Cortisone

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 (17-hydroxy-11-dehydrocorticosterone) is a naturally occurring steroid hormone that functions in carbohydrate metabolism and is used medically for the treatment of various ailments, including rheumatoid arthritis and certain allergies. Its chemical formula is 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 can develop when abnormally low quantities of those hormones are produced by the adrenal gland, and it can be fatal.

Human creativity and curiosity about nature and the human body led to research culminating in the isolation of cortisone and the understanding of its medicinal uses. The process of its discovery ranged over 100 years, since Thomas Addison first described Addison's disease in 1849 and published a classic paper on the disease and anemia in 1855. Over time, researchers identified and isolated the hormone that would become known as cortisone, culminating in a useful drug in 1949.

Contents

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 metabolism, 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 administered 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 percent of the effects of the glucocorticosteroids while cortisone is about four or five percent.

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 ulcers, 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

  • Addison, T. On The Constitutional And Local Effects Of Disease Of The Supra-Renal Capsules. London: Samual Highley, 1855. Retrieved July 16, 2007.
  • Goodlad, G. A. J., and H. N. Munro. “Diet and the action of cortione on protein metabolism.” Biochem J. 73(2): 343–348, 1959.
  • Gramene. Summary for carbohydrate metabolism. Gramene website. 2007. Retrieved July 16, 2007.
  • Ingle, D. J. “The biologic properties of cortisone: A review.” Journal of Clinical Endocrinology 10: 1312-1354, 1950.
  • Merck. Merck Index, 11th Edition. Merck & Company, 1989. ISBN 091191028X
  • Woodward R. B., F. Sondheimer, and D. Taub. “The total synthesis of cortisone.” Journal of the American Chemical Society 73: 4057, 1951.

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