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=CN=C(C=C1)C#CC2=CC=C3SCCC(C)(C)C3=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.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 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 1 times / day multiple, topical dose: 5 mg route of administration: Topical experiment type: MULTIPLE 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 1 times / day multiple, topical dose: 5 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
TAZAROTENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
18 h |
2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: |
TAZAROTENIC ACID plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: |
TAZAROTENIC ACID plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN 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: |
unhealthy, 39 – 72 |
DLT: Hypercalcaemia, Hypertriglyceridaemia... Dose limiting toxicities: Hypercalcaemia (grade 3, 17%) Sources: Hypertriglyceridaemia (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: |
unhealthy, 39 – 72 |
DLT: Musculoskeletal pain... Dose limiting toxicities: Musculoskeletal pain (grade 3, 17%) Sources: |
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: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Disorder fetal, Skin irritation... AEs leading to discontinuation/dose reduction: Disorder fetal Sources: Skin 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: |
unhealthy, 39 – 72 |
| 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: |
unhealthy, 39 – 72 |
| 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: |
unhealthy, 39 – 72 |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
| 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: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2006-02-01 |
|
| The p73 gene is an anti-tumoral target of the RARbeta/gamma-selective retinoid tazarotene. | 2004-12 |
|
| 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. | 2004-12 |
|
| 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. | 2004-12 |
|
| Comparison of topical retinoids in the treatment of acne. | 2004-11-24 |
|
| Phase II trial of the antiangiogenic agent IM862 in metastatic renal cell carcinoma. | 2004-11-01 |
|
| Topical tazarotene in acne vulgaris: treatment approaches. | 2004-10 |
|
| Meta-analysis of topical tazarotene in the treatment of mild to moderate acne. | 2004-10 |
|
| Topical tazarotene: The BEST (balancing efficacy, speed, and tolerability) in acne trial. | 2004-10 |
|
| Topical retinoids in the management of acne: the best path to clear results. | 2004-10 |
|
| Retinoid therapy for psoriasis. | 2004-10 |
|
| Keratosis punctata palmoplantaris controlled with topical retinoids: a case report and review of the literature. | 2004-09 |
|
| Elephantiasis nostrum verrucosa of the abdomen: clinical results with tazarotene. | 2004-08-12 |
|
| Current management strategies for cutaneous T-cell lymphoma. | 2004-07-21 |
|
| Topical tazarotene chemoprevention reduces Basal cell carcinoma number and size in Ptch1+/- mice exposed to ultraviolet or ionizing radiation. | 2004-07-01 |
|
| Topical treatment of basal cell carcinoma with tazarotene: a clinicopathological study on a large series of cases. | 2004-07 |
|
| Questions & answers. Of all the treatments that promise to improve the appearance of aging skin, which ones have been medically proven to actually work? | 2004-07 |
|
| 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. | 2004-06 |
|
| Established treatments of psoriasis. | 2004-06 |
|
| Topical retinoid and antibiotic combination therapy for acne management. | 2004-04-22 |
|
| Oral tazarotene and oral pimecrolimus: novel oral therapies in development for psoriasis. | 2004-04-22 |
|
| Tazarotene 0.1% cream for the treatment of photodamage. | 2004-04 |
|
| Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene. | 2004-04 |
|
| Seborrheic keratoses: a study comparing the standard cryosurgery with topical calcipotriene, topical tazarotene, and topical imiquimod. | 2004-04 |
|
| Tazarotene 0.1% gel for refractory mycosis fungoides lesions: an open-label pilot study. | 2004-04 |
|
| [Prescribe topical treatments for psoriasis]. | 2004-01-15 |
|
| Treatment of lentigo maligna with tazarotene 0.1% gel. | 2004-01 |
|
| 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 |
|
| Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23. | 2003-12-18 |
|
| Wrinkles. | 2003-12 |
|
| The efficacy of topical tazarotene monotherapy and combination therapies in psoriasis. | 2003-12 |
|
| [Medication of the month. Tazarotene 0.05%-0.1% (Zorac)]. | 2003-11 |
|
| Comparison of prognostic factors in patients in phase I trials of cytotoxic drugs vs new noncytotoxic agents. | 2003-10-06 |
|
| Tazarotene-induced gene 3 is suppressed in basal cell carcinomas and reversed in vivo by tazarotene application. | 2003-10 |
|
| A phase 1 study of tazarotene in adults with advanced cancer. | 2003-09-01 |
|
| Investigational therapies for psoriasis. | 2003-08 |
|
| Tazarotene: therapeutic strategies in the treatment of psoriasis, acne and photoaging. | 2003-07-03 |
|
| Tazarotene 0.1% gel for psoriasis of the fingernails and toenails: an open, prospective study. | 2003-07 |
|
| Cumulative irritation comparison of adapalene gel and solution with 2 tazarotene gels and 3 tretinoin formulations. | 2003-07 |
|
| Type I lamellar ichthyosis improved by tazarotene 0.1% gel. | 2003-07 |
|
| 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. | 2003-05 |
|
| Confluent and reticulated papillomatosis: response to tazarotene. | 2003-05 |
|
| Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans. | 2003-04 |
|
| Retrospective analysis of the treatment of psoriasis of the palms and soles. | 2003 |
|
| Treatment of occupational koilonychia with tazarotene gel. | 2003 |
|
| 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 |
|
| Short-contact therapy with tazarotene in psoriasis vulgaris. | 2003 |
|
| Tazarotene: the first receptor-selective topical retinoid for the treatment of psoriasis. | 1997-08 |
Patents
Sample Use Guides
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
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| Record UNII |
81BDR9Y8PS
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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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