Record Information
Version1.0
Creation Date2016-05-22 03:46:42 UTC
Update Date2026-08-20 04:58:58 UTC
Accession NumberCHEM016893
Identification
Common NameSulindac
ClassSmall Molecule
Description
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acidChEBI
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acidChEBI
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acidChEBI
ClinorilChEBI
SulindacoChEBI
SulindacumChEBI
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetateGenerator
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetateGenerator
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acidGenerator
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetateGenerator
cis-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetateGenerator
cis-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acidGenerator
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetateGenerator
cis-5-Fluoro-2-methyl-1-((p-methylsulphinyl)benzylidene)indene-3-acetateGenerator
cis-5-Fluoro-2-methyl-1-((p-methylsulphinyl)benzylidene)indene-3-acetic acidGenerator
AclinHMDB
ArthrobidHMDB
Cahill may roberts brand OF sulindacHMDB
Chemia brand OF sulindacHMDB
CopalHMDB
Novo-sundacHMDB
Nu pharm brand OF sulindacHMDB
SulindalHMDB
Apo-sulinHMDB
Kendrick brand OF sulindacHMDB
Merck sharp and dohme brand OF sulindacHMDB
Apotex brand OF sulindacHMDB
ArthrocineHMDB
ChibretHMDB
KenalinHMDB
KlinorilHMDB
Novo sundacHMDB
Novopharm brand OF sulindacHMDB
Alphapharm brand OF sulindacHMDB
Apo sulinHMDB
Merck brand OF sulindacHMDB
Nu sulindacHMDB
Nu-pharm brand OF sulindacHMDB
Nu-sulindacHMDB
Chemical FormulaC20H17FO3S
Average Molecular Mass356.411 g/mol
Monoisotopic Mass356.088 g/mol
CAS Registry Number38194-50-2
IUPAC Name2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
Traditional Namesulindac
SMILESCC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O
InChI IdentifierInChI=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 KeyMLKXDPUZXIRXEP-MFOYZWKCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndenes and isoindenes
Sub ClassNot Available
Direct ParentIndenes and isoindenes
Alternative Parents
Substituents
  • Phenyl sulfoxide
  • Indene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Sulfoxide
  • Sulfinyl compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP2.96ALOGPS
logP2.93ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.56 m³·mol⁻¹ChemAxon
Polarizability37.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00605
HMDB IDHMDB0014743
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulindac
Chemspider ID1265915
ChEBI ID9352
PubChem Compound ID1548887
Kegg Compound IDC01531
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11569947
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11927004
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12406542
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15020200
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15123337
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19884509
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23689354
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23804703