Cortisone

Not to be confused with cortisol (a.k.a. hydrocortisone), a similar compound with a similar name, genesis, and function.

Cortisone
IUPAC name (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11-dione
Identifiers
CAS number	53-06-5 Y
PubChem	222786
ChemSpider	193441 Y
UNII	V27W9254FZ Y
KEGG	D07749 Y
MeSH	Cortisone
ChEBI	CHEBI:16962 Y
ChEMBL	CHEMBL111861 N
Jmol-3D images	Image 1
SMILES O=C(CO)[C@@]3(O)CC[C@H]2[C@@H]4CC\C1=C\C(=O)CC[C@]1(C)[C@H]4C(=O)C[C@@]23C
InChI InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1 Y Key: MFYSYFVPBJMHGN-ZPOLXVRWSA-N Y InChI=1/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1 Key: MFYSYFVPBJMHGN-ZPOLXVRWBW
Properties
Molecular formula	C21H28O5
Molar mass	376.0g/mol
Melting point	220–224 °C
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cortisone ( /ˈkɔrtɨsoʊn/ or /ˈkɔrtɨzoʊn/; 17-hydroxy-11-dehydrocorticosterone) is a steroid hormone. It is one of the main hormones released by the adrenal gland in response to stress. In chemical structure, it is a corticosteroid closely related to corticosterone. It is used to treat a variety of ailments and can be administered intravenously, orally, intraarticularly, or transcutaneously. Cortisone suppresses the immune system, thus reducing inflammation and attendant pain and swelling at the site of the injury. Risks exist, in particular in the long-term use of cortisone.^[1][2]

History

Cortisone was first identified by the American chemist Edward Calvin Kendall while a researcher at the Mayo Clinic.^[3] 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 their 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.^{[chronology citation needed]} This eliminated the need to use osmium tetroxide, a rare, expensive, and dangerous 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 fasciculata and zona reticularis, in response to ACTH, secrete glucocorticoids, in particular cortisol. In the peripheral tissues, cortisol is converted to cortisone by the enzyme 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.^[4]

Effects and uses

Cortisone, 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.

A cortisone injection can also be used to give short-term pain relief and reduce the swelling from inflammation of a joint, tendon, or bursa in, for example, the joints of the knee, elbow, and shoulder.^[5]

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.^[6]

Last, cortisone is a common treatment for a severe sore throat that occurs commonly with EBV infectious mononucleosis. It is important to note that cortisone does not help lessen the duration of the virus, and is used purely to increase the comfort of a patient with trouble speaking or swallowing as a result of the mononucleosis-induced swollen throat.

Side-effects

Oral use of cortisone has a number of potential side-effects: hyperglycemia, insulin resistance, diabetes mellitus, osteoporosis, anxiety, depression, amenorrhoea, cataracts and glaucoma, among other problems.^{[1][2][citation needed]}

See also

• Central serous retinopathy
• Corticosterol

References

Notes

1. ^ ^{a b} "Cortisone shots: Risks". MayoClinic.com. 2010-11-16. http://www.mayoclinic.com/health/cortisone-shots/MY00268/DSECTION=risks. Retrieved 2011-09-03. 
2. ^ ^{a b} "Prednisone and other corticosteroids: Balance the risks and benefits". MayoClinic.com. 2010-06-05. http://www.mayoclinic.com/health/steroids/HQ01431. Retrieved 2011-09-03. 
3. ^ "Cortisone Discovery and the Nobel Prize". http://www.mayoclinic.org/tradition-heritage/cortisone-discovery.html. Retrieved 2009-07-04. 
4. ^ Samuels, Theophilus "Cortisol vs. corticosterone"
5. ^ [1]^{[dead link]}
6. ^ "Cortisol vs. corticosterone". Bio.net. http://www.bio.net/bionet/mm/immuno/2000-April/015756.html. Retrieved 2011-09-03. 

Bibliography

• Bonagura J., DVM. et al. (2000). Current Veterinary Therapy. 13. pp. 321–381. 
• Ingle DJ (October 1950). "The biologic properties of cortisone: a review". J. Clin. Endocrinol. Metab. 10 (10): 1312–54. doi:10.1210/jcem-10-10-1312. PMID 14794756. http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=14794756. 
• Woodward R. B., Sondheimer F., Taub D. (1951). "The Total Synthesis of Cortisone". Journal of the American Chemical Society 73 (8): 4057–4057. doi:10.1021/ja01152a551. 

External links

• Cortisone: The Wonder Drug
• "How Hormone Team Is Saving Lives" , by John E. Pleiffer 1951 article on the new drug cortisone and how it works