Natural Product (NP) Details

General Information of the NP (ID: NP7706)
Name
Tazarotene
Synonyms
tazarotene; 118292-40-3; Tazorac; Zorac; Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate; Avage; AGN-190168; Fabior; AGN 190168; Tazarotene (Avage); UNII-81BDR9Y8PS; C21H21NO2S; 81BDR9Y8PS; CHEMBL1657; ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate; CHEBI:32184; NCGC00167525-01; ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]nicotinate; DSSTox_CID_26691; DSSTox_RID_81825; DSSTox_GSID_46691; tazaroteno; tazarotenum; Suretin; Tazoral; Zora; 6-(4,4-Dimethyl-thiochroman-6-ylethynyl)-nicotinic acid ethyl ester; ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate; Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate;6-(4,4-dimethyl-thiochroman-6-ylethynyl)-nicotinic acid ethyl ester; Tazorac (TN); Avage (TN); CAS-118292-40-3; Acnitaz; ethyl 6-(2-(4,4-dimethylthiochroman-6-yl)-ethynyl)nicotinate; Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)-ethynyl]nicotinate; Tazarotene (JAN/USAN/INN); Tazarotene [USAN:INN:BAN]; Zorac; ; ; Tazorac; Tazarotene,(S); ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]pyridine-3-carboxylate; Fabior (TN); 3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-, ethyl ester; PubChem24431; SCHEMBL3134; MLS003915630; BIDD:GT0293; GTPL6952; DTXSID5046691; HMS3655K05; HMS3747C19; HMS3747E19; ACT06773; AMY31169; BCP22966; EBD38650; ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl] nicotinate; ZINC1542199; Tox21 112522; Tox21_112522; ABP000994; AC-755; ANW-45265; BDBM50265951; MFCD00867628; s1569; AKOS015902872; Tox21_112522_1; BS-1012; CCG-268046; CS-1029; DB00799; NCGC00167525-02; NCGC00167525-03; 6-[(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester; HY-15388; SMR002096194; BCP0726000163; AB0012671; DB-014992; FT-0652578; SW220026-1; AGN190168, AGN-190168; C12531; D01132; S-7551; 15146-EP2275420A1; 15146-EP2295055A2; 15146-EP2295416A2; 15146-EP2298748A2; 15146-EP2298764A1; 15146-EP2298765A1; 15146-EP2298768A1; 15146-EP2305642A2; 15146-EP2308861A1; 15146-EP2311453A1; 15146-EP2311808A1; 15146-EP2311829A1; 15146-EP2314590A1; 15146-EP2316832A1; 15146-EP2316833A1; AB01274801-01; AB01274801_02; 292T403; SR-01000931253; Q-102516; Q3981685; SR-01000931253-2; Ethyl 6-[2-(4,4-dimethylthiochroman-6-yl)ethynyl]nicotinate; 6-(4,4-dimethylthiochroman-6-ylethynyl) nicotinic acid ethyl ester; (+/-)OCTAHYDROCYCLOPENTA[B]PYRROLE-2-CARBOXYLICACIDHYDROCHLORIDE; 6-(2-(4,4-dimethyl-thiochroman-6yl)ethynyl)-nicotinic acid ethyl ester; Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]pyridine-3-carboxylate; 6-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]- 3-pyridinecarboxylic Acid Ethyl Ester; 6-[2-(3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylic acid ethyl ester; 6-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-3-pyridinecarboxylicacidethylester
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Plaque psoriasis [ICD-11: EA90] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.956
 
MDCK Permeability
 -4.876
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 0.622
 
PPB
 99.3%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 +++
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 ++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 6.564
 
T1/2
 0.444
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 -
 
FDAMDD
 ++
 
Respiratory
 ++
 
Human Hepatotoxicity
 - - -
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 - - -
 
Drug-induced Neurotoxicity
 - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C21H21NO2S
PubChem CID
5381
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
CAS Number
CAS 118292-40-3
ChEBI ID
CHEBI:32184
TTD Drug ID
D0BM5G
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Imiquimod      Skin cancer     Click to Show/Hide the Molecular Data of This Drug
                 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
                    Experimental
                    Result(s)		 Tazarotene enhanced the penetration of imiquimod, and could be a therapeutic option in cases where surgical intervention is not possible.
Target and Pathway
Target(s) Retinoic acid receptor gamma (RARG)  Molecule Info  [3]
Reactome Nuclear Receptor transcription pathway Click to Show/Hide
WikiPathways Vitamin A and Carotenoid Metabolism Click to Show/Hide
2 Nuclear Receptors in Lipid Metabolism and Toxicity
3 Mesodermal Commitment Pathway
4 Endoderm Differentiation
5 Nuclear Receptors
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: 6952).
Reference 2 Lentigo maligna successfully treated with combination therapy of topical tazarotene and imiquimod. Clin Exp Dermatol. 2017 Jun;42(4):468-470.
Reference 3 Recent developments in receptor-selective retinoids. Curr Pharm Des. 2000 Jun;6(9):919-31.
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