Identification

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Name
Mometasone furoate
Accession Number
DB14512  (DBSALT002454)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

Mometasone furoate is a corticosteroid drug that can be used for the treatment of asthma, rhinitis, and certain skin conditionsLabel10,11. It has a glucocorticoid receptor binding affinity 22 times stronger than dexamethasone and higher than many other corticosteroids as well2. Mometasone furoate is formulated as a dry powder inhaler, nasal spray, and ointment for its different indicationsLabel10,11.

Structure
Thumb
Synonyms
  • Mometasone furoate
  • Mometasone furoate anhydrous
External IDs
SCH 32088 / SCH-32088
Product Ingredients
IngredientUNIICASInChI Key
Mometasone furoate monohydrateMTW0WEG809141646-00-6AQCCVUHZMIMSIB-HRVPQZBTSA-N
Active Moieties
NameKindUNIICASInChI Key
Mometasoneprodrug8HR4QJ6DW8105102-22-5QLIIKPVHVRXHRI-CXSFZGCWSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AsmanexInhalant220 ug/1Respiratory (inhalation)Physicians Total Care, Inc.2006-03-09Not applicableUs
AsmanexInhalant110 ug/1Respiratory (inhalation)Merck Sharp & Dohme Corp.2005-03-30Not applicableUs
AsmanexInhalant220 ug/1Respiratory (inhalation)Merck Sharp & Dohme Corp.2005-03-30Not applicableUs
Asmanex HFAAerosol200 ug/1Respiratory (inhalation)Merck Sharp & Dohme Corp.2014-04-25Not applicableUs
Asmanex HFAAerosol100 ug/1Respiratory (inhalation)Merck Sharp & Dohme Corp.2014-04-25Not applicableUs
Asmanex HFAAerosol50 ug/1Respiratory (inhalation)Merck Sharp & Dohme Corp.2019-08-12Not applicableUs
Asmanex TwisthalerPowderRespiratory (inhalation)Merck Ltd.2011-12-21Not applicableCanada
Asmanex TwisthalerPowderRespiratory (inhalation)Merck Ltd.2011-12-21Not applicableCanada
Asmanex TwisthalerPowderRespiratory (inhalation)Merck Ltd.2015-04-08Not applicableCanada
Elocom CreamCreamTopicalMerck Ltd.1991-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-mometasoneSpray, meteredNasalApotex Corporation2013-03-25Not applicableCanada
Mometasone FuroateCream1 mg/1gTopicalA-S Medication Solutions2008-05-28Not applicableUs
Mometasone FuroateOintment1 mg/1gTopicalPerrigo New York Inc2008-07-18Not applicableUs
Mometasone FuroateLotion1 mg/1gTopicalImpax Generics2007-11-212017-06-01Us
Mometasone FuroateOintment1 mg/1TopicalTorrent Pharmaceuticals Limited2018-07-13Not applicableUs
Mometasone FuroateOintment1 mg/1gTopicalRemedy Repack2017-01-25Not applicableUs
Mometasone FuroateSolution1 mg/1mLTopicalTaro Pharmaceuticals U.S.A., Inc.2006-03-15Not applicableUs
Mometasone FuroateOintment1 mg/1gTopicalAlmus2006-06-20Not applicableUs
Mometasone FuroateSolution1 mg/1mLTopicalHarris Pharmaceutical, Inc.2014-03-04Not applicableUs
Mometasone FuroateSolution1 mg/1mLTopicalGw Pharmaceuticals Ltd.2014-03-04Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MosaspraySpray, meteredNasalSandoz Canada Incorporated2016-06-17Not applicableCanada
Nasal Allergy and Congestion ReliefSpray, meteredNasalApotex CorporationNot applicableNot applicableCanada
Nasonex Allergy and CongestionSpray, meteredNasalMerck Ltd.Not applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DuleraMometasone furoate (200 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
DuleraMometasone furoate (100 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
DuleraMometasone furoate (200 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)A-S Medication Solutions2010-06-22Not applicableUs
DuleraMometasone furoate (50 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2019-08-12Not applicableUs
QuinixilMometasone furoate (1 mg/1g) + Dimethicone (50 mg/1g)KitTopicalV2 Pharma, LLC2019-06-03Not applicableUs
ZenhaleMometasone furoate (50 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)Merck Ltd.2011-06-20Not applicableCanada
ZenhaleMometasone furoate (200 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)Merck Ltd.2011-06-17Not applicableCanada
ZenhaleMometasone furoate (100 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)Merck Ltd.2011-03-10Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Hyaluronic Acid Sodium Salt 2% / Mometasone Furoate 0.1% / Niacinamide 4%Mometasone furoate (0.1 g/100g) + Hyaluronic acid (2 g/100g) + Nicotinamide (4 g/100g)CreamTopicalSincerus Florida, LLC2019-05-21Not applicableUs
Categories
UNII
04201GDN4R
CAS number
83919-23-7
Weight
Average: 521.429
Monoisotopic: 520.141944106
Chemical Formula
C27H30Cl2O6
InChI Key
WOFMFGQZHJDGCX-ZULDAHANSA-N
InChI
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
IUPAC Name
(1R,2R,3aS,3bS,9aS,9bR,10S,11aS)-9b-chloro-1-(2-chloroacetyl)-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl furan-2-carboxylate
SMILES
[H][C@@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@]([H])(O)C[C@]2(C)[C@@]1(OC(=O)C1=CC=CO1)C(=O)CCl

