U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H17NO2S
Molecular Weight 323.409
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAZAROTENIC ACID

SMILES

CC1(C)CCSC2=CC=C(C=C12)C#CC3=CC=C(C=N3)C(O)=O

InChI

InChIKey=IQIBKLWBVJPOQO-UHFFFAOYSA-N
InChI=1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula C19H17NO2S
Molecular Weight 323.409
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tazarotene a novel acetylenic retinoid is known to be effective in the topical treatment of psoriasis and acne. Tazarotene is rapidly and completely metabolized to its active metabolite tazarotenic acid. The exact mechanism of action of tazarotenic acid in the treatment of psoriasis and acne is not clearly defined. However, it is thought that the selective interaction of tazarotenic acid with the retinoic acid receptor (RAR) family (RARα, RARβ, and RARγ) and the subsequent induction of both positive and negative gene regulatory effects may be involved.

Approval Year

PubMed

PubMed

TitleDatePubMed
Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis.
1997 Aug
Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.
2006 Feb 1
Patents

Patents

Sample Use Guides

In Vitro Use Guide
In vitro enzyme kinetic parameters were determined for tazarotenic acid metabolite formation using 5 nM CYP26A1 or CYP26B1, 25 nM purified human reductase, and 0–10 μM tazarotenic acid. Incubations were carried out for 10 minutes at 37°C to ensure product linearity with regard to time and protein concentration. Additional experiments to determine the kinetic parameters for the sequential metabolism of tazarotenic acid metabolite sulfoxide used substrate concentrations ranging from 0 to 50 μM. Samples were prepared as described for in vitro metabolic profiling experiments.
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:08:09 UTC 2019
Edited
by admin
on Tue Oct 22 13:08:09 UTC 2019
Record UNII
85FDJ14553
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAZAROTENIC ACID
Common Name English
AGN-190299
Code English
3-PYRIDINECARBOXYLIC ACID, 6-(2-(3,4-DIHYDRO-4,4-DIMETHYL-2H-1-BENZOTHIOPYRAN-6-YL)ETHYNYL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
118292-41-4
Created by admin on Tue Oct 22 13:08:09 UTC 2019 , Edited by admin on Tue Oct 22 13:08:09 UTC 2019
PRIMARY
CAS
118292-41-4
Created by admin on Tue Oct 22 13:08:09 UTC 2019 , Edited by admin on Tue Oct 22 13:08:09 UTC 2019
PRIMARY
PUBCHEM
147525
Created by admin on Tue Oct 22 13:08:09 UTC 2019 , Edited by admin on Tue Oct 22 13:08:09 UTC 2019
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Esterase metabolism
Related Record Type Details
ACTIVE MOIETY