U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30Cl2O6
Molecular Weight 521.4304
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOMETASONE FUROATE

SMILES

C[C@]1([H])C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@]3([C@]([H])(C[C@]2(C)[C@]1(C(=O)CCl)OC(=O)c5ccco5)O)Cl

InChI

InChIKey=WOFMFGQZHJDGCX-ZULDAHANSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019796s026lbl.pdf

Mometasone is a medium-potency synthetic corticosteroid with antiinflammatory, antipruritic, and vasoconstrictive properties. Studies in asthmatic patients have demonstrated that mometasone provides a favorable ratio of topical to systemic activity due to its primary local effect along with the extensive hepatic metabolism and the lack of active metabolites. Though effective for the treatment of asthma, glucocorticoids do not affect asthma symptoms immediately. Maximum improvement in symptoms following inhaled administration of mometasone furoate may not be achieved for 1 to 2 weeks or longer after starting treatment. When glucocorticoids are discontinued, asthma stability may persist for several days or longer. Mometasone has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 12 times that of dexamethasone, 7 times that of triamcinolone acetonide, 5 times that of budesonide, and 1.5 times that of fluticasone. Mometasone inhaler is indicated for the maintenance treatment of asthma as prophylactic therapy. The nasal spray is indicated for the treatment of the nasal symptoms of seasonal allergic and perennial allergic rhinitis. ELOCON Lotion (Mometasone) is indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ELOCON

Approved Use

ELOCON Lotion is a corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients ≥12 years of age.

Launch Date

5.47171205E11
Preventing
ASMANEX

Approved Use

ASMANEX TWISTHALER is a corticosteroid indicated for: • Maintenance treatment of asthma as prophylactic therapy in patients 4 years of age and older.

Launch Date

1.11205443E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
183 pg/mL
320 μg 1 times / day steady-state, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.56 pg/mL
100 μg single, nasal
dose: 100 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1560 pg × h/mL
320 μg 1 times / day steady-state, respiratory
dose: 320 μg
route of administration: Respiratory
experiment type: STEADY-STATE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
92 pg × h/mL
100 μg single, nasal
dose: 100 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
19.24 h
100 μg single, nasal
dose: 100 μg
route of administration: Nasal
experiment type: SINGLE
co-administered:
MOMETASONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1.5%
MOMETASONE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
Other AEs: Glucocorticoid decreased, Skin and subcutaneous conditions NEC...
Other AEs:
Glucocorticoid decreased (1 patient)
Skin and subcutaneous conditions NEC (1 patient)
Skin bacterial infection (1 patient)
Sources:
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
Other AEs: Pruritus, Skin atrophy...
Other AEs:
Pruritus (4.8%)
Skin atrophy (4.8%)
Tingling (4.8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Glucocorticoid decreased 1 patient
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
Skin and subcutaneous conditions NEC 1 patient
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
Skin bacterial infection 1 patient
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, 0.5 - 2 yeas
n = 63
Health Status: unhealthy
Condition: dermatoses
Age Group: 0.5 - 2 yeas
Sex: unknown
Population Size: 63
Sources:
Pruritus 4.8%
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
Skin atrophy 4.8%
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
Tingling 4.8%
0.1 % 1 times / day steady, topical
Recommended
Dose: 0.1 %, 1 times / day
Route: topical
Route: steady
Dose: 0.1 %, 1 times / day
Sources:
unhealthy, adult
n = 812
Health Status: unhealthy
Condition: dermatoses
Age Group: adult
Sex: unknown
Population Size: 812
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.327 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
yes
unlikely (co-administration study)
Comment: ketoconazole 200 mg (as well as placebo) were given twice daily concomitantly on Days 4 to 9. Mometasone furoate plasma concentrations were <150 pcg/mL on Day 3 prior to coadministration of ketoconazole or placebo. Following concomitant administration of ketoconazole, 4 out of 12 subjects in the ketoconazole treatment group (n=12) had peak plasma concentrations of mometasone furoate >200 pcg/mL on Day 9 (211-324 pcg/mL)
Page: 22,23
PubMed

PubMed

TitleDatePubMed
Safety of the newer inhaled corticosteroids in childhood asthma.
2003
Relief of cough and nasal symptoms associated with allergic rhinitis by mometasone furoate nasal spray.
2003 Apr
A prospective study on the efficacy of mometasone furoate monohydrate aqueous nasal spray on Chinese patients with allergic rhinitis.
2003 Apr
Randomized, double-masked comparison of olopatadine ophthalmic solution, mometasone furoate monohydrate nasal spray, and fexofenadine hydrochloride tablets using the conjunctival and nasal allergen challenge models.
2003 Aug
A comparison of nasal clearance after treatment of perennial allergic rhinitis with budesonide and mometasone.
2003 Feb
Montelukast as an adjuvant to mainstay therapies in patients with seasonal allergic rhinitis.
2003 Jun
Systemic bioactivity of intranasal triamcinolone and mometasone in perennial allergic rhinitis.
2003 Mar
Intranasal steroid sprays in the treatment of rhinitis: is one better than another?
2003 Nov
Differential modulation of glucocorticoid action by FK506 in A549 cells.
2003 Nov 15
Pharmaceutical characteristics that influence the clinical efficacy of inhaled corticosteroids.
2003 Oct
Features of mometasone furoate nasal spray and its utility in the management of allergic rhinitis.
2003 Sep
Influence of preservatives and topical steroids on ciliary beat frequency in vitro.
2004 Apr
State and trait anxiety in patients affected by nasal polyposis before and after medical treatment.
2004 Dec
Local and systemic administration of corticosteroids in the treatment of olfactory loss.
2004 Jan-Feb
Significant receptor affinities of metabolites and a degradation product of mometasone furoate.
2004 Jul 22
[Effects of systemic or topical administration of corticosteroids and vitamin B in patients with olfactory loss].
2004 Nov
Add-on therapy options in asthma not adequately controlled by inhaled corticosteroids: a comprehensive review.
2004 Oct 27
Nasal allergies and beyond: a clinical review of the pharmacology, efficacy, and safety of mometasone furoate.
2005
Hydrocortisone butyrate 0.1% cream in the treatment of chronic dermatitis.
2005 Feb
Effects of inhaled corticosteroids on bone.
2005 Jan
Effects of mometasone furoate on a rat allergic rhinitis model.
2005 Nov 7
Cough and its importance in COPD.
2006
Alternative therapies in antibiotic-resistant infection.
2006
Antimicrobial silk clothing in the treatment of atopic dermatitis proves comparable to topical corticosteroid treatment.
2006
Differences in the glucocorticoid to progesterone receptor selectivity of inhaled glucocorticoids.
2006 Mar
Mometasone and beclomethasone comparison article observations.
2006 May
Novel insights into the aetiology and pathophysiology of increased airway inflammation during COPD exacerbations.
2006 May 22
Inhaled corticosteroids in children with asthma: pharmacologic determinants of safety and efficacy and other clinical considerations.
2007
Pathological features and inhaled corticosteroid response of eosinophilic and non-eosinophilic asthma.
2007 Dec
Evidence-based selection of inhaled corticosteroid for treatment of chronic asthma.
2007 Jan-Feb
Exogenous Cushing syndrome with inhaled fluticasone in a child receiving lopinavir/ritonavir.
2007 Jul
Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate.
2007 Jul 25
Onset of action of azelastine nasal spray compared with mometasone nasal spray and placebo in subjects with seasonal allergic rhinitis evaluated in an environmental exposure chamber.
2007 Jul-Aug
Airways inflammation and treatment during acute exacerbations of COPD.
2008
Vancomycin-induced DRESS syndrome in a female patient.
2008
New approaches to managing asthma: a US perspective.
2008 Apr
Expression of chloride channel protein CLC-3 in patients with allergic rhinitis: effect of topical corticosteroid treatment.
2008 Mar
Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis.
2008 Oct
Local cytokines and clinical symptoms in children with allergic rhinitis after different treatments.
2009
Comparison of corticosteroid nasal sprays in relation to concomitant use and cost of other prescription medications to treat allergic rhinitis symptoms: retrospective cohort analysis of pharmacy claims data.
2009
A double-blind randomised placebo-controlled trial of topical intranasal corticosteroids in 4- to 11-year-old children with persistent bilateral otitis media with effusion in primary care.
2009 Aug
Mometasone furoate: an inhaled glucocorticoid for the management of asthma in adults and children.
2009 Aug
Topical intranasal corticosteroids in 4-11 year old children with persistent bilateral otitis media with effusion in primary care: double blind randomised placebo controlled trial.
2009 Dec 16
Inhaled corticosteroids for asthma: are they all the same?
2009 Feb
Effect of the inhaled corticosteroid mometasone on small airway patency in patients with asthma.
2009 May-Jun
Treatment of postviral olfactory loss with glucocorticoids, Ginkgo biloba, and mometasone nasal spray.
2009 Oct
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Alitretinoin--its use in intractable hand eczema and other potential indications.
2009 Sep 21
Mapping analyses to estimate health utilities based on responses to the OM8-30 Otitis Media Questionnaire.
2010 Feb
Allergic contact dermatitis to inhalation corticosteroids.
2010 Jan-Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Can also be used as inhalation powder http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021067s013lbl.pdf
Apply a few drops to the affected skin areas once daily and massage lightly until it disappears.
Route of Administration: Topical
Mac-1 expression and human eosinophil migration were effectively downregulated by preincubation with Mometasone at 1, 10 and 100 nM
Name Type Language
MOMETASONE FUROATE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
MOMETASONE FUROATE [EP MONOGRAPH]
Common Name English
(11.BETA.,16.ALPHA.)-9,21-DICHLORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Common Name English
SINUVA
Brand Name English
LYR-210
Code English
9,21-DICHLORO-11.BETA.,17-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE 17-(2-FUROATE)
Common Name English
MOMETASONE FUROATE [USP MONOGRAPH]
Common Name English
MOMETASONE FUROATE [ORANGE BOOK]
Common Name English
SCH 32088
Code English
MOMETASONE FUROATE [WHO-DD]
Common Name English
MOMETASONE FUROATE COMPONENT OF DULERA
Common Name English
SCH-32088
Code English
MOMETASONE FUROATE [USAN]
Common Name English
MOMETASONE FUROATE [USP-RS]
Common Name English
ASMANEX
Brand Name English
MOMETASONE FUROATE [JAN]
Common Name English
DULERA COMPONENT MOMETASONE FUROATE
Common Name English
MOMETASONE FUROATE [GREEN BOOK]
Common Name English
MOMETASONE FUROATE ANHYDROUS
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 9,21-DICHLORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)
Common Name English
ELOCON
Brand Name English
NSC-760077
Code English
LYR210
Code English
MOMETASONE FUROATE [VANDF]
Common Name English
MOMETASONE FUROATE [MART.]
Common Name English
NSC-746171
Code English
MOMETASONE FUROATE [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 691019
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
NCI_THESAURUS C29505
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
Code System Code Type Description
FDA UNII
04201GDN4R
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
EVMPD
SUB166214
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
EPA CompTox
83919-23-7
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
CAS
83919-23-7
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
EVMPD
SUB03318MIG
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL1161
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
WIKIPEDIA
MOMETASONE FUROATE
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
MERCK INDEX
M7597
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY Merck Index
RXCUI
30145
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY RxNorm
PUBCHEM
441336
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
NCI_THESAURUS
C29268
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
DRUG CENTRAL
1832
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY
USP_CATALOG
1445470
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB14512
Created by admin on Fri Jun 25 20:34:09 UTC 2021 , Edited by admin on Fri Jun 25 20:34:09 UTC 2021
PRIMARY