Tazarotene

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

  P405：Unter Verschluss aufbewahren.

  P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Tazarotene Chemische Eigenschaften,Einsatz,Produktion Methoden

• Chemische Eigenschaften

  White Solid

• Originator

  Avage,Allergan

• Verwenden

  Used to treat psoriasis, acne and sun damaged skin.

• Verwenden

  An acetylenic retinoid prodrug converted to the active metabolite, Tazarotenic acid, with selective affinity for retinoic acid receptors RAR?and RAR. Antiacne; antipsoriatic. Used in treatment of photodamaged skin

• Verwenden

  Tazarotene is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). It is commonly sold in two concentrations: 0.05% and 0.1%. In addition to tretinoin, wh

• Verwenden

  anticholelithic

• Definition

  ChEBI: The ethyl ester of tazarotenic acid. A prodrug for tazarotenic acid, it is used for the treatment of psoriasis, acne, and sun-damaged skin.

• Indications

  Like other retinoids, tazarotene (Tazorac) acts by binding to RARs and altering gene expression. Tazarotene appears to be particularly selective for the retinoid receptors RAR-β and RAR-γ, but the clinical significance of this observation is unknown.

• Manufacturing Process

  A mixture of 14.91 g (135.324 mmol) of thiophenol and 5.5 g (137.5 mmol) of NaOH in 100 ml acetone was heated at reflux for 2.5 h and then treated dropwise with a solution of 20 g (134.19 mmol) of 1-bromo-3-methyl-2- butene in 20 ml acetone. This solution was refluxed for 40 h and then stirred at room temperature for 24 h. Solvent was then removed in vacuo, the residue taken up in water, and extracted with 3 times 50 ml ether. Ether extracts were combined and washed with 3 times 30 ml of 5% NaOH solution, then water, saturated NaCl solution and dried. Solvent was then removed in vacuo and the residue further purified by kugelrohr distillation (80°C, 0.75 mm) to give the phenyl-3-methylbut-2-enylsulfide as a pale yellow oil.
  To a solution of 15.48 g (86.824 mmol) of phenyl-3-methylbut-2-enylsulfide in 160 ml benzene were added successively 12.6 g (88.767 mmol) of phosphorus pentoxide and 11 ml of 85% phosphoric acid. This solution was refluxed with vigorous stirring under argon for 20 h, then cooled to room temperature. The supernatant organic layer was decanted and the syrupy residue extracted with 3 times 50 ml ether. Organic fractions were combined and washed with water, saturated NaHCO3 and saturated NaCl solution and then dried. Solvent was removed in vacuo and the residue purified by kugelrohr distillation (80°C, 0.5 mm) to give the 4,4-dimethylthiochroman as a pale yellow oil.
  A solution of 14.3 g (80.21 mmol) of 4,4-dimethyl thiochroman and 6.76 g (86.12 mmol) of acetyl chloride in 65 ml benzene was cooled in an ice bath and treated dropwise with 26.712 g (102.54 mmol) of stannic chloride. The mixture was stirred at room temperature for 12 h, then treated with 65 ml water and 33 ml conc. hydrogen chloride and heated at reflux for 0.5 h. After being cooled to room temperature, the organic layer was separated and the aqueous layer extracted with 5 times 50 ml benzene. The recovered organic fractions were combined and washed with 5% sodium carbonate solution, water, saturated NaCl solution and then dried. The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes) followed by kugelrohr distillation (150°C, 0.7 mm) to give the 4,4-dimethyl-6-acetylthiochroman as a pale yellow oil.
  To a solution of 1.441 g (14.2405 mmol) of diisopropylamine in 30 ml dry tetrahydrofuran under argon at -78°C was added dropwise 9 ml of 1.6 M (14.4 mmol) n-butyl lithium in hexane. After stirring this solution at -78°C for 1 h, it was treated dropwise with a solution of 2.95 g (13.389 mmol) of 4,4- dimethyl-6-acetylthiochroman in 5 ml of dry tetrahydrofuran. After another hour of stirring at -78°C, the solution was treated with 2.507 g (14.53 mmol) of diethyl chlorophosphate and brought to room temperature, where it was stirred for 3.75 h. This solution was then transferred using a double ended needle to a solution of lithium diisopropylamide (prepared as above using 2.882 g (28.481 mmol) of diisopropylamine and 18 ml of 1.6 M (28.8 mmol) n-butyl lithium in hexane) in 60 ml dry tetrahydrofuran at -78°C. The cooling bath was removed and the solution stirred at room temperature for 15 h, then quenched with water and acidified to pH 1 with 3 N hydrogen chloride. The mixture was stirred at room temperature for 12 h, then treated with 65 ml water and 33 ml conc. hydrogen chloride and heated at reflux for 0.5 h. After being cooled to room temperature, the organic layer was separated and the aqueous layer extracted with 5 times 50 ml benzene. The recovered organic fractions were combined and washed with 5% sodium carbonate solution, water, saturated NaCl solution and then dried. The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 5% ethyl acetate in hexanes) followed by kugelrohr distillation (150°C, 0.7 mm) to give the 4,4-dimethyl-6-ethynylthiochroman as a pale yellow oil.
  A mixture of 15.75 g (0.1 mol) 6-chloronicotinic acid, 6.9 g (0.15

• Trademarks

  Avage (Allergan); Tazorac (Allergan).

• Therapeutic Function

  Keratolytic

• Biochem/physiol Actions

  Tazarotene induces the expression of tazarotene-induced gene 3 (TIG3), a tumor suppressor gene. It is a prodrug of tazarotenic acid, which specifically activates RARb and RARg, only weakly activates RARa, and is inactive at retinoid X receptors (RXRs). In psoriasis, tazarotene normalizes abnormal keratinocyte differentiation and reduces their hyperproliferation.

• Clinical Use

  In the United States, tazarotene has been approved for topical treatment of psoriasis (involving up to 20% body surface area) and mild to moderate facial acne. Application site burning, stinging, and desquamation are common side effects, especially with acne. Tazarotene is contraindicated in women who are pregnant.

• Nebenwirkungen

  Tazorac is a category X drug and must be avoided in pregnancy. This drug can be irritating and should be avoided in patients with sensitive skin or seborrheic dermatitis.

• Structure and conformation

  Retinoid prodrug, converted to active form, the carboxylic acid of tazarotene by rapid de-esterification. This drug binds to all three retinoic acid receptors with some increased affinity for the β and γ receptors.

Tazarotene Upstream-Materialien And Downstream Produkte

Tazarotene Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global(335)Suppliers

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