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Details

Stereochemistry ACHIRAL
Molecular Formula C21H21NO2S
Molecular Weight 351.462
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAZAROTENE

SMILES

CCOC(=O)C1=CN=C(C=C1)C#CC2=CC=C3SCCC(C)(C)C3=C2

InChI

InChIKey=OGQICQVSFDPSEI-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Tazarotene is a prodrug and a member of the acetylenic class of retinoids. Following topical application, tazarotene undergoes esterase hydrolysis to form its active metabolite, tazarotenic acid. When treating acne tazarotene may be taken in conjunction with an oral antibiotic. Tazarotene has been shown in peer-reviewed double blinded studies to reduce: mottling and hyperpigmentation, sallowness, fine wrinkling and coarse wrinkling in sun damaged skin. Histological studies have shown that long term (greater than 1 year) use of Tazarotene is associated with a significant reduction in atypical melanocytes and keratocytes - cells considered to be precursors of skin cancer. Some studies have shown long term use of Tazarotene to be associated with increased collagen production and better organization of skin collagen bundles. Although the exact mechanism of tazarotene action is not known, studies have shown that the active form of the drug (tazarotenic acid) binds to all three members of the retinoic acid receptor (RAR) family: RARa, RARb, and RARg, but shows relative selectivity for RARb, and RARg and may modify gene expression. It also has affinity for RXR receptors. Tazarotene is used to treat psoriasis, acne and sun damaged skin (photodamage). Tazarotene is marketed as Tazorac, Avage, Zorac, and Fabior.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Management of scalp psoriasis: guidelines for corticosteroid use in combination treatment.
2001
Efficacy and tolerability of once-daily tazarotene 0.1% gel versus once-daily tretinoin 0.025% gel in the treatment of facial acne vulgaris: a randomized trial.
2001 Jun
Randomized facial tolerability studies comparing gel formulations of retinoids used to treat acne vulgaris.
2001 Jun
Comparison of treatment of acne vulgaris with alternate-day applications of tazarotene 0.1% gel and once-daily applications of adapalene 0.1% gel: a randomized trial.
2001 Jun
Retinoids for the treatment of psoriasis: outlook for the future.
2001 May
1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects.
2001 May
Treatment of psoriasis. Part 1. Topical therapy and phototherapy.
2001 Oct
Developments in topical retinoid therapy for acne.
2001 Sep
Retinoids--which dermatological indications will benefit in the near future?
2001 Sep-Oct
The modern age of acne therapy: a review of current treatment options.
2001 Sep-Oct
Wrinkles.
2003 Dec
Spotlight on adapalene in acne vulgaris.
2004
The p73 gene is an anti-tumoral target of the RARbeta/gamma-selective retinoid tazarotene.
2004 Dec
Histological effects of tazarotene 0.1% cream vs. vehicle on photodamaged skin: a 6-month, multicentre, double-blind, randomized, vehicle-controlled study in patients with photodamaged facial skin.
2004 Dec
Topical tazarotene in acne vulgaris: treatment approaches.
2004 Oct
Meta-analysis of topical tazarotene in the treatment of mild to moderate acne.
2004 Oct
Topical tazarotene: The BEST (balancing efficacy, speed, and tolerability) in acne trial.
2004 Oct
Topical retinoids in the management of acne: the best path to clear results.
2004 Oct
Keratosis punctata palmoplantaris controlled with topical retinoids: a case report and review of the literature.
2004 Sep
Comparison of topical retinoids in the treatment of acne.
2004 Sep-Oct
Patents

Patents

Sample Use Guides

In Vivo Use Guide
For psoriasis: It is recommended that treatment start with TAZORAC (Tazarotene) 0.05% Gel, with strength increased to 0.1% if tolerated and medically indicated. Apply TAZORAC® Gel once a day, in the evening, to psoriatic lesions, using enough (2 mg/cm2) to cover only the lesion with a thin film to no more than 20% of body surface area. If a bath or shower is taken prior to application, the skin should be dry before applying the gel. If emollients are used, they should be applied at least an hour before application of TAZORAC® Gel.
Route of Administration: Topical
In Vitro Use Guide
Tazarotene treatment caused a dose-dependent reduction in cell proliferation in BCC cell line ASZ001 cells (the strongest effect on cell proliferation was at 10 umol/L)
Name Type Language
TAZAROTENE
INCI   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INCI   USAN   INN  
Official Name English
AVAGE
Brand Name English
TAZAROTENE [USAN]
Common Name English
TAZAROTENE [MI]
Common Name English
TAZAROTENE [WHO-DD]
Common Name English
TAZAROTENE [JAN]
Common Name English
TAZAROTENE [VANDF]
Common Name English
TAZAROTENE [INN]
Common Name English
TAZORAC
Brand Name English
ETHYL 6-((4,4-DIMETHYLTHIOCHROMAN-6-YL)ETHYNYL)NICOTINATE
Systematic Name English
TAZAROTENE [ORANGE BOOK]
Common Name English
AGN-190168
Code English
AGN 190168
Code English
3-PYRIDINECARBOXYLIC ACID, 6-((3,4-DIHYDRO-4,4-DIMETHYL-2H-1-BENZOTHIOPYRAN-6-YL)ETHYNYL)-, ETHYL ESTER
Common Name English
TAZAROTENE [MART.]
Common Name English
TAZAROTENE [INCI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007700
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
NDF-RT N0000007700
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
NDF-RT N0000007700
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
WHO-ATC D05AX05
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
WHO-VATC QD05AX05
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
NDF-RT N0000007700
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
NDF-RT N0000175607
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
NDF-RT N0000007700
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
Code System Code Type Description
MESH
C086827
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
PUBCHEM
5381
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY SWITZERF
CAS
118292-40-3
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
RXCUI
83947
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY RxNorm
DRUG BANK
DB00799
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
LactMed
118292-40-3
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
WIKIPEDIA
TAZAROTENE
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
EPA CompTox
118292-40-3
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
MERCK INDEX
M10488
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL1657
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
EVMPD
SUB10844MIG
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
IUPHAR
6952
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
INN
7328
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY
NCI_THESAURUS
C29487
Created by admin on Tue Mar 06 10:23:50 UTC 2018 , Edited by admin on Tue Mar 06 10:23:50 UTC 2018
PRIMARY