MOMETASONE FUROATE MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H30Cl2O6.H2O
Molecular Weight	539.445
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of MOMETASONE FUROATE MONOHYDRATE

Structure Search

SMILES

O.[H][C@@]12C[C@@H](C)[C@](OC(=O)C3=CC=CO3)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]4(Cl)[C@@]2([H])CCC5=CC(=O)C=C[C@]45C

InChI

InChIKey=AQCCVUHZMIMSIB-HRVPQZBTSA-N

InChI=1S/C27H30Cl2O6.H2O/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;1H2/t15-,18+,19+,21+,24+,25+,26+,27+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C27H30Cl2O6
Molecular Weight	521.429
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 2637

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatoses 23 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019796s026lbl.pdf	Primary		Approved 8307	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
Asthma 234 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021067s013lbl.pdf	Preventing		Approved 8307	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

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 1670

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 869	BCRP 545 P-gp 1491

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C8 923	inhibitor 3185 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 545	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/16442095/	likely
P-gp 1491	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/16442095/	likely
CYP3A4 1670	substrate 3264 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
A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate.	2001 Sep	11589253
Efficacy of budesonide in moderate to severe asthma.	2002 Jun	12117080
[Allergic contact eczema caused by henna tattoo].	2002 Sep-Oct	12396964
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	14512132
Comparison of the flow properties of aqueous suspension corticosteroid nasal sprays under differing sampling conditions.	2003 Oct	14606664
[Effects of systemic or topical administration of corticosteroids and vitamin B in patients with olfactory loss].	2004 Nov	15538662
Effects of inhaled corticosteroids on bone.	2005 Jan	15702810
Pimecrolimus permeates less than tacrolimus through normal, inflamed, or corticosteroid-pretreated skin.	2005 Oct	16176283
Alternative therapies in antibiotic-resistant infection.	2006	17357317
Antimicrobial silk clothing in the treatment of atopic dermatitis proves comparable to topical corticosteroid treatment.	2006	17033173
The glucocorticoid RU24858 does not distinguish between transrepression and transactivation in primary human eosinophils.	2006 Jul 12	16834783
Novel insights into the aetiology and pathophysiology of increased airway inflammation during COPD exacerbations.	2006 May 22	16716229
Future therapeutic treatment of COPD: struggle between oxidants and cytokines.	2007	18229560
Pathological features and inhaled corticosteroid response of eosinophilic and non-eosinophilic asthma.	2007 Dec	17356056
Evidence-based selection of inhaled corticosteroid for treatment of chronic asthma.	2007 Jan-Feb	17365197
Seborrhoeic dermatitis.	2007 Jul 1	19454093
Airways inflammation and treatment during acute exacerbations of COPD.	2008	18686731
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
Effect of allergic rhinitis on the use and cost of health services by children with asthma.	2008 Aug 30	18729293
Relative oral corticosteroid-sparing effect of 7 inhaled corticosteroids in chronic asthma: a meta-analysis.	2008 Jul	18681088
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
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
Effect of the inhaled corticosteroid mometasone on small airway patency in patients with asthma.	2009 May-Jun	19549430

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

Substance Class	Chemical Created by `admin` on `Fri Dec 16 18:45:33 UTC 2022` Edited by `admin` on `Fri Dec 16 18:45:33 UTC 2022`
Record UNII	MTW0WEG809
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MOMETASONE FUROATE MONOHYDRATE

Common Name

English

NASONEX

Brand Name

English

Mometasone furoate monohydrate [WHO-DD]

Common Name

English

MOMETASONE FUROATE MONOHYDRATE [VANDF]

Common Name

English

MOMETASONE FUROATE MONOHYDRATE [EP MONOGRAPH]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 9,21-DICHLORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-, HYDRATE (1:1), (11.BETA.,16.ALPHA.)-

Common Name

English

MOMETASONE FUROATE MONOHYDRATE [GREEN BOOK]

Common Name

English

RYALTRIS COMPONENT MOMETASONE FUROATE MONOHYDRATE

Brand Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 9,21-DICHLORO-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)-MONOHYDRATE

Common Name

English

MOMETASONE FUROATE HYDRATE [JAN]

Common Name

English

MOMETASONE FUROATE MONOHYDRATE [MI]

Common Name

English

MOMETASONE FUROATE MONOHYDRATE [ORANGE BOOK]

Common Name

English

MOMETASONE FUROATE HYDRATE

Common Name

English

MOMETASONE FUROATE MONOHYDRATE COMPONENT OF RYALTRIS

Brand Name

English

MOMETASONE FUROATE (AS MONOHYDRATE)

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 524.1610