Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H28Cl2O4 |
Molecular Weight | 427.361 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]3(Cl)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
InChI
InChIKey=QLIIKPVHVRXHRI-CXSFZGCWSA-N
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
DescriptionSources: http://www.drugbank.ca/drugs/DB00764Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019796s026lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00764
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/019796s026lbl.pdf
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. Mometasone 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. ELOCON Lotion (Mometasone) is indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00764 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ELOCON Approved UseELOCON Lotion is a corticosteroid indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients ≥12 years of age. Launch Date5.47171205E11 |
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Preventing | ASMANEX Approved UseASMANEX TWISTHALER is a corticosteroid indicated for:
• Maintenance treatment of asthma as prophylactic therapy in patients 4 years of age and older. Launch Date1.11205443E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
183 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26845343 |
320 μg 1 times / day steady-state, respiratory dose: 320 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: |
MOMETASONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.56 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29669668 |
100 μg single, nasal dose: 100 μg route of administration: Nasal experiment type: SINGLE co-administered: |
MOMETASONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1560 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26845343 |
320 μg 1 times / day steady-state, respiratory dose: 320 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered: |
MOMETASONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
92 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29669668 |
100 μg single, nasal dose: 100 μg route of administration: Nasal experiment type: SINGLE co-administered: |
MOMETASONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29669668 |
100 μg single, nasal dose: 100 μg route of administration: Nasal experiment type: SINGLE co-administered: |
MOMETASONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5% |
MOMETASONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: |
Other AEs: Glucocorticoid decreased, Skin and subcutaneous conditions NEC... Other AEs: Glucocorticoid decreased (1 patient) Sources: Skin and subcutaneous conditions NEC (1 patient) Skin bacterial infection (1 patient) |
0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: |
Other AEs: Pruritus, Skin atrophy... Other AEs: Pruritus (4.8%) Sources: Skin atrophy (4.8%) Tingling (4.8%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Glucocorticoid decreased | 1 patient | 0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: |
Skin and subcutaneous conditions NEC | 1 patient | 0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: |
Skin bacterial infection | 1 patient | 0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, 0.5 - 2 yeas n = 63 Health Status: unhealthy Condition: dermatoses Age Group: 0.5 - 2 yeas Sex: unknown Population Size: 63 Sources: |
Pruritus | 4.8% | 0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: |
Skin atrophy | 4.8% | 0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: |
Tingling | 4.8% | 0.1 % 1 times / day steady, topical Recommended Dose: 0.1 %, 1 times / day Route: topical Route: steady Dose: 0.1 %, 1 times / day Sources: |
unhealthy, adult n = 812 Health Status: unhealthy Condition: dermatoses Age Group: adult Sex: unknown Population Size: 812 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/ Page: 6.0 |
yes [IC50 0.327 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205641Orig1s000ClinPharmR.pdf#page=22 Page: 22,23 |
yes | unlikely (co-administration study) Comment: ketoconazole 200 mg (as well as placebo) were given twice daily concomitantly on Days 4 to 9. Mometasone furoate plasma concentrations were <150 pcg/mL on Day 3 prior to coadministration of ketoconazole or placebo. Following concomitant administration of ketoconazole, 4 out of 12 subjects in the ketoconazole treatment group (n=12) had peak plasma concentrations of mometasone furoate >200 pcg/mL on Day 9 (211-324 pcg/mL) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205641Orig1s000ClinPharmR.pdf#page=22 Page: 22,23 |
PubMed
Title | Date | PubMed |
---|---|---|
Investigation of an enhanced resolution triple quadrupole mass spectrometer for high-throughput liquid chromatography/tandem mass spectrometry assays. | 2002 |
|
Divergent effect of mometasone on human eosinophil and neutrophil apoptosis. | 2002 Aug 16 |
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A meta-analysis of the dose-response relationship of inhaled corticosteroids in adolescents and adults with mild to moderate persistent asthma. | 2002 Jan |
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Instrumental evaluation of retinoid-induced skin irritation. | 2002 May |
|
Safety of the newer inhaled corticosteroids in childhood asthma. | 2003 |
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A comparison of nasal clearance after treatment of perennial allergic rhinitis with budesonide and mometasone. | 2003 Feb |
|
Efficacy of betamethasone valerate mousse in comparison with standard therapies on scalp psoriasis: an open, multicentre, randomized, controlled, cross-over study on 241 patients. | 2003 Jan |
