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Identification
Name Mometasone
Accession Number DB00764 (APRD00289)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Asmanex
Asmanex Twisthaler
Elocom
Elocon
Mometasone furoate
Nasonex
Brand mixtures
Brand Name Ingredients
Combisor Mometasone + Salicyclic Acid
Categories
  • Anti-inflammatory Agents
  • Anti-Allergic Agents
CAS number 105102-22-5
Weight Average: 427.361
Monoisotopic: 426.136464798
Chemical Formula C22H28Cl2O4
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
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.
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.
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.

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Substrate Enzymes Product
Mometasone
    		6-beta-hydroxy-mometasone furoate Details
    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
    • Humans and other mammals
    Pathways Not Available
    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
    Form Route Strength
    Cream Topical
    Lotion Topical
    Ointment Topical
    Spray Intrasinal
    Prices
    Unit description Cost Unit
    Asmanex 120 Metered Doses 220 mcg/inh Aerosol 0.24 gm Inhaler 230.27 USD inhaler
    Asmanex twisthaler 220 mcg #30 131.47 USD inhaler
    Asmanex twisthaler 110 mcg #30 121.76 USD inhaler
    Nasonex 50 mcg/act Suspension 50 mcg Nasal Spray 116.82 USD inhaler
    Elocon 0.1% Lotion 60ml Bottle 86.71 USD bottle
    Elocon 0.1% Cream 45 gm Tube 79.13 USD tube
    Elocon 0.1% Ointment 45 gm Tube 76.45 USD tube
    Mometasone Furoate 0.1% Solution 60ml Bottle 64.99 USD bottle
    Mometasone Furoate 0.1% Cream 45 gm Tube 50.96 USD tube
    Elocon 0.1% Lotion 30ml Bottle 49.85 USD bottle
    Elocon 0.1% Ointment 15 gm Tube 49.85 USD tube
    Elocon 0.1% Cream 15 gm Tube 47.68 USD tube
    Mometasone Furoate 0.1% Ointment 45 gm Tube 35.99 USD tube
    Mometasone Furoate 0.1% Solution 30ml Bottle 32.99 USD bottle
    Mometasone Furoate 0.1% Cream 15 gm Tube 29.99 USD tube
    Mometasone Furoate 0.1% Ointment 15 gm Tube 19.19 USD tube
    Nasonex 50 mcg nasal spray 6.37 USD g
    Elocon 0.1% cream 2.69 USD g
    Mometasone furoate 0.1% cream 1.42 USD g
    Elocom 0.1 % Cream 0.7 USD g
    Elocom 0.1 % Ointment 0.63 USD g
    Elocom 0.1 % Lotion 0.47 USD g
    Pms-Mometasone 0.1 % Ointment 0.35 USD g
    Ratio-Mometasone 0.1 % Ointment 0.35 USD g
    Taro-Mometasone 0.1 % Ointment 0.35 USD g
    Taro-Mometasone 0.1 % Lotion 0.33 USD g
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    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    Patents
    Country Patent Number Approved Expires (estimated)
    United States 6503537 1998-09-17 2018-09-17
    United States 5394868 1995-06-25 2012-06-25
    Canada 2282360 2004-11-09 2018-03-16
    Canada 2091360 1997-04-08 2011-09-06
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 218-220 °C Not Available
    water solubility Practically insoluble. Not Available
    logP 2.1 Not Available
    Predicted Properties
    Property Value Source
    water solubility 5.23e-03 g/l ALOGPS
    logP 2.81 ALOGPS
    logP 3.5 ChemAxon
    logS -4.9 ALOGPS
    pKa (strongest acidic) 12.48 ChemAxon
    pKa (strongest basic) -3.3 ChemAxon
    physiological charge 0 ChemAxon
    hydrogen acceptor count 4 ChemAxon
    hydrogen donor count 2 ChemAxon
    polar surface area 74.6 ChemAxon
    rotatable bond count 2 ChemAxon
    refractivity 110.29 ChemAxon
    polarizability 43.82 ChemAxon
    References
    Synthesis Reference Not Available
    General Reference Not Available
    External Links
    Resource Link
    KEGG Compound C07816 Link_out
    ChEBI 6970 Link_out
    ChEMBL 6970 Link_out
    Therapeutic Targets Database DAP001042 Link_out
    PharmGKB PA450541 Link_out
    HET MOF Link_out
    Drug Product Database 2244769 Link_out
    RxList http://www.rxlist.com/cgi/generic2/momet1.htm Link_out
    Drugs.com http://www.drugs.com/cdi/mometasone-spray.html Link_out
    PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/nas1518.shtml Link_out
    Wikipedia http://en.wikipedia.org/wiki/Mometasone Link_out
    ATC Codes
    • D07AC13
    • D07XC03
    • R01AD09
    • R03BA07
    AHFS Codes
    • 52:08.08
    • 84:06.00
    PDB Entries Not Available
    FDA label show (152 KB)
    MSDS Not Available
    Interactions
    Drug Interactions Searched, but no interactions found.
    Food Interactions Not Available
    Targets

    1. Glucocorticoid receptor

    Pharmacological action: yes
    Actions: agonist

    Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

    Organism class: human
    UniProt ID: P04150 Link_out
    Gene: NR3C1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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
    Enzymes

    1. Cytochrome P450 2C8

    Actions: inhibitor

    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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

    UniProt ID: P10632 Link_out
    Gene: CYP2C8
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    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 February 08, 2013 16:19