Drug Details

General Information of the Drug (ID: DR8341)
Name
Sulindac
Synonyms
Aclin; Aflodac; Arthrobid; Arthrocine; Chibret; Clinoril; Copal; Copals; Kenalin; Klinoril; Mobilin; Sulindaco; Sulindacum; Sulindal; Alphapharm Brand of Sulindac; Apo Sulin; Apotex Brand of Sulindac; Cahill May Roberts Brand of Sulindac; Chemia Brand of Sulindac; Copal resin; Copal rosin varnish; Gum copal; KendrickBrand of Sulindac; Merck Brand of Sulindac; Novo Sundac; Novopharm Brand of Sulindac; Nu Pharm Brand of Sulindac; Nu Sulindac; Resin copal; Sulindac sulfoxide; MK 231; MK231; S 8139; Apo-Sulin; Clinoril (TN); MK-231; Merck Sharp & Dohme Brand of Sulindac; Novo-Sundac; Nu-Pharm Brand of Sulindac; Nu-Sulindac; Sulindaco [INN-Spanish]; Sulindacum [INN-Latin]; Sulindac (JAN/USP/INN); Sulindac [USAN:BAN:INN:JAN]; Z-5-Fluoro-2-methyl-1-[p-(methlsulfinyl)benzylidene]indene-3-acetic acid; Cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid; {5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1h-inden-3-yl}acetic acid; Cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid; [(1E)-5-fluoro-2-methyl-1-{[4-(methylsulfinyl)phenyl]methylidene}-1H-inden-3-yl]acetic acid; {(1E)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-inden-3-yl}acetic acid; {(1Z)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-inden-3-yl}acetic acid; (E)-(1)-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid; (Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid; (Z)-5-Fluoro-2-methyl-1-[[4-(methyl-sulfinyl)phenyl]methylene]-1H-indene-3-acetic acid; (Z)-5-Fluoro-2-methyl-1-[p-(methylsulfinyl)benzylidene]indene-3-acetic acid; 2-[(3E)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid; 2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid; 2-[6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid; 5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid
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Molecular Type
Small molecule
Disease Rheumatoid arthritis [ICD-11: FA20] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption
The absorption of drug is approximately 90% following oral administration
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
88% of drug becomes completely available to its intended biological destination(s)
Clearance
The renal clearance of drug is 68.12 +/- 27.56 mL/min
Elimination
1% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 7.8 hours
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 16.0325 micromolar/kg/day
Water Solubility
The ability of drug to dissolve in water is measured as 0.0028 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C20H17FO3S
PubChem CID
1548887
Canonical SMILES
CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
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-
InChIKey
MLKXDPUZXIRXEP-MFOYZWKCSA-N
CAS Number
CAS 38194-50-2
ChEBI ID
CHEBI:9352
TTD Drug ID
D0Z5IU
DrugBank ID
DB00605
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Epigallocatechin gallate      Hamamelis virginiana     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Up-regulation Apoptosis
                    In-vivo Model Colon carcinogenesis in five-week-old male was induced by azoxymethane.
                    Experimental
                    Result(s)		 EGCG with sulindac synergistically suppresses ACF formation by enhancing apoptosis.
Target and Pathway
Target(s) Aldose reductase (AKR1B1)  Molecule Info  [3]
BioCyc Methylglyoxal degradation III Click to Show/Hide
2 Acetone degradation I (to methylglyoxal)
KEGG Pathway Pentose and glucuronate interconversions Click to Show/Hide
2 Fructose and mannose metabolism
3 Galactose metabolism
4 Glycerolipid metabolism
5 Metabolic pathways
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TGF_beta_Receptor Signaling Pathway
Pathwhiz Pathway Fructose and Mannose Degradation Click to Show/Hide
2 Pyruvate Metabolism
3 Pterine Biosynthesis
4 Glycerolipid Metabolism
5 Galactose Metabolism
WikiPathways Metapathway biotransformation Click to Show/Hide
2 Polyol Pathway
3 Metabolism of steroid hormones and vitamin D
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5425).
Reference 2 Synergistic effects of (-)-epigallocatechin gallate with sulindac against colon carcinogenesis of rats treated with azoxymethane. Cancer Lett. 2002 Mar 8;177(1):49-56.
Reference 3 Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin. Biochem Pharmacol. 1983 Jul 1;32(13):1995-8.
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