U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TAZAROTENE

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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.44 pg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
105.72 pg × h/mL
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

Doses

DosePopulationAdverse 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: 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: Page: p.812
DLT: Hypercalcaemia, Hypertriglyceridaemia...
Dose limiting toxicities:
Hypercalcaemia (grade 3, 17%)
Hypertriglyceridaemia (grade 4, 17%)
Sources: 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: 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: Page: p.812
DLT: Musculoskeletal pain...
Dose limiting toxicities:
Musculoskeletal pain (grade 3, 17%)
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
AEs

AEs

AESignificanceDosePopulation
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: 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: 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: 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: 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: 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: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Plaque psoriasis|Acne vulgaris
Sources: Page: p.1
PubMed

PubMed

TitleDatePubMed
Management of scalp psoriasis: guidelines for corticosteroid use in combination treatment.
2001
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
Retinoids for the treatment of psoriasis: outlook for the future.
2001 May
1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects.
2001 May
Tazarotene 0.1% gel in the treatment of fingernail psoriasis: a double-blind, randomized, vehicle-controlled study.
2001 Nov
Treatment of psoriasis. Part 1. Topical therapy and phototherapy.
2001 Oct
Developments in topical retinoid therapy for acne.
2001 Sep
Retinoids--which dermatological indications will benefit in the near future?
2001 Sep-Oct
The modern age of acne therapy: a review of current treatment options.
2001 Sep-Oct
Practical management of psoriasis in the elderly: epidemiology, clinical aspects, quality of life, patient education and treatment options.
2002
Treatment of cutaneous T cell lymphoma: current status and future directions.
2002
Successful treatment of acne vulgaris using a new method: results of a randomized vehicle-controlled trial of short-contact therapy with 0.1% tazarotene gel.
2002 Apr
Is TIG1 a new tumor suppressor in prostate cancer?
2002 Apr 3
Treatment of warty dyskeratoma with tazarotenic acid.
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
Topical tazarotene therapy for psoriasis, acne vulgaris, and photoaging.
2002 Mar
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
Drug interactions in psoriasis: the pros and cons of combining topical psoriasis therapies.
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
Treating keratosis pilaris.
2002 Sep
Retrospective analysis of the treatment of psoriasis of the palms and soles.
2003
Treatment of occupational koilonychia with tazarotene gel.
2003
Optimizing treatment with topical tazarotene.
2003
The rationale for using a topical retinoid for inflammatory acne.
2003
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-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application.
2003 Oct
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
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
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
Current management strategies for cutaneous T-cell lymphoma.
2004 May-Jun
Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma.
2004 Nov 1
Topical retinoids in the management of acne: the best path to clear results.
2004 Oct
Comparison of topical retinoids in the treatment of acne.
2004 Sep-Oct
Patents

Sample Use Guides

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
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)
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
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
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
NDF-RT N0000007700
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
NDF-RT N0000007700
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
WHO-ATC D05AX05
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
WHO-VATC QD05AX05
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
NCI_THESAURUS C804
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
NDF-RT N0000007700
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
EU-Orphan Drug EU/3/06/423
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
NDF-RT N0000175607
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
NDF-RT N0000007700
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
Code System Code Type Description
USAN
FF-57
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
MESH
C086827
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
PUBCHEM
5381
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
CAS
118292-40-3
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
CHEBI
32184
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
RXCUI
83947
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY RxNorm
DRUG BANK
DB00799
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
WIKIPEDIA
TAZAROTENE
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
EPA CompTox
DTXSID5046691
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
MERCK INDEX
M10488
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY Merck Index
FDA UNII
81BDR9Y8PS
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
ChEMBL
CHEMBL1657
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
LACTMED
Tazarotene
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
DRUG CENTRAL
2571
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
DAILYMED
81BDR9Y8PS
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
EVMPD
SUB10844MIG
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
IUPHAR
6952
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
INN
7328
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY
NCI_THESAURUS
C29487
Created by admin on Sun Dec 18 19:43:23 UTC 2022 , Edited by admin on Sun Dec 18 19:43:23 UTC 2022
PRIMARY