Sulindac (CHEM016893)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:46:42 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016893
Identification
Common NameSulindac
ClassSmall Molecule
DescriptionSulindac 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 TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-2049000000-ee0d75c6250b16c1d750Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03ki-9026500000-09ffdf8287c75b771d27Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001j-1290000000-33b23a68145a3ef2000cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0019000000-fec3a7dbf1ba6b64f03eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-0019000000-6a9b19701aa1af58166dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001l-0095000000-1aef30e1f36f3fcc9ea2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001j-0090000000-4f30705a14fab7bb25e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-8bf873219e6e4353be1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000y-0095000000-0a507959838acf3f73cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0059000000-3ad0cecc4eb73cce225eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0069000000-be643d55172bd2292511Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001j-1290000000-33b23a68145a3ef2000cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0009000000-aa01817d10171df35e25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0229000000-cf8ae62ab9c9a2b04d59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-3591000000-a4e5854feef934299dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-2029000000-1008aba76fe664bb42e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4059000000-059edf52b4661bfc81efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9031000000-f66b9288554dc37968c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0009000000-72d296d26dcda3b7ae09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-0009000000-892fc6f6c746c9f48f15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-0191000000-4bbbf45eea7d16fde5bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0009000000-f37cc66528ef3b96ffcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-2009000000-e7c5432f2cda09c51a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0292-4093000000-259994ac6b903c437345Spectrum
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
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