Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1536)
Drug Name
Tazarotene
Prodrug Info Tazarotene is the prodrug of Tazarotenic acid
Synonyms
Tazarotene (Avage); Tazarotene [USAN:INN]; Tazorac; tazarotene; 118292-40-3; 3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-, ethyl ester; Fabior; OGQICQVSFDPSEI-UHFFFAOYSA-N; 81BDR9Y8PS; AGN 190168; AGN-190168; Avage; C21H21NO2S; CHEBI:32184; CHEMBL1657; Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate; NCGC00167525-01; UNII-81BDR9Y8PS; Zora; Zorac; ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]pyridine-3-carboxylate
Indication Psoriasis vulgaris [ICD11: EA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 351.5 Topological Polar Surface Area 64.5
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5381
PubChem SID
582921 ; 4405151 ; 7848195 ; 8153307 ; 12014289 ; 14754274 ; 29224433 ; 46508992 ; 50031802 ; 50112778 ; 53789348 ; 56352905 ; 57322745 ; 68530738 ; 79123421 ; 85246194 ; 92719256 ; 93166451 ; 103629338 ; 104113517 ; 104253218 ; 104253308 ; 104309077 ; 124757343 ; 125164147 ; 125338838 ; 126620953 ; 126658167 ; 126670670 ; 127300883 ; 127300884 ; 127300885 ; 127300886 ; 127300887 ; 127300888 ; 127300889 ; 127300890 ; 127300891 ; 127300892 ; 127300893 ; 127300894 ; 127300895 ; 127300896 ; 127300897 ; 128806208 ; 134337757 ; 135017550 ; 135692178 ; 136376512 ; 136946544
ChEBI ID
ChEBI:32184
CAS Number
118292-40-3
TTD Drug ID
D0BM5G
Formula
C21H21NO2S
Canonical SMILES
CCOC(=O)C1=CN=C(C=C1)C#CC2=CC3=C(C=C2)SCCC3(C)C
InChI
1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
AGN 190832 DM000459 N. A. Oxidation - Oxidation 1 [3]
Tazarotenic acid DM000456
147525
Hydrolysis - Hydrolysis 1 [3]
AGN 190833 DM000460 N. A. Oxidation - Oxidation 2 [3]
AGN 190844 DM000457 N. A. Hydrolysis - Hydrolysis 2 [3]
AGN 190844 DM000457 N. A. Oxidation - Oxidation 2 [3] , [2] , [4]
AGN 190843 DM000458 N. A. Hydrolysis - Hydrolysis 3 [3]
AGN 190843 DM000458 N. A. Oxidation - Oxidation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002348 Tazarotene Tazarotenic acid Hydrolysis - Hydrolysis LE [3]
MR002349 Tazarotene AGN 190832 Oxidation - Oxidation Unclear [3]
MR002345 AGN 190832 AGN 190844 Hydrolysis - Hydrolysis Unclear [3]
MR002346 AGN 190832 AGN 190833 Oxidation - Oxidation Unclear [3]
MR002343 Tazarotenic acid AGN 190844 Oxidation - Oxidation CYP2C8 ... [3], [2], [4]
MR002347 AGN 190833 AGN 190843 Hydrolysis - Hydrolysis Unclear [3]
MR002344 AGN 190844 AGN 190843 Oxidation - Oxidation Unclear [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
References
1 Tazarotene was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans. Drug Metab Dispos. 2003 Apr;31(4):476-81.
3 Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis Clin Pharmacokinet. 1999 Oct;37(4):273-87. doi: 10.2165/00003088-199937040-00001.
4 LABEL:AZAROTENE aerosol, foam

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