Pharmacology

Indication

There are 3 formulations of mometasone furoate with various indications. The inhaler is indicated for prophylaxis of asthma in patients ≥4 yearsLabel. The nasal spray is indicated for treating nasal symptoms of allergic rhinitis in patients ≥2 years, treating symptoms of nasal congestion from seasonal allergic rhinitis in patients ≥2 years, treating nasal polyps in patients ≥18 years, and prophylaxis of seasonal allergic rhinitis in patients ≥12 years10. The ointment is indicated for symptomatic treatment of dermatitis and pruritis in patients ≥2 years11.

Associated Conditions
Pharmacodynamics

Mometasone is a synthetic corticosteroid with an affinity for glucocorticoid receptors 22 times higher than that of dexamethasone2. Mometasone furoate also has a lower affinity to mineralocorticoid receptors than natural corticosteroids, making it more selective in its action2. Mometasone furoate diffuses across cell membranes to activate pathways responsible for reducing inflammationLabel1,2,3,10,11.

Mechanism of action

In asthma, mometasone is believed to inhibit mast cells, eosinophils, basophils, and lymphocytes3. There is also evidence of inhibition of histamine, leukotrienes, and cytokines3.

Corticosteroids diffuse across cell membranes into the cytosol of cells where they bind to glucocorticoid receptors to produce their activity2. Mometasone furoate has a particularly high receptor affinity compare to other corticosteroids, 22 times higher than that of dexamethasone2. Mometasone furoate binding to a glucocorticoid receptor causes conformational changes in the receptor, separation from chaperones, and the receptor moves to the nucleus3. Once at the nucleus, receptors dimerize and bind to a DNA sequence known as the glucocorticoid response element which either increases expression of anti-inflammatory molecules or inhibits expression of pro-inflammatory molecules (such as interleukins 4 and 5)3. Mometasone furoate also reduces inflammation by blocking transcription factors such as activator-protein-1 and nuclear factor kappa B (NF-kappaB)2,3.

TargetActionsOrganism
AGlucocorticoid receptorNot AvailableHumans
UProgesterone receptorNot AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The mean time to peak concentration is 1.0 to 2.5 hoursLabel. Bioavailability has been reported as <1%Label but studies of repeat doses of inhaled corticosteroids suggest a bioavailability of 11%3. The 0.1% ointment may have a bioavailability of 0.7%11.

