Identification
- Name
- Mometasone
- Accession Number
- DB00764 (APRD00289)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Description
Mometasone is a medium-potency synthetic corticosteroid with anti-inflammatory, 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. The anti-inflammatory 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
- Synonyms
- (+)-Mometasone
- Mometason
- Mometasona
- Mométasone
- Mometasone
- Mometasonum
- External IDs
- LAS-41002 / LAS41002
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Mometasone Furoate Spray, metered 50 ug/1 Nasal Remedy Repack 2018-03-20 Not applicable US Mometasone Furoate Spray, metered 50 ug/1 Nasal Golden State Medical Supply, Inc. 2016-03-29 Not applicable US Mometasone Furoate Spray, metered 50 ug/1 Nasal Apotex Corporation 2016-03-22 Not applicable US Momexin Cream 1 mg/1g Topical Innocutis Holdings, LLC 2009-05-01 2011-12-20 US - International/Other Brands
- Ecural (Essex pharma) / Elocom (Merck) / Elomet (Schering-Plough) / Eziwin (Intas) / mometAid (Progreś Laboratories) / Novasone (Schering-Plough)
- Categories
- Adrenal Cortex Hormones
- Adrenals
- Adrenergics, Inhalants
- Agents to Treat Airway Disease
- Anti-Allergic Agents
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Drugs for Obstructive Airway Diseases
- Glucocorticoids
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Nasal Preparations
- Pregnadienediols
- Pregnadienes
- Pregnanes
- Steroids
- UNII
- 8HR4QJ6DW8
- CAS number
- 105102-22-5
- Weight
- Average: 427.361
Monoisotopic: 426.136464798 - Chemical Formula
- C22H28Cl2O4
- InChI Key
- 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,2R,3aS,3bS,9aS,9bR,10S,11aS)-9b-chloro-1-(2-chloroacetyl)-1,10-dihydroxy-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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
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.
Target Actions Organism AGlucocorticoid receptor agonistHumans UProgesterone receptor agonistHumans - 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
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The therapeutic efficacy of (R)-warfarin can be increased when used in combination with Mometasone. (S)-Warfarin The therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Mometasone. 1-Testosterone The risk or severity of edema formation can be increased when 1-Testosterone is combined with Mometasone. 1,10-Phenanthroline The therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Mometasone. 16-Bromoepiandrosterone The risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Mometasone. 19-norandrostenedione The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Mometasone. 1alpha-Hydroxyvitamin D5 The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Mometasone. 2-Methoxyethanol The risk or severity of adverse effects can be increased when Mometasone is combined with 2-Methoxyethanol. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Mometasone. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Mometasone. - Food Interactions
- Not 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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014902
- KEGG Drug
- D08227
- KEGG Compound
- C07816
- PubChem Compound
- 441335
- PubChem Substance
- 46505288
- ChEBI
- 6970
- ChEMBL
- CHEMBL1201404
- Therapeutic Targets Database
- DAP001042
- PharmGKB
- PA450541
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Mometasone
- ATC Codes
- D07AC13 — Mometasone
- D07AC — Corticosteroids, potent (group III)
- D07A — CORTICOSTEROIDS, PLAIN
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- R03BA — Glucocorticoids
- R03B — OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R01AD — Corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- D07XC — Corticosteroids, potent, other combinations
- D07X — CORTICOSTEROIDS, OTHER COMBINATIONS
- D07 — CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
- D — DERMATOLOGICALS
- AHFS Codes
- 68:04.00 — Adrenals
- 84:06.00 — Anti-inflammatory Agents
- 52:08.08 — Corticosteroids
- FDA label
- Download (152 KB)
Clinical Trials
- Clinical Trials
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
- A-S Medication Solutions LLC
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Dixie Chem Tec Inc.
- E. Fougera and Co.
- G & W Labs
- Glenmark Generics Ltd.
- Harris Pharmaceutical Inc.
- JSJ Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Nycomed Inc.
- Perrigo Co.
- Pharmedix
- Physicians Total Care Inc.
- Sandoz
- Schering Corp.
- Schering-Plough Inc.
- Taro Pharmaceuticals USA
- Tolmar Inc.
