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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28Cl2O4
Molecular Weight 427.362
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOMETASONE

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)O)O)Cl

InChI

InChIKey=QLIIKPVHVRXHRI-CXSFZGCWSA-N
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

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
Efficacy and safety of ketotifen eye drops as adjunctive therapy to mometasone nasal spray in subjects with seasonal allergic rhinoconjunctivitis.
2003
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
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
Efficacy of betamethasone valerate mousse in comparison with standard therapies on scalp psoriasis: an open, multicentre, randomized, controlled, cross-over study on 241 patients.
2003 Jan
Montelukast as an adjuvant to mainstay therapies in patients with seasonal allergic rhinitis.
2003 Jun
Features of mometasone furoate nasal spray and its utility in the management of allergic rhinitis.
2003 Sep
Safety and tolerability of treatments for allergic rhinitis in children.
2004
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
[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
Eosinophilic airway inflammation in COPD.
2006
Cough and its importance in COPD.
2006
The benefits of combined treatment with corticosteroids and long-acting beta agonists.
2006
Pharmacological treatment of chronic obstructive pulmonary disease.
2006
Alternative therapies in antibiotic-resistant infection.
2006
Antimicrobial silk clothing in the treatment of atopic dermatitis proves comparable to topical corticosteroid treatment.
2006
The glucocorticoid RU24858 does not distinguish between transrepression and transactivation in primary human eosinophils.
2006 Jul 12
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
Plasma concentrations of inhaled corticosteroids in relation to airflow obstruction in asthma.
2006 Oct
Cross-reactions to desoximetasone and mometasone furoate in a patient with multiple topical corticosteroid allergies.
2006 Sep
Future therapeutic treatment of COPD: struggle between oxidants and cytokines.
2007
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
Montelukast in the management of allergic rhinitis.
2007 Jun
The role of mometasone furoate aqueous nasal spray in the treatment of adenoidal hypertrophy in the pediatric age group: preliminary results of a prospective, randomized study.
2007 Jun
Synergistic effect of formoterol and mometasone in a mouse model of allergic lung inflammation.
2007 Sep
Onset and duration of action of nasal sprays in seasonal allergic rhinitis patients: olopatadine hydrochloride versus mometasone furoate monohydrate.
2007 Sep-Oct
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
Long-term follow-up of children undergoing topical intranasal steroid therapy for adenoidal hypertrophy.
2008 Aug
A prospective clinical review of "multi model" approach for treating ear keloids.
2008 Jan
Relative oral corticosteroid-sparing effect of 7 inhaled corticosteroids in chronic asthma: a meta-analysis.
2008 Jul
Chronic hypokalemia due to excessive cola consumption: a case report.
2008 Jul 14
Expression of chloride channel protein CLC-3 in patients with allergic rhinitis: effect of topical corticosteroid treatment.
2008 Mar
[The effect of desloratadine on quality of life of patients with seasonal allergic rhinitis].
2008 May
Antibacterial activity of mometasone furoate.
2008 May
Comparative adrenocortical suppression in dogs with otitis externa following topical otic administration of four different glucocorticoid-containing medications.
2008 Summer
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
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
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
INN   VANDF   WHO-DD  
INN  
Official Name English
LAS-41002
Code English
9,21-DICHLORO-11.BETA.,17-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE
Systematic Name English
LAS41002
Code English
MOMETASONE [VANDF]
Common Name English
MOMETASONE [INN]
Common Name English
(+)-MOMETASONE
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 9,21-DICHLORO-11,17-DIHYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)-
Systematic Name English
MONOVO
Brand Name English
MOMETASONE FUROATE IMPURITY G [EP]
Common Name English
MOMETASONE [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.957
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
NDF-RT N0000175450
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-VATC QR03BA07
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-ATC D07AC13
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-ATC R03AK09
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
NCI_THESAURUS C211
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-VATC QR01AD09
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-ATC R01AD09
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-VATC QS02CA91
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-VATC QR03AK09
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-VATC QD07AC13
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
NDF-RT N0000175576
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-ATC R03BA07
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-ATC D07XC03
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
CFR 21 CFR 524.1044H
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
WHO-VATC QD07XC03
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
Code System Code Type Description
MESH
C053915
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
INN
6030
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
NCI_THESAURUS
C66181
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
FDA UNII
8HR4QJ6DW8
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
LACTMED
Mometasone, Nasal
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
PUBCHEM
441335
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
RXCUI
108118
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00764
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
CAS
105102-22-5
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
EPA CompTox
105102-22-5
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL1161
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
EVMPD
SUB09045MIG
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
WIKIPEDIA
MOMETASONE
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY
LACTMED
Mometasone, Topical
Created by admin on Fri Jun 25 20:34:50 UTC 2021 , Edited by admin on Fri Jun 25 20:34:50 UTC 2021
PRIMARY