Cortisone

From Wikipedia, the free encyclopedia

This article needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (December 2008)

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 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.

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

[edit] History

Cortisone was first identified by the American chemist Carl Petersson while a researcher at KTH.^[1] He was awarded 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..

[edit] Production

This section does not cite any references or sources. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (December 2008)

Cortisone is one of several end products of a process called steroidogenesis. This process starts with the synthesis of cholesterol which then proceeds through a series of modifications in the adrenal gland (suprarenal) to become any one of many steroid hormones. One end product of this pathway is cortisol. For cortisol to be released from the adrenal gland a cascade of signaling occurs. Corticotropin releasing hormone released from the hypothalamus stimulates corticotrophs in the anterior pituitary to release ACTH which relays the signal to the adrenal cortex. Here, the zona fasiculata and zona reticularis in response to ACTH secrete glucocorticoids, in particular cortisol. In the peripheral tissues cortisol is converted to cortisone by an enzyme called 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 hydrogenation of the 11-keto-group and cortisol is thus sometimes referred to as hydrocortisone.

[edit] Effects and uses

Cortisol, a glucocorticoid, 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.

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.

Cortisone can be used as a drug to treat a variety of ailments. It can be administered intravenously, orally, intraarticularly,^[2] or cutaneously.

Cortisone may also be used to deliberately suppress immune response in persons with autoimmune diseases or following an organ transplant to prevent transplant rejection. The suppression of the immune system may also be important in the treatment of inflammatory conditions such as severe IgE-mediated allergies.

[edit] References

1. ^ "Cortisone Discovery and the Nobel Prize". http://www.mayoclinic.org/tradition-heritage/cortisone-discovery.html. Retrieved on 2009-07-04. 
2. ^ Kruse DW (December 2008). "Intraarticular cortisone injection for osteoarthritis of the hip. Is it effective? Is it safe?". Curr Rev Musculoskelet Med 1 (3-4): 227–33. doi:10.1007/s12178-008-9029-0. PMID 19468910. PMC: 2682414. http://dx.doi.org/10.1007/s12178-008-9029-0. 

• 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 DJ (October 1950). "The biologic properties of cortisone: a review". J. Clin. Endocrinol. Metab. 10 (10): 1312–54. PMID 14794756. http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=14794756. 

[edit] See also

• Central serous retinopathy
• Corticosterol

[edit] External links

• Cortisone: The Wonder Drug

v • d • e Corticosteroids - glucocorticoid/receptor and mineralocorticoid/receptor (A07EA, C05AA, D07, D10AA, H02, R01AD, R03BA, S01BA, S02B, and S03B) (Endogenous in CAPS) Mineralocorticoids (3-one, 4-ene, no FG at 16) Pregnenedione: ALDOSTERONE · 11-DEOXYCORTICOSTERONE · HALOGENATED AT 9: Fludrocortisone Glucocorticoids (3-one, 4-ene, 11-FG, 17-hydroxy) Pregnene CORTISONE Pregnenedione (+20-one) HYDROCORTISONE/CORTISOL# (Hydrocortisone aceponate, Hydrocortisone buteprate, Hydrocortisone butyrate) · Budesonide · Ciclesonide · Deflazacort · Medrysone · Tixocortol · HALOGENATED AT 6: Cloprednol · HALOGENATED, WITH FG AT 16: Halcinonide Pregnadiene (+1-ene) Rimexolone · HALOGENATED, WITH FG AT 16: Flunisolide · Triamcinolone · Amcinonide · Fluocinolone acetonide (Fluocinonide) Pregnadienediol (+21-hydroxy) Prednisone (Meprednisone) · HALOGENATED AT 9: Fluorometholone · HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone, Diflucortolone, Fluocortin) · Desoximetasone Pregnadienetriol (+11-hydroxy) Prednisolone# (Methylprednisolone, Methylprednisolone aceponate, Prednicarbate, Prednylidene) · Desonide · HALOGENATED: Fluprednisolone (Difluprednate, Fluperolone) · HALOGENATED, WITH FG AT 16: Dexamethasone# · Betamethasone (Clobetasol, Clobetasone, Diflorasone, Halometasone, Ulobetasol) · Beclometasone · Paramethasone  · Alclometasone · Fluclorolone · Flumetasone · Fluprednidene Pregnatriene (+2-ene) Cortivazol Androstene HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate, Fluticasone furoate) Other/ungrouped HALOGENATED: Loteprednol · HALOGENATED, WITH FG AT 16: Fludroxycortide · Formocortal · Mometasone furoate Aldosterone antagonists Spironolactone · Eplerenone · Potassium canrenoate · Canrenone Synthesis Trilostane · Carbenoxolone · Aminoglutethimide · Metyrapone #WHO-EM. †Undergoing clinical trials, not FDA approved. ‡Withdrawn from market. §Development halted.

v • d • e Cholesterol and steroid metabolic intermediates Mevalonate pathway to HMG-CoA Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA Ketone bodies Acetone · Acetoacetic acid · beta-Hydroxybutyric acid to DMAPP Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate Geranyl- Geranyl pyrophosphate · Geranylgeranyl pyrophosphate Carotenoid Prephytoene diphosphate · Phytoene Non-mevalonate pathway DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP To Cholesterol Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol Steroid Corticosteroids (C21 pregnane) Mineralocorticoids Pregnenolone · Progesterone · 11-Deoxycorticosterone · Corticosterone · Aldosterone Glucocorticoids Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · 11-Deoxycortisol · Cortisol Cortisol · Cortisone Sex steroids Androgens (C19 andrane) DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone DHEA sulfate · Epitestosterone Estrogens (C18 estrane) Estrone · Estradiol · Estriol Nonhuman Phytosterols Stigmasterol · Brassicasterol Ergosterols Ergosterol · Ergocalciferol see also enzymes, disorders Major families of biochemicals Saccharides/Carbohydrates/Glycosides · Amino acids/Peptides/Proteins/Glycoproteins · Lipids/Terpenes/Steroids/Carotenoids · Alkaloids/Nucleobases/Nucleic acids · Cofactors/Flavonoids/Polyketides/Tetrapyrroles