- Dosage forms
Form Route Strength Spray, metered Nasal 50 ug/1 Cream Topical 1 mg/1g - Prices
Unit description Cost Unit Asmanex 120 Metered Doses 220 mcg/inh Aerosol 0.24 gm Inhaler 230.27USD inhaler Asmanex twisthaler 220 mcg #30 131.47USD inhaler Asmanex twisthaler 110 mcg #30 121.76USD inhaler Nasonex 50 mcg/act Suspension 50 mcg Nasal Spray 116.82USD inhaler Elocon 0.1% Lotion 60ml Bottle 86.71USD bottle Elocon 0.1% Cream 45 gm Tube 79.13USD tube Elocon 0.1% Ointment 45 gm Tube 76.45USD tube Mometasone Furoate 0.1% Solution 60ml Bottle 64.99USD bottle Mometasone Furoate 0.1% Cream 45 gm Tube 50.96USD tube Elocon 0.1% Lotion 30ml Bottle 49.85USD bottle Elocon 0.1% Ointment 15 gm Tube 49.85USD tube Elocon 0.1% Cream 15 gm Tube 47.68USD tube Mometasone Furoate 0.1% Ointment 45 gm Tube 35.99USD tube Mometasone Furoate 0.1% Solution 30ml Bottle 32.99USD bottle Mometasone Furoate 0.1% Cream 15 gm Tube 29.99USD tube Mometasone Furoate 0.1% Ointment 15 gm Tube 19.19USD tube Nasonex 50 mcg nasal spray 6.37USD g Elocon 0.1% cream 2.69USD g Mometasone furoate 0.1% cream 1.42USD g Elocom 0.1 % Cream 0.7USD g Elocom 0.1 % Ointment 0.63USD g Elocom 0.1 % Lotion 0.47USD g Pms-Mometasone 0.1 % Ointment 0.35USD g Ratio-Mometasone 0.1 % Ointment 0.35USD g Taro-Mometasone 0.1 % Ointment 0.35USD g Taro-Mometasone 0.1 % Lotion 0.33USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5394868 No 1995-03-07 2012-06-25 US CA2282360 No 2004-11-09 2018-03-16 Canada CA2091360 No 1997-04-08 2011-09-06 Canada US6127353 Yes 2000-10-03 2018-04-03 US US6240918 Yes 2001-06-05 2017-08-20 US US8173172 Yes 2012-05-08 2018-09-17 US US6503537 Yes 2003-01-07 2018-09-17 US US5829434 Yes 1998-11-03 2016-05-03 US US6068832 No 2000-05-30 2017-08-27 US US7067502 No 2006-06-27 2020-05-21 US US7566705 No 2009-07-28 2020-05-21 US US8109918 No 2012-02-07 2024-03-12 US US7951131 No 2011-05-31 2024-03-12 US US8025635 No 2011-09-27 2027-06-12 US US9585681 No 2017-03-07 2026-04-04 US US7951130 No 2011-05-31 2024-03-12 US US7544192 No 2009-06-09 2026-11-29 US US7951133 No 2011-05-31 2024-03-12 US US7713255 No 2010-05-11 2024-03-12 US US7662141 No 2010-02-16 2024-03-12 US US8763222 No 2014-07-01 2032-02-08 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 218-220 °C Not Available water solubility Practically insoluble. Not Available logP 2.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00523 mg/mL ALOGPS logP 2.81 ALOGPS logP 3.5 ChemAxon logS -4.9 ALOGPS pKa (Strongest Acidic) 12.49 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 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 110.29 m3·mol-1 ChemAxon Polarizability 43.82 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.8572 CYP450 2D6 inhibitor Non-inhibitor 0.8429 CYP450 2C19 inhibitor Non-inhibitor 0.8966 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / Halogenated steroids / 3-oxo delta-1,4-steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Alpha-chloroketones / Secondary alcohols show 7 more
- Substituents
- Progestogin-skeleton / 20-oxosteroid / Hydroxysteroid / Halo-steroid / 9-halo-steroid / Oxosteroid / 11-beta-hydroxysteroid / 11-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid show 23 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 11beta-hydroxy steroid, 17alpha-hydroxy steroid, 20-oxo steroid, 3-oxo-Delta(1),Delta(4)-steroid, chlorinated steroid (CHEBI:6970)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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
- 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
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- 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 June 13, 2005 07:24 / Updated on February 17, 2019 16:46