Mometasone furoate

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Mometasone furoate Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  Mometasone furoate is a topical steroidal antiinflammatory useful in the treatment of corticosteroid-responsive dermatoses. As a steroidal antiinflammatory of grade II potency, mometasone furoate is characterized by a once-daily dose regimen and a relatively wide safety margin.

• Chemische Eigenschaften

  White-to-Off-White Solid

• Originator

  Schering-Plough (USA)

• Verwenden

  Mometasone furoate is a deuterated topical corticosteroid used as an anti-inflammatory. Mometasone furoate has been used to study its effect on Leishmania major amastigotes. It could as labeled Mometasone, intended for use as an internal standard for the quantification of Mometasone by GC- or LC-mass spectrometry. Formulations containing mometasone furoate have been used in the treatment of allergic rhinitis, atopic dermatitis, and asthma. Intranasal administration of mometasone furoate (1 μg/nostril) reduces the frequency of sneezing and nasal rubbing in a rat model of histamine-induced allergic rhinitis. Topical application of mometasone furoate reduces croton oil-induced ear edema in mice (ED50 = 0.31 μg/ml).

• Definition

  ChEBI: Mometasone furoate is a 2-furoate ester, a steroid ester, an 11beta-hydroxy steroid, a 20-oxo steroid, an organochlorine compound and a 3-oxo-Delta(1),Delta(4)-steroid. It has a role as an anti-inflammatory drug and an anti-allergic agent. It is functionally related to a mometasone.

• Manufacturing Process

  METHOD I (Patent U.S. 4,472,393)
  A. 21-Chloro-9β,11β-epoxy-17α-hydroxy-16α-methyl-1,4-pregnadiene-3,20- dione
  Prepare a solution of 5.0 g. of 9β,11β-epoxy-17α,21-dihydroxy-16α-methyl- 1,4-pregnadiene-3,20-dione in 20 ml of dry pyridine. Cool on an ice bath; to the stirred solution under nitrogen, add dropwise 1.1 ml of mesyl chloride. Remove the ice bath and continue stirring at room temperature for 30 min. Add 2.0 g of lithium chloride and continue stirring for a further 150 min. Add to a mixture of 150 ml ethyl acetate and 100 ml distilled water. Wash the organic phase with dilute 3% aqueous hydrochloric acid, then saturated aqueous sodium chloride solution and finally saturated sodium bicarbonate solution. Dry the organic phase over magnesium sulfate, filter and remove the solvent to give 4.62 g of 21-chloro-9β,11β-epoxy-17α-hydroxy-16α-methyl- 1,4-pregnadiene-3,20-dione.
  B. 21-Chloro-9β,11β-epoxy-17α-hydroxy-16α-methyl-1,4-pregnadiene-3,20- dione 17-(2'-furoate)
  Prepare under argon a solution of 8 g of 4-dimethylaminopyridine in 250 ml of dry methylene chloride. Cool on an ice bath and add to the stirred solution 6.0 ml of 2-furoyl chloride. Remove from the ice bath, allow the temperature to rise to room temperature and then add 11.5 g of the 21-chloro-9β,11β-epoxy- 17α-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione. After 24 hours add 500 ml of ethyl acetate saturated with water. Filter off the precipitate and then evaporate off the solvent to give the crude 21-chloro-9β,11β-epoxy-17α- hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione 17-(2'-furoate).
  C. 9α,21-Dichloro-11β,17α-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione 17-(2'-furoate)
  To the crude 21-chloro-9β,11β-epoxy-17α-hydroxy-16α-methyl-1,4- pregnadiene-3,20-dione 17-(2'-furoate) add 50 ml of glacial acetic acid, then add a solution of 3.5 g of anhydrous hydrogen chloride in 125 ml of glacial acetic acid. Stir for 15 minutes and then quench with 500 ml of distilled water. Filter off the solids, recrystallise from methanol:water, dry for 24 hours under vacuum to give 12.6 g 9α,21-dichloro-11β,17α-hydroxy-16α-methyl-1,4- pregnadiene-3,20-dione 17-(2'-furoate) (yield 83% of theory).
  Prepare under nitrogen a solution of 1.80 g of 21-chloro-17α-hydroxy-16α- methyl-1,4,9(11)-pregnatriene-3,20-dione 17-(2'-furoate). Add, with stirring, a solution of 1.15 ml of 70% perchloric acid in 2.53 ml of distilled water, and immediately thereafter 604 mg of 1,3-dichloro-5,5-dimethylhydantoin. Stir the reaction mixture for twenty minutes and then raise the temperature to ambient temperature. Monitor the consumption of starting material by thin layer chromatography of aliquots using chloroform:1,3-dichloro-5,5- dimethylhydantoinyl acetate (9:1) and hexane:ethyl acetate (1:1). When the starting material is consumed, pour the reaction mixture into 500 ml of distilled water containing the 1,3-dichloro-5,5-dimethylhydantoin and 7 g of sodium bisulphite. Add sodium chloride until the solution is saturated. Filter the precipitated solid, wash and dry at 50°C under vacuum. Purify the resulting crude product by preparative chromatography on 1000 micron silica gel plates using chloroform: ethyl acetate (19:1). Elute the desired band with ethyl acetate, filter the eluate and evaporate at room temperature to give crude product (1.3 g). Recrystallize the product by dissolving in refluxing methylene chloride, filtering and then replacing the methylene chloride at reflux with methanol and then the methanol with distilled water. Cool the suspension to room temperature, filter and dry under vacuum at 50°C to give the pure pregna-1,4-diene-3,20-dione, 9,21-dichloro-17-((2- furanylcarbonyl)oxy)-11-hydroxy-16-methyl-, (11β-,16α)-.
  METHOD II
  The present invention (Patent U.S. 6,177,560) refers to a new process for the preparation of mometasone furoate carried out by esterifiication of the 17 hydroxy group of mometasone without prior protection of the 11 hydroxy group. Mom

