Mometasone

Last updated

Mometasone
Mometasone furoate.svg
Mometasone furoate ball-and-stick.png
Clinical data
Trade names Nasonex, 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.com Monograph
License data
Pregnancy
category
Routes of
administration
Topical, inhalation (nasal spray)
Drug class Corticosteroid; Glucocorticoid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Nasal spray is virtually undetectable in plasma; but systemic availability is comparable to fluticasone [9]
Protein binding 98% to 99%
Metabolism Liver
Elimination half-life 5.8 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 InfoCard 100.125.600 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C22H28Cl2O4 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 Yes check.svgY
  • Key:QLIIKPVHVRXHRI-CXSFZGCWSA-N Yes check.svgY

  • 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
 X mark.svgNYes check.svgY  (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]

Contents

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

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

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

Contraindications

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

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:

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

Side effects

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:

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:

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

Pharmacology

Pharmacodynamics

Mometasone furoate reduces inflammation by causing several effects: [6] [28] [29]

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

Mometasone -- the metabolite of mometasone furoate. Mometasone.svg
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

Metabolism

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

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

Availability

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

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

CombinationCommercial NameNotes
azelastine Nasaflex
clotrimazole and gentamicin Mometamax, MometavetVeterinary use
clotrimazole and mupirocin Derma Q
florfenicol and terbinafine ClaroVeterinary use
formoterol Dulera, Hexaler Bronquial Duo, Zenhale
fusidic acid Bactirest-M, Dermotil Fusid, Momate-F
gentamicin and posaconazole Mometamax UltraVeterinary 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 HundeVeterinary 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

Related Research Articles

<span class="mw-page-title-main">Corticosteroid</span> Class of steroid hormones

Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involved in a wide range of physiological processes, including stress response, immune response, and regulation of inflammation, carbohydrate metabolism, protein catabolism, blood electrolyte levels, and behavior.

<span class="mw-page-title-main">Allergic rhinitis</span> Nasal inflammation due to allergens in the air

Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. It is classified as a type I hypersensitivity reaction. Signs and symptoms include a runny or stuffy nose, sneezing, red, itchy, and watery eyes, and swelling around the eyes. The fluid from the nose is usually clear. Symptom onset is often within minutes following allergen exposure, and can affect sleep and the ability to work or study. Some people may develop symptoms only during specific times of the year, often as a result of pollen exposure. Many people with allergic rhinitis also have asthma, allergic conjunctivitis, or atopic dermatitis.

A decongestant, or nasal decongestant, is a type of pharmaceutical drug that is used to relieve nasal congestion in the upper respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine. Intranasal corticosteroids can also be used as decongestants and antihistamines can be used to alleviate runny nose, nasal itch, and sneezing.

<span class="mw-page-title-main">Glucocorticoid</span> Class of corticosteroids

Glucocorticoids are a class of corticosteroids, which are a class of steroid hormones. Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor that is present in almost every vertebrate animal cell. The name "glucocorticoid" is a portmanteau and is composed from its role in regulation of glucose metabolism, synthesis in the adrenal cortex, and its steroidal structure.

<span class="mw-page-title-main">Prednisolone</span> Corticosteroid medication

Prednisolone is a corticosteroid, a steroid hormone used to treat certain types of allergies, inflammatory conditions, autoimmune disorders, and cancers. Some of these conditions include adrenocortical insufficiency, high blood calcium, rheumatoid arthritis, dermatitis, eye inflammation, asthma, and multiple sclerosis. It can be taken by mouth, injected into a vein, used topically as a skin cream, or as eye drops. It differs from the similarly named prednisone in having a hydroxyl at the 11th carbon instead of a ketone.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the brand name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

<span class="mw-page-title-main">Triamcinolone</span> Steroid medication

Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others. It is also used to prevent worsening of asthma and chronic obstructive pulmonary disease (COPD). It can be taken in various ways including by mouth, injection into a muscle, and inhalation.

<span class="mw-page-title-main">Nasal spray</span> Spray that delivers medications locally in the nasal cavities or systemically

Nasal sprays are used to deliver medications locally in the nasal cavities or systemically. They are used locally for conditions such as nasal congestion and allergic rhinitis. In some situations, the nasal delivery route is preferred for systemic therapy because it provides an agreeable alternative to injection or pills. Substances can be assimilated extremely quickly and directly through the nose. Many pharmaceutical drugs exist as nasal sprays for systemic administration. Other applications include hormone replacement therapy, treatment of Alzheimer's disease and Parkinson's disease. Nasal sprays are seen as a more efficient way of transporting drugs with potential use in crossing the blood–brain barrier.

