Identification
- Summary
Mometasone is a corticosteroid with no indications.
- Generic Name
- Mometasone
- DrugBank Accession Number
- DB00764
- Background
Mometasone is a corticosteroid not currently used in medical products. Mometasone furoate however, is still in use.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Mometasone (DB00764)
- Weight
- Average: 427.361
Monoisotopic: 426.136464798 - Chemical Formula
- C22H28Cl2O4
- Synonyms
- (+)-Mometasone
- Mometason
- Mometasona
- Mométasone
- Mometasone
- Mometasonum
- External IDs
- LAS-41002
- LAS41002
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Allergic rhinitis (ar) •••••••••••• •••••••••• Management of Asthma •••••••••••• •••••• Management of Bacterial sinusitis •••••••••••• •••••••••• Treatment of Pruritus •••••••••••• ••••••••• •••••••• Management of Sinusitis •••••••••••• •••••••••• - Contraindications & Blackbox Warnings
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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.
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- Route of elimination
Not Available
- Half-life
5.8 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Mometasone can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Mometasone is combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Mometasone. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Mometasone. Acarbose The risk or severity of hyperglycemia can be increased when Mometasone is combined with Acarbose. - Food Interactions
- No interactions found.
Products
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Categories
- ATC Codes
- R03AL12 — Indacaterol, glycopyrronium bromide and mometasone
- R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
- R03A — ADRENERGICS, 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
- Drug Categories
- Adrenal Cortex Hormones
- Adrenals
- 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 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs for Obstructive Airway Diseases
- Fused-Ring Compounds
- Glucocorticoids
- Hyperglycemia-Associated Agents
- Immunosuppressive Agents
- Nasal Preparations
- Pregnadienediols
- Pregnadienes
- Pregnanes
- Steroids
- Thyroxine-binding globulin inhibitors
- Chemical TaxonomyProvided by Classyfire
- 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
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl chloride 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8HR4QJ6DW8
- CAS number
- 105102-22-5
- 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
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
- ChemSpider
- 390090
- BindingDB
- 50237628
- 108118
- ChEBI
- 6970
- ChEMBL
- CHEMBL1201404
- ZINC
- ZINC000004097440
- Therapeutic Targets Database
- DAP001042
- PharmGKB
- PA450541
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Mometasone
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Allergic Rhinitis (AR) 1 4 Completed Treatment Allergic Rhinosinusitis / Chronic Sinusitis / Eosinophilic Chronic Rhinosinusitis 1 4 Completed Treatment Asthma / Seasonal Allergic Rhinitis 1 4 Completed Treatment Asthma / Sinusitis 1 4 Completed Treatment Otitis Media With Effusion (OME) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder Respiratory (inhalation) 200 mcg Powder Respiratory (inhalation) 400 mcg Powder, metered Respiratory (inhalation) 200 MICROGRAMMI Powder, metered Respiratory (inhalation) 400 MICROGRAMMI Suspension Intrasinal; Nasal 50 mg Cream Topical 1 MG/G Cream Cream 0.1 % Ointment Cutaneous 0.1 % Solution Topical Solution Topical 0.1 % Powder, metered Respiratory (inhalation) Ointment Cutaneous 1 MG/G Lotion 0.1 % Cream Topical 1 MG/ML Ointment Cutaneous 1 MG/ML Ointment Cutaneous Cream 1 MG/G Emulsion Topical 1 MG/G Emulsion Cutaneous 1 MG/G Spray Nasal Spray Nasal 0.05 % Spray Nasal 50 MICROGRAMMI Solution Cutaneous; Topical 1 MG/G Cream Cutaneous 1 MG/G Spray Nasal 50 MCG Suspension Intrasinal; Nasal 0.05 % Spray, suspension Nasal 50 mcg/1dose - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region 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 Yes 2006-06-27 2020-11-21 US US7566705 Yes 2009-07-28 2020-11-21 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.455293 predictedDarkChem Lite v0.1.0 [M-H]- 196.00305 predictedDeepCCS 1.0 (2019) [M-H]- 196.455293 predictedDarkChem Lite v0.1.0 [M-H]- 196.00305 predictedDeepCCS 1.0 (2019) [M+H]+ 197.989193 predictedDarkChem Lite v0.1.0 [M+H]+ 197.89847 predictedDeepCCS 1.0 (2019) [M+H]+ 197.989193 predictedDarkChem Lite v0.1.0 [M+H]+ 197.89847 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.863193 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.88713 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.863193 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.88713 predictedDeepCCS 1.0 (2019)
Targets
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- 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. [Article]
- 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. [Article]
- Smith CL, Kreutner W: In vitro glucocorticoid receptor binding and transcriptional activation by topically active glucocorticoids. Arzneimittelforschung. 1998 Sep;48(9):956-60. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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. [Article]
- Foti RS, Diaz P, Douguet D: Comparison of the ligand binding site of CYP2C8 with CYP26A1 and CYP26B1: a structural basis for the identification of new inhibitors of the retinoic acid hydroxylases. J Enzyme Inhib Med Chem. 2016;31(sup2):148-161. doi: 10.1080/14756366.2016.1193734. Epub 2016 Jul 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInducer
- 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. [Article]
- 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. [Article]
- Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Oxygen binding
- 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
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Dvorak Z, Pavek P: Regulation of drug-metabolizing cytochrome P450 enzymes by glucocorticoids. Drug Metab Rev. 2010 Nov;42(4):621-35. doi: 10.3109/03602532.2010.484462. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:55