Cortisone

This article describes the largely inactive biomolecule. Hydrocortisone, which is often abbreviated as "cortisone" , has its systematic name cortisol .

Structural formula
General
Non-proprietary name	Cortisone
other names	11-dehydro-17-hydroxycorticosterone ( IUPAC ) 11-dehydro-17-hydroxycorticosterone-21-acetate (cortisone acetate)
Molecular formula	C 21 H 28 O 5 (cortisone) C 23 H 30 O 6 (cortisone acetate)
External identifiers / databases
CAS number 53-06-5 (cortisone) 50-04-4 (cortisone acetate) EC number 200-162-4 ECHA InfoCard 100,000,149 PubChem 222786 ChemSpider 193441 DrugBank DB01380 Wikidata Q423185
Drug information
ATC code	H02 AB10
Drug class	Glucocorticoids
properties
Molar mass	360.45 g · mol -1 (cortisone) 402.5 g · mol -1 (cortisone acetate)
Melting point	222 ° C (cortisone) 235 ° C (cortisone acetate)
boiling point	Decomposition from 240 ° C
solubility	Water: 280 mg l −1 at 25 ° C
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cortisone (from Latin cortex 'bark', spelling also cortisone ) is a steroid hormone that was found in the adrenal cortex of humans around 1935 and can also be produced synthetically. Cortisone is the oxidation- inactivated form of the glucocorticoid cortisol , which is important in the carbohydrate balance, fat metabolism and protein turnover. The acetic acid ester cortisone acetate was used for therapeutic purposes. Colloquially, glucocorticoids , drugs with cortisol effects - above all prednisolone and dexamethasone  - are often referred to as "cortisone". When we talk about the side effects of cortisone, we are talking about the side effects of the glucocorticoids.

Discovery story

In 1929/30 it was discovered that animals that had had their adrenal glands removed remained alive when they were given extracts from the adrenal cortex. In the years 1935–1940, cortisone was isolated from animal adrenal cortex by various working groups and named differently: as "compound F" by Oskar Wintersteiner , as "substance Fa" by Tadeus Reichstein and as "compound E" by the working group around Edward Calvin Kendall . The hydrogenated form cortisol or hydrocortisone was produced by Reichstein in 1937/38. It was later found that cortisone is an oxidation product of the actual hormone cortisol. The partial synthesis of cortisone from deoxycholic acid was first achieved by Lewis Hastings Sarett at Merck during the Second World War . In 1948, the physician Philip Hench first injected cortisone into a patient with severe rheumatism , who was then painless. Two years later, Kendall, Reichstein and Hench were jointly awarded the Nobel Prize for Medicine “for their discoveries about the hormones of the adrenal cortex, their structure and their biological effects” . In 1951 Robert Woodward first found a way for the total synthesis of cortisone.

Physiological effect

Cortisone itself has no effect on the organism, as it is neither the glucocorticoid - receptor nor the mineralocorticoid binds receptor. Therefore topical application , for example on the skin, does not make sense. In local therapy, instead of cortisone, corticosteroids are used, which do not have to be metabolized in order to be biologically active. When ingested orally or intravenously , cortisone is converted by the enzyme 11 β -hydroxysteroid dehydrogenase 1 in the liver to cortisol , which shows the actual effect (see cortisol effect ) .

Therapeutic use

The synthetically produced absorption ester cortisone acetate is suitable for therapeutic purposes because it is quickly absorbed after oral administration . After hydrolysis to cortisone, the biologically active cortisol is formed in the liver .

operation area

Cortisone acetate is intended for systemic absorption in the form of tablets. The active ingredient can be used to compensate for a deficiency in the body's own cortisol, such as occurs in primary adrenal insufficiency (substitution therapy). Today, however, other glucocorticoids are used for such therapeutic purposes, for example hydrocortisone (cortisol) and prednisolone .

Pharmacological properties

Cortisone acetate has glucocorticoid and mineralocorticoid properties. The latter are more pronounced than other (newer) synthetic steroids. The bioavailability of cortisol from cortisone acetate corresponds to about 80% of a comparable, orally administered dose of cortisol. The duration of action is about eight to twelve hours, making cortisone (acetate) a short-acting glucocorticoid. The half-life in blood plasma is around one hour.

