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Identification
NameMometasone
Accession NumberDB00764  (APRD00289)
Typesmall molecule
Groupsapproved
Description

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. he 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.

Structure
Thumb
Synonyms
SynonymLanguageCode
MometasonGermanINN
Mometason furoat-1-WasserNot AvailableIS
MometasonaSpanishINN
MométasoneFrenchINN
Mométasone (furoate de)FrenchPH: Ph. Eur. 7
Mometasone FuroateNot AvailablePH: BP 2011, USP 34
Mometasone Furoate HydrateNot AvailableJAN
Mometasonfuroat Not AvailablePH: Ph. Eur. 7
Mometasoni furoas Not AvailablePH: Ph. Eur. 7
MometasonumLatinINN
SaltsNot Available
Brand names
NameCompany
AsmanexMerck
Asmanex TwisthalerMerck
EcuralEssex pharma
ElocomMerck
EloconMerck
ElometSchering-Plough
EziwinIntas
mometAidProgreś Laboratories
NasonexMerck
NovasoneSchering-Plough
Brand mixtures
Brand NameIngredients
CombisorMometasone and Salicyclic Acid
ElosalicMometasone and Salicylic acid
CategoriesNot Available
CAS number105102-22-5
WeightAverage: 427.361
Monoisotopic: 426.136464798
Chemical FormulaC22H28Cl2O4
InChI KeyInChIKey=QLIIKPVHVRXHRI-CXSFZGCWSA-N
InChI
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
IUPAC Name
(1R,2S,10S,11S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Halogenated Steroids; Iridoids and Derivatives; Cyclohexanols; Tertiary Alcohols; Ketones; Chlorohydrins; Cyclic Alcohols and Derivatives; Polyamines; Enolates; Organochlorides; Alkyl Chlorides
Substituents3-keto-steroid; 20-keto-steroid; 9-halo-steroid; 17-hydroxy-steroid; 11-hydroxy-steroid; 11-noriridane monoterpene; monoterpene; cyclohexanol; tertiary alcohol; cyclic alcohol; secondary alcohol; ketone; halohydrin; chlorohydrin; polyamine; enolate; alcohol; organochloride; organohalogen; carbonyl group; alkyl halide; alkyl chloride
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationThe 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.
PharmacodynamicsMometasone 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 actionUnbound 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.
AbsorptionNasal spray is virtually undetectable in plasma
Volume of distributionNot Available
Protein binding98% 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.