Volume of distribution

Steady state volume of distribution of 152LLabel.

Protein binding

98% to 99% (in vitro concentration of 5 to 500ng/mL)Label10.

Metabolism

Metabolism of mometasone furoate is largely performed hepatically by cytochrome P450 3A4 producing a number of metabolitesLabel10,1,3. Some of these metabolites include free mometasone and 6-beta-hydroxy-mometasone furoate1,3,4.

Route of elimination

For an inhaled dose, approximately 74% is excreted in the feces and 8% is excreted in the urineLabel10.

Half life

The terminal half life of an inhaled dose is approximately 5 hoursLabel though it has been reported as 5.8 hours by other sources10,2.

Clearance

The clearance rate of mometasone furoate is not readily available1, though it may be close to 90L/h2.

Toxicity

Overdose with a mometasone furoate inhaler may occur with chronic overuseLabel10. Symptoms of chronic overuse may present as hypercorticism and adrenal suppression, and patients may not require any more treatment than monitoringLabel10.

In animal studies of pregnancy, some fetal toxic effects were seen at or above the maximum recommended human dose, though rodents are more sensitive to these effects than humansLabel10,11. The benefits and risks of use should be considered in pregnant patients10,11

It is unknown if mometasone furoate is excreted in breast milk but other corticosteroids are and therefore caution should be exercised when administering to nursing mothersLabel10,11.

Safety and effectiveness in pediatric populations has been established through clinical trials, though there may be a reduction in expected growth of about 1cm per year depending on the dose and duration of treatmentLabel. Pediatric patients should be titrated to the lowest effective dose for mometasone furoate inhalersLabel.

A trial of geriatric patients showed no difference in safety or efficacy compared to younger patients, however patients of an even greater age may still be more sensitive to mometasone furoateLabel10,11.

The use of a mometasone furoate inhaler in moderate or severe hepatic impairment rarely leads to detectable plasma concentrations though caution may be prudent with increasing degrees of severityLabel10.

