tazarotene   

GtoPdb Ligand ID: 6952

Synonyms: AGN-190168 | Tazorac® | Zorac®
tazarotene is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Tazarotene is a vitamin A-like retinoid that binds all isoforms of the retinoic acid receptor, but may show selectivity for the β, and γ isoforms acting via which may result in altered gene expression that provides the beneficial effects on skin condition. Tazarotene is essentailly a prodrug, with tazarotenic acid (PubChem CID 147525) being the active metabolite.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 64.49
Molecular weight 351.13
XLogP 5.62
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
Isomeric SMILES CCOC(=O)c1ccc(nc1)C#Cc1ccc2c(c1)C(C)(C)CCS2
InChI 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
InChI Key OGQICQVSFDPSEI-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1997))
IUPAC Name
ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
International Nonproprietary Names
INN number INN
7328 tazarotene
Synonyms
AGN-190168 | Tazorac® | Zorac®
Database Links
CAS Registry No. 118292-40-3
ChEMBL Ligand CHEMBL1657
DrugBank Ligand DB00799
DrugCentral Ligand 2571
GtoPdb PubChem SID 178103534
PubChem CID 5381
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Wikipedia Tazarotene

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Tocris
Tazarotene
Cat. No. 3997