Cortisone
From DrugPedia: A Wikipedia for Drug discovery
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| + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1033&show=SHOW-3D Show 3-D Structure] | ||
| + | {{Drugbox | ||
| + | | 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 | ||
| + | | CAS_number = 53-06-5 | ||
| + | | CAS_supplemental = | ||
| + | | ATC_suffix = | ||
| + | | ATC_supplemental = | ||
| + | | PubChem = 123917 | ||
| + | | ChemSpiderID = | ||
| + | | chemical_formula =C<sub>21</sub>H<sub>28</sub>O<sub>5</sub> | ||
| + | | molecular_weight = 360.44 | ||
| + | | smiles = CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C | ||
| + | | synonyms = Cortogen | ||
| + | | density = | ||
| + | | melting_point = 222 | ||
| + | | boiling_point = | ||
| + | | solubility = 280 mg/L 25<sup>o</sup>C EXP | ||
| + | | specific_rotation = | ||
| + | | sec_combustion = | ||
| + | | bioavailability = | ||
| + | | protein_bound = | ||
| + | | metabolism = | ||
| + | | elimination_half-life = | ||
| + | | excretion = | ||
| + | | pregnancy_category= | ||
| + | | dependency_liability = | ||
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| + | }} | ||
'''Cortisone''' ({{pronEng|ˈkɔrtɨsoʊn}} or {{IPA|/ˈkɔrtɨzoʊn/}} (ˈkôrtəˌsōn or -zōn)) (17-hydroxy-11-dehydrocorticosterone) is a [[steroid]] [[hormone]]. Chemically, it is a [[corticosteroid]] closely related to [[corticosterone]]. | '''Cortisone''' ({{pronEng|ˈkɔrtɨsoʊn}} or {{IPA|/ˈkɔrtɨzoʊn/}} (ˈkôrtəˌsōn or -zōn)) (17-hydroxy-11-dehydrocorticosterone) is a [[steroid]] [[hormone]]. Chemically, it is a [[corticosteroid]] closely related to [[corticosterone]]. | ||
| + | A naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver to the active metabolite HYDROCORTISONE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p726). | ||
==History== | ==History== | ||
Cortisone was first discovered by the American chemist [[Edward Calvin Kendall]] while a researcher at the [[Mayo Clinic]]. 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 discovered by the American chemist [[Edward Calvin Kendall]] while a researcher at the [[Mayo Clinic]]. 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.]]. | ||
| - | + | ==PhysioChemical Properties== | |
| + | ===Melting Point=== | ||
| + | 222 deg C EXP | ||
| + | ===log P (octanol-water)=== | ||
| + | 1.47 EXP | ||
| + | ===Water Solubility=== | ||
| + | 280 mg/L 25 EXP | ||
| + | ===Vapor Pressure=== | ||
| + | 5.80E-13 mm Hg 25 EST | ||
| + | ===Henry's Law Constant=== | ||
| + | 6.03E-10 atm-m3/mole 25 EST | ||
| + | ===Atmospheric OH Rate Constant=== | ||
| + | 1.10E-10 cm3/molecule-sec 25 EST | ||
==Production== | ==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 is thus sometimes referred to as [[hydrocortisone]]. | 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 is thus sometimes referred to as [[hydrocortisone]]. | ||
Current revision
| Cortisone
| |
| Systematic (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 | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C21H28O5 |
| Mol. mass | 360.44 |
| SMILES | & |
| Synonyms | Cortogen |
| Physical data | |
| Melt. point | 222 °C |
| Solubility in water | 280 mg/L 25oC EXP mg/mL |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Cortisone (Template:PronEng or Template:IPA (ˈkôrtəˌsōn or -zōn)) (17-hydroxy-11-dehydrocorticosterone) is a steroid hormone. Chemically, it is a corticosteroid closely related to corticosterone. A naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver to the active metabolite HYDROCORTISONE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p726).
Contents |
[edit] History
Cortisone was first discovered by the American chemist Edward Calvin Kendall while a researcher at the Mayo Clinic. 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..
[edit] PhysioChemical Properties
[edit] Melting Point
222 deg C EXP
[edit] log P (octanol-water)
1.47 EXP
[edit] Water Solubility
280 mg/L 25 EXP
[edit] Vapor Pressure
5.80E-13 mm Hg 25 EST
[edit] Henry's Law Constant
6.03E-10 atm-m3/mole 25 EST
[edit] Atmospheric OH Rate Constant
1.10E-10 cm3/molecule-sec 25 EST
[edit] 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 is thus sometimes referred to as hydrocortisone.
[edit] 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.
Cortisone is sometimes used as a drug to treat a variety of ailments. It can be administered intravenously or cutaneously.
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. The suppression of the immune system may be important in the treatment of inflammatory conditions such as severe IgE-mediated allergies.
Cortisone is less powerful than a similar steroid cortisol. Cortisol is responsible for 95% of the effects of the glucocorticosteroids while cortisone is about 4 or 5%. Corticosterone is even less important.Template:Fact Cortisol decreases the uptake of glucose by cells and increases glucose release by the liver. This may cause hyperglycemia in a well-fed state but can maintain blood glucose levels in (stressful) fasting states.
[edit] References
- Merck Index, 11th Edition, 2533
- Woodward R. B., Sondheimer F., Taub D. (1951). "The Total Synthesis of Cortisone". Journal of the American Chemical Society 73: 4057–4057. doi:.
- Ingle D. J. (1950). "The biologic properties of cortisone: a review". Journal of Clinical Endocrinology 10: 1312–1354.
