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Mometasone

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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
Pharmacokineticdata
BioavailabilityNasal spray is virtually undetectable in plasma; but systemic availability is comparable tofluticasone[7]
Protein binding98% to 99%
MetabolismLiver
Eliminationhalf-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
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.125.600Edit this at Wikidata
Chemical and physical data
FormulaC22H28Cl2O4for mometasone
C27H30O6Cl2as 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/s1checkY
  • Key:QLIIKPVHVRXHRI-CXSFZGCWSA-NcheckY

  • 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 asmometasone y 3 s,is asteroid(specifically, aglucocorticoid) medication used to treat certainskin conditions,hay fever,andasthma.[8][9][10]Specifically it is used to prevent rather than treat asthma attacks.[8]It can be applied to the skin, inhaled, or used in the nose.[8][9][10]Mometasonefuroate,not mometasone, is used in medical products.[11]

Common side effects when used for asthma include asthma andthrush.[8]It is therefore recommended to rinse the mouth after use.[8]Long-term use may increase the risk forglaucomaandcataracts.[8]Common side effects when used in the nose includeupper respiratory tract infectionsandnose bleeds.[10]Common side effects when applied on the skin includeacne,skin atrophy,and itchiness.[9]It works by decreasinginflammation.[8]

Mometasone furoate was patented in 1981 and came into medical use in 1987.[12]It is on theWorld Health Organization's List of Essential Medicines[13]and is available as ageneric medication.[14][15]In 2021, it was the 266th most commonly prescribed medication in the United States, with more than 1million prescriptions.[16][17]

Medical uses[edit]

Mometasone furoate is used in the treatment of inflammatory skin disorders (such aseczema[18]andpsoriasis) (topical form),allergic rhinitis(such ashay fever) (topical form),asthma(inhalation form)[19][20]for patients unresponsive to less potentcorticosteroids,and penilephimosis.[21]In terms of steroid strength, it is more potent thanhydrocortisone,and less potent thandexamethasone.[22]

Some low-quality evidence suggests the use of mometasone for symptomatic improvement in children withadenoid hypertrophy.[23]

Mometasone is used to alleviate inflammation and itchiness in skin conditions that respond to treatment with glucocorticoids such as psoriasis and atopic dermatitis.[24][25]

Nasalmometasone 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 treatnasal polyps.[4]

It is not useful for thecommon cold.[26]

Asthma[edit]

Mometasone furoate can be used withformoterolfor the treatment of asthma, due to its anti-inflammatory properties.[23][20]

Contraindications[edit]

People should not use inhaled mometasone or mometasonenasal sprayif 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 forglaucomaandcataractsand 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 followingside 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 andadrenal 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 ofosteoporosis,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 isadrenal insufficiency.

Pharmacology[edit]

Pharmacodynamics[edit]

Mometasone furoate reduces inflammation by causing several effects:[4][27][28]

  • 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 theglucocorticoidproperties of mometasone furoate, it is a very potentagonistof theprogesterone receptoras well as apartial agonistof themineralocorticoid receptor.[29]

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 enzymecytochrome P450 2C8which participates in the activity of monooxygenase.[30]

The inflammation is reduced in decreasing the liberation ofhydrolaseacids ofleukocytes,the prevention of the accumulation ofmacrophagesin the sites of inflammation, the interference with adhesion of leukocytes tocapillarywalls, the reduction of the permeability of the capillary membranes and consequentlyedema,the reduction of complementary components, inhibition of histamine andkininliberation, and interference with scar tissue formation.[31]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 ofphospholipase A2,collectively called lipocortins. The lipocortins, in turn, control the biosynthesis of potent mediators of inflammation as theprostaglandinsandleukotrienes,inhibiting the liberation of the molecular precursors ofarachidonic acid.Intranasal mometasone alleviates symptoms such asrhinorrheaaquosa,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. Afterin vitroincubation, one of the minor metabolites formed is furoate 6β-hydroxymometasone. In human hepatic microsomes, the formation of these metabolites is regulated byCYP3A4.[4]

