Cortisone

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
CAS Number	53-06-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16962 Y
ChEMBL	ChEMBL111861 N
ChemSpider	193441 Y
ECHA InfoCard	100.000.149
IUPHAR/BPS	5171
KEGG	D07749 Y
MeSH	Cortisone
PubChem CID	222786
UNII	V27W9254FZ Y
CompTox Dashboard (EPA)	DTXSID5022857
InChI 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 Y Key: MFYSYFVPBJMHGN-ZPOLXVRWSA-N Y 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
SMILES 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
Chemical formula	C21H28O5
Molar mass	360.450 g·mol−1
Melting point	220 to 224 °C (428 to 435 °F; 493 to 497 K)
Pharmacology
ATC code	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 YN ?) Infobox references

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.