Identification

Name
Mometasone furoate
Accession Number
DB14512  (DBSALT002454)
Type
Small Molecule
Groups
Approved, Vet approved
Description
Not Available
Structure
Thumb
Synonyms
  • Mometasone furoate anhydrous
External IDs
SCH 32088 / SCH-32088
Product Ingredients
IngredientUNIICASInChI Key
Mometasone furoate monohydrateMTW0WEG809141646-00-6AQCCVUHZMIMSIB-HRVPQZBTSA-N
Active Moieties
NameKindUNIICASInChI Key
Mometasoneprodrug8HR4QJ6DW8105102-22-5QLIIKPVHVRXHRI-CXSFZGCWSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AsmanexInhalant220 ug/1Respiratory (inhalation)Physicians Total Care, Inc.2006-03-09Not applicableUs
AsmanexInhalant110 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2005-03-30Not applicableUs
AsmanexInhalant220 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2005-03-30Not applicableUs
Asmanex HFAAerosol200 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2014-04-25Not applicableUs
Asmanex HFAAerosol100 ug/1Respiratory (inhalation)Merck Sharp & Dohme Limited2014-04-25Not applicableUs
Asmanex TwisthalerPowder400 mcgRespiratory (inhalation)Merck Ltd.2011-12-21Not applicableCanada
Asmanex TwisthalerPowder200 mcgRespiratory (inhalation)Merck Ltd.2011-12-21Not applicableCanada
Asmanex TwisthalerPowder100 mcgRespiratory (inhalation)Merck Ltd.2015-04-08Not applicableCanada
Elocom CreamCream0.1 %TopicalMerck Ltd.1991-12-31Not applicableCanada
Elocom LotionLotion0.1 %TopicalMerck Ltd.1991-12-31Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-mometasoneSpray, metered50 mcgNasalApotex Corporation2013-03-25Not applicableCanada
Mometasone FuroateCream1 mg/1gTopicalA-S Medication Solutions2004-12-212017-05-31Us
Mometasone FuroateCream1 mg/1gTopicalSandoz2007-04-182014-09-30Us
Mometasone FuroateOintment1 mg/1gTopicalAlmus2006-06-20Not applicableUs
Mometasone FuroateCream1 mg/1gTopicalA-S Medication Solutions2008-05-28Not applicableUs
Mometasone FuroateCream1 mg/1gTopicalNucare Pharmaceuticals,inc.2008-05-28Not applicableUs
Mometasone FuroateCream1 mg/1gTopicalRebel Distributors2006-08-23Not applicableUs
Mometasone FuroateSpray, metered50 ug/1NasalAmneal Pharmaceuticals2017-04-04Not applicableUs
Mometasone FuroateCream1 mg/1gTopicalA-S Medication Solutions2006-08-23Not applicableUs
Mometasone FuroateSolution1 mg/1mLTopicalPhysicians Total Care, Inc.2006-03-30Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MosaspraySpray, metered50 mcgNasalSandoz Canada IncorporatedNot applicableNot applicableCanada
Nasal Allergy and Congestion ReliefSpray, metered50 mcgNasalApotex CorporationNot applicableNot applicableCanada
Nasonex Allergy and CongestionSpray, metered50 mcgNasalMerck Ltd.Not applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DuleraMometasone furoate (200 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)A-S Medication Solutions2010-06-22Not applicableUs
DuleraMometasone furoate (200 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
DuleraMometasone furoate (100 ug/1) + Formoterol fumarate (5 ug/1)AerosolRespiratory (inhalation)Merck Sharp & Dohme Corp.2010-06-22Not applicableUs
ZenhaleMometasone furoate (100 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)Merck Ltd.2011-03-10Not applicableCanada
ZenhaleMometasone furoate (50 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)Merck Ltd.2011-06-20Not applicableCanada
ZenhaleMometasone furoate (200 mcg) + Formoterol fumarate (5 mcg)Aerosol, meteredRespiratory (inhalation)Merck Ltd.2011-06-17Not applicableCanada
Categories
UNII
04201GDN4R
CAS number
83919-23-7
Weight
Average: 521.429
Monoisotopic: 520.141944106
Chemical Formula
C27H30Cl2O6
InChI Key
WOFMFGQZHJDGCX-ZULDAHANSA-N
InChI
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
IUPAC Name
(1R,2R,3aS,3bS,9aS,9bR,10S,11aS)-9b-chloro-1-(2-chloroacetyl)-10-hydroxy-2,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl furan-2-carboxylate
SMILES
[H][C@@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@]([H])(O)C[C@]2(C)[C@@]1(OC(=O)C1=CC=CO1)C(=O)CCl

Pharmacology

Indication

The 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.

Associated Conditions
Pharmacodynamics

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. The clinical significance of these findings is unknown.

Mechanism of action

Unbound corticosteroids cross cell membranes and bind with high affinity to specific cytoplasmic receptors. Inflammation is decreased by diminishing the release of leukocytic acid hydrolases, prevention of macrophage accumulation at inflamed sites, interference with leukocyte adhesion to the capillary wall, reduction of capillary membrane permeability, reduction of complement components, inhibition of histamine and kinin release, and interference with the formation of scar tissue. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Mometasone furoate 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.

TargetActionsOrganism
AGlucocorticoid receptorNot AvailableHuman
UProgesterone receptorNot AvailableHuman
Absorption

Nasal spray is virtually undetectable in plasma

Volume of distribution
Not Available
Protein binding

98% to 99% (in a concentration range of 5 to 500 ng/mL).

Metabolism

Hepatic. Extensive metabolism to multiple metabolites. There are no major metabolites detectable in plasma. Upon in vitro incubation, one of the minor metabolites formed is 6ß-hydroxy-mometasone furoate. In human liver microsomes, the formation of the metabolite is regulated by cytochrome P-450 3A4.

Route of elimination
Not Available
Half life

5.8 hours

Clearance
Not Available
Toxicity

The potential for acute toxic effects following overdose with the mometasone inhaler is low. However, habitual overuse of the product can cause symptoms of steroid overload, including menstrual irregularities, acne, obesity, and muscle weakness. Single oral doses up to 8000 µg have been studied on human volunteers with no adverse events reported.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Mometasone furoate.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Mometasone furoate.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Mometasone furoate.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Mometasone furoate.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Mometasone furoate.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Mometasone furoate.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Mometasone furoate.
4-HydroxytestosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Mometasone furoate.
5-androstenedioneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Mometasone furoate.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Mometasone furoate.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C07817
ChemSpider
390091
BindingDB
50148733
ChEBI
47564
ChEMBL
CHEMBL1161
HET
MOF
Wikipedia
Mometasone_furoate
AHFS Codes
  • 68:04.00 — Adrenals
  • 84:06.00 — Anti-inflammatory Agents
  • 52:08.08 — Corticosteroids
PDB Entries
1sr7 / 4e2j / 4p6w

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAtopic Dermatitis (AD)1
3CompletedTreatmentChronic Rhinosinusitis / Nasal Polyposis1
4Not Yet RecruitingOtherHypothyroidism1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InhalantRespiratory (inhalation)110 ug/1
InhalantRespiratory (inhalation)220 ug/1
AerosolRespiratory (inhalation)100 ug/1
AerosolRespiratory (inhalation)200 ug/1
PowderRespiratory (inhalation)100 mcg
PowderRespiratory (inhalation)200 mcg
PowderRespiratory (inhalation)400 mcg
AerosolRespiratory (inhalation)
CreamTopical0.1 %
LotionTopical0.1 %
OintmentTopical0.1 %
CreamTopical1 mg/1g
OintmentTopical1 mg/1g
CreamTopical1 g/100g
LotionTopical1 mg/1g
LotionTopical1 mg/1mL
OintmentTopical1 mg/1
SolutionTopical1 mg/1mL
Spray, meteredNasal50 ug/1
Spray, meteredNasal50 mcg
CreamTopical.1 %
LotionTopical.1 %
ImplantIntrasinal1350 ug/1
Aerosol, meteredRespiratory (inhalation)
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6127353Yes1998-04-032018-04-03Us
US6240918Yes1997-08-202017-08-20Us
US8173172Yes1998-09-172018-09-17Us
US6503537Yes1998-09-172018-09-17Us
US5829434Yes1996-05-032016-05-03Us
US6068832No1997-08-272017-08-27Us
US7067502No2000-05-212020-05-21Us
US7566705No2000-05-212020-05-21Us
US8109918No2004-03-122024-03-12Us
US7951131No2004-03-122024-03-12Us
US8025635No2007-06-122027-06-12Us
US9585681No2006-04-042026-04-04Us
US7951130No2004-03-122024-03-12Us
US7544192No2006-11-292026-11-29Us
US7951133No2004-03-122024-03-12Us
US7713255No2004-03-122024-03-12Us
US7662141No2004-03-122024-03-12Us
US8763222No2012-02-082032-02-08Us

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0108 mg/mLALOGPS
logP4.27ALOGPS
logP5.06ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area93.81 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity132.5 m3·mol-1ChemAxon
Polarizability52.57 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03mj-3891000000-64a4294ec7bf5ac82d6c

Taxonomy

Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Steroid esters / 20-oxosteroids / 11-beta-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Furoic acid esters / Alpha-chloroketones / Heteroaromatic compounds / Secondary alcohols
show 10 more
Substituents
Progestogin-skeleton / 20-oxosteroid / Steroid ester / Halo-steroid / Hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Oxosteroid / 11-hydroxysteroid
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, 11beta-hydroxy steroid, steroid ester, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, 2-furoate ester (CHEBI:47564)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Isogai M, Shimizu H, Esumi Y, Terasawa T, Okada T, Sugeno K: Binding affinities of mometasone furoate and related compounds including its metabolites for the glucocorticoid receptor of rat skin tissue. J Steroid Biochem Mol Biol. 1993 Feb;44(2):141-5. [PubMed:8439518]
  2. Lumry WR: A review of the preclinical and clinical data of newer intranasal steroids used in the treatment of allergic rhinitis. J Allergy Clin Immunol. 1999 Oct;104(4 Pt 1):S150-8. [PubMed:10518812]
  3. Smith CL, Kreutner W: In vitro glucocorticoid receptor binding and transcriptional activation by topically active glucocorticoids. Arzneimittelforschung. 1998 Sep;48(9):956-60. [PubMed:9793625]
  4. Zhang X, Moilanen E, Adcock IM, Lindsay MA, Kankaanranta H: Divergent effect of mometasone on human eosinophil and neutrophil apoptosis. Life Sci. 2002 Aug 16;71(13):1523-34. [PubMed:12127907]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Madauss KP, Deng SJ, Austin RJ, Lambert MH, McLay I, Pritchard J, Short SA, Stewart EL, Uings IJ, Williams SP: Progesterone receptor ligand binding pocket flexibility: crystal structures of the norethindrone and mometasone furoate complexes. J Med Chem. 2004 Jun 17;47(13):3381-7. [PubMed:15189034]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Berger WE, Milgrom H, Chervinsky P, Noonan M, Weinstein SF, Lutsky BN, Staudinger H: Effects of treatment with mometasone furoate dry powder inhaler in children with persistent asthma. Ann Allergy Asthma Immunol. 2006 Nov;97(5):672-80. doi: 10.1016/S1081-1206(10)61099-X. [PubMed:17165278]
  2. Sharpe M, Jarvis B: Inhaled mometasone furoate: a review of its use in adults and adolescents with persistent asthma. Drugs. 2001;61(9):1325-50. [PubMed:11511026]

Drug created on July 12, 2018 09:10 / Updated on October 16, 2018 08:44