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=C1C=C(C=C2)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.drugbank.ca/drugs/DB00799https://www.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf

Tazarotene a novel acetylenic retinoid is known to be effective in the topical treatment of psoriasis and acne. Tazarotene is rapidly and completely metabolized to its active metabolite tazarotenic acid. The exact mechanism of action of tazarotenic acid in the treatment of psoriasis and acne is not clearly defined. However, it is thought that the selective interaction of tazarotenic acid with the retinoic acid receptor (RAR) family (RARα, RARβ, and RARγ) and the subsequent induction of both positive and negative gene regulatory effects may be involved.

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 2637
Retinoic acid receptor alpha 11 Target ID: CHEMBL2055 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2637
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2637
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Agonist 2637	40.0 nM [EC50]
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: http://www.drugbank.ca/drugs/DB00799	Agonist 2637	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 2637	63.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2554
Facial acne vulgaris 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Primary	Approved 8307	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 15 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf	Primary	Approved 8307	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
Focal acral hyperkeratosis.	2001 Feb	11328631
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	11236213
A pilot study to determine the effect of tazarotene gel 0.1% on steroid-induced epidermal atrophy.	2001 Jul	11679006
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
Randomized facial tolerability studies comparing gel formulations of retinoids used to treat acne vulgaris.	2001 Jun	11499328
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	11422529
New developments in the treatment of psoriasis.	2001 May-Jun	11408843
Treatment of psoriasis. Part 1. Topical therapy and phototherapy.	2001 Oct	11568737
Developments in topical retinoid therapy for acne.	2001 Sep	11594670
Optimizing the use of tazarotene for the treatment of facial acne vulgaris through combination therapy.	2002 Feb	12095065
Tazarotene is an effective therapy for elastosis perforans serpiginosa.	2002 Feb	11843635
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
Instrumental evaluation of retinoid-induced skin irritation.	2002 May	12060479
Drug interactions in psoriasis: the pros and cons of combining topical psoriasis therapies.	2002 May-Jun	11976987
[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis].	2002 Nov	12501485
Short-contact therapy with tazarotene in psoriasis vulgaris.	2003	12771482
The rationale for using a topical retinoid for inflammatory acne.	2003	12553848
Wrinkles.	2003 Dec	15555188
Type I lamellar ichthyosis improved by tazarotene 0.1% gel.	2003 Jul	12823301
The topical treatment of psoriasis.	2003 Mar-Apr	12637782
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	12734506
Spotlight on adapalene in acne vulgaris.	2004	15554742
Seborrheic keratoses: a study comparing the standard cryosurgery with topical calcipotriene, topical tazarotene, and topical imiquimod.	2004 Apr	15090020
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
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
Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene.	2004 Jul-Aug	15303792
Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis.	2004 Mar-Apr	15098968
Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging.	2004 May-Jun	15087589
Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma.	2004 Nov 1	15354209
Topical tazarotene in acne vulgaris: treatment approaches.	2004 Oct	15543715
Retinoid therapy for psoriasis.	2004 Oct	15450342
Comparison of topical retinoids in the treatment of acne.	2004 Sep-Oct	15556727

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 `Sun Dec 18 00:07:10 UTC 2022` Edited by `admin` on `Sun Dec 18 00:07:10 UTC 2022`
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

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

DTXSID60152094