Jump to content

Mometasone

From Wikipedia, the free encyclopedia
(Redirected from Mometasone Furoate)

Mometasone
Clinical data
Trade namesNasonex, Asmanex, Elocon, others[1]
Other namesLAS-41002, 9α,21-Dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 17α-(2-furoate)
AHFS/Drugs.comMonograph
License data
Pregnancy
category
Routes of
administration		Topical, inhalation (nasal spray)
Drug classCorticosteroid; Glucocorticoid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityNasal spray is virtually undetectable in plasma; but systemic availability is comparable to fluticasone[9]
Protein binding98% to 99%
MetabolismLiver
Elimination half-life5.8 hours
Identifiers
  • (9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2-chloroacetyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl furan-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.125.600 Edit this at Wikidata
Chemical and physical data
FormulaC22H28Cl2O4 for mometasone
C27H30O6Cl2 as furoate
3D model (JSmol)
  • CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CCl)O)C)O)Cl)C

  • as furoate: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CCl)OC(=O)C5=CC=CO5)C)O)Cl)C
  • InChI=1S/C22H28Cl2O4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1 checkY
  • Key:QLIIKPVHVRXHRI-CXSFZGCWSA-N checkY

  • as furoate: InChI=1S/C27H30Cl2O6/c1-15-11-19-18-7-6-16-12-17(30)8-9-24(16,2)26(18,29)21(31)13-25(19,3)27(15,22(32)14-28)35-23(33)20-5-4-10-34-20/h4-5,8-10,12,15,18-19,21,31H,6-7,11,13-14H2,1-3H3/t15-,18+,19+,21+,24+,25+,26+,27+/m1/s1
  • Key:WOFMFGQZHJDGCX-ZULDAHANSA-N
 ☒NcheckY (what is this?)  (verify)

Mometasone, also known as mometasone furoate, is a steroid (specifically, a glucocorticoid) medication used to treat certain skin conditions, hay fever, and asthma.[10][11][12] Specifically it is used to prevent rather than treat asthma attacks.[10] It can be applied to the skin, inhaled, or used in the nose.[10][11][12] Mometasone furoate, not mometasone, is used in medical products.[13]

Common side effects when used for asthma include headache, sore throat and thrush.[10] It is therefore recommended to rinse the mouth after use.[10] Long-term use may increase the risk for glaucoma and cataracts.[10] Common side effects when used in the nose include upper respiratory tract infections and nose bleeds.[12] Common side effects when applied on the skin include acne, skin atrophy, and itchiness.[11] It works by decreasing inflammation.[10]

Mometasone furoate was patented in 1981 and came into medical use in 1987.[14] It is on the World Health Organization's List of Essential Medicines[15] and is available as a generic medication.[16][17] In 2021, it was the 266th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[18][19]

Medical uses

[edit]

Mometasone furoate is used in the treatment of inflammatory skin disorders (such as eczema[20] and psoriasis) (topical form), allergic rhinitis (such as hay fever) (topical form), asthma (inhalation form)[21][22] for patients unresponsive to less potent corticosteroids, and penile phimosis.[23] In terms of steroid strength, it is more potent than hydrocortisone, and less potent than dexamethasone.[24]

Some low-quality evidence suggests the use of mometasone for symptomatic improvement in children with adenoid hypertrophy.[25]

Mometasone is used to alleviate inflammation and itchiness in skin conditions that respond to treatment with glucocorticoids such as psoriasis and atopic dermatitis.[26][27]

Nasal mometasone is used in people over two years of age to diminish the symptoms of hay fever (seasonal allergic rhinitis) and other allergies (perennial rhinitis), including nasal congestion, discharge, pruritus, and sneezing and to treat nasal polyps.[6]

It is not useful for the common cold.[28]

Asthma

[edit]

Mometasone furoate can be used with formoterol for the treatment of asthma, due to its anti-inflammatory properties.[25][22]

Contraindications

[edit]

People should not use inhaled mometasone or mometasone nasal spray if they have:

  • glaucoma or cataracts
  • hypersensitivity, or are allergic to any ingredient in mometasone

Those who are using mometasone nasal or inhaled for a long period of time (e.g. more than three months) should get regular eye exams to check for glaucoma and cataracts and should take precautions to avoid infections such as taking a vitamin D supplement, staying away from those with an infection (chickenpox, measles, colds or flu, COVID-19), washing foods, hand washing and calling a family doctor at the first sign of a severe infection.

