sulindac   

GtoPdb Ligand ID: 5425

Synonyms: Clinoril®
sulindac is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Useful in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene. It has COX inhibitory activity, but the full details of its anti-inflammatory and and proapoptotic (anti-tumour) mechanisms remain to be resolved. Antagonism of RXRα has been implicated in its apoptosis-promoting effects in cancer cells [2]. Recent report suggests potential use for cystic fibrosis [1].
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 73.58
Molecular weight 356.09
XLogP 3.62
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)CC1=C(C)C(=Cc2ccc(cc2)S(=O)C)c2c1cc(F)cc2
Isomeric SMILES OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)S(=O)C)/c2c1cc(F)cc2
InChI InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
InChI Key MLKXDPUZXIRXEP-MFOYZWKCSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1978))
IUPAC Name
2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
International Nonproprietary Names
INN number INN
3791 sulindac
Synonyms
Clinoril®
Database Links
CAS Registry No. 38194-50-2
ChEBI CHEBI:9352
ChEMBL Ligand CHEMBL15770
DrugBank Ligand DB00605
DrugCentral Ligand 2534
GtoPdb PubChem SID 178102078
PubChem CID 1548887
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Wikipedia Sulindac