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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 of TAZAROTENIC ACID

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
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
Focal acral hyperkeratosis.
2001 Feb
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
A pilot study to determine the effect of tazarotene gel 0.1% on steroid-induced epidermal atrophy.
2001 Jul
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
Randomized facial tolerability studies comparing gel formulations of retinoids used to treat acne vulgaris.
2001 Jun
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
New developments in the treatment of psoriasis.
2001 May-Jun
Treatment of psoriasis. Part 1. Topical therapy and phototherapy.
2001 Oct
Developments in topical retinoid therapy for acne.
2001 Sep
Optimizing the use of tazarotene for the treatment of facial acne vulgaris through combination therapy.
2002 Feb
Tazarotene is an effective therapy for elastosis perforans serpiginosa.
2002 Feb
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
Instrumental evaluation of retinoid-induced skin irritation.
2002 May
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
Short-contact therapy with tazarotene in psoriasis vulgaris.
2003
The rationale for using a topical retinoid for inflammatory acne.
2003
Wrinkles.
2003 Dec
Type I lamellar ichthyosis improved by tazarotene 0.1% gel.
2003 Jul
The topical treatment of psoriasis.
2003 Mar-Apr
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
Spotlight on adapalene in acne vulgaris.
2004
Seborrheic keratoses: a study comparing the standard cryosurgery with topical calcipotriene, topical tazarotene, and topical imiquimod.
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
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
Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene.
2004 Jul-Aug
Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis.
2004 Mar-Apr
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
Retinoid therapy for psoriasis.
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)
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
  • Download
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
Created by admin on Sun Dec 18 00:07:10 UTC 2022 , Edited by admin on Sun Dec 18 00:07:10 UTC 2022
PRIMARY
DAILYMED
85FDJ14553
Created by admin on Sun Dec 18 00:07:10 UTC 2022 , Edited by admin on Sun Dec 18 00:07:10 UTC 2022
PRIMARY
CAS
118292-41-4
Created by admin on Sun Dec 18 00:07:10 UTC 2022 , Edited by admin on Sun Dec 18 00:07:10 UTC 2022
PRIMARY
CHEBI
73129
Created by admin on Sun Dec 18 00:07:10 UTC 2022 , Edited by admin on Sun Dec 18 00:07:10 UTC 2022
PRIMARY
FDA UNII
85FDJ14553
Created by admin on Sun Dec 18 00:07:10 UTC 2022 , Edited by admin on Sun Dec 18 00:07:10 UTC 2022
PRIMARY
PUBCHEM
147525
Created by admin on Sun Dec 18 00:07:10 UTC 2022 , Edited by admin on Sun Dec 18 00:07:10 UTC 2022
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC