cortisol   

GtoPdb Ligand ID: 2868

Synonyms: Acticort® | Plenadren®
cortisol is an approved drug (FDA (1953, prior history unavailable), EMA (2011))
Comment: Cortisol is an endogenous adrenal glucocorticoid with immunosuppressant action. Approved as hydrocortisone. Hydrocortisone is a glucocorticoid receptor agonist.
Marketed formulations may contain hydrocortisone acetate (PubChem CID 5744).
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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 362.21
XLogP 0.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC(=O)C1(O)CCC2C1(C)CC(O)C1C2CCC2=CC(=O)CCC12C
Isomeric SMILES OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
InChI InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
InChI Key JYGXADMDTFJGBT-VWUMJDOOSA-N
No information available.
Summary of Clinical Use
Hydrocortisone is used to treat many immune and allergic disorders, adrenal insufficiency disorders (eg Addison's disease) and corticosteroid-responsive dermatological disorders (eg psoriasis, atopic dermatitis, and contact dermatitis).
Mechanism Of Action and Pharmacodynamic Effects
The glucocorticoid receptor-drug complex acts as a transcription factor at glucocorticoid response elements in gene promoter regions, resulting in increased expression of specific target genes. Notably synthesis of prostaglandins and leukotrienes (two of the main pro-inflammatory mediators) is inhibited by the action of glucocorticoids.
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