Drug Information
Drug General Information | Top | |||
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Drug ID |
D0Z5IU
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Former ID |
DAP000569
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Drug Name |
Sulindac
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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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Drug Type |
Small molecular drug
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Indication | Rheumatoid arthritis [ICD-11: FA20] | Approved | [1], [2] | |
Therapeutic Class |
Antiinflammatory Agents
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Company |
Merck & Co
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Structure |
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Download2D MOL |
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Formula |
C20H17FO3S
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Canonical SMILES |
CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
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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-
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InChIKey |
MLKXDPUZXIRXEP-MFOYZWKCSA-N
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CAS Number |
CAS 38194-50-2
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PubChem Compound ID | ||||
PubChem Substance ID |
4693, 7847188, 7980709, 8149543, 8653294, 11111823, 11111824, 11114189, 11534177, 14828051, 17405626, 26611935, 26680385, 26732639, 26747172, 26747173, 32248851, 46506570, 47216762, 47736459, 47959726, 47959727, 47959728, 48035101, 48035102, 48259216, 49699049, 49982642, 50106970, 50106971, 53778176, 53789046, 57409048, 75972879, 85231236, 85787894, 90341400, 91011398, 92124295, 92303413, 92307725, 99301689, 103179013, 103925149, 104170038, 104253449, 110524953, 118307514, 121361866, 121362536
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ChEBI ID |
CHEBI:9352
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ADReCS Drug ID | BADD_D02097 | |||
SuperDrug ATC ID |
M01AB02
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SuperDrug CAS ID |
cas=038194502
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Interaction between the Drug and Microbe | Top | |||
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The Metabolism of Drug Affected by Studied Microbe(s) | ||||
The Order in the Taxonomic Hierarchy of the following Microbe(s): Gut microbiota | ||||
Studied Microbe: Anaerobic bacterium unspecific | [3], [4] | |||
Metabolic Reaction | Sulfoxide reduction | |||
Resulting Metabolite | Sulindac sulfide; sulinpyrzone sulfide | |||
Metabolic Effect | Increase activity | |||
Description | Sulindac can be metabolized to Sulindac sulfide and sulinpyrzone sulfide by unspecific Anaerobic bacterium through sulfoxide reduction, which results in the increase of the drug's activity. | |||
Studied Microbe: Gut microbiota unspecific | [3], [4], [5], [6] | |||
Metabolic Reaction | Sulfur oxidation | |||
Resulting Metabolite | Sulindac sulfide; sulinpyrzone sulfide | |||
Metabolic Effect | Increase activity; Increase side effect | |||
Description | Sulindac can be metabolized to Sulindac sulfide and sulinpyrzone sulfide by gut microbiota through sulfur oxidation , which results in the increase of drug's activity and side effect. |
Target and Pathway | Top | |||
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Target(s) | Aldose reductase (AKR1B1) | Target Info | Inhibitor | [7], [8] |
BioCyc | Methylglyoxal degradation III | |||
Acetone degradation I (to methylglyoxal) | ||||
KEGG Pathway | Pentose and glucuronate interconversions | |||
Fructose and mannose metabolism | ||||
Galactose metabolism | ||||
Glycerolipid metabolism | ||||
Metabolic pathways | ||||
NetPath Pathway | IL1 Signaling Pathway | |||
TGF_beta_Receptor Signaling Pathway | ||||
Pathwhiz Pathway | Fructose and Mannose Degradation | |||
Pyruvate Metabolism | ||||
Pterine Biosynthesis | ||||
Glycerolipid Metabolism | ||||
Galactose Metabolism | ||||
WikiPathways | Metapathway biotransformation | |||
Polyol Pathway | ||||
Metabolism of steroid hormones and vitamin D |
References | Top | |||
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REF 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). | |||
REF 2 | New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202. | |||
REF 3 | The influence of gut microbiota on drug metabolism and toxicity. Expert Opin Drug Metab Toxicol. 2016;12(1):31-40. | |||
REF 4 | Faecal microflora and beta-glucuronidase expression are altered in an irinotecan-induced diarrhea model in rats. Cancer Biol Ther. 2008 Dec;7(12):1919-25. | |||
REF 5 | The effect of gut microbiota on drug metabolism. Expert Opin Drug Metab Toxicol. 2013 Oct;9(10):1295-308. | |||
REF 6 | Personalized Mapping of Drug Metabolism by the Human Gut Microbiome. Cell. 2020 Jun 25;181(7):1661-1679.e22. | |||
REF 7 | Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin. Biochem Pharmacol. 1983 Jul 1;32(13):1995-8. | |||
REF 8 | Diabetic complications in lens and nerve and their prevention by sulindac or sorbinil: two novel aldose reductase inhibitors. Invest Ophthalmol Vis Sci. 1983 Oct;24(10):1426-9. |
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