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.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdfhttps://www.drugbank.ca/drugs/DB00799Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26937021 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdfhttps://www.drugbank.ca/drugs/DB00799
Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020600s008lbl.pdf
Tazarotene is a prodrug and a member of the acetylenic class of retinoids. Following topical application, tazarotene undergoes esterase hydrolysis to form its active metabolite, tazarotenic acid. When treating acne tazarotene may be taken in conjunction with an oral antibiotic. Tazarotene has been shown in peer-reviewed double blinded studies to reduce: mottling and hyperpigmentation, sallowness, fine wrinkling and coarse wrinkling in sun damaged skin. Histological studies have shown that long term (greater than 1 year) use of Tazarotene is associated with a significant reduction in atypical melanocytes and keratocytes - cells considered to be precursors of skin cancer. Some studies have shown long term use of Tazarotene to be associated with increased collagen production and better organization of skin collagen bundles. Although the exact mechanism of tazarotene action is not known, studies have shown that the active form of the drug (tazarotenic acid) binds to all three members of the retinoic acid receptor (RAR) family: RARa, RARb, and RARg, but shows relative selectivity for RARb, and RARg and may modify gene expression. It also has affinity for RXR receptors. Tazarotene is used to treat psoriasis, acne and sun damaged skin (photodamage). Tazarotene is marketed as Tazorac, Avage, Zorac, and Fabior.
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 |
---|---|---|
Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis. | 1997 Aug |
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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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Oral lichen planus: a preliminary clinical study on treatment with tazarotene. | 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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[Psoriatic onycho-pachydermo- periostitis]. | 2002 Oct |
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A comparison of psoralen plus ultraviolet A (PUVA) monotherapy, tacalcitol plus PUVA and tazarotene plus PUVA in patients with chronic plaque-type psoriasis. | 2002 Oct |
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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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Pharmacokinetics of tazarotene cream 0.1% after a single dose and after repeat topical applications at clinical or exaggerated application rates in patients with acne vulgaris or photodamaged skin. | 2003 |
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Optimizing treatment with topical tazarotene. | 2003 |
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The rationale for using a topical retinoid for inflammatory acne. | 2003 |
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Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans. | 2003 Apr |
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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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A systematic review of adverse effects associated with topical treatments for psoriasis. | 2003 Feb |
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Acne cream can reverse sun damage. | 2003 Feb |
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Cumulative irritation comparison of adapalene gel and solution with 2 tazarotene gels and 3 tretinoin formulations. | 2003 Jul |
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Type I lamellar ichthyosis improved by tazarotene 0.1% gel. | 2003 Jul |
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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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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 |
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Established treatments of psoriasis. | 2004 Jun |
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Topical retinoid and antibiotic combination therapy for acne management. | 2004 Mar-Apr |
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Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis. | 2004 Mar-Apr |
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Current management strategies for cutaneous T-cell lymphoma. | 2004 May-Jun |
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Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging. | 2004 May-Jun |
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Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma. | 2004 Nov 1 |
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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 |
|
Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways. | 2006 Feb 1 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26937021
In vitro enzyme kinetic parameters were determined for tazarotenic acid metabolite formation using 5 nM CYP26A1 or CYP26B1, 25 nM purified human reductase, and 0–10 μM tazarotenic acid. Incubations were carried out for 10 minutes at 37°C to ensure product linearity with regard to time and protein concentration. Additional experiments to determine the kinetic parameters for the sequential metabolism of tazarotenic acid metabolite sulfoxide used substrate concentrations ranging from 0 to 50 μM. Samples were prepared as described for in vitro metabolic profiling experiments.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 14:11:42 UTC 2023
by
admin
on
Thu Jul 06 14:11:42 UTC 2023
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Record UNII |
85FDJ14553
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Record Status |
Validated (UNII)
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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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