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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
Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis.
1997 Aug
The efficacy of 308nm laser treatment of psoriasis compared to historical controls.
2001 Dec
Practical management of psoriasis in the elderly: epidemiology, clinical aspects, quality of life, patient education and treatment options.
2002
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment.
2002
A multicenter, double-blind, randomized comparison study of the efficacy and tolerability of once-daily tazarotene 0.1% gel and adapalene 0.1% gel for the treatment of facial acne vulgaris.
2002 Feb
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
Refining retinoids with heteroatoms.
2002 Jun
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
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
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
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
The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis.
2003 Dec
Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23.
2003 Dec 18
Management of acne.
2003 Jan
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
The topical treatment of psoriasis.
2003 Mar-Apr
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
Spotlight on adapalene in acne vulgaris.
2004
Tazarotene does not affect the pharmacokinetics and efficacy of a norethindrone/ethinylestradiol oral contraceptive.
2004
Adapalene: a review of its use in the treatment of acne vulgaris.
2004
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
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
Established treatments of psoriasis.
2004 Jun
Current management strategies for cutaneous T-cell lymphoma.
2004 May-Jun
Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging.
2004 May-Jun
Topical tazarotene in acne vulgaris: treatment approaches.
2004 Oct
Retinoid therapy for psoriasis.
2004 Oct
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

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.
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