TAZAROTENIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H17NO2S
Molecular Weight	323.409
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdfhttps://www.drugbank.ca/drugs/DB00799
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf

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

Targets

Primary Target	Pharmacology	Potency
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2752
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2752
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2752
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2752	40.0 nM [EC50]
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: http://www.drugbank.ca/drugs/DB00799	Agonist 2752	0.8 nM [EC50]
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2752	63.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2596
Facial acne vulgaris 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Primary	Approved 8583	TAZORAC Approved Use TAZORAC® (tazarotene) Gel 0.05% and 0.1% are indicated for the topical treatment of patients with stable plaque psoriasis of up to 20% body surface area involvement. TAZORAC® (tazarotene) Gel 0.1% is also indicated for the topical treatment of patients with facial acne vulgaris of mild to moderate severity. Launch Date 2000
Plaque psoriasis 17 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Primary	Approved 8583	TAZORAC Approved Use TAZORAC® (tazarotene) Gel 0.05% and 0.1% are indicated for the topical treatment of patients with stable plaque psoriasis of up to 20% body surface area involvement. TAZORAC® (tazarotene) Gel 0.1% is also indicated for the topical treatment of patients with facial acne vulgaris of mild to moderate severity. Launch Date 2000

C_max

Value	Dose	Co-administered	Analyte	Population
5.44 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31641413	5 mg 1 times / day multiple, topical dose: 5 mg route of administration: Topical experiment type: MULTIPLE co-administered:		TAZAROTENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
105.72 pg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31641413	5 mg 1 times / day multiple, topical dose: 5 mg route of administration: Topical experiment type: MULTIPLE co-administered:		TAZAROTENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
18 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered:		TAZAROTENIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered:		TAZAROTENIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
33.6 mg 1 times / day multiple, oral Highest studied dose Dose: 33.6 mg, 1 times / day Route: oral Route: multiple Dose: 33.6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	unhealthy, 39 – 72 Health Status: unhealthy Age Group: 39 – 72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	DLT: Hypercalcaemia, Hypertriglyceridaemia... Dose limiting toxicities: Hypercalcaemia (grade 3, 17%) Hypertriglyceridaemia (grade 4, 17%) Sources: https://pubmed.ncbi.nlm.nih.gov/12942109
25.2 mg 1 times / day multiple, oral MTD Dose: 25.2 mg, 1 times / day Route: oral Route: multiple Dose: 25.2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	unhealthy, 39 – 72 Health Status: unhealthy Age Group: 39 – 72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	DLT: Musculoskeletal pain... Dose limiting toxicities: Musculoskeletal pain (grade 3, 17%) Sources: https://pubmed.ncbi.nlm.nih.gov/12942109
0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	Disc. AE: Disorder fetal, Skin irritation... AEs leading to discontinuation/dose reduction: Disorder fetal Skin irritation Pruritus Burning skin Skin red Skin peeling Photosensitivity Sunburn Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf

AEs

AE	Significance	Dose	Population
Hypercalcaemia	grade 3, 17% DLT	33.6 mg 1 times / day multiple, oral Highest studied dose Dose: 33.6 mg, 1 times / day Route: oral Route: multiple Dose: 33.6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	unhealthy, 39 – 72 Health Status: unhealthy Age Group: 39 – 72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12942109
Hypertriglyceridaemia	grade 4, 17% DLT	33.6 mg 1 times / day multiple, oral Highest studied dose Dose: 33.6 mg, 1 times / day Route: oral Route: multiple Dose: 33.6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	unhealthy, 39 – 72 Health Status: unhealthy Age Group: 39 – 72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12942109
Musculoskeletal pain	grade 3, 17% DLT	25.2 mg 1 times / day multiple, oral MTD Dose: 25.2 mg, 1 times / day Route: oral Route: multiple Dose: 25.2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12942109	unhealthy, 39 – 72 Health Status: unhealthy Age Group: 39 – 72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12942109
Burning skin	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Disorder fetal	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Photosensitivity	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Pruritus	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Skin irritation	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Skin peeling	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Skin red	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf
Sunburn	Disc. AE	0.1 % 1 times / day multiple, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf

