Sulindac sulfone (CHEM017534)

Record Information
Version1.0
Creation Date2016-05-22 04:26:38 UTC
Update Date2026-08-20 04:58:59 UTC
Accession NumberCHEM017534
Identification
Common NameSulindac sulfone
ClassSmall Molecule
Description
A sulfone metabolite of sulindac that inhibits cell growth by inducing apoptosis independently of cyclooxygenase inhibition. It inhibits the development and induces regression of premalignant adenomatous polyps. Lipoxygenase and Cox-2 inhibitor.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Fluoro-2-methyl-1-((Z)-p-(methylsulfonyl)benzylidene)indene-3-acetic acidChEBI
cis-5-Fluoro-2-methyl-1-(p-methylsulfonylbenzylidenyl)indene-3-acetic acidChEBI
ExisulindChEBI
5-Fluoro-2-methyl-1-((Z)-p-(methylsulfonyl)benzylidene)indene-3-acetateGenerator
5-Fluoro-2-methyl-1-((Z)-p-(methylsulphonyl)benzylidene)indene-3-acetateGenerator
5-Fluoro-2-methyl-1-((Z)-p-(methylsulphonyl)benzylidene)indene-3-acetic acidGenerator
cis-5-Fluoro-2-methyl-1-(p-methylsulfonylbenzylidenyl)indene-3-acetateGenerator
cis-5-Fluoro-2-methyl-1-(p-methylsulphonylbenzylidenyl)indene-3-acetateGenerator
cis-5-Fluoro-2-methyl-1-(p-methylsulphonylbenzylidenyl)indene-3-acetic acidGenerator
Sulindac sulphoneGenerator
(5-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-(N-benzyl)-indene)-acetamideMeSH
FGN-1MeSH
AptosynMeSH
Sulindac sulfone, (Z)-isomerMeSH
2-[(3Z)-6-fluoro-2-Methyl-3-[(4-methylsulfonylphenyl)methylidene]inden-1-yl]acetateGenerator
2-[(3Z)-6-fluoro-2-Methyl-3-[(4-methylsulphonylphenyl)methylidene]inden-1-yl]acetateGenerator
2-[(3Z)-6-fluoro-2-Methyl-3-[(4-methylsulphonylphenyl)methylidene]inden-1-yl]acetic acidGenerator
Sulindac sulfoneMeSH
Chemical FormulaC20H17FO4S
Average Molecular Mass372.410 g/mol
Monoisotopic Mass372.083 g/mol
CAS Registry Number59973-80-7
IUPAC Name2-[(1Z)-5-fluoro-1-[(4-methanesulfonylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
Traditional Namesulindac sulfone
SMILES[H]\C(=C1/C(C)=C(CC(O)=O)C2=C1C=CC(F)=C2)C1=CC=C(C=C1)S(C)(=O)=O
InChI IdentifierInChI=1S/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)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 KeyMVGSNCBCUWPVDA-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
  • Benzenesulfonyl group
  • Indene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Sulfonyl
  • Sulfone
  • 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 Solubility0.0016 g/LALOGPS
logP2.94ALOGPS
logP3.03ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.2 m³·mol⁻¹ChemAxon
Polarizability38.06 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 IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkExisulind
Chemspider IDNot Available
ChEBI ID64212
PubChem Compound ID5472495
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17016604
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20332437
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20374023
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21515355
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21735687
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22364235