Sulindac sodiumProduct ingredient for Sulindac

Name
Sulindac sodium
Drug Entry
Sulindac

Sulindac is a nonsteroidal anti-inflammatory drug (NSAID) of the arylalkanoic acid class that is marketed by Merck under the brand name Clinoril. Like other NSAIDs, it may be used in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene, that is converted in vivo to an active sulfide compound by liver enzymes. There is evidence from some studies that sulindac may be associated with fewer gastrointestinal side effects than other NSAIDs, except for the cyclooxygenase-2 (COX-2) inhibitor drug class. This may be due to the sulfide metabolite undergoing enterohepatic circulation thus maintaining constant blood levels of the compound without inducing gastrointestinal effects, where the drug is excreted in the bile and then reabsorbed from the intestines. While its full mechanism of action is not fully understood, sulindac is thought to primarily mediate its action by inhibiting prostaglandin synthesis by inhibiting COX-1 and COX-2.

Accession Number
DBSALT002293
Structure
Synonyms
Not Available
UNII
NJV14I2XPC
CAS Number
63804-15-9
Weight
Average: 378.39
Monoisotopic: 378.07018799
Chemical Formula
C20H16FNaO3S
InChI Key
YMXUJDLCLXHYBO-WPTDRQDKSA-M
InChI
InChI=1S/C20H17FO3S.Na/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);/q;+1/p-1/b17-9-;
IUPAC Name
sodium 2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetate
SMILES
[Na+].C[S+]([O-])C1=CC=C(\C=C2\C(C)=C(CC([O-])=O)C3=CC(F)=CC=C23)C=C1
ChemSpider
4938097
Predicted Properties
PropertyValueSource
Water Solubility0.0541 mg/mLALOGPS
logP3.59ALOGPS
logP2.93Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.09Chemaxon
pKa (Strongest Basic)-8.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area57.2 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity110.4 m3·mol-1Chemaxon
Polarizability36.77 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon