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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
(+)-MometasoneNot AvailableNot Available
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
DuleraMometasone + Formoterol
ElosalicMometasone and Salicylic acid
CategoriesNot Available
CAS number105102-22-5
WeightAverage: 427.361
Monoisotopic: 426.136464798
Chemical FormulaC22H28Cl2O4
InChI KeyQLIIKPVHVRXHRI-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
Not Available
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

Targets

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

Enzymes

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

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