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Cortisone information


Cortisone
Names
Pronunciation /ˈkɔːrtɪsn/, /ˈkɔːrtɪzn/
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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16962 checkY
ChEMBL
  • ChEMBL111861 ☒N
ChemSpider
  • 193441 checkY
ECHA InfoCard 100.000.149 Edit this at Wikidata
IUPHAR/BPS
  • 5171
KEGG
  • D07749 checkY
MeSH Cortisone
PubChem CID
  • 222786
UNII
  • V27W9254FZ checkY
CompTox Dashboard (EPA)
  • DTXSID5022857 Edit this at Wikidata
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 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
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 checkY☒N ?)
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.

  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.

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Cortisone

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Cortisone is a pregnene (21-carbon) steroid hormone. It is a naturally-occurring corticosteroid metabolite that is also used as a pharmaceutical prodrug...

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Cortisone acetate

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Cortisone acetate (brand names Adreson, Cortison, Cortisone, Cortisone Acetate, Cortone, Cortistab, Cortisyl, others) is a synthetic glucocorticoid corticosteroid...

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Corticosteroid

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21H 30O 5), corticosterone (C 21H 30O 4), cortisone (C 21H 28O 5) and aldosterone (C 21H 28O 5) (cortisone and aldosterone are isomers). The main corticosteroids...

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Prednisone

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synthetic pregnane corticosteroid and derivative of cortisone and is also known as δ1-cortisone or 1,2-dehydrocortisone or as 17α,21-dihydroxypregna-1...

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Cortisol

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biologically inert cortisone to biologically active cortisol 11-beta HSD2 uses the cofactor NAD+ to convert cortisol to cortisone Overall, the net effect...

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Cortisone reductase deficiency

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Cortisone reductase deficiency is caused by dysregulation of the 11β-hydroxysteroid dehydrogenase type 1 enzyme (11β-HSD1), otherwise known as cortisone...

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Philip Showalter Hench

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Prize for Physiology or Medicine in 1950 for the discovery of the hormone cortisone, and its application for the treatment of rheumatoid arthritis. The Nobel...

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Upjohn

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the time. Upjohn developed a process for the large scale production of cortisone. The oxygen atom at the 11 position in this steroid is an absolute requirement...

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Percy Lavon Julian

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work laid the foundation for the steroid drug industry's production of cortisone, other corticosteroids, and birth control pills. He later started his...

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Bigger Than Life

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teacher and family man whose life spins out of control when he misuses cortisone. It is based on a 1955 article by medical writer Berton Roueché in The...

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Crystal polymorphism

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second polymorph was found with more suitable compressive properties. Cortisone acetate exists in at least five different polymorphs, four of which are...

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Pregnene

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A pregnene is an alkene derivative of a pregnane. An example is cortisone. Cortisone Ethisterone Spironolactone Pregnenes at the U.S. National Library...

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Kenneth Callow

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the isolation and characterisation of vitamin D, and the synthesis of cortisone from naturally occurring steroids. After he retired from the NIMR in 1966...

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Adrenal gland

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blood pressure and electrolyte balance. The glucocorticoids cortisol and cortisone are synthesized in the zona fasciculata; their functions include the regulation...

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List of doping cases in cycling

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the 1975 Tour de France by using cortisone. In 1982, after retiring from racing, he said "I was doped with cortisone for three years and there were many...

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Clark Middleton

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its effects in an interview: "At first it distorted my hands. Then the cortisone I had to take made my cheeks fat. At 8, I lost movement in my neck. When...

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Edward Calvin Kendall

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used to treat rheumatoid arthritis. The compound was eventually named cortisone. In 1950, Kendall and Hench, along with Swiss chemist Tadeus Reichstein...

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Prednisolone

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Natural Cortisone Cortisone acetate Cortodoxone (cortexolone, 11-deoxycortisol) Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone) Desoxycortone...

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Tadeusz Reichstein

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Medicine laureate (1950), which was awarded for his work on the isolation of cortisone. Reichstein was born into a Polish-Jewish family at Włocławek, Russian...

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Erythropoietin

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Hypothalamic– pituitary Adrenal axis Adrenal cortex Aldosterone Cortisol Cortisone DHEA DHEA-S Androstenedione Adrenal medulla Adrenaline Norepinephrine...

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Rhizopus

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Sweet potato and is used in commercial production of fumaric acid and cortisone. Various species, including R. stolonifer, may cause soft rot in sweet...

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Hydrocortisone

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Hydrocortisone is metabolized by 11β-hydroxysteroid dehydrogenases (11β-HSDs) into cortisone, an inactive metabolite. It is additionally 5α-, 5β-, and 3α-reduced into...

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Hydrodilatation

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assisted by a radiographer. Contrast medium, a local anaesthetic and cortisone are injected into the joint. Then up to 40ml of sterile saline solution...

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Liquorice

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(1990). "The Influence of Glycyrrhetinic Acid on Plasma Cortisol and Cortisone in Healthy Young Volunteers". The Journal of Clinical Endocrinology &...

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Deflazacort

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activity of 7.5 mg of deflazacort is approximately equivalent to 25 mg cortisone, 20 mg hydrocortisone, 5 mg of prednisolone or prednisone, 4 mg of methylprednisolone...

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