Cortisone

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 (17-hydroxy-11-dehydrocorticosterone) is a naturally occuring steroid hormone that functions in carbohydrate metabolism and is used medically for the treatment of various ailments, including rheumatoid arthritis and certain allergies. Its formula is formula C₂₁H₂₈O₅ and IUPAC name is 17,21-dihydroxypregn-4-ene-3,11,20-trione.

Cortisone is a corticosteroid, a term that refers to steroid hormones that are produced in the adrenal cortex of the body. Cortisone is essential for life. Addison's disease is a case of abnormally low quantities of those hormones are produced by the adrenal gland, and it can be fatal.

Overview

Cortisone is synthesized from cholesterol in the adrenal cortex via the stimulation of adrenocorticotropin hormone (ACTH) (Gramene 2007).

Cortisone is the inactive precursor molecule of the active hormone cortisol, the "stress hormone." 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.

Both cortisone and cortisol are classified as glucocorticoids, a group of corticosteroids that controls protein, fat, carbohydrate, and calcium metabolism. (Minealocorticoids, the other group of corticosteroids, regulates salt and potassium levels and water retention.) Another hormone produced in the adrenal glands, albeit in the adrenal medulla, not the adrenal cortex like corticosteroids, is adrenaline (epinephrine), which like cortisol, deals with stress.

Cortisone is involved in carbohydrate metablolism, with such effects listed as increased glucose release from the liver, increased liver glycogen synthesis, and decreased utilization of glucose by the tissues (Gramene 2007). Cortisone also stimulates protein catabolism and decreased protein synthesis. Goodlad and Munro (1958) noted that administred cortisone results in loss of protein from the body and accumulation of glycogen and protein in the liver. Cortisol also effects salt retention in the kidneys.

Cortisone is considered to be less important than cortisol. Cortisol is responsible for 95% of the effects of the glucocorticosteroids. while cortisone is about 4 or 5%.

Cortisone was first isolated 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. It was discovered that it could treat arthritis and was named "cortisone" on July 1, 1949.

Medical use

Cortisone is sometimes used as a drug to treat a variety of ailments. It can be administered intravenously or cutaneously.

Cortisone has an anti-inflammatory effect in the short-term, and thus has been found helpful in treating rheumatoid arthritis. It also has been used to treat allergies, dematology diseases, respiratory diseases, and endocrine disorders. It can be one of the most effective treatments for people with severe allergies. Cortisone can help in dissolving scar tissue and speed the healing process.

One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. Thus, bacterial infection can be increased. This is one explanation for the apparent correlation between high stress and sickness. On the other hand, the ability of cortisone to minimize the immune reaction has helped in terms of organ transplants. Some other side effects are peptic ulsers, depression, and even mood swings and insomnia.

Cortisone has been an effective medical tool. However, other drugs that are more effective, longer lasting, and have less side effects have largely replaced cortisone in medical treatment.

References

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• Goodlad, G. A. J., and H. N. Munro. 1959. Diet and the action of cortione on protein metabolism. Biochem J. 73(2): 343–348.
• Gramene. 2007. Summary for carbohydrate metabolism. Gramene website. Retrieved November 9, 2007.
• Ingle, D. J. 1950. The biologic properties of cortisone: A review. Journal of Clinical Endocrinology 10: 1312-1354.
• Merck. 1989. Merck Index, 11th Edition. Merck & Company. ISBN 091191028X
• Woodward R. B., F. Sondheimer, and D. Taub. 1951. The total synthesis of cortisone. Journal of the American Chemical Society 73: 4057.

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