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

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
A review of the pharmacology and pharmacokinetics of inhaled fluticasone propionate and mometasone furoate.	2001 Sep	11589253
Mediator antagonists in the treatment of allergic disease.	2001 Sep-Oct	11715214
A comparison of nasal clearance after treatment of perennial allergic rhinitis with budesonide and mometasone.	2003 Feb	12601318
Systemic bioactivity of intranasal triamcinolone and mometasone in perennial allergic rhinitis.	2003 Mar	12630983
Comparison of the flow properties of aqueous suspension corticosteroid nasal sprays under differing sampling conditions.	2003 Oct	14606664
Pharmaceutical characteristics that influence the clinical efficacy of inhaled corticosteroids.	2003 Oct	14582810
Local and systemic administration of corticosteroids in the treatment of olfactory loss.	2004 Jan-Feb	15035568
The benefits of combined treatment with corticosteroids and long-acting beta agonists.	2006	18046857
Inhaled corticosteroids in children with asthma: pharmacologic determinants of safety and efficacy and other clinical considerations.	2007	17523699
Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate.	2007 Jul 25	17650349
Onset and duration of action of nasal sprays in seasonal allergic rhinitis patients: olopatadine hydrochloride versus mometasone furoate monohydrate.	2007 Sep-Oct	18034980
Relative oral corticosteroid-sparing effect of 7 inhaled corticosteroids in chronic asthma: a meta-analysis.	2008 Jul	18681088
One-year treatment with mometasone furoate in chronic obstructive pulmonary disease.	2008 Nov 13	19014549
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
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
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

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 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