PubMed

Title	Date	PubMed
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.	2006-02-01	16178010
The p73 gene is an anti-tumoral target of the RARbeta/gamma-selective retinoid tazarotene.	2004-12	15610529
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.	2004-12	15606521
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.	2004-12	15383624
Comparison of topical retinoids in the treatment of acne.	2004-11-24	15556727
Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma.	2004-11-01	15354209
Topical tazarotene in acne vulgaris: treatment approaches.	2004-10	15543715
Meta-analysis of topical tazarotene in the treatment of mild to moderate acne.	2004-10	15543714
Topical tazarotene: The BEST (balancing efficacy, speed, and tolerability) in acne trial.	2004-10	15543713
Topical retinoids in the management of acne: the best path to clear results.	2004-10	15543712
Retinoid therapy for psoriasis.	2004-10	15450342
Keratosis punctata palmoplantaris controlled with topical retinoids: a case report and review of the literature.	2004-09	15499759
Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene.	2004-08-12	15303792
Current management strategies for cutaneous T-cell lymphoma.	2004-07-21	15262305
Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation.	2004-07-01	15231643
Topical treatment of basal cell carcinoma with tazarotene: a clinicopathological study on a large series of cases.	2004-07	15270884
Questions & answers. Of all the treatments that promise to improve the appearance of aging skin, which ones have been medically proven to actually work?	2004-07	15239171
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.	2004-06	15203997
Established treatments of psoriasis.	2004-06	15180467
Topical retinoid and antibiotic combination therapy for acne management.	2004-04-22	15098969
Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis.	2004-04-22	15098968
Tazarotene 0.1% cream for the treatment of photodamage.	2004-04	15146262
Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene.	2004-04	15102095
Seborrheic keratoses: a study comparing the standard cryosurgery with topical calcipotriene, topical tazarotene, and topical imiquimod.	2004-04	15090020
Tazarotene 0.1% gel for refractory mycosis fungoides lesions: an open-label pilot study.	2004-04	15034511
[Prescribe topical treatments for psoriasis].	2004-01-15	15049598
Treatment of lentigo maligna with tazarotene 0.1% gel.	2004-01	14699375
Spotlight on adapalene in acne vulgaris.	2004	15554742
Tazarotene does not affect the pharmacokinetics and efficacy of a norethindrone/ethinylestradiol oral contraceptive.	2004	15244497
Adapalene: a review of its use in the treatment of acne vulgaris.	2004	15212561
Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23.	2003-12-18	14675762
Wrinkles.	2003-12	15555188
The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis.	2003-12	14640932
[Medication of the month. Tazarotene 0.05%-0.1% (Zorac)].	2003-11	14748200
Comparison of prognostic factors in patients in phase I trials of cytotoxic drugs vs new noncytotoxic agents.	2003-10-06	14520440
Tazarotene-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application.	2003-10	14632211
A phase 1 study of tazarotene in adults with advanced cancer.	2003-09-01	12942109
Investigational therapies for psoriasis.	2003-08	12894137
Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging.	2003-07-03	15087589
Tazarotene 0.1% gel for psoriasis of the fingernails and toenails: an open, prospective study.	2003-07	12890227
Cumulative irritation comparison of adapalene gel and solution with 2 tazarotene gels and 3 tretinoin formulations.	2003-07	12889719
Type I lamellar ichthyosis improved by tazarotene 0.1% gel.	2003-07	12823301
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.	2003-05	12734506
Confluent and reticulated papillomatosis: response to tazarotene.	2003-05	12734485
Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans.	2003-04	12642475
Retrospective analysis of the treatment of psoriasis of the palms and soles.	2003	14578095
Treatment of occupational koilonychia with tazarotene gel.	2003	12926806
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	12885265
Short-contact therapy with tazarotene in psoriasis vulgaris.	2003	12771482
Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis.	1997-08	9270551

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

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 `Mon Mar 31 22:16:52 GMT 2025` Edited by `admin` on `Mon Mar 31 22:16:52 GMT 2025`
Record UNII	85FDJ14553
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AGN-190299

Preferred Name

English

TAZAROTENIC ACID

Common Name

English

AGN190299

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

DTXSID60152094