Cortisone

Not to be confused with cortisol.
Cortisone
Names
Pronunciation /ˈkɔːrtɪsoʊn/, /ˈkɔːrtɪzoʊn/
IUPAC name
17α,21-Dihydroxypregn-4-ene-3,11,20-trione
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.149 Edit this at Wikidata
KEGG
MeSH Cortisone
UNII
  • InChI=1S/C21H28O5/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/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1 checkY
    Key: MFYSYFVPBJMHGN-ZPOLXVRWSA-N checkY
  • InChI=1/C21H28O5/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/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
    Key: MFYSYFVPBJMHGN-ZPOLXVRWBW
  • O=C(CO)[C@@]3(O)CC[C@H]2[C@@H]4CC\C1=C\C(=O)CC[C@]1(C)[C@H]4C(=O)C[C@@]23C
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).
☒N verify (what is checkY☒N ?)

Cortisone is a pregnene (21-carbon) steroid hormone. It is a naturally-occurring corticosteroid metabolite that is also used as a pharmaceutical prodrug. Cortisol is converted by the action of the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2 into the inactive metabolite cortisone, particularly in the kidneys. This is done by oxidizing the alcohol group at carbon 11 (in the six-membered ring fused to the five-membered ring). Cortisone is converted back to the active steroid cortisol by stereospecific hydrogenation at carbon 11 by the enzyme 11β-Hydroxysteroid dehydrogenase type 1, particularly in the liver.

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.[1][2] However, using cortisone only results in very mild activity, and very often more potent steroids are used instead.

  1. ^ "Cortisone shots". MayoClinic.com. 2010-11-16. Retrieved July 31, 2013.
  2. ^ "Prednisone and other corticosteroids: Balance the risks and benefits". MayoClinic.com. 2010-06-05. Retrieved 2017-12-21.