|
Treatment of recurrent chronic hyperplastic sinusitis with nasal polyposis. | 2003 Jun |
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Intranasal steroid sprays in the treatment of rhinitis: is one better than another? | 2003 Nov |
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Influence of preservatives and topical steroids on ciliary beat frequency in vitro. | 2004 Apr |
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Local and systemic administration of corticosteroids in the treatment of olfactory loss. | 2004 Jan-Feb |
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Comparative potency of formulations of mometasone furoate in terms of inhibition of 'PIRHR' in the forearm skin of normal human subjects measured with laser doppler velocimetry. | 2005 May-Jun |
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Effects of mometasone furoate on a rat allergic rhinitis model. | 2005 Nov 7 |
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Novel insights into the aetiology and pathophysiology of increased airway inflammation during COPD exacerbations. | 2006 May 22 |
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Cross-reactions to desoximetasone and mometasone furoate in a patient with multiple topical corticosteroid allergies. | 2006 Sep |
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Evidence-based selection of inhaled corticosteroid for treatment of chronic asthma. | 2007 Jan-Feb |
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Exogenous Cushing syndrome with inhaled fluticasone in a child receiving lopinavir/ritonavir. | 2007 Jul |
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Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate. | 2007 Jul 25 |
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Airways inflammation and treatment during acute exacerbations of COPD. | 2008 |
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Effect of illicit direct to consumer advertising on use of etanercept, mometasone, and tegaserod in Canada: controlled longitudinal study. | 2008 Sep 2 |
|
Comparative adrenocortical suppression in dogs with otitis externa following topical otic administration of four different glucocorticoid-containing medications. | 2008 Summer |
|
Local cytokines and clinical symptoms in children with allergic rhinitis after different treatments. | 2009 |
|
Comparison of corticosteroid nasal sprays in relation to concomitant use and cost of other prescription medications to treat allergic rhinitis symptoms: retrospective cohort analysis of pharmacy claims data. | 2009 |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Mapping analyses to estimate health utilities based on responses to the OM8-30 Otitis Media Questionnaire. | 2010 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Can also be used as inhalation powder http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021067s013lbl.pdf
Apply a few drops to the affected skin areas once daily and
massage lightly until it disappears.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15454120
Mac-1 expression and human eosinophil migration were effectively downregulated by preincubation with Mometasone at 1, 10 and 100 nM
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 524.957
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NDF-RT |
N0000175450
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WHO-VATC |
QR03BA07
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WHO-ATC |
D07AC13
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WHO-ATC |
R03AK09
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NCI_THESAURUS |
C211
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WHO-VATC |
QR01AD09
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WHO-ATC |
R01AD09
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WHO-VATC |
QS02CA91
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WHO-VATC |
QR03AK09
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WHO-VATC |
QD07AC13
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NDF-RT |
N0000175576
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WHO-ATC |
R03BA07
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WHO-ATC |
D07XC03
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CFR |
21 CFR 524.1044H
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WHO-VATC |
QD07XC03
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Code System | Code | Type | Description | ||
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C053915
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8HR4QJ6DW8
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6970
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6030
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C66181
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8HR4QJ6DW8
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Mometasone, Nasal
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441335
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108118
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DB00764
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105102-22-5
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DTXSID10872412
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CHEMBL1161
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SUB09045MIG
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100000080358
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MOMETASONE
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Mometasone, Topical
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ACTIVE MOIETY