Cortisone
| Names | |
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| Pronunciation | /ˈkɔːrtɪsoʊn/, /ˈkɔːrtɪzoʊn/ ⓘ |
| IUPAC name
17α,21-Dihydroxypregn-4-ene-3,11,20-trione
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| Systematic IUPAC name
(1R,3aS,3bS,9aR,9bS,11aS)-1-Hydroxy-1-(hydroxyacetyl)-9a,11a-dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-7H-cyclopenta[a]phenanthrene-7,10(1H)-dione | |
| Other names
17α,21-Dihydroxy-11-ketoprogesterone; 17α-Hydroxy-11-dehydrocorticosterone
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.149 |
| KEGG | |
| MeSH | Cortisone |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C21H28O5 | |
| Molar mass | 360.450 g·mol−1 |
| Melting point | 220 to 224 °C (428 to 435 °F; 493 to 497 K) |
| Pharmacology | |
| H02AB10 (WHO) S01BA03 (WHO) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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.
Cortisone can be administered as a prodrug, meaning it has to be converted by the body (specifically the liver, converting it into cortisol) after administration to be effective. It is used to treat a variety of ailments and can be administered intravenously, orally, intra-articularly (into a joint), or transcutaneously. Cortisone suppresses various elements of the immune system, thus reducing inflammation and attendant pain and swelling. Risks exist, in particular in the long-term use of cortisone. However, using cortisone only results in very mild activity, and very often more potent steroids are used instead.