People should not use mometasone topical (skin cream) if:

  • hypersensitive or allergic to any ingredient in the skin cream

The risks of Mometasone furoate to the baby during pregnancy cannot be ruled out.

Side effects

[edit]

The nasal spray form of mometasone may cause the following side effects:

Serious side effects include: Thrush (fungal infection in the nose or throat), slow wound healing, eye problems such as glaucoma or cataracts, weakened immune system (immunodeficiency) which causes an increased susceptibility to infections and adrenal insufficiency.

The inhaled form of mometasone for asthma may cause the following side effects:

  • headache
  • stuffy or runny nose
  • dry throat
  • swelling of nose, throat and sinuses
  • flu-like symptoms
  • painful menstrual periods

Serious side effects may include: allergic reactions (anaphylaxis), increased risk of osteoporosis, glaucoma and cataracts, thrush in the mouth or throat, growth retardation in children, bronchospasms, adrenal insufficiency and weakened immune system which causes an increased susceptibility to infections.

The topical (skin cream) version may cause:

  • burning and itching at the application site
  • acne
  • changes in skin color
  • dryness at application site
  • skin sores

The only serious side effect that is known with mometasone topical is adrenal insufficiency.

Pharmacology

[edit]

Pharmacodynamics

[edit]

Mometasone furoate reduces inflammation by causing several effects:[6][29][30]

  • Reversing the activation of inflammatory proteins
  • Activating the secretion of anti-inflammatory proteins
  • Stabilizing cell membranes
  • Decreasing the influx of inflammatory cells

In addition to the glucocorticoid properties of mometasone furoate, it is a very potent agonist of the progesterone receptor as well as a partial agonist of the mineralocorticoid receptor.[31]

Mechanism of action

[edit]
Mometasone — the metabolite of mometasone furoate.

Mometasone, like other corticosteroids, possesses anti-inflammatory, antipruritic, and vasoconstrictive properties. For allergies, corticosteroids reduce the allergic reactions in various types of cells (mastocytes and eosinophils) that are responsible for allergic reactions. Mometasone and other corticosteroids circulate in the blood easily, crossing cellular membranes and binding with cytoplasmic receptors, resulting in the transcription and synthesis of proteins. It also inhibits the actions of the enzyme cytochrome P450 2C8 which participates in the activity of monooxygenase.[32]

The inflammation is reduced in decreasing the liberation of hydrolase acids of leukocytes, the prevention of the accumulation of macrophages in the sites of inflammation, the interference with adhesion of leukocytes to capillary walls, the reduction of the permeability of the capillary membranes and consequently edema, the reduction of complementary components, inhibition of histamine and kinin liberation, and interference with scar tissue formation.[33] The proliferation of fibroblasts and collagen deposits is also reduced. It is believed that the action of corticosteroid anti-inflammatory agents is bound to inhibitive proteins of phospholipase A2, collectively called lipocortins. The lipocortins, in turn, control the biosynthesis of potent mediators of inflammation as the prostaglandins and leukotrienes, inhibiting the liberation of the molecular precursors of arachidonic acid. Intranasal mometasone alleviates symptoms such as rhinorrhea aquosa, nasal congestion, nasal drip, sneezing, and pharyngeal itching. Topical administration applied to skin reduces the inflammation associated with chronic or acute dermatosis.

Although mometasone furoate does not have significant systemic immunomodulatory effects, it can be considered a local immunosuppressive drug because clinical studies have shown reductions (vs. baseline ) in neutrophils (a white blood cell) in the nasal mucosa.[citation needed] It could be also considered an antihistamine along with its glucocorticoid effects because it significantly reduces histamine and eosinophil cationic protein levels.[citation needed]

Pharmacokinetics

[edit]

Metabolism

[edit]

Extensive metabolic hepatic metabolism of mometasone furoate to multiple metabolites occurs. No principal metabolites are detectable in plasma. After in vitro incubation, one of the minor metabolites formed is furoate 6β-hydroxymometasone. In human hepatic microsomes, the formation of these metabolites is regulated by CYP3A4.[6]

Mometasone

[edit]

Mometasone by itself is a synthetic, steroidal glucocorticoid or corticosteroid that was never marketed.[34][35][36] The C17α furoate ester of mometasone, is the marketed medication.[34][35][36] Mometasone furoate acts as a prodrug of mometasone.[37] In addition to its glucocorticoid activity, mometasone also has very potent progestogenic activity and acts as a partial agonist of the mineralocorticoid receptor.[31]

Society and culture

[edit]

Availability

[edit]

As of 2016, mometasone furoate is available worldwide in formulations for nasal, oral inhalation, and topical administration, for human and for veterinary use, either as the single active agent or in combinations with other drugs, under many brand names.[1]

Combinations

[edit]

The following combination medications are available as of 2022:[38]

Combination Commercial Name Notes
azelastine Nasaflex
clotrimazole and gentamicin Mometamax, Mometavet Veterinary use
clotrimazole and mupirocin Derma Q
florfenicol and terbinafine Claro Veterinary use
formoterol Dulera, Hexaler Bronquial Duo, Zenhale
fusidic acid Bactirest-M, Dermotil Fusid, Momate-F
gentamicin and posaconazole Mometamax Ultra Veterinary use
hydroquinone and tretinoin Acnezac-MH
miconazole Elica M, Elica-M, and Sensicort-F
mupirocin Sensicort-B
orbifloxacin and posaconazole Posatex, Posatex voor honden, Posatex für Hunde Veterinary use
salicylic acid Cortimax-S, Elicasal, Elocom Plus, Elosalic, Mezo-S, Momate-S, Momesalic,

Momtas-S, Monsalic, Sensicort-S

terbinafine Cutizone-T, Mezo-T, MomelomTerbi-Humanity
tiotropium Tiomom

References

[edit]
  1. ^ a b "International brands for Mometasone". Drugs.com. Archived from the original on 17 November 2016. Retrieved 17 November 2016.
  2. ^ "Mometasone Use During Pregnancy". Drugs.com. 14 February 2020. Archived from the original on 26 October 2020. Retrieved 1 April 2020.
  3. ^ "Nasonex Allergy mometasone furoate 50 micrograms/ actuation (as monohydrate) aqueous nasal spray (215798)". Therapeutic Goods Administration (TGA). 15 July 2020. Retrieved 22 August 2024.
  4. ^ "Nasonex aqueous nasal spray mometasone furoate 50 microgram/actuation (as monohydrate) spray bottle (77112)". Therapeutic Goods Administration (TGA). 10 October 2023. Retrieved 22 August 2024.
  5. ^ "Noumed Mometasone Hayfever & Allergy Relief (Noumed Pharmaceuticals PTY LTD)". Therapeutic Goods Administration (TGA). 13 September 2024. Retrieved 15 September 2024.
  6. ^ a b c d "Nasonex- mometasone furoate spray, metered". DailyMed. 26 January 2011. Archived from the original on 5 November 2022. Retrieved 19 June 2022.
  7. ^ "Nasonex- mometasone furoate spray". DailyMed. 15 December 2022. Archived from the original on 17 April 2023. Retrieved 17 April 2023.
  8. ^ "List of nationally authorised medicinal products" (PDF). European Medicines Agency. Archived (PDF) from the original on 7 March 2023. Retrieved 6 March 2023.
  9. ^ Tayab ZR, Fardon TC, Lee DK, Haggart K, McFarlane LC, Lipworth BJ, et al. (November 2007). "Pharmacokinetic/pharmacodynamic evaluation of urinary cortisol suppression after inhalation of fluticasone propionate and mometasone furoate". British Journal of Clinical Pharmacology. 64 (5): 698–705. doi:10.1111/j.1365-2125.2007.02919.x. PMC 2203259. PMID 17509041.
  10. ^ a b c d e f g "Mometasone Furoate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 7 October 2016. Retrieved 11 March 2019.
  11. ^ a b c "Mometasone Furoate topical Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 5 August 2020. Retrieved 11 March 2019.
  12. ^ a b c "Mometasone Furoate eent Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 30 April 2016. Retrieved 11 March 2019.
  13. ^ "Mometasone". DrugBank. Archived from the original on 29 June 2019. Retrieved 30 April 2020.
  14. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 488. ISBN 9783527607495.
  15. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  16. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  17. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 265. ISBN 9780857113382.
  18. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  19. ^ "Mometasone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  20. ^ Lax SJ, Harvey J, Axon E, Howells L, Santer M, Ridd MJ, et al. (Cochrane Skin Group) (March 2022). "Strategies for using topical corticosteroids in children and adults with eczema". The Cochrane Database of Systematic Reviews. 2022 (3): CD013356. doi:10.1002/14651858.CD013356.pub2. PMC 8916090. PMID 35275399.{{cite journal}}: CS1 maint: overridden setting (link)
