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Cortisone



Cortisone
IUPAC name 17,21-dihydroxypregn
-4-ene-3,11,20-trione
Identifiers
CAS number 53-06-5
MeSH Cortisone
SMILES C[C@@](C3)4[C@](CC[C@@](O)4
[C@@](CO)=O)([H])[C@]2([H])CCC1=CC
(CC[C@@](C)1[C@]([H])2C3=O)=O
Properties
Molecular formula C21H28O5
Molar mass 360.46 g/mol
Melting point

220-224 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Cortisone (pronounced /ˈkɔrtɨsoʊn/ or /ˈkɔrtɨzoʊn/ (ˈkôrtəˌsōn or -zōn)) (17-hydroxy-11-dehydrocorticosterone) is a steroid hormone. Chemically, it is a corticosteroid closely related to corticosterone.

Additional recommended knowledge

Contents

Production

Cortisone is one of several end products of a process called steroidogenesis. This process starts with cholesterol which then goes through a series of reactions in the adrenal gland to produce a variety of steroid hormones. One end product of this pathway is cortisol, which is then released from the adrenal gland by ACTH signaling from the anterior pituitary, which is stimulated by corticotropin-releasing hormone from the hypothalamus in the brain. In the peripheral tissues cortisol is converted to cortisone by 11-beta-steroid dehydrogenase. Cortisol has much greater glucocorticoid activity than cortisone and thus cortisone can be considered an inactive metabolite of cortisol. However 11-beta-steroid dehydrogenase can catalyze the reverse reaction as well and thus cortisone is also the inactive precursor molecule of the active hormone cortisol. Cortisone is activated through hydroxylation of the 11-keto-group by an enzyme called 11-beta-steroid dehydrogenase. The active form, cortisol, is thus sometimes referred to as hydrocortisone.

Effects and uses

Cortisol and adrenaline are the main hormones released by the body as a reaction to stress. They elevate blood pressure and prepare the body for a fight or flight response.

Cortisone is sometimes used as a drug to treat a variety of ailments. It can be administered intravenously or cutaneously.

One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This could be the explanation for the apparent correlation between high stress and sickness. The suppression of the immune system may be important in the treatment of inflammatory conditions such as severe IgE-mediated allergies.

Cortisone is less important than a similar steroid cortisol. Cortisol is responsible for 95% of the effects of the glucocorticosteroids while cortisone is about 4 or 5%. Corticosterone is even less important.

Cortisone shots also may leave "dents" in the injection area, in some cases.

History

Cortisone was first discovered by the American chemist Edward Calvin Kendall while a researcher at the Mayo Clinic. He won the 1950 Nobel Prize for Physiology or Medicine along with Philip S. Hench and Tadeus Reichstein for the discovery of adrenal cortex hormones, their structures, and functions. Cortisone was first produced commercially by Merck & Co. under the leadership of George W. Merck.

References

  • Merck Index, 11th Edition, 2533
  • Woodward R. B., Sondheimer F., Taub D. (1951). "The Total Synthesis of Cortisone". Journal of the American Chemical Society 73: 4057 - 4057. doi:10.1021/ja01152a551.
  • Ingle D. J. (1950). "The biologic properties of cortisone: a review". Journal of Clinical Endocrinology 10: 1312-1354.

See also

  • Central serous retinopathy
  • Corticosterol
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Cortisone". A list of authors is available in Wikipedia.
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