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
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)
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 |
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 Date9.700992E11 |
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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 Date9.700992E11 |
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 |
---|---|---|
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 |
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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 |
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New developments in the treatment of psoriasis. | 2001 May-Jun |
|
Treatment of psoriasis. Part 1. Topical therapy and phototherapy. | 2001 Oct |
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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 |
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Tazarotene is an effective therapy for elastosis perforans serpiginosa. | 2002 Feb |
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Topical tazarotene therapy for psoriasis, acne vulgaris, and photoaging. | 2002 Mar |
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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 |
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Instrumental evaluation of retinoid-induced skin irritation. | 2002 May |
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Drug interactions in psoriasis: the pros and cons of combining topical psoriasis therapies. | 2002 May-Jun |
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[Immunosuppresive agents, retinoids and new trends in the therapy of psoriasis]. | 2002 Nov |
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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 |
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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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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 |
|
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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Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene. | 2004 Jul-Aug |
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Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis. | 2004 Mar-Apr |
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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
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
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admin
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Edited
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Record UNII |
85FDJ14553
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Record Status |
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Record Version |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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