The effects of mometasone furoate in renal impairment, and across gender and race have not been studiedLabel10.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinMometasone furoate may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinMometasone furoate may increase the anticoagulant activities of (S)-Warfarin.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Mometasone furoate.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Mometasone furoate.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Mometasone furoate.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Mometasone furoate.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Mometasone furoate.
1alpha,24S-Dihydroxyvitamin D2The therapeutic efficacy of 1alpha,24S-Dihydroxyvitamin D2 can be decreased when used in combination with Mometasone furoate.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Mometasone furoate.
2,4-thiazolidinedioneThe risk or severity of hyperglycemia can be increased when Mometasone furoate is combined with 2,4-thiazolidinedione.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Szefler SJ: Pharmacokinetics of intranasal corticosteroids. J Allergy Clin Immunol. 2001 Jul;108(1 Suppl):S26-31. [PubMed:11449203]
  2. Hubner M, Hochhaus G, Derendorf H: Comparative pharmacology, bioavailability, pharmacokinetics, and pharmacodynamics of inhaled glucocorticosteroids. Immunol Allergy Clin North Am. 2005 Aug;25(3):469-88. doi: 10.1016/j.iac.2005.05.004. [PubMed:16054538]
  3. Crim C, Pierre LN, Daley-Yates PT: A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate. Clin Ther. 2001 Sep;23(9):1339-54. [PubMed:11589253]
  4. Teng XW, Cutler DJ, Davies NM: Mometasone furoate degradation and metabolism in human biological fluids and tissues. Biopharm Drug Dispos. 2003 Nov;24(8):321-33. doi: 10.1002/bdd.362. [PubMed:14595701]
  5. FDA Approved Drug Products: Asmanex Mometasone Furoate Inhalation Powder [Link]
  6. FDA Approved Drug Products: Nasonex Mometasone Furoate Nasal Spray [Link]
  7. FDA Approved Drug Products: Elocon Mometasone Furoate Lotion [Link]
  8. FDA Approved Drug Products: Sinuva Mometasone Furoate Sinus Implant [Link]
  9. FDA Approved Drug Products: Elocon Mometasone Furoate Ointment [Link]
  10. Mometasone Furoate Nasonex FDA Label [File]
  11. Mometasone Furoate Elocon FDA Label [File]
External Links
KEGG Compound
C07817
ChemSpider
390091
BindingDB
50148733
ChEBI
47564
ChEMBL
CHEMBL1161
HET
MOF
Wikipedia
Mometasone_furoate
AHFS Codes
  • 68:04.00 — Adrenals
  • 84:06.00 — Anti-inflammatory Agents
  • 52:08.08 — Corticosteroids
PDB Entries
1sr7 / 4e2j / 4p6w
FDA label
Download (609 KB)
MSDS
Download (185 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentOtitis Media With Effusion1
1Active Not RecruitingTreatmentChronic Rhinosinusitis1
1Active Not RecruitingTreatmentSpinal Cord Injuries (SCI)1
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentAtopic Dermatitis (AD)1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
1CompletedTreatmentTreatment of the Signs and Symptoms of Seasonal Allergic Rhinitis1
1RecruitingOtherHypersensitivity1
1, 2CompletedNot AvailableSeasonal Allergic Rhinitis (SAR)1
2CompletedNot AvailablePsoriasis Vulgaris (Plaque Psoriasis)1
2CompletedTreatmentAcute Rhinosinusitis1
2CompletedTreatmentAirway Inflammation / Asthma1
2CompletedTreatmentAsthma9
2CompletedTreatmentAtopic Dermatitis (AD)1
2CompletedTreatmentChronic Rhinosinusitis1
2CompletedTreatmentPolyps, Nasal1
2CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2CompletedTreatmentRhinitis, Allergic, Perennial1
2CompletedTreatmentSeasonal Allergic Rhinitis (SAR)3
2CompletedTreatmentSickle Cell Disorders1
2Enrolling by InvitationTreatmentPolyps, Nasal1
2SuspendedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
2TerminatedTreatmentOesophagitis, Eosinophilic1
2WithdrawnTreatmentAsthma1
2, 3CompletedTreatmentChronic Rhinosinusitis / Polyps, Nasal1
3Active Not RecruitingTreatmentNasal Polyposis1
3Active Not RecruitingTreatmentPolyps, Nasal1
3CompletedNot AvailablePerennial Allergic Rhinitis (PAR)1
3CompletedSupportive CareBreast Cancer / Dermatologic Complications / Radiation Toxicity / Skin Reactions Secondary to Radiation Therapy1
3CompletedTreatmentAcute Rhinosinusitis1
3CompletedTreatmentAdenoids Hypertrophy1
3CompletedTreatmentAllergic Rhinitis (AR)4
3CompletedTreatmentAllergic Rhinitis (AR) / Asthma1
3CompletedTreatmentAllergies / Conjunctivitis / Rhinitis / Rhinoconjunctivitis2
3CompletedTreatmentAsthma9
3CompletedTreatmentAsthma / Chronic Obstructive Pulmonary Disease (COPD)1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
3CompletedTreatmentChronic Rhinosinusitis Phenotype With Nasal Polyps (CRSwNP) / Polyps, Nasal2
3CompletedTreatmentChronic Rhinosinusitis / Nasal Polyposis1
3CompletedTreatmentMild Asthma1
3CompletedTreatmentPerennial Allergic Rhinitis (PAR)4
3CompletedTreatmentPerennial Allergic Rhinitis (PAR) / Rhinitis, Allergic, Perennial1
3CompletedTreatmentPolyps, Nasal3
3CompletedTreatmentRhinitis, Allergic, Nonseasonal / Rhinitis, Allergic, Perennial1
3CompletedTreatmentRhinitis, Allergic, Perennial4
3CompletedTreatmentRhinitis, Allergic, Seasonal4
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR)8
3Not Yet RecruitingTreatmentAllergic Rhinitis (AR)2
3Unknown StatusNot AvailableItching / Nasal Obstruction / Sneezing1
3Unknown StatusTreatmentMild to Moderate Persistent Allergic Rhinitis1
3WithdrawnTreatmentAsthma1
3WithdrawnTreatmentObstructive Sleep Apnea (Mild, Moderate, Severe) as Per Polysomnography1
4Active Not RecruitingTreatmentSeasonal Allergic Rhinitis (SAR)1
4CompletedNot AvailableAtopic Dermatitis (AD)1
4CompletedOtherRhinitis, Allergic, Perennial and Seasonal1
4CompletedTreatmentAdenoidal Hypertrophy1
4CompletedTreatmentAdenoids1
4CompletedTreatmentAllergic Rhinitis (AR)4
4CompletedTreatmentAsthma6
4CompletedTreatmentAsthma / Rhinitis, Allergic, Seasonal1
4CompletedTreatmentAsthma / Rhinitis / Sinusitis1
4CompletedTreatmentObstructive Sleep Apnea (OSA) / Perennial Allergic Rhinitis (PAR) / Sleep Disorder1
4CompletedTreatmentPsoriasis1
4CompletedTreatmentSeasonal Allergic Rhinitis (SAR)2
4RecruitingHealth Services ResearchEarly Radiation Dermatitis1
4RecruitingTreatmentAllergic Rhinosinusitis / Chronic Eosinophilic Rhinosinusitis / Chronic Rhinosinusitis (Diagnosis)1
4TerminatedBasic SciencePolyps, Nasal1
4TerminatedTreatmentAdenoidectomy / Adenoids Hypertrophy / Nasal Obstruction1
4TerminatedTreatmentAsthma2
4TerminatedTreatmentPerennial Allergic Rhinitis (PAR)1
4TerminatedTreatmentSeasonal Allergic Rhinitis (SAR)1
4Unknown StatusTreatmentAsthma / Polyps, Nasal / Sinusitis1
4Unknown StatusTreatmentPhimosis1
4Unknown StatusTreatmentVitiligo2
4WithdrawnTreatmentEnuresis / Obstructive Sleep Apnea (OSA) / Sleep Disordered Breathing (SDB)1
Not AvailableCompletedNot AvailableAllergic Rhinitis (AR)1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableRhinitis, Allergic, Perennial / Rhinitis, Allergic, Seasonal1
Not AvailableCompletedNot AvailableSeasonal Allergic Rhinitis (SAR)1
Not AvailableCompletedOtherAsthma1
Not AvailableRecruitingNot AvailableAsthma1
Not AvailableRecruitingNot AvailableAsthma in Children1
Not AvailableRecruitingTreatmentObstructive Sleep Apnea Hypopnea Syndrome (OSAHS) and Malocclusion1
Not AvailableSuspendedTreatmentAsthma / Rhinitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InhalantRespiratory (inhalation)110 ug/1
InhalantRespiratory (inhalation)220 ug/1
AerosolRespiratory (inhalation)100 ug/1
AerosolRespiratory (inhalation)200 ug/1
AerosolRespiratory (inhalation)50 ug/1
PowderRespiratory (inhalation)
AerosolRespiratory (inhalation)
CreamTopical
OintmentTopical
CreamTopical1 mg/1g
OintmentTopical1 mg/1g
CreamTopical
CreamTopical1 g/100g
LotionTopical1 mg/1mL
LotionTopical1 mg/1g
OintmentTopical1 mg/1
SolutionTopical1 mg/1mL
Spray, meteredNasal50 mcg
Spray, meteredNasal50 ug/1
Spray, meteredNasal
LotionTopical
KitTopical
ImplantIntrasinal1350 ug/1
Aerosol, meteredRespiratory (inhalation)
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6127353Yes2000-10-032018-04-03Us
US6240918Yes2001-06-052017-08-20Us
US8173172Yes2012-05-082018-09-17Us
US6503537Yes2003-01-072018-09-17Us
US5829434Yes1998-11-032016-05-03Us
US6068832No2000-05-302017-08-27Us
US7067502Yes2006-06-272020-11-21Us
US7566705Yes2009-07-282020-11-21Us
US8109918No2012-02-072024-03-12Us
US7951131No2011-05-312024-03-12Us
US8025635No2011-09-272027-06-12Us
US9585681No2017-03-072026-04-04Us
US7951130No2011-05-312024-03-12Us
US7544192No2009-06-092026-11-29Us
US7951133No2011-05-312024-03-12Us
US7713255No2010-05-112024-03-12Us
US7662141No2010-02-162024-03-12Us
US8763222No2014-07-012032-02-08Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)215-228Not Available
water solubilityInsolubleNot Available
logP4.115Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0108 mg/mLALOGPS
logP4.27ALOGPS
logP5.06ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area93.81 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity132.5 m3·mol-1ChemAxon
Polarizability52.57 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03mj-3891000000-64a4294ec7bf5ac82d6c

