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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

Molecular Formula C21H21NO2S
Molecular Weight 351.462
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Focal acral hyperkeratosis.
2001 Feb
Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction.
2001 Feb
Duration of improvement in psoriasis after treatment with tazarotene 0.1% gel plus clobetasol propionate 0.05% ointment: comparison of maintenance treatments.
2001 Jan
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
[Successful symptomatic tazarotene treatment of juvenile acanthosis nigricans of the familial obesity-associated type in insulin resistance].
2001 Jun
Investigator-masked comparison of tazarotene gel q.d. plus mometasone furoate cream q.d. vs. mometasone furoate cream b.i.d. in the treatment of plaque psoriasis.
2001 Mar
Retinoids for the treatment of psoriasis: outlook for the future.
2001 May
Altered expression of angiopoietins and Tie2 endothelium receptor in psoriasis.
2001 May
Treatment of psoriasis. Part 1. Topical therapy and phototherapy.
2001 Oct
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment.
2002
Treatment of cutaneous T cell lymphoma: current status and future directions.
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
Combination of calcipotriene (Dovonex) ointment and tazarotene (Tazorac) gel versus clobetasol ointment in the treatment of plaque psoriasis: a pilot study.
2002 Jun
Tazarotene (tazorac) for acne.
2002 Jun 10
Topical tazarotene therapy for psoriasis, acne vulgaris, and photoaging.
2002 Mar
A clinical evaluation of tazarotene 0.1% gel, with and without a high- or mid-high-potency corticosteroid, in patients with stable plaque psoriasis.
2002 Mar-Apr
Instrumental evaluation of retinoid-induced skin irritation.
2002 May
Potential anti-inflammatory effects of topical retinoids and retinoid analogues.
2002 May-Jun
[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis].
2002 Nov
Retrospective analysis of the treatment of psoriasis of the palms and soles.
2003
Treatment of occupational koilonychia with tazarotene gel.
2003
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
Investigational therapies for psoriasis.
2003 Aug
The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis.
2003 Dec
Tazarotene 0.1% gel for psoriasis of the fingernails and toenails: an open, prospective study.
2003 Jul
Cumulative irritation comparison of adapalene gel and solution with 2 tazarotene gels and 3 tretinoin formulations.
2003 Jul
Type I lamellar ichthyosis improved by tazarotene 0.1% gel.
2003 Jul
[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
Comparison of prognostic factors in patients in phase I trials of cytotoxic drugs vs new noncytotoxic agents.
2003 Oct 6
A phase 1 study of tazarotene in adults with advanced cancer.
2003 Sep 1
Tazarotene 0.1% cream for the treatment of photodamage.
2004 Apr
Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene.
2004 Apr
Seborrheic keratoses: a study comparing the standard cryosurgery with topical calcipotriene, topical tazarotene, and topical imiquimod.
2004 Apr
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
A retinoic acid receptor beta/gamma-selective prodrug (tazarotene) plus a retinoid X receptor ligand induces extracellular signal-regulated kinase activation, retinoblastoma hypophosphorylation, G0 arrest, and cell differentiation.
2004 Dec
Treatment of lentigo maligna with tazarotene 0.1% gel.
2004 Jan
Topical treatment of basal cell carcinoma with tazarotene: a clinicopathological study on a large series of cases.
2004 Jul
Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene.
2004 Jul-Aug
Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis.
2004 Mar-Apr
Current management strategies for cutaneous T-cell lymphoma.
2004 May-Jun
Retinoid therapy for psoriasis.
2004 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)
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:46:24 UTC 2019
Edited
by admin
on Mon Oct 21 20:46:24 UTC 2019
Record UNII
81BDR9Y8PS
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
METABOLITE INACTIVE -> PARENT
FECAL; URINE
METABOLITE INACTIVE -> PARENT
FECAL; URINE
METABOLITE ACTIVE -> PRODRUG
Esterase metabolism