• Trademarks

  Asmanex (Schering);Elocon (Schering).

• Therapeutic Function

  Glucocorticoid

• Biologische Funktion

  Mometasone furoate has strong local anti-inflammatory activity equivalent to that of fluticasone propionate. It has a quick onset of action relative to the other inhaled/intranasal steroids with the least systemic availability and, consequently, the fewest systemic side effects.

• Allgemeine Beschreibung

  Mometasone furoate (Asmanex,Nasonex) undergoes extensive metabolism to multiplemetabolites. No major metabolites are detectable in humanplasma after oral administration, but the 6β-hydroxy metaboliteis detectable by use of human liver microsomes. Thismetabolite is formed via the CYP3A4 pathway.

• Allgemeine Beschreibung

  Mometasone furoate,9,21-dichloro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methylpregna-1,4-diene-3,20-dione (Elocon), is a highpotencyGC available in cream, lotion, or ointment formulationsfor topical use. In addition, mometasone furoatemonohydrate is formulated for treating allergic rhinitis andasthma.

• Biochem/physiol Actions

  Mometasone furoate is a 17-heterocyclic intranasal corticosteroid. It is effectively used as a first-line daily intranasal therapeutic for allergic rhinitis and nasal polyposis. Mometasone furoate is also used as an adjunct to anti-bacterials for treating acute rhinosinusitis. In addition, it relieves the symptoms of asthma in both adults and adolescents by exhibiting a broad spectrum of anti-inflammatory properties.

• Mechanism of action

  Mometasone furoate is the most recent glucocorticoid to be developed and commercialized. It has a number of unique functional groups that confer enhanced glucocorticoid activity as well as pharmacokinetic advantages. The combination of the C-21 chloro and the furoic acid ester at C-17 results in the highest glucocorticoid receptor affinity of any topical corticosteroid. The 16α- methyl decreases the mineralocorticoid effects, and the 9α-chloro group increases both glucocorticoid and mineralocorticoid activities. Inhaled mometasone furoate acts locally as an anti-inflammatory treatment for asthma and has the least systemic bioavailability of all the inhaled glucocorticoids (<1%).

• Clinical Use

  Mometasone furoate was originally marketed as a topically applied corticosteroid, but because of its low systemic bioavailability, it was found to be more useful in the treatment of allergic disorders and lung diseases (107).

• Stoffwechsel

  It is extensively metabolized, with 6β-hydroxymometasone and 21-hydroxymometasone being found among the metabolites. Inhaled mometasone furoate in mainly excreted in the feces (~74%) as metabolites and only minimally excreted in the urine (~8%). It has a relatively long half-life in the lung and is administered once daily, usually in the evening.

Mometasone furoate Upstream-Materialien And Downstream Produkte

Mometasone furoate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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