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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
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 2022, it was the 311th most commonly prescribed medication in the United States, with more than 200,000 prescriptions.[18]

Medical uses

[edit]

Mometasone furoate is used in the treatment of inflammatory skin disorders (such as eczema[19] and psoriasis) (topical form), allergic rhinitis (such as hay fever) (topical form), asthma (inhalation form)[20][21] for patients unresponsive to less potent corticosteroids, and penile phimosis.[22] In terms of steroid strength, it is more potent than hydrocortisone, and less potent than dexamethasone.[23]

Some low-quality evidence suggests the use of mometasone for symptomatic improvement in children with adenoid hypertrophy.[24]

Mometasone is used to alleviate inflammation and itchiness in skin conditions that respond to treatment with glucocorticoids such as psoriasis and atopic dermatitis.[25][26]

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, sneezing, and treat nasal polyps.[6]

It is not useful for the common cold.[27]

Asthma

[edit]

Mometasone furoate can be used with formoterol for the treatment of asthma, due to its anti-inflammatory properties.[24][21]

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 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 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 the 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][28][29]

  • 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.[30]

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.[31]

The inflammation is reduced by decreasing the liberation of hydrolase acids of leukocytes, the prevention of the accumulation of macrophages in the sites of inflammation, the interference with the 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.[32] 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 the 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.[33][34][35] The C17α furoate ester of mometasone, is the marketed medication.[33][34][35] Mometasone furoate acts as a prodrug of mometasone.[36] In addition to its glucocorticoid activity, mometasone also has very potent progestogenic activity and acts as a partial agonist of the mineralocorticoid receptor.[30]

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 veterinary use, either as a single active agent or in combination with other medications, under many brand names.[1]

Combinations

[edit]

The following combination medications are available as of 2022:[37]

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]
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  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.
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