File:Cortison.svg · Wikimedia Commons · See Wikimedia Commons
cortisone
Sign in to saveAlso known as COS237, 11-dehydro-17-hydroxycorticosterone, 17-hydroxy-11-dehydrocorticosterone, Kortison, Cortison, Delta(4)-pregnene-17alpha,21-diol-3,11,20-trione, 4-pregnene-17alpha,21-diol-3,11,20-trione, 17alpha,21-dihydroxy-4-pregnene-3,11,20-trione
Cortisone is a naturally occurring, mostly inactive pregnene (21-carbon) steroid hormone. In the body, cortisone is produced as part of the Cortisol-Cortisone shunt, which protects vulnerable organs like the kidneys from cortisol. These organs produce the enzyme 11β-HSD2 which locally converts cortisol into inactive cortisone. Cortisone is later converted back into the active steroid cortisol by the enzyme 11β-HSD1, particularly in the liver, which maintains blood cortisol levels. Without the reaction converting cortisol into cortisone, cortisol binds with the mineralocorticoid receptors of th
Chemical data
- Formula
- C21H28O5
- Molecular weight
- 360.4 g/mol
- IUPAC name
- (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
- SMILES
- C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
- InChIKey
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N
- XLogP
- 1.5
- Polar surface area
- 91.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
24,526 papers- CORTISONE.British medical journal · 1955
- CORTISONE and tuberculosis.British medical journal · 1951
- [Cortisone].Il Lattante · 1951
- [Cortisone].Minerva farmaceutica · 1953
- Cortisone and the adrenal cortex.Transactions of the Association of American Physicians · 1986
via PubMed
Wikidata facts
- Mass
- 360.193674
Show 8 more facts
- MCN code
- 2937.21.10
- chemical formula
- C₂₁H₂₈O₅
- Commons category
- Cortisone
- melting point
- 225.5
- isomeric SMILES
- C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C
- canonical SMILES
- CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C
- World Health Organisation international non-proprietary name
- cortisone
- defined daily dose
- 37.5
Sources (8)
via Wikidata · CC0
~7 min read
Article
9 sectionsContents
- Effects and uses
- Side effects
- History
- Production
- Popular culture
- See also
- External links
- Notes
- Bibliography
Cortisone is a naturally occurring, mostly inactive pregnene (21-carbon) steroid hormone. In the body, cortisone is produced as part of the Cortisol-Cortisone shunt, which protects vulnerable organs like the kidneys from cortisol. These organs produce the enzyme 11β-HSD2 which locally converts cortisol into inactive cortisone. Cortisone is later converted back into the active steroid cortisol by the enzyme 11β-HSD1, particularly in the liver, which maintains blood cortisol levels. Without the reaction converting cortisol into cortisone, cortisol binds with the mineralocorticoid receptors of the kidney, causing hypertension along with the other symptoms of apparent mineralocorticoid excess syndrome. Because it gets converted into cortisol by the body, it is sometimes used as a pharmaceutical prodrug as an alternative to directly taking cortisol.
The term "cortisone" is frequently misused to mean either any corticosteroid or hydrocortisone, which is in fact cortisol. Many who speak of receiving a "cortisone shot" or taking "cortisone" are more likely receiving hydrocortisone or one of many other, much more potent synthetic corticosteroids.