MOMETASONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28Cl2O4
Molecular Weight	427.361
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]3(Cl)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

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
Sources: http://www.drugbank.ca/drugs/DB00764
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00764	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatoses 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019796s026lbl.pdf	Primary		Approved 8429	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 1987
Asthma 241 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021067s013lbl.pdf	Preventing		Approved 8429	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 2005

C_max

Value	Dose	Co-administered	Analyte	Population
183 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26845343	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29669668	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

Value	Dose	Co-administered	Analyte	Population
1560 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26845343	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29669668	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
19.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29669668	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020762s053lbl.pdf			MOMETASONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	Other AEs: Pruritus, Skin atrophy... Other AEs: Pruritus (4.8%) Skin atrophy (4.8%) Tingling (4.8%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf	unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019543s024lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911	BCRP 561 P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/ Page: 6.0	yes [IC50 0.327 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16442095/	likely
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16442095/	likely
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205641Orig1s000ClinPharmR.pdf#page=22 Page: 22,23	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) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205641Orig1s000ClinPharmR.pdf#page=22 Page: 22,23

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6970	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6970
ZINC	ZINC000004097440	http://zinc15.docking.org/substances/ZINC000004097440

PubMed

Title	Date	PubMed
Efficacy and safety of ketotifen eye drops as adjunctive therapy to mometasone nasal spray in subjects with seasonal allergic rhinoconjunctivitis.	2003	17535073
Eosinophilic airway inflammation in COPD.	2006	18046901
Cough and its importance in COPD.	2006	18046867
The benefits of combined treatment with corticosteroids and long-acting beta agonists.	2006	18046857
Pharmacological treatment of chronic obstructive pulmonary disease.	2006	18044097
Future therapeutic treatment of COPD: struggle between oxidants and cytokines.	2007	18229560
Exogenous Cushing syndrome with inhaled fluticasone in a child receiving lopinavir/ritonavir.	2007 Jul	17535841
Seborrhoeic dermatitis.	2007 Jul 1	19454093
Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate.	2007 Jul 25	17650349
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	17882923
Montelukast in the management of allergic rhinitis.	2007 Jun	18360641
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	17533178
Synergistic effect of formoterol and mometasone in a mouse model of allergic lung inflammation.	2007 Sep	17618304
Onset and duration of action of nasal sprays in seasonal allergic rhinitis patients: olopatadine hydrochloride versus mometasone furoate monohydrate.	2007 Sep-Oct	18034980
[Patient preference survey on the lack of taste and odor of Nasonex nasal spray. Which impact on compliance to treatment?].	2008	18777767
Airways inflammation and treatment during acute exacerbations of COPD.	2008	18686731
Vancomycin-induced DRESS syndrome in a female patient.	2008	18607115
New treatment options in allergic rhinitis: patient considerations and the role of ciclesonide.	2008 Apr	18728855
New approaches to managing asthma: a US perspective.	2008 Apr	18728834
Long-term follow-up of children undergoing topical intranasal steroid therapy for adenoidal hypertrophy.	2008 Aug	18499270
Effect of allergic rhinitis on the use and cost of health services by children with asthma.	2008 Aug 30	18729293
Mometasone furoate in the management of asthma: a review.	2008 Dec	19337427
Foxp3+ T regulatory cells (Tregs) are increased in nasal polyps (NP) after treatment with intranasal steroid.	2008 Dec	18793874
A prospective clinical review of "multi model" approach for treating ear keloids.	2008 Jan	19753193
Relative oral corticosteroid-sparing effect of 7 inhaled corticosteroids in chronic asthma: a meta-analysis.	2008 Jul	18681088
Chronic hypokalemia due to excessive cola consumption: a case report.	2008 Jul 14	18625064
Expression of chloride channel protein CLC-3 in patients with allergic rhinitis: effect of topical corticosteroid treatment.	2008 Mar	18347257
[The effect of desloratadine on quality of life of patients with seasonal allergic rhinitis].	2008 May	18720881
Antibacterial activity of mometasone furoate.	2008 May	18490574
One-year treatment with mometasone furoate in chronic obstructive pulmonary disease.	2008 Nov 13	19014549
Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis.	2008 Oct	19209282
Effect of illicit direct to consumer advertising on use of etanercept, mometasone, and tegaserod in Canada: controlled longitudinal study.	2008 Sep 2	18765444
Comparative adrenocortical suppression in dogs with otitis externa following topical otic administration of four different glucocorticoid-containing medications.	2008 Summer	18597249
Local cytokines and clinical symptoms in children with allergic rhinitis after different treatments.	2009	19851472
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	19591513
Bronchial diffusing capacity of nitric oxide is increased in patients with allergic rhinitis.	2009	18802360
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	19671372
Mometasone furoate: an inhaled glucocorticoid for the management of asthma in adults and children.	2009 Aug	19618993
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	20015903
Using nasal steroids to treat nasal obstruction caused by adenoid hypertrophy: does it work?	2009 Feb	19201278
Inhaled corticosteroids for asthma: are they all the same?	2009 Feb	19125898
Inhaled corticosteroids for asthma: impact of practice level device switching on asthma control.	2009 Jan 2	19121204
Use of mometasone furoate to prevent polyp relapse after endoscopic sinus surgery.	2009 Mar	19289710
Twelve years' experience with direct-to-consumer advertising of prescription drugs in Canada: a cautionary tale.	2009 May 27	19479084
Effect of the inhaled corticosteroid mometasone on small airway patency in patients with asthma.	2009 May-Jun	19549430
Treatment of postviral olfactory loss with glucocorticoids, Ginkgo biloba, and mometasone nasal spray.	2009 Oct	19841338
Drugs associated with more suicidal ideations are also associated with more suicide attempts.	2009 Oct 2	19798416
Alitretinoin--its use in intractable hand eczema and other potential indications.	2009 Sep 21	19920921
Mapping analyses to estimate health utilities based on responses to the OM8-30 Otitis Media Questionnaire.	2010 Feb	19941078
Allergic contact dermatitis to inhalation corticosteroids.	2010 Jan-Feb	19825528

Patents

Sample Use Guides

In Vivo Use Guide

Apply a few drops to the affected skin areas once daily and massage lightly until it disappears.

Route of Administration: Topical

In Vitro Use Guide

Mac-1 expression and human eosinophil migration were effectively downregulated by preincubation with Mometasone at 1, 10 and 100 nM

Name

Type

Language

MOMETASONE

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

MOMETASONE FUROATE IMPURITY G [EP IMPURITY]

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 [WHO-DD]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 524.957