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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]].
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| - | 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).
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| - | ==History==
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| - | 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.]].
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| - | ==Production== | + | <table align='right' border=1> |
| - | 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]].
| + | <tr><td> |
| | + | <jmol><jmolApplet> |
| | + | <size>200</size> |
| | + | <script>spin on;color atoms amino;</script> |
| | + | <uploadedFileContents>NPH133.SDF</uploadedFileContents> |
| | + | <color>black</color> |
| | + | </jmolApplet> |
| | + | </jmol> |
| | + | </td></tr></table> |
| | + | ==Description== |
| | + | 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) |
| | + | ==General Properties== |
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| - | ==Effects and uses==
| + | <b>*Molecular Weight</b> |
| - | 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]].
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| - | Cortisone is sometimes used as a drug to treat a variety of ailments. It can be administered [[intravenous]]ly or [[cutaneous]]ly.
| + | 360.44 |
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| - | 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 (medicine)|stress]] and sickness. The suppression of the immune system may be important in the treatment of inflammatory conditions such as severe [[IgE]]-mediated [[allergies]].
| + | <b>*Molecular Formula</b> |
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| - | 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.{{Fact|date=January 2008}} 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.
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| - | ==References==
| + | C<sub>2</sub><sub>1</sub>H<sub>2</sub><sub>8</sub>O<sub>5</sub> |
| - | *''Merck Index'', 11th Edition, 2533
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| - | *{{cite journal
| + | |
| - | | author= Woodward R. B., Sondheimer F., Taub D.
| + | |
| - | | title= The Total Synthesis of Cortisone
| + | |
| - | | journal=Journal of the American Chemical Society
| + | |
| - | | year=1951
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| - | | pages=4057–4057
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| - | | volume=73
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| - | | doi=10.1021/ja01152a551 }}
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| - | *{{cite journal
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| - | | author= Ingle D. J.
| + | |
| - | | title= The biologic properties of cortisone: a review
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| - | | journal=Journal of Clinical Endocrinology
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| - | | year=1950
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| - | | pages=1312–1354
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| - | | volume=10 }}
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| - | ==See also==
| + | <b>*IUPAC NAME</b> |
| - | * [[Central serous retinopathy]] | + | |
| - | * [[Corticosterol]]
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| - | ==External links==
| + | (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 |
| - | *[http://www.chem.yorku.ca/hall_of_fame/essays97/cortisone/cortison.htm Cortisone: The Wonder Drug]
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| - | {{Corticosteroids}}
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| - | [[Category:Corticosteroids]]
| + | <b>*Canonical Smiles</b> |
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| | + | CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4(C(=O)CO)O)C |
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| - | KEGG Pathway(C00762,D07749)
| + | <b>*Isomeric Smiles</b> |
| - | *C21-Steroid hormone metabolism | + | |
| - | *Prostate cancer
| + | |
| | | | |
| - | Activity Adrenal cortex hormone, glucocorticoid
| + | C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | |
| - | |+'''List of PDB file having CORTISONE as Ligands'''
| + | |
| - | |-
| + | ==PhysioChemical Properties== |
| - | ! style="background:brown; color:white" |MMDB ID
| + | |
| - | ! style="background:brown; color:white" |PDB ID
| + | <b>*Melting Point</b> |
| - | ! style="background:brown; color:white" |Reference
| + | |
| - | |-
| + | 222(EXP) |
| - | |66962
| + | |
| - | |3EB3
| + | <b>*LogP</b> |
| - | |Gulbis JM, Zhou M, Mann S, MacKinnon RStructure of the cytoplasmic beta subunit-T1 assembly of voltage-dependent K+ channelsScience v289, p.123-127
| + | |
| - | |-
| + | 1.47(EXP) |
| - | |}
| + | |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | <b>*Water Solubility</b> |
| - | |+'''Physiochemical Properties'''
| + | |
| - | |-
| + | 280(EXP) at 25C |
| - | ! style="background:brown; color:white" |Physical Property
| + | |
| - | ! style="background:brown; color:white" |Value
| + | ==External Links== |
| - | ! style="background:brown; color:white" |Units
| + | *[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=222786]Pubchem |
| - | ! style="background:brown; color:white" |Temp (deg C)
| + | *[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=3EB3]]3EB3, |
| - | ! style="background:brown; color:white" |Source
| + | *[http://www.genome.jp/dbget-bin/www_bget?compound+C00762]]KEGG Compound |
| - | |-
| + | *[http://www.genome.jp/dbget-bin/www_bget?drug+D07749]]KEGG Drug |
| - | |Melting Point
| + | *[http://www.hmdb.ca/metabolites/HMDB02802]Human Metabolome DataBase |
| - | |222
| + | |
| - | |deg C
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| + | [[Categories:Hormones]] |
| - | |EXP
| + | |
| - | |-
| + | |
| - | |log P (octanol-water)
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| - | |1.47
| + | |
| - | |(none)
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| - | |
| + | |
| - | |EXP
| + | |
| - | |-
| + | |
| - | |Water Solubility
| + | |
| - | |280
| + | |
| - | |mg/L
| + | |
| - | |25
| + | |
| - | |EXP
| + | |
| - | |-
| + | |
| - | |Vapor Pressure
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| - | |5.80E-13
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| - | |mm Hg
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| - | |25
| + | |
| - | |EST
| + | |
| - | |-
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| - | |Henry's Law Constant
| + | |
| - | |6.03E-10
| + | |
| - | |atm-m3/mole
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| - | |25
| + | |
| - | |EST
| + | |
| - | |-
| + | |
| - | |Atmospheric OH Rate Constant
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| - | |1.10E-10
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| - | |cm3/molecule-sec
| + | |
| - | |25
| + | |
| - | |EST
| + | |
| - | |-
| + | |
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)
(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
