Cortisone: Difference between revisions

Cortisone
Names
	IUPAC names 17,21-dihydroxypregn; -4-ene-3,11,20-trione
Identifiers
CAS Number	53-06-5 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.000.149
MeSH	Cortisone
CompTox Dashboard (EPA)	DTXSID5022857 ;
	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
Chemical formula	C21H28O5
Molar mass	360.46 g/mol
Melting point	220-224 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 02:34, 13 September 2009

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

History

Cortisone was first identified by the American chemist Edward Calvin Kendall while a researcher at the Mayo Clinic.^[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.. On September 30, 1949, Percy Julian announced an improvement in the process of producing cortisone from bile acids. This eliminated the need to use osmium tetroxide (a rare and expensive chemical).

Production

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.http://www.bio.net/bionet/mm/immuno/2000-April/015756.html

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. http://www.bio.net/bionet/mm/immuno/2000-April/015756.html

Veterinary Use

Because of corisone's effects on the immune system, dogs treated with even moderate doses show an increase in thirst and urination frequency. The urine that is created is not concentrated. Higher doses increase the likelyhood of life threaning side effects which includes fluid in the abdomen and an increased risk of myocardial arrest (Bonagura et al, 2000).*

References

^ "Cortisone Discovery and the Nobel Prize". Retrieved 2009-07-04.
^ Kruse DW (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. PMC 2682414. PMID 19468910. {{cite journal}}: Unknown parameter |month= ignored (help)

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Ingle DJ (1950). "The biologic properties of cortisone: a review". J. Clin. Endocrinol. Metab. 10 (10): 1312–54. PMID 14794756. {{cite journal}}: Unknown parameter |month= ignored (help)

http://www.bio.net/bionet/mm/immuno/2000-April/015756.html

Bonagura J., DVM.; et al. (2000). Current Veterinary Therapy. Vol. 13. pp. 321–381. {{cite book}}: Cite has empty unknown parameter: |1= (help); Explicit use of et al. in: |author= (help)

External links

Cortisone: The Wonder Drug

[urlCortisone_Discovery_and_the_Nobel_Prize-1] "Cortisone Discovery and the Nobel Prize". Retrieved 2009-07-04.

[pmid19468910-2] Kruse DW (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. PMC 2682414. PMID 19468910. {{cite journal}}: Unknown parameter |month= ignored (help)

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[2]

@@ Line 34: / Line 34: @@
 ==History==
-Cortisone was first identified by the American chemist [[Edward Calvin Kendall]] while a researcher at the [[Mayo Clinic]].<ref name="urlCortisone Discovery and the Nobel Prize">{{cite web |url=http://www.mayoclinic.org/tradition-heritage/cortisone-discovery.html |title=Cortisone Discovery and the Nobel Prize |format= |work= |accessdate=2009-07-04}}</ref> 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.]].
+Cortisone was first identified by the American chemist [[Edward Calvin Kendall]] while a researcher at the [[Mayo Clinic]].<ref name="urlCortisone Discovery and the Nobel Prize">{{cite web |url=http://www.mayoclinic.org/tradition-heritage/cortisone-discovery.html |title=Cortisone Discovery and the Nobel Prize |format= |work= |accessdate=2009-07-04}}</ref> 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.]]. On September 30, 1949, [[Percy Julian]] announced an improvement in the process of producing cortisone from bile acids. This eliminated the need to use osmium tetroxide (a rare and expensive chemical).
 ==Production==

v t e Mineralocorticoids and antimineralocorticoids (H02)
Mineralocorticoids	11-Deoxycorticosterone (desoxycortone) 11-Deoxycortisol (cortodoxone) Aldosterone Corticosterone Cortisol (hydrocortisone) Desoxycortone acetate Desoxycortone enanthate Fludrocortisone Fludrocortisone acetate
Antimineralocorticoids	Amlodipine Benidipine Canrenoate potassium (potassium canrenoate) Canrenoic acid Canrenone Drospirenone Eplerenone Felodipine Finerenone Gestodene Nifedipine Nimodipine Nitrendipine Progesterone Spironolactone
Synthesis modifiers	Acetoxolone Aminoglutethimide Carbenoxolone Enoxolone Ketoconazole Metyrapone Mitotane Osilodrostat Trilostane
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III