Cortisone

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Cortisone
Chemical structure of cortisone
Systematic name 17,21-dihydroxypregn-4-ene-3,11,20-trione
Chemical formula C21H28O5
Molecular mass 360.46 g/mol
Density  ? g/cm3
Melting point 220-224 °C
CAS number [53-06-5]
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
Disclaimer and references

Cortisone (IPA:ˈkôrtəˌsōn) (17-hydroxy-11-dehydrocorticosterone) is a steroid hormone. Chemically, it is a corticosteroid with formula C21H28O5 and IUPAC name 17,21-dihydroxypregn-4-ene-3,11,20-trione. It is closely related to corticosterone.

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 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.

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.

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.

[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.

[edit] See also

[edit] External links


Corticosteroids - glucocorticoid/receptor and mineralocorticoid/receptor edit
(A07EA, C05AA, D07, D10AA, H02, R01AD, R03BA, S01BA, S02B, and S03B)

Alclometasone, Aldosterone, Amcinonide, Beclometasone, Betamethasone, Budesonide, Ciclesonide, Clobetasol, Clobetasone, Clocortolone, Cloprednol, Cortisone, Cortivazol, Deflazacort, Deoxycorticosterone, Desonide, Desoximetasone, Desoxycortone, Dexamethasone, Diflorasone, Diflucortolone, Difluprednate, Fluclorolone, Fludrocortisone, Fludroxycortide, Flumetasone, Flunisolide, Fluocinolone acetonide, Fluocinonide, Fluocortin, Fluocortolone, Fluorometholone, Fluperolone, Fluprednidene, Fluticasone, Formocortal, Halcinonide, Halometasone, Hydrocortisone/cortisol, Hydrocortisone aceponate, Hydrocortisone buteprate, Hydrocortisone butyrate, Loteprednol, Medrysone, Meprednisone, Methylprednisolone, Methylprednisolone aceponate, Mometasone furoate, Paramethasone, Prednicarbate, Prednisone/Prednisolone, Prednylidene, Rimexolone, Tixocortol, Triamcinolone, Ulobetasol
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