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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
Practical management of psoriasis in the elderly: epidemiology, clinical aspects, quality of life, patient education and treatment options.
2002
Successful treatment of acne vulgaris using a new method: results of a randomized vehicle-controlled trial of short-contact therapy with 0.1% tazarotene gel.
2002 Apr
Is TIG1 a new tumor suppressor in prostate cancer?
2002 Apr 3
Optimizing the use of tazarotene for the treatment of facial acne vulgaris through combination therapy.
2002 Feb
Once-daily tazarotene 0.1 % gel versus once-daily tretinoin 0.1 % microsponge gel for the treatment of facial acne vulgaris: a double-blind randomized trial.
2002 Feb
Tazarotene is an effective therapy for elastosis perforans serpiginosa.
2002 Feb
Treatment of warty dyskeratoma with tazarotenic acid.
2002 Feb
Refining retinoids with heteroatoms.
2002 Jun
Potential anti-inflammatory effects of topical retinoids and retinoid analogues.
2002 May-Jun
Drug interactions in psoriasis: the pros and cons of combining topical psoriasis therapies.
2002 May-Jun
Topical agents for the treatment of psoriasis, past, present and future.
2002 May-Jun
[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis].
2002 Nov
Oral lichen planus: a preliminary clinical study on treatment with tazarotene.
2002 Nov
Questionable techniques for evaluating photodamage.
2002 Nov
Efficacy of 0.1% tazarotene cream for the treatment of photodamage: a 12-month multicenter, randomized trial.
2002 Nov
[Psoriatic onycho-pachydermo- periostitis].
2002 Oct
A comparison of psoralen plus ultraviolet A (PUVA) monotherapy, tacalcitol plus PUVA and tazarotene plus PUVA in patients with chronic plaque-type psoriasis.
2002 Oct
Treating keratosis pilaris.
2002 Sep
Pharmacokinetics of tazarotene cream 0.1% after a single dose and after repeat topical applications at clinical or exaggerated application rates in patients with acne vulgaris or photodamaged skin.
2003
Short-contact therapy with tazarotene in psoriasis vulgaris.
2003
Optimizing treatment with topical tazarotene.
2003
The rationale for using a topical retinoid for inflammatory acne.
2003
Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans.
2003 Apr
Wrinkles.
2003 Dec
Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23.
2003 Dec 18
Tazarotene 0.1% gel for psoriasis of the fingernails and toenails: an open, prospective study.
2003 Jul
Type I lamellar ichthyosis improved by tazarotene 0.1% gel.
2003 Jul
Tazarotene cream in the treatment of psoriasis: Two multicenter, double-blind, randomized, vehicle-controlled studies of the safety and efficacy of tazarotene creams 0.05% and 0.1% applied once daily for 12 weeks.
2003 May
Confluent and reticulated papillomatosis: response to tazarotene.
2003 May
[Medication of the month. Tazarotene 0.05%-0.1% (Zorac)].
2003 Nov
Tazarotene-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application.
2003 Oct
A phase 1 study of tazarotene in adults with advanced cancer.
2003 Sep 1
Spotlight on adapalene in acne vulgaris.
2004
Tazarotene 0.1% gel for refractory mycosis fungoides lesions: an open-label pilot study.
2004 Apr
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
Treatment of lentigo maligna with tazarotene 0.1% gel.
2004 Jan
[Prescribe topical treatments for psoriasis].
2004 Jan 15
Topical treatment of basal cell carcinoma with tazarotene: a clinicopathological study on a large series of cases.
2004 Jul
Questions & answers. Of all the treatments that promise to improve the appearance of aging skin, which ones have been medically proven to actually work?
2004 Jul
Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation.
2004 Jul 1
Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene.
2004 Jul-Aug
Topical retinoid and antibiotic combination therapy for acne management.
2004 Mar-Apr
Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis.
2004 Mar-Apr
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
IDP-123
Common Name English
TAZAROTENE [USAN]
Common Name English
TAZAROTENE [MI]
Common Name English
IDP-118 COMPONENT TAZAROTENE
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
TAZAROTENE COMPONENT OF DUOBRII
Brand Name English
AGN 190168
Code English
DUOBRII COMPONENT TAZAROTENE
Brand Name 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 Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
WHO-ATC D05AX05
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
WHO-VATC QD05AX05
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
NCI_THESAURUS C804
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
EU-Orphan Drug EU/3/06/423
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
NDF-RT N0000175607
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
NDF-RT N0000007700
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
Code System Code Type Description
MESH
C086827
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
PUBCHEM
5381
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
CAS
118292-40-3
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
RXCUI
83947
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB00799
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
LactMed
118292-40-3
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
WIKIPEDIA
TAZAROTENE
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
EPA CompTox
118292-40-3
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
MERCK INDEX
M10488
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1657
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
EVMPD
SUB10844MIG
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
IUPHAR
6952
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
INN
7328
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY
NCI_THESAURUS
C29487
Created by admin on Mon Oct 21 20:46:24 UTC 2019 , Edited by admin on Mon Oct 21 20:46:24 UTC 2019
PRIMARY