Side effects

In the case of substitution therapy with physiologically adjusted doses - as provided for according to the indication - no side effects are to be expected.

After an overdose over a long period of time, symptoms of Cushing's syndrome can develop, which include muscle weakness or muscle wasting ( cortisone myopathy ), osteoporosis , aseptic bone necrosis (head of the upper arm and thigh bone), stretch marks (striae rubrae) , delayed wound healing, steroid acne , punctiform skin bleeding ( petechiae ), bruises , increase in intraocular pressure ( glaucoma ), opacity of the lens ( cataract ), inhibition of gastric mucus production, in rare cases long-lasting hiccups, increased blood sugar level, diabetes ( diabetes mellitus ), water retention in the tissue , full moon face , increased potassium excretion , Growth disorders in children, disorders of sex hormone secretion (lack of menstrual bleeding, abnormal hair growth, impotence ), “ bull's neck ”, changes in the blood count ( leukocytosis , lymphopenia , eosinopenia, polyglobulia ), increased risk of infection and immunodeficiency .

Short-term, high-dose systemic use:

In the case of short-term, high-dose systemic use, neuropsychiatric symptoms in particular can occur, such as convulsions , dizziness , headaches , insomnia , euphoria , depression and psychoses . In addition, this application can lead to the manifestation of latent epilepsy .

Commercial preparations

According to the manufacturer, the last ready-to-use product available on the German market , Cortisone CIBA , was withdrawn from the market in 2008 due to the supplier's quality problems .

literature

• Lea Haller: Cortisone. History of a Hormone, 1900–1955. Chronos, Zurich 2012. ISBN 978-3-0340-1115-0 .
• Hanns Kaiser , Norbert Klinkenberg: Cortisone. The story of a drug. Scientific Book Society, Darmstadt 1988, ISBN 978-3-534-80037-7 .

Web links

Wiktionary: Cortisone  - explanations of meanings, word origins, synonyms, translations

• Cortisone, the miracle drug against rheumatism . kraniopharyngeom.de
• Why does cortisone have to be tapered off? rheuma-online.de - Introduction to cortisone in general and cortisone in rheumatism therapy

Individual evidence

1. ↑ ^{a b} Entry on cortisone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
2. ↑ ^{a b c} A. W Frahm, HHJ Hager, F. v. Bruchhausen, M. Albinus, H. Hager: Hager's Handbook of Pharmaceutical Practice: Volume 4: Substances A – K. , Birkhäuser, 1999, p. 1099, ISBN 978-3-540-52688-9 .
3. ↑ ^{a b} Data sheet Cortisone, ≥ 98% from Sigma-Aldrich , accessed on September 14, 2011 ( PDF ).
4. ↑ This refers to artificial glucocorticoids.
5. ^ ^{A b} Peter Dilg: Cortisone. In: Werner E. Gerabek , Bernhard D. Haage, Gundolf Keil , Wolfgang Wegner (eds.): Enzyklopädie Medizingeschichte. De Gruyter, Berlin / New York 2005, ISBN 3-11-015714-4 , p. 275.
6. ^ Arthur A. Patchett: Lewis Hastings Sarett 1917–1999 (PDF; 156 kB) . (PDF) Biographical Memoirs, Vol. 81, 2002, The National Academy Press, Washington, DC
7. ↑ Florian Horn: Biochemistry of humans: The textbook for medical studies , 3rd edition, Thieme-Verlag 2005; P. 371. ISBN 3-13-130883-4 .
8. ↑ ^{a b} Entry on cortisone at Vetpharm, accessed on June 23, 2012.
9. ↑ ^{a b} K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 4.0, cortisone acetate. Loose-leaf collection, 18th delivery 2004, Wissenschaftliche Verlagsgesellschaft Stuttgart
10. ↑ VJ Heazelwood, JP Galligan, GR Cannell, F. Bochner, RH Mortimer: Plasma cortisol delivery from oral cortisol and cortisone acetate: relative bioavailability. In: Br. J. Clin. Pharmacol , 17 (1), 1984, pp. 55-59; PMC 1463287 (free full text, PDF).
11. ↑ Specialist information on Cortisone Ciba®
12. ↑ Important information! In: Glandula , Novartis Pharma GmbH, issue 01/08, p. 23, glandula-online.de (PDF)
13. ↑ Reviews at Perlentaucher .

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !