mometasone   Click here for help

GtoPdb Ligand ID: 9029

Synonyms: Elocon® (topical) | Nasonex®
Approved drug Immunopharmacology Ligand
mometasone is an approved drug (1987 (FDA))
Compound class: Synthetic organic
Comment: Mometasone is a corticosteroid anti-inflammatory drug.
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View more information in the IUPHAR Pharmacology Education Project: mometasone

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 74.6
Molecular weight 426.14
XLogP 2.12
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES ClCC(=O)C1(O)C(C)CC2C1(C)CC(O)C1(C2CCC2=CC(=O)C=CC12C)Cl
Isomeric SMILES ClCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)Cl
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
InChI Key QLIIKPVHVRXHRI-CXSFZGCWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Mometasone is used intranasally in the management of asthma, allergic rhinitis and nasal polyposis, and topically for allergic skin disorders. Prescribed formulations contain mometasone furoate (PubChem CID 441336).

A fixed-dose combination of indacaterol/glycopyrrolate/mometasone furoate (QVM149, Enerzair® Breezhaler®) has completed Phase 3 evaluation as a once-daily therapy for uncontrolled asthma [1]. Results confirmed non-inferiority to twice-daily salmeterol/fluticasone high-dose + tiotropium, and using a medium-dose had comparable efficacy but at a corresponding lower steroid dose.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The antiinflammatory actions of corticosteroids are thought to involve inhibition of several pathways involved in resolution of inflammation, including inhibition of cytosolic phospholipase A2 (through activation of lipocortin-1 (annexin)) which controls the biosynthesis of pro-inflammatory prostaglandins and leukotrienes.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03158311 Study to Compare QVM149 and Free Triple Combination of Salmeterol/Fluticasone + Tiotropium Phase 3 Interventional Novartis Based on results from this trial, this combination therapy is under regulatory review in multiple countries to gain clinical approval. 1
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com