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
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
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 |
DescriptionSources: https://www.drugbank.ca/drugs/DB00799https://www.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdfCurator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2003 |
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Target ID: CHEMBL2055 |
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Target ID: CHEMBL2008 |
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Target ID: CHEMBL2003 |
40.0 nM [EC50] | ||
Target ID: CHEMBL2008 Sources: http://www.drugbank.ca/drugs/DB00799 |
0.8 nM [EC50] | ||
Target ID: CHEMBL2055 |
63.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TAZORAC Approved UseTAZORAC® (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 Date2000 |
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Primary | TAZORAC Approved UseTAZORAC® (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 Date2000 |
Cmax
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: 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%) Sources: Page: p.812Hypertriglyceridaemia (grade 4, 17%) |
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 Sources: Page: p.1Skin irritation Pruritus Burning skin Skin red Skin peeling Photosensitivity Sunburn |
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: 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
Title | Date | PubMed |
---|---|---|
Practical management of psoriasis in the elderly: epidemiology, clinical aspects, quality of life, patient education and treatment options. | 2002 |
|
Refining retinoids with heteroatoms. | 2002 Jun |
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[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis]. | 2002 Nov |
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Questionable techniques for evaluating photodamage. | 2002 Nov |
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Efficacy of 0.1% tazarotene cream for the treatment of photodamage: a 12-month multicenter, randomized trial. | 2002 Nov |
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Retrospective analysis of the treatment of psoriasis of the palms and soles. | 2003 |
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Treatment of occupational koilonychia with tazarotene gel. | 2003 |
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The rationale for using a topical retinoid for inflammatory acne. | 2003 |
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Investigational therapies for psoriasis. | 2003 Aug |
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Wrinkles. | 2003 Dec |
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The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis. | 2003 Dec |
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Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23. | 2003 Dec 18 |
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Management of acne. | 2003 Jan |
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Tazarotene 0.1% gel for psoriasis of the fingernails and toenails: an open, prospective study. | 2003 Jul |
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The topical treatment of psoriasis. | 2003 Mar-Apr |
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Confluent and reticulated papillomatosis: response to tazarotene. | 2003 May |
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[Medication of the month. Tazarotene 0.05%-0.1% (Zorac)]. | 2003 Nov |
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Tazarotene-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application. | 2003 Oct |
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Comparison of prognostic factors in patients in phase I trials of cytotoxic drugs vs new noncytotoxic agents. | 2003 Oct 6 |
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A phase 1 study of tazarotene in adults with advanced cancer. | 2003 Sep 1 |
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Spotlight on adapalene in acne vulgaris. | 2004 |
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Tazarotene does not affect the pharmacokinetics and efficacy of a norethindrone/ethinylestradiol oral contraceptive. | 2004 |
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Adapalene: a review of its use in the treatment of acne vulgaris. | 2004 |
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Tazarotene 0.1% cream for the treatment of photodamage. | 2004 Apr |
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Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene. | 2004 Apr |
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Seborrheic keratoses: a study comparing the standard cryosurgery with topical calcipotriene, topical tazarotene, and topical imiquimod. | 2004 Apr |
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Tazarotene 0.1% gel for refractory mycosis fungoides lesions: an open-label pilot study. | 2004 Apr |
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The p73 gene is an anti-tumoral target of the RARbeta/gamma-selective retinoid tazarotene. | 2004 Dec |
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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 |
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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 |
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Treatment of lentigo maligna with tazarotene 0.1% gel. | 2004 Jan |
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[Prescribe topical treatments for psoriasis]. | 2004 Jan 15 |
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Topical treatment of basal cell carcinoma with tazarotene: a clinicopathological study on a large series of cases. | 2004 Jul |
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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 |
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Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation. | 2004 Jul 1 |
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Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene. | 2004 Jul-Aug |
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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 |
|
Established treatments of psoriasis. | 2004 Jun |
|
Topical retinoid and antibiotic combination therapy for acne management. | 2004 Mar-Apr |
|
Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis. | 2004 Mar-Apr |
|
Current management strategies for cutaneous T-cell lymphoma. | 2004 May-Jun |
|
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 |
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Meta-analysis of topical tazarotene in the treatment of mild to moderate acne. | 2004 Oct |
|
Topical tazarotene: The BEST (balancing efficacy, speed, and tolerability) in acne trial. | 2004 Oct |
|
Topical retinoids in the management of acne: the best path to clear results. | 2004 Oct |
|
Retinoid therapy for psoriasis. | 2004 Oct |
|
Keratosis punctata palmoplantaris controlled with topical retinoids: a case report and review of the literature. | 2004 Sep |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18483315
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
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Record UNII |
81BDR9Y8PS
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Validated (UNII)
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Record Version |
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N0000007700
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C804
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N0000007700
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EU/3/06/423
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N0000175607
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TAZAROTENE
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
FECAL; URINE
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METABOLITE INACTIVE -> PARENT |
FECAL; URINE
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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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