TAZAROTENE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C1=CC=C(N=C1)C#CC2=CC3=C(SCCC3(C)C)C=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	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 2662
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2662
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2662
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2662	40.0 nM [EC50]
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: http://www.drugbank.ca/drugs/DB00799	Agonist 2662	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 2662	63.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2565
Facial acne vulgaris 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Primary	Approved 8360	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 9.700992E11
Plaque psoriasis 16 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Primary	Approved 8360	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 9.700992E11

C_max

Value	Dose	Co-administered	Analyte	Population
5.44 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31641413	5 mg single, topical dose: 5 mg route of administration: Topical experiment type: SINGLE 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 single, topical dose: 5 mg route of administration: Topical experiment type: SINGLE co-administered:		TAZAROTENE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE 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 Page: p.812	unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812	DLT: Hypercalcaemia, Hypertriglyceridaemia... Dose limiting toxicities: Hypercalcaemia (grade 3, 17%) Hypertriglyceridaemia (grade 4, 17%) Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812
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 Page: p.812	unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812	DLT: Musculoskeletal pain... Dose limiting toxicities: Musculoskeletal pain (grade 3, 17%) Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1	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 Page: p.1

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 Page: p.812	unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812
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 Page: p.812	unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812
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 Page: p.812	unhealthy, 39 – 72 n = 6 Health Status: unhealthy Condition: Advanced cancer Age Group: 39 – 72 Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/12942109 Page: p.812
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Plaque psoriasis\|Acne vulgaris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020600s010lbl.pdf Page: p.1

PubMed

Title	Date	PubMed
Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis.	1997 Aug	9270551
The efficacy of 308nm laser treatment of psoriasis compared to historical controls.	2001 Dec	12165220
Duration of improvement in psoriasis after treatment with tazarotene 0.1% gel plus clobetasol propionate 0.05% ointment: comparison of maintenance treatments.	2001 Jan	11277960
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	11499329
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	11499327
[Successful symptomatic tazarotene treatment of juvenile acanthosis nigricans of the familial obesity-associated type in insulin resistance].	2001 Jun	11428078
1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects.	2001 May	11519864
New developments in the treatment of psoriasis.	2001 May-Jun	11408843
Developments in topical retinoid therapy for acne.	2001 Sep	11594670
Retinoids--which dermatological indications will benefit in the near future?	2001 Sep-Oct	11586072
Practical management of psoriasis in the elderly: epidemiology, clinical aspects, quality of life, patient education and treatment options.	2002	12428994
Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment.	2002	12079221
Treatment of cutaneous T cell lymphoma: current status and future directions.	2002	11978140
Optimizing the use of tazarotene for the treatment of facial acne vulgaris through combination therapy.	2002 Feb	12095065
Topical tazarotene therapy for psoriasis, acne vulgaris, and photoaging.	2002 Mar	12007011
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	11992180
Topical agents for the treatment of psoriasis, past, present and future.	2002 May-Jun	11976984
[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis].	2002 Nov	12501485
Questionable techniques for evaluating photodamage.	2002 Nov	12437464
Treatment of occupational koilonychia with tazarotene gel.	2003	12926806
Investigational therapies for psoriasis.	2003 Aug	12894137
Wrinkles.	2003 Dec	15555188
Tazarotene 0.1% gel for psoriasis of the fingernails and toenails: an open, prospective study.	2003 Jul	12890227
Cumulative irritation comparison of adapalene gel and solution with 2 tazarotene gels and 3 tretinoin formulations.	2003 Jul	12889719
Type I lamellar ichthyosis improved by tazarotene 0.1% gel.	2003 Jul	12823301
Tazarotene-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application.	2003 Oct	14632211
Spotlight on adapalene in acne vulgaris.	2004	15554742
Adapalene: a review of its use in the treatment of acne vulgaris.	2004	15212561
Tazarotene 0.1% cream for the treatment of photodamage.	2004 Apr	15146262
Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene.	2004 Apr	15102095
The p73 gene is an anti-tumoral target of the RARbeta/gamma-selective retinoid tazarotene.	2004 Dec	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 Dec	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 Dec	15383624
Topical treatment of basal cell carcinoma with tazarotene: a clinicopathological study on a large series of cases.	2004 Jul	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 Jul	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 Jun	15203997
Topical retinoid and antibiotic combination therapy for acne management.	2004 Mar-Apr	15098969
Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging.	2004 May-Jun	15087589
Topical tazarotene in acne vulgaris: treatment approaches.	2004 Oct	15543715
Keratosis punctata palmoplantaris controlled with topical retinoids: a case report and review of the literature.	2004 Sep	15499759
Comparison of topical retinoids in the treatment of acne.	2004 Sep-Oct	15556727
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	16178010

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 `Thu Jul 06 22:30:13 UTC 2023` Edited by `admin` on `Thu Jul 06 22:30:13 UTC 2023`
Record UNII	81BDR9Y8PS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAZAROTENE

Official Name

English

AVAGE

Brand Name

English

IDP-123

Common Name

English

TAZAROTENE [USAN]

Common Name

English

TAZAROTENE [MI]

Common Name

English

Tazarotene [WHO-DD]

Common Name

English

IDP-118 COMPONENT TAZAROTENE

Common Name

English

TAZAROTENE [JAN]

Common Name

English

TAZAROTENE [VANDF]

Common Name

English

tazarotene [INN]

Common Name

English

TAZORAC

Brand Name

English

ARAZLO

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