  21. ^ Tan RA, Corren J (December 2008). "Mometasone furoate in the management of asthma: a review". Therapeutics and Clinical Risk Management. 4 (6): 1201–8. doi:10.2147/TCRM.S3261. PMC 2643101. PMID 19337427.
  22. ^ a b Bousquet J (May 2009). "Mometasone furoate: an effective anti-inflammatory with a well-defined safety and tolerability profile in the treatment of asthma". International Journal of Clinical Practice. 63 (5): 806–19. doi:10.1111/j.1742-1241.2009.02003.x. PMID 19392928. S2CID 2040993.
  23. ^ Khope S (March 2010). "Topical mometasone furoate for phimosis". Indian Pediatrics. 47 (3): 282. PMID 20371899.
  24. ^ Williams DM (2005). "What does potency actually mean for inhaled corticosteroids?". The Journal of Asthma. 42 (6): 409–17. doi:10.1081/jas-57878. PMID 16293535. S2CID 43138631.
  25. ^ a b Passali D, Spinosi MC, Crisanti A, Bellussi LM (2 May 2016). "Mometasone furoate nasal spray: a systematic review". Multidisciplinary Respiratory Medicine. 11: 18. doi:10.1186/s40248-016-0054-3. PMC 4852427. PMID 27141307.
  26. ^ Green C, Colquitt JL, Kirby J, Davidson P, Payne E (November 2004). "Clinical and cost-effectiveness of once-daily versus more frequent use of same potency topical corticosteroids for atopic eczema: a systematic review and economic evaluation". Health Technology Assessment. 8 (47): iii, iv, 1–120. doi:10.3310/hta8470. PMID 15527669.
  27. ^ Prakash A, Benfield P (January 1998). "Topical mometasone. A review of its pharmacological properties and therapeutic use in the treatment of dermatological disorders". Drugs. 55 (1): 145–63. doi:10.2165/00003495-199855010-00009. PMID 9463794. S2CID 46976211.
  28. ^ "Mometasone Nasal Spray: MedlinePlus Drug Information". MedlinePlus. 19 March 2020. Archived from the original on 20 March 2020. Retrieved 19 March 2020. Mometasone nasal spray should not be used to treat symptoms (e.g., sneezing, stuffy, runny, itchy nose) caused by the common cold. Mometasone nasal spray is in a class of medications called corticosteroids. It works by blocking the release of certain natural substances that cause allergy symptoms.
  29. ^ Nurse's Drug Handbook 2010. Jones & Bartlett Learning. 15 July 2009. p. 677. ISBN 978-0-7637-7900-9.
  30. ^ Kavuru MS (2007). "Chapter 9: Anti-inflammatory agents". Diagnosis and Management of Asthma. Professional Communications. ISBN 978-1-932610-38-3.
  31. ^ a b Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, et al. (December 2002). "Mometasone furoate is a less specific glucocorticoid than fluticasone propionate". The European Respiratory Journal. 20 (6): 1386–92. doi:10.1183/09031936.02.02472001. PMID 12503693.
  32. ^ Walsky RL, Gaman EA, Obach RS (January 2005). "Examination of 209 drugs for inhibition of cytochrome P450 2C8". Journal of Clinical Pharmacology. 45 (1): 68–78. doi:10.1177/0091270004270642. PMID 15601807. S2CID 670198.
  33. ^ Blaiss MS (2011). "Safety update regarding intranasal corticosteroids for the treatment of allergic rhinitis". Allergy and Asthma Proceedings. 32 (6): 413–8. doi:10.2500/aap.2011.32.3473. PMID 22221434.
  34. ^ a b Elks H (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 834–. ISBN 978-1-4757-2085-3. Archived from the original on 10 January 2023. Retrieved 11 March 2019.
  35. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 701–. ISBN 978-3-88763-075-1.
  36. ^ a b Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 185–. ISBN 978-0-7514-0499-9. Archived from the original on 10 January 2023. Retrieved 11 March 2019.
  37. ^ Vardanyan R, Hruby V (7 January 2016). "Steroid Hormones". Synthesis of Best-Seller Drugs. Elsevier Science. pp. 463–. ISBN 978-0-12-411524-8.
  38. ^ "Mometasone". Archived from the original on 17 November 2016. Retrieved 17 November 2016.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Mometasone&oldid=1259065412"