<span class="mw-page-title-main">Olopatadine</span> Chemical compound

Olopatadine, sold under the brand name Patanol among others, is an antihistamine medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis. It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

<span class="mw-page-title-main">Post-nasal drip</span> Medical condition

Post-nasal drip (PND), also known as upper airway cough syndrome (UACS), occurs when excessive mucus is produced by the nasal mucosa. The excess mucus accumulates in the back of the nose, and eventually in the throat once it drips down the back of the throat. It can be caused by rhinitis, sinusitis, gastroesophageal reflux disease (GERD), or by a disorder of swallowing. Other causes can be allergy, cold, flu, and side effects from medications.

<span class="mw-page-title-main">Beclometasone</span> Chemical compound

Beclometasone or beclomethasone, also known as beclomethasone dipropionate, and sold under the brand name Qvar among others, is a steroid medication. It is available as an inhaler, cream, pills, and nasal spray. The inhaled form is used in the long-term management of asthma. The cream may be used for dermatitis and psoriasis. The pills have been used to treat ulcerative colitis. The nasal spray is used to treat allergic rhinitis and nasal polyps.

<span class="mw-page-title-main">Fluticasone propionate</span> Medication

Fluticasone propionate, sold under the brand names Flovent and Flonase among others, is a glucocorticoid steroid medication. When inhaled it is used for the long term management of asthma and COPD. In the nose it is used for hay fever and nasal polyps. It can also be used for mouth ulcers. It works by decreasing inflammation.

<span class="mw-page-title-main">Triamcinolone acetonide</span> Medicinal chemical compound, steroid

Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions, to relieve the discomfort of mouth sores, and by injection into joints to treat various joint conditions. It is also injected into lesions to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat allergic rhinitis. It is used for the treatment of macular edema associated with uveitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.

<span class="mw-page-title-main">Flunisolide</span> Chemical compound

Flunisolide is a corticosteroid often prescribed as a treatment for allergic rhinitis. Intranasal corticosteroids are the most effective medication for controlling symptoms.

Topical steroids are the topical forms of corticosteroids. Topical steroids are the most commonly prescribed topical medications for the treatment of rash and eczema. Topical steroids have anti-inflammatory properties and are classified based on their skin vasoconstrictive abilities. There are numerous topical steroid products. All the preparations in each class have the same anti-inflammatory properties but essentially differ in base and price.

<span class="mw-page-title-main">Fluticasone furoate</span> Corticosteroid

Fluticasone furoate, sold under the brand name Flonase Sensimist among others, is a corticosteroid for the treatment of non-allergic and allergic rhinitis administered by a nasal spray. It is also available as an inhaled corticosteroid to help prevent and control symptoms of asthma. It is derived from cortisol. Unlike fluticasone propionate, which is only approved for children four years and older, fluticasone furoate is approved in children as young as two years of age when used for allergies.

<span class="mw-page-title-main">Budesonide</span> Type of corticosteroid medication

Budesonide, sold under the brand name Pulmicort, among others, is a steroid medication. It is available as an inhaler, nebulization solution, pill, nasal spray, and rectal forms. The inhaled form is used in the long-term management of asthma and chronic obstructive pulmonary disease (COPD). The nasal spray is used for allergic rhinitis and nasal polyps. Modified-release pills or capsules and rectal forms may be used for inflammatory bowel disease including Crohn's disease, ulcerative colitis, and microscopic colitis.

Olopatadine/mometasone, sold under the brand name Ryaltris, is a fixed-dose combination medication for the treatment of allergic rhinitis and rhinoconjunctivitis in adults and adolescents twelve years of age and older. It contains olopatadine hydrochloride and mometasone furoate monohydrate. It is sprayed into the nose.

<span class="mw-page-title-main">Topical glucocorticoids</span>

Topical glucocorticoids are the topical forms of glucocorticoids. Topical glucocorticoids are used in the treatment of many skin conditions. They provide anti-inflammatory, antimitotic, and immune-system suppressing actions through various mechanisms.

Anti-allergic agents are medications used to treat allergic reactions. Anti-allergic agents have existed since 3000 B.C in countries such as China and Egypt. It was not until 1933 when antihistamines, the first type of anti-allergic agents, were developed. Common allergic diseases include allergic rhinitis, allergic asthma and atopic dermatitis with varying symptoms, including runny nose, watery eyes, itchiness, coughing, and shortness of breath. More than one-third of the world's population is currently being affected by one or more allergic conditions.

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