Taxonomy

Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Steroid esters / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Furoic acid esters / Alpha-chloroketones / Heteroaromatic compounds / Secondary alcohols
show 10 more
Substituents
Progestogin-skeleton / 20-oxosteroid / Steroid ester / Halo-steroid / Hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Oxosteroid / 11-hydroxysteroid
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, 11beta-hydroxy steroid, steroid ester, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, 2-furoate ester (CHEBI:47564)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Isogai M, Shimizu H, Esumi Y, Terasawa T, Okada T, Sugeno K: Binding affinities of mometasone furoate and related compounds including its metabolites for the glucocorticoid receptor of rat skin tissue. J Steroid Biochem Mol Biol. 1993 Feb;44(2):141-5. [PubMed:8439518]
  2. Lumry WR: A review of the preclinical and clinical data of newer intranasal steroids used in the treatment of allergic rhinitis. J Allergy Clin Immunol. 1999 Oct;104(4 Pt 1):S150-8. [PubMed:10518812]
  3. Smith CL, Kreutner W: In vitro glucocorticoid receptor binding and transcriptional activation by topically active glucocorticoids. Arzneimittelforschung. 1998 Sep;48(9):956-60. [PubMed:9793625]
  4. Zhang X, Moilanen E, Adcock IM, Lindsay MA, Kankaanranta H: Divergent effect of mometasone on human eosinophil and neutrophil apoptosis. Life Sci. 2002 Aug 16;71(13):1523-34. [PubMed:12127907]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Mometasone Furoate Twisthaler Label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Madauss KP, Deng SJ, Austin RJ, Lambert MH, McLay I, Pritchard J, Short SA, Stewart EL, Uings IJ, Williams SP: Progesterone receptor ligand binding pocket flexibility: crystal structures of the norethindrone and mometasone furoate complexes. J Med Chem. 2004 Jun 17;47(13):3381-7. [PubMed:15189034]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Berger WE, Milgrom H, Chervinsky P, Noonan M, Weinstein SF, Lutsky BN, Staudinger H: Effects of treatment with mometasone furoate dry powder inhaler in children with persistent asthma. Ann Allergy Asthma Immunol. 2006 Nov;97(5):672-80. doi: 10.1016/S1081-1206(10)61099-X. [PubMed:17165278]
  2. Sharpe M, Jarvis B: Inhaled mometasone furoate: a review of its use in adults and adolescents with persistent asthma. Drugs. 2001;61(9):1325-50. [PubMed:11511026]
  3. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [PubMed:20482443]

Drug created on July 12, 2018 09:10 / Updated on November 12, 2019 22:54