Tazarotene
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Tazarotene
structure -
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CAS No:
118292-40-3
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Formula:
C21H21NO2S
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Chemical Name:
Tazarotene
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Synonyms:
3-Pyridinecarboxylic acid,6-[2-(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-,ethyl ester;3-Pyridinecarboxylic acid,6-[(3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl]-,ethyl ester;2H-1-Benzothiopyran,3-pyridinecarboxylic acid deriv.;AGN 190168;Tazarotene;Zorac;Tazorac;Acnitaz
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CAS No:
Description
It is as white-like or pale yellow solid. White SolidChEBI: The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.Tazarotene belongs to a third generation prescription topical retinoid. It is marketed in different forms including cream (brand name: Avage), foam (brand name: Fabuir) and gel (brand name: Tazorac). It is mainly used for the treatment of psoriasis, acne, and sun damaged skin. The detailed mech
Solid
Tazarotene is the ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin. It has a role as a keratolytic drug, a prodrug and a teratogenic agent. It is a retinoid, a thiochromane, a member of pyridines, an acetylenic compound and an ethyl ester. It derives from a tazarotenic acid.|Tazarotene, commonly marketed as Tazorac®, Avage®, and Zorac®, is member of the acetylenic class of retinoids. It is a prodrug that is found in topical formulations used in the treatment of various conditons, such as psoriasis, acne, and sun damaged skin (photodamage).|Tazarotene is a Retinoid.|Tazarotene is a synthetic, topical retinoid. Tazarotene induces the expression of tazarotene-induced gene 3 (TIG3), a tumor suppressor gene. In psoriasis, tazarotene normalizes abnormal keratinocyte differentiation and reduces their hyperproliferation. (NCI04)
Tazarotene Basic Attributes
351.46
351.46
1308068-626-2
81BDR9Y8PS
DTXSID5046691
C29487
D - Dermatologicals
2934999090
Characteristics
64.5
4.9
white to very faintly yellow
1.22±0.1 g/cm3(Predicted)
97-98 °C @ Solvent: Hexane
499.8±45.0 °C(Predicted)
256.1±28.7 °C
1.625
H2O: soluble ;DMSO: >15mg/mL
Store at +4°C
4.03E-10mmHg at 25°C
Safety Information
NONH for all modes of transport
3
US5675100
P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P263, P264, P270, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Toxicity
Excessive topical use may lead to marked redness, peeling, or discomfort. Oral ingestion of the drug may affect liver function causing hypertriglyceridemia. Other symptoms may include conjunctival irritation, hair loss, headache, edema, fatigue, dermatitis, nausea, and visual disturbances. Oral administration of this material to rats and rabbits at doses of 0.20 mg/kg/day (rabbits) and 0.25 mg/kg/day (rats) resulted in developmental toxicity. A no effect level of 0.05 mg/kg/day was established. Similar teratogenic effects have been reported for other retinoid compounds.
The active form of the drug, tazarotenic acid, is highly bound to plasma proteins (>99%).
Drug Information
Used to treat psoriasis, acne and sun damaged skin (photodamage).|FDA Label|Treatment of lamellar ichthyosis
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.
Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)|Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. (See all compounds classified as Keratolytic Agents.)|An agent that causes the production of physical defects in the developing embryo. (See all compounds classified as Teratogens.)
Minimal systemic absorption of tazarotene occurs due to its rapid metabolism in the skin to the active metabolite, tazarotenic acid, which can be systemically absorbed and further metabolized. Gender had no influence on the systemic bioavailability of tazarotenic acid.|Tazarotene and tazarotenic acid were metabolized to sulfoxides, sulfones and other polar metabolites which were eliminated through urinary and fecal pathways.
Undergoes esterase hydrolysis in skin to form its active metabolite, tazarotenic acid. Tazarotenic acid is further metabolized in skin and, after systemic absorption, hepatically metabolized to sulfoxides, sulfones, and other polar products for elimination.
The half-life of the active form of the drug, tazarotenic acid, is approximately 18 hours in normal and psoriatic patients.
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.
AGN 190168
Tazarotene Use and Manufacturing
Charged ethyl 6-chloronicotinate (10.0 gm) in a R.B. Flask arranged with reflux condenser on oil bath, containing toluene (100 ml). Stirred and charged potassium carbonate (30.0 gm), triphenylphosphine (4.0 gm) and 5percent Pd/C (4.0 gm) to the reaction solution. Gradually raised the temperature to 45-50 C and maintained under stirring at 45 - 50To 188 ml of toluene was added palladium on carbon (10 g) under N2 atmosphere. The mixture was heated to 105-115 °C to remove water by azeotropic distillation. Thereaction mass was cooled to 50-55 °C. To the above mixture, anhydrous sodium sulphate(12.5 g), anhydrous potassium carbonate (37.5 g), triphenylphosphine (5 g), ethyl 6-chioronicotinoate (12.5 g) and toluene (12.5 ml) were added at 50-55 °C and stirred for 2hours. To the above mixture, 4, 4-dimethyl-6-ethynylthiochroman (10 g), cuprous iodide(0.06 g) and toluene (12.5 ml) were added and the reaction mixture was heated to 105-115 °C for 10-12 hours. The reaction mixture was cooled to 25-30 °C and water (125 ml)was added. The biphasi reaction mixture was filtered and from the filtrate, product enriched organic layer was separated. The organic layer was washed with water (2 X 65. ml) and brine solution (2 X 65 ml), dried over anhydrous sodium sulphate (5 g) and all the solvent was distilled off to get residual mass. The residual mass was dissolved in n20 heptane (50 ml) at 75-80 °C, which was treated with activated charcoal, neutral aluminaand filtered. The filtrate was stirred at 25-30 °C for 20 hours. The resulted solid was filtered off, washed with n-heptane (12.5 ml) and dried to yield 9 g of tazarotene. (HPLC purity of tazarotene— 97.64percent; Content of dimer impurity - 1.31percent).
Used to treat psoriasis, acne and sun damaged skin.
Human drugs -> Rare disease (orphan)|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:351.5
XLogP3:4.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:351.12930009
Monoisotopic Mass:351.12930009
Topological Polar Surface Area:64.5
Heavy Atom Count:25
Complexity:547
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
This product is a prodrug of vitamin A for external use on the skin, which has the functions of regulating epidermal cell differentiation and proliferation. In most biological systems, it is converted into the active form, the homologous carboxylic acid of tazarotene, through rapid deesterification. This active product can relatively selectively bind to the β and γ subtypes of the retinoic acid receptor, but its exact mechanism for treating psoriasis is still unclear.
Registered Holders
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ALIVUS LIFE SCIENCES LTD
Active
United States
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Pcas
Active
United States
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OLON S.P.A.
Active
Italy
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