SubstrateEnzymesProduct
Mometasone
    6-beta-hydroxy-mometasone furoateDetails
    Route of eliminationNot Available
    Half life5.8 hours
    ClearanceNot Available
    ToxicityThe 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
    • Humans and other mammals
    PathwaysNot Available
    SNP Mediated EffectsNot Available
    SNP Mediated Adverse Drug ReactionsNot Available
    ADMET
    Predicted ADMET features
    Property Value Probability
    Human Intestinal Absorption + 0.995
    Blood Brain Barrier + 0.9721
    Caco-2 permeable + 0.7845
    P-glycoprotein substrate Substrate 0.7849
    P-glycoprotein inhibitor I Non-inhibitor 0.7635
    P-glycoprotein inhibitor II Non-inhibitor 0.656
    Renal organic cation transporter Non-inhibitor 0.7753
    CYP450 2C9 substrate Non-substrate 0.852
    CYP450 2D6 substrate Non-substrate 0.9135
    CYP450 3A4 substrate Substrate 0.8028
    CYP450 1A2 substrate Non-inhibitor 0.9383
    CYP450 2C9 substrate Non-inhibitor 0.8572
    CYP450 2D6 substrate Non-inhibitor 0.8429
    CYP450 2C19 substrate Non-inhibitor 0.8966
    CYP450 3A4 substrate Non-inhibitor 0.6761
    CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8898
    Ames test Non AMES toxic 0.8962
    Carcinogenicity Non-carcinogens 0.9393
    Biodegradation Not ready biodegradable 1.0
    Rat acute toxicity 1.9124 LD50, mol/kg Not applicable
    hERG inhibition (predictor I) Weak inhibitor 0.9254
    hERG inhibition (predictor II) Non-inhibitor 0.6092
    Pharmacoeconomics
    Manufacturers
    • Schering corp sub schering plough corp
    • Altana inc
    • G and w laboratories inc
    • Glenmark generics inc usa
    • Taro pharmaceuticals usa inc
    • Tolmar inc
    • Nycomed us inc
    • Perrigo co
    • Perrigo new york inc
    • Schering corp
    • Schering plough healthcare products inc
    • Schering-Plough
    Packagers
    Dosage forms
    FormRouteStrength
    CreamTopical
    LotionTopical
    OintmentTopical
    SprayIntrasinal
    Prices
    Unit descriptionCostUnit
    Asmanex 120 Metered Doses 220 mcg/inh Aerosol 0.24 gm Inhaler230.27USDinhaler
    Asmanex twisthaler 220 mcg #30131.47USDinhaler
    Asmanex twisthaler 110 mcg #30121.76USDinhaler
    Nasonex 50 mcg/act Suspension 50 mcg Nasal Spray116.82USDinhaler
    Elocon 0.1% Lotion 60ml Bottle86.71USDbottle
    Elocon 0.1% Cream 45 gm Tube79.13USDtube
    Elocon 0.1% Ointment 45 gm Tube76.45USDtube
    Mometasone Furoate 0.1% Solution 60ml Bottle64.99USDbottle
    Mometasone Furoate 0.1% Cream 45 gm Tube50.96USDtube
    Elocon 0.1% Lotion 30ml Bottle49.85USDbottle
    Elocon 0.1% Ointment 15 gm Tube49.85USDtube
    Elocon 0.1% Cream 15 gm Tube47.68USDtube
    Mometasone Furoate 0.1% Ointment 45 gm Tube35.99USDtube
    Mometasone Furoate 0.1% Solution 30ml Bottle32.99USDbottle
    Mometasone Furoate 0.1% Cream 15 gm Tube29.99USDtube
    Mometasone Furoate 0.1% Ointment 15 gm Tube19.19USDtube
    Nasonex 50 mcg nasal spray6.37USDg
    Elocon 0.1% cream2.69USDg
    Mometasone furoate 0.1% cream1.42USDg
    Elocom 0.1 % Cream0.7USDg
    Elocom 0.1 % Ointment0.63USDg
    Elocom 0.1 % Lotion0.47USDg
    Pms-Mometasone 0.1 % Ointment0.35USDg
    Ratio-Mometasone 0.1 % Ointment0.35USDg
    Taro-Mometasone 0.1 % Ointment0.35USDg
    Taro-Mometasone 0.1 % Lotion0.33USDg
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    Patents
    CountryPatent NumberApprovedExpires (estimated)
    United States65035371998-09-172018-09-17
    United States53948681995-06-252012-06-25
    Canada22823602004-11-092018-03-16
    Canada20913601997-04-082011-09-06
    Properties
    Statesolid
    Experimental Properties
    PropertyValueSource
    melting point218-220 °CNot Available
    water solubilityPractically insoluble.Not Available
    logP2.1Not Available
    Predicted Properties
    PropertyValueSource
    water solubility5.23e-03 g/lALOGPS
    logP2.81ALOGPS
    logP3.5ChemAxon
    logS-4.9ALOGPS
    pKa (strongest acidic)12.48ChemAxon
    pKa (strongest basic)-3.3ChemAxon
    physiological charge0ChemAxon
    hydrogen acceptor count4ChemAxon
    hydrogen donor count2ChemAxon
    polar surface area74.6ChemAxon
    rotatable bond count2ChemAxon
    refractivity110.29ChemAxon
    polarizability43.82ChemAxon
    number of rings4ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterYesChemAxon
    Veber's ruleNoChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    SpectraNot Available
    References
    Synthesis Reference

    Pui-Ho Yuen, Charles Eckhart, Teresa Etlinger, Nancy Levine, “Mometasone furoate monohydrate, process for making same and pharmaceutical compositions.” U.S. Patent US6127353, issued April, 1988.

    US6127353
    General ReferenceNot Available
    External Links
    ResourceLink
    KEGG CompoundC07816
    ChEBI6970
    ChEMBLCHEMBL1201404
    Therapeutic Targets DatabaseDAP001042
    PharmGKBPA450541
    HETMOF
    Drug Product Database2244769
    RxListhttp://www.rxlist.com/cgi/generic2/momet1.htm
    Drugs.comhttp://www.drugs.com/cdi/mometasone-spray.html
    PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/nas1518.shtml
    WikipediaMometasone
    ATC CodesD07AC13D07XC03R01AD09R03BA07
    AHFS Codes
    • 52:08.08
    • 84:06.00
    PDB EntriesNot Available
    FDA labelshow(152 KB)
    MSDSNot Available
    Interactions
    Drug InteractionsSearched, but no interactions found.
    Food InteractionsNot Available

    1. Glucocorticoid receptor

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: agonist

    Components

    Name UniProt ID Details
    Glucocorticoid receptor P04150 Details

    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
    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
    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
    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
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

    1. Cytochrome P450 2C8

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 2C8 P10632 Details

    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
    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. Epub 2009 Nov 24. Pubmed

    Comments
    Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12