Cortisone

Source: Wikipedia, the free encyclopedia.
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
IUPHAR/BPS
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

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

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.

Effects and uses

Cortisone itself is inactive.

11β-hydroxysteroid dehydrogenase type 1.[4]
This primarily happens in the liver, the main site at which cortisone becomes cortisol after oral or systemic injection, and can thus have a pharmacological effect. After application to the skin or injection into a joint, local cells that express 11β-hydroxysteroid dehydrogenase type 1 instead convert it to active cortisol.

A cortisone injection may provide short-term pain relief and may reduce the swelling from

bursa in, for example, the joints of the knee, elbow and shoulder[1] and into a broken coccyx.[5]

Cortisone is used by

eczema and atopic dermatitis,[7] and stop the development of sarcoidosis.[8]

Side effects

Oral use of cortisone has a number of potential systemic adverse effects, including

abscesses).[9]

History

Cortisone was first identified by the American chemists Edward Calvin Kendall and Harold L. Mason while researching at the Mayo Clinic.[10][11][12] During the discovery process, cortisone was known as compound E (while cortisol was known as compound F).

In 1949,

Nobel Prize for Physiology or Medicine along with Philip Showalter Hench and Tadeusz Reichstein for the discovery of the structure and function of adrenal cortex hormones including cortisone.[14][15] Both Reichstein and the team of O. Wintersteiner and J. Pfiffner had separately isolated the compound prior to the discovery made by Mason and Kendall, but failed to recognize its biological significance.[11] Mason's contributions to the crystallization and characterization of the compound have generally been forgotten outside of the Mayo Clinic.[11]

Cortisone was first produced commercially by

Glaxo to produce cortisone from hecogenin from sisal plants.[18]

Production

Cortisone is one of several end-products of a process called

ACTH, which relays the signal to the adrenal cortex. Here, the zona fasciculata and zona reticularis, in response to ACTH, secrete glucocorticoids, in particular cortisol. In various peripheral tissues, notably the kidneys, cortisol is inactivated to cortisone by the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2. This is crucial because cortisol is a potent mineralocorticoid and would cause havoc with electrolyte levels (raising blood sodium and lowering blood potassium levels) and raise blood pressure if it were not inactivated in the kidneys.[4]

Because cortisone must be converted to cortisol before being active as a glucocorticoid, its activity is less than simply administering cortisol directly (80–90%).[19]

Popular culture

Addiction to cortisone was the subject of the 1956 motion picture Bigger Than Life, produced by and starring James Mason. Though it was a box-office flop upon its initial release,[20] many modern critics hail the film as a masterpiece and brilliant indictment of contemporary attitudes toward mental illness and addiction.[21] In 1963, Jean-Luc Godard named it one of the ten greatest American sound films ever made.[22]

John F. Kennedy was regularly administered corticosteroids such as cortisone as a treatment for Addison's disease.[23]

See also

Notes

  1. ^ a b c "Cortisone shots". MayoClinic.com. 2010-11-16. Retrieved July 31, 2013.
  2. ^ a b "Prednisone and other corticosteroids: Balance the risks and benefits". MayoClinic.com. 2010-06-05. Retrieved 2017-12-21.
  3. ISBN 978-0853693000
    .
  4. ^
    PMID 19837912
    .
  5. ^ "injections and needles for coccyx pain". www.coccyx.org.
  6. PMID 1582609
    .
  7. ^ "All About Atopic Dermatitis". National Eczema Association. Archived from the original on 2012-01-30. Retrieved 2013-05-07.
  8. PMID 13182965
    .
  9. S2CID 18658724
    .
  10. ^ "Cortisone Discovery and the Nobel Prize". Mayo Clinic. Retrieved 2009-07-04.
  11. ^ a b c "I Went to See the Elephant" autobiography of Dwight J. Ingle, published by Vantage Press (1963), pg 94, 109
  12. doi:10.1016/S0021-9258(18)74790-X
    . Retrieved 2014-09-07.
  13. ^
    ISBN 978-0-7817-6879-5
    .
  14. ^ "The Nobel Prize in Physiology or Medicine 1950". The Nobel Prize. The Nobel Foundation. 2021. Retrieved 2 April 2021.
  15. PMID 10070369
    .
  16. PMID 13875857
    .
  17. ^ Gibbons, Ray (1949). "Science gets synthetic key to rare drug; discovery is made in Chicago". Chicago Tribune. Chicago. p. 1.
  18. PMID 16337555
    .
  19. ^ "Corticosteroid Dose Equivalents". Medscape. Retrieved 20 December 2016.
  20. ^ Cossar 2011, p. 273.
  21. ^ Halliwell 2013, pp. 159–162.
  22. ^ Marshall, Colin (December 2, 2013). "A Young Jean-Luc Godard Picks the 10 Best American Films Ever Made (1963)". Open Culture.
  23. ^ Altman, Lawrence (October 6, 1992). "The doctor's world; Disturbing Issue of Kennedy's Secret Illness". The New York Times.

Bibliography

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