Mometasone

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAllergic rhinitis (ar)••••••••••••••••••••••
Management ofAsthma••••••••••••••••••
Management ofBacterial sinusitis••••••••••••••••••••••
Treatment ofPruritus••••••••••••••••••••• ••••••••
Management ofSinusitis••••••••••••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Humans
UProgesterone receptor
agonist
Humans
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
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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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbametapirThe serum concentration of Mometasone can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Mometasone is combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Mometasone.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Mometasone.
AcarboseThe risk or severity of hyperglycemia can be increased when Mometasone is combined with Acarbose.
Food Interactions
No interactions found.

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Categories

ATC Codes
R03AL12 — Indacaterol, glycopyrronium bromide and mometasoneR01AD59 — Mometasone, combinationsR03AK14 — Indacaterol and mometasone
Drug Categories
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
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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
Human Metabolome Database
HMDB0014902
KEGG Drug
D08227
KEGG Compound
C07816
PubChem Compound
441335
PubChem Substance
46505288
ChemSpider
390090
BindingDB
50237628
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAllergic Rhinosinusitis / Chronic Sinusitis / Eosinophilic Chronic Rhinosinusitis1
4CompletedTreatmentAsthma / Seasonal Allergic Rhinitis1
4CompletedTreatmentAsthma / Sinusitis1
4CompletedTreatmentOtitis Media With Effusion (OME)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
PowderRespiratory (inhalation)200 mcg
PowderRespiratory (inhalation)400 mcg
Powder, meteredRespiratory (inhalation)200 MICROGRAMMI
Powder, meteredRespiratory (inhalation)400 MICROGRAMMI
SuspensionIntrasinal; Nasal50 mg
CreamTopical1 MG/G
Cream
Cream0.1 %
OintmentCutaneous0.1 %
SolutionTopical
SolutionTopical0.1 %
Powder, meteredRespiratory (inhalation)
OintmentCutaneous1 MG/G
Lotion0.1 %
CreamTopical1 MG/ML
OintmentCutaneous1 MG/ML
OintmentCutaneous
Cream1 MG/G
EmulsionTopical1 MG/G
EmulsionCutaneous1 MG/G
SprayNasal
SprayNasal0.05 %
SprayNasal50 MICROGRAMMI
SolutionCutaneous; Topical1 MG/G
CreamCutaneous1 MG/G
SprayNasal50 MCG
SuspensionIntrasinal; Nasal0.05 %
Spray, suspensionNasal50 mcg/1dose
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5394868No1995-03-072012-06-25US flag
CA2282360No2004-11-092018-03-16Canada flag
CA2091360No1997-04-082011-09-06Canada flag
US6127353Yes2000-10-032018-04-03US flag
US6240918Yes2001-06-052017-08-20US flag
US8173172Yes2012-05-082018-09-17US flag
US6503537Yes2003-01-072018-09-17US flag
US5829434Yes1998-11-032016-05-03US flag
US6068832No2000-05-302017-08-27US flag
US7067502Yes2006-06-272020-11-21US flag
US7566705Yes2009-07-282020-11-21US flag
US8109918No2012-02-072024-03-12US flag
US7951131No2011-05-312024-03-12US flag
US8025635No2011-09-272027-06-12US flag
US9585681No2017-03-072026-04-04US flag
US7951130No2011-05-312024-03-12US flag
US7544192No2009-06-092026-11-29US flag
US7951133No2011-05-312024-03-12US flag
US7713255No2010-05-112024-03-12US flag
US7662141No2010-02-162024-03-12US flag
US8763222No2014-07-012032-02-08US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)218-220 °CNot Available
water solubilityPractically insoluble.Not Available
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00523 mg/mLALOGPS
logP2.81ALOGPS
logP3.5Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.49Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity110.29 m3·mol-1Chemaxon
Polarizability43.82 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.9721
Caco-2 permeable+0.7845
P-glycoprotein substrateSubstrate0.7849
P-glycoprotein inhibitor INon-inhibitor0.7635
P-glycoprotein inhibitor IINon-inhibitor0.656
Renal organic cation transporterNon-inhibitor0.7753
CYP450 2C9 substrateNon-substrate0.852
CYP450 2D6 substrateNon-substrate0.9135
CYP450 3A4 substrateSubstrate0.8028
CYP450 1A2 substrateNon-inhibitor0.9383
CYP450 2C9 inhibitorNon-inhibitor0.8572
CYP450 2D6 inhibitorNon-inhibitor0.8429
CYP450 2C19 inhibitorNon-inhibitor0.8966
CYP450 3A4 inhibitorNon-inhibitor0.6761
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8898
Ames testNon AMES toxic0.8962
CarcinogenicityNon-carcinogens0.9393
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9124 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9254
hERG inhibition (predictor II)Non-inhibitor0.6092
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05uu-1911000000-7b8ff84d92407510c9d8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05i3-0009700000-e2cc0ef6983fc0c77b73
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0001900000-98c3a3d9e54b016d7708
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9006200000-a661ad0b97af97c27b21
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pxu-0425900000-7c6057e59c27471b77ab
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00os-0109200000-b98ccc00f2994e37a9be
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0591000000-4afdc4f14d9436fb4c39
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05i3-0009700000-e2cc0ef6983fc0c77b73
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0001900000-98c3a3d9e54b016d7708
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9006200000-a661ad0b97af97c27b21
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pxu-0425900000-7c6057e59c27471b77ab
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00os-0109200000-b98ccc00f2994e37a9be
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0591000000-4afdc4f14d9436fb4c39
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-196.455293
predicted
DarkChem Lite v0.1.0
[M-H]-196.00305
predicted
DeepCCS 1.0 (2019)
[M-H]-196.455293
predicted
DarkChem Lite v0.1.0
[M-H]-196.00305
predicted
DeepCCS 1.0 (2019)
[M+H]+197.989193
predicted
DarkChem Lite v0.1.0
[M+H]+197.89847
predicted
DeepCCS 1.0 (2019)
[M+H]+197.989193
predicted
DarkChem Lite v0.1.0
[M+H]+197.89847
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.863193
predicted
DarkChem Lite v0.1.0
[M+Na]+203.88713
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.863193
predicted
DarkChem Lite v0.1.0
[M+Na]+203.88713
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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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
  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. [Article]
  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. [Article]
  3. Smith CL, Kreutner W: In vitro glucocorticoid receptor binding and transcriptional activation by topically active glucocorticoids. Arzneimittelforschung. 1998 Sep;48(9):956-60. [Article]
  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. [Article]
  5. 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
  1. 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
  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. [Article]
  2. 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
Substrate
Inducer
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
  1. 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]
  2. 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]
  3. 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
  1. 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