Mometasone[edit]

Mometasone by itself is asynthetic,steroidalglucocorticoidorcorticosteroidthat was never marketed.[32][33][34]The C17αfuroateesterof mometasone, is the marketed medication.[32][33][34]Mometasone furoate acts as aprodrugof mometasone.[35]In addition to its glucocorticoid activity, mometasone also has very potentprogestogenicactivity and acts as apartial agonistof themineralocorticoid receptor.[29]

Society and culture[edit]

Brand names[edit]

As of 2016, mometasone furoate is available worldwide in formulations for nasal, oral inhalation, and topical administration, for human and for veterinary use, and in combinations with other drugs, under many brand names.[1]It was available as the single active agent in the following brands: Alcom, Altosone, Asmanex, Atozon, Aureox, Belloseta, Bioelementa, Biometasona, Bloctimo, Borgasone, Breso, Broner, Codermo, Cortynase, Cutimom, Cutizone, Cutticom, Dance, Demoson, Dergentil, Derimod, Dermacortine, Dermaten, Dermome, Dermosona, Dermotasone, Dermovel, Desdek, Ecelecort, Ecural, Edelan, Elica, Elisone, Elisox, Elitasone, Elna, Elocan, Elocom, Elocon, Elocortin, Elofute, Elomet, Elomox, Eloskin, Eloson, Elosone, Elovent, Elox, Etacid, Eversone, Eztom, F-Din, Fenisona, Flazcort, Flogocort, Fremomet, Frondava, Fu Mei Song, Fulmeta, Furo, Furoato de Mometasona, Furoderm, Gistan-H, Honmet, Iflacort, Intercon, Ivoxel, Kalmente, Konex, Ladexol, Lisoder, Logren, Loksin, Lomeane, M-Furo, Makiren, Mefurosan, Melocort, Mena, Mesone, Metacortil, Metactiv, Metaflam, Metagra, Metasafe, Metason, Metasone, Metaspray, Metatop, Metaz, Metmin, Metsone, Midermin, Mifusin, Minyear, Mofacort, Mofulex, Mofur, Mofuroate, Molison, Momate, Momax, Momecon, Momecort, Momecutan, Momederm, MomeGalen, Momegen, Momekort, Momelab, Momentum, Momeplus, Momerid, Momeson, Momesone, Momester, Momet, Mometa, Mometagen, Mometason, Mometasona, Mometasona Furoato, Mometasone Furoate, Mometasone Furoate Hydrate, Mometasonfuroaat, Mometasonfuroat, Mometasoni Furoas, Mometasonum, Mometasyn, Mometasyn, Mometax, Mometazon, Mometazona, Mometazona Fuorat, Mometazonfuroat, Mometix-AQ, Momevate, Momexa, Mommex, Mommox, Momtas, Monaliz, Monez, Monovel, Monovo, Mosone, Motaderm, Motaneal, Movesan, Mtaz, Mundoson, Murozo, Myrey, Narinex, Nasamet, Nasehaler, Nasocure, Nasomet, Nasometin, Nasonex, Nassomet, Nazofix, Nazoster, Netonox, Nexomist, Novasone, Ovison, Ovixan, Oximax, Pharmecort, Pluster, Pronasal, Propel, Prospiril, Pydercon, Rinelon, Rinitek, Rino-Val, Rinobudex, Rinonex, Rinosal, Rinosona, Rinoval, Risonel, Rinocort, Sensicort, Septopic, Silkaren, Soneta, Suavicort, Suqi, Synaller, Tabunex, Topcort, Topison, Uniclar, Uniderm, Vizomet, Yperod, Zalconex, and Zynovate.[1]

Combinations[edit]

The following combination medications are available as of 2022:[36]

References[edit]

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