Cortisone

From Wikipedia, the free encyclopedia

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 (IPA:ˈkôrtəˌsōn) (17-hydroxy-11-dehydrocorticosterone) is a steroid hormone. Chemically, it is a corticosteroid closely related to corticosterone.

1 Production
2 Effects and uses
3 History
4 References
5 See also
6 External links

[edit] Production

Cortisone is the inactive precursor molecule of the active hormone cortisol. It 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.

[edit] Effects and uses

Cortisone 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 is an explanation for the apparent correlation between high stress and sickness.

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.

[edit] History

Cortisone was first discovered by the American chemist Edward Calvin Kendall. 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.

[edit] 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.