025 , Edited by admin on Mon Mar 31 18:11:04 GMT 2025
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DRUG BANK
DB14097
Created by admin on Mon Mar 31 18:11:04 GMT 2025 , Edited by admin on Mon Mar 31 18:11:04 GMT 2025
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Related Record Type Details
ACTIVE MOIETY