dexamethasone   

GtoPdb Ligand ID: 2768

Synonyms: Decadron® | desametasone | fluormethylprednisolone
dexamethasone is an approved drug (FDA (1958), EMA (2010))
Compound class: Synthetic organic
Comment: Dexamethasone is a glucocorticoid receptor agonist with anti-inflammatory action.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 94.83
Molecular weight 392.2
XLogP 1.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC(=O)C1(O)C(C)CC2C1(C)CC(O)C1(C2CCC2=CC(=O)C=CC12C)F
Isomeric SMILES OCC(=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)F
InChI InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
InChI Key UREBDLICKHMUKA-CXSFZGCWSA-N
No information available.
Summary of Clinical Use
Dexamethasone may be administered by various routes to treat myriad inflammatory condtions, including inflammatory dermatoses, asthma, allergic or inflammatory nasal conditions, and nasal polyps, endocrine disorders and many more. Ozurdex® has EMA authorisation as a treatment for macular edema and uveitis, and Neofordex® can be used to treat multiple myeloma.

SARS-CoV-2 infection (COVID-19): On June 16th 2020, it was reported that results from the UK recovery trial have shown a clear survival benefit of low-dose dexamethasone in COVID-19 patients with severe respiratory complications. It cut the risk of death by a third for patients on ventilators and by 20% for those on oxygen [4]. This disclosure is preliminary, and pending peer review and publication.
Mechanism Of Action and Pharmacodynamic Effects
Dexamethasone binds to the glucocorticoid receptor and the drug-receptor complex translocates to the nucleus and acts as transcription factor for target gene expression. The antiinflammatory actions of dexamethasone are thought to involve phospholipase A2 inhibitory proteins such as the annexins (aka lipocortins), which control the biosynthesis of the major mediators of inflammation, prostaglandins and leukotrienes. Increased expression of the gene coding for annexin-1 is one of the mechanisms by which glucocorticoids inhibit inflammation.
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