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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 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
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
Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans.
2003 Apr
Investigational therapies for psoriasis.
2003 Aug
Wrinkles.
2003 Dec
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
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
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
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
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
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
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
[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
Tazarotene 0.1% cream versus tretinoin 0.05% emollient cream in the treatment of photodamaged facial skin: a multicenter, double-blind, randomized, parallel-group study.
2004 Jun
Established treatments of psoriasis.
2004 Jun
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
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
Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma.
2004 Nov 1
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
Retinoid therapy for psoriasis.
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
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.
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
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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
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ACTIVE MOIETY