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			{{Short description|Corticosteroid precursor and metabolite of cortisol}}
	{{distinguish2|] (a.k.a. hydrocortisone), a similar compound with a similar name, genesis, and function}}
			{{distinguish|cortisol}}
	{{lead too short|date=November 2009}}
	{{Refimprove|date=December 2008}}
	{{chembox		{{chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 396318449		| verifiedrevid = 456660597
			| pronounce = {{IPAc-en|ˈ|k|ɔːr|t|ᵻ|s|oʊ|n}}, {{IPAc-en|ˈ|k|ɔːr|t|ᵻ|z|oʊ|n}}
	| ImageFile = Cortison.svg
			| ImageFile1 = {{wikidata|property|raw|P117}}
	| ImageSize = 200px
			| ImageFile2 = {{wikidata|property|raw|P8224}}
	| ImageFile1 = Cortisone-3D-balls.png
			| IUPACName = 17α,21-Dihydroxypregn-4-ene-3,11,20-trione
	| ImageSize1 = 200px
	| IUPACName = (8S,9S,10R,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopentaphenanthrene-3,11-dione		| SystematicName = (1''R'',3a''S'',3b''S'',9a''R'',9b''S'',11a''S'')-1-Hydroxy-1-(hydroxyacetyl)-9a,11a-dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-7''H''-cyclopentaphenanthrene-7,10(1''H'')-dione
			| OtherNames = 17α,21-Dihydroxy-11-ketoprogesterone; 17α-Hydroxy-11-dehydrocorticosterone
	| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = V27W9254FZ		| UNII = V27W9254FZ
			| IUPHAR_ligand = 5171
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| ChEMBL = 1499		| ChEMBL = 111861
	| InChI = 1/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1		| InChI = 1/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
	| InChIKey = MFYSYFVPBJMHGN-ZPOLXVRWBW		| InChIKey = MFYSYFVPBJMHGN-ZPOLXVRWBW
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	| StdInChIKey = MFYSYFVPBJMHGN-ZPOLXVRWSA-N		| StdInChIKey = MFYSYFVPBJMHGN-ZPOLXVRWSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 193441		| ChemSpiderID = 193441
	| CASNo = 53-06-5		| CASNo = 53-06-5
	| PubChem = 222786		| PubChem = 222786
	| KEGG_Ref = {{keggcite|changed|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D07749		| KEGG = D07749
	| ChEBI_Ref = {{ebicite|changed|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 16962		| ChEBI = 16962
	| SMILES = O=C(CO)3(O)CC24CC\C1=C\C(=O)CC1(C)4C(=O)C23C		| SMILES = O=C(CO)3(O)CC24CC\C1=C\C(=O)CC1(C)4C(=O)C23C
	| MeSHName = Cortisone		| MeSHName = Cortisone
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=21 | H=28 | O=5
	| Formula = C<sub>21</sub>H<sub>28</sub>O<sub>5</sub>
			| Appearance =
	| MolarMass = 360.46 g/mol
	| Appearance =		| Density =
	| Density =		| MeltingPtC = 220 to 224
			| BoilingPt =
	| MeltingPt = 220–224 °C
	| BoilingPt =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section6={{Chembox Pharmacology
	| Solubility =		| ATCCode_prefix = H02
	| MainHazards =		| ATCCode_suffix = AB10
			| ATC_Supplemental = {{ATC|S01|BA03}}
	| FlashPt =
			}}
	| Autoignition =
			|Section7={{Chembox Hazards
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
	}}		}}
	}}		}}
			'''Cortisone''' is a ] (21-carbon) ]. It is a naturally-occurring ] metabolite that is also used as a pharmaceutical ]. ] is converted by the action of the enzyme ] into the inactive metabolite cortisone, particularly in the kidneys. This is done by ] the alcohol group at carbon 11 (in the six-membered ring fused to the five-membered ring). Cortisone is converted back to the active steroid cortisol by ] ] at carbon 11 by the enzyme ], particularly in the liver.
			The term "cortisone" is frequently misused to mean either any ] or ], which is in fact ]. Many who speak of receiving a "cortisone shot" or taking "cortisone" are more likely receiving hydrocortisone or one of many other, much more potent synthetic corticosteroids.
			Cortisone can be administered as a prodrug, meaning it has to be converted by the body (specifically the liver, converting it into cortisol) after administration to be effective. It is used to treat a variety of ailments and can be administered ]ly, ]ly, ]ly (into a joint), or ]ly. Cortisone suppresses various elements of the immune system, thus reducing inflammation and attendant pain and swelling. Risks exist, in particular in the long-term use of cortisone.<ref name=mayo>{{cite web|url=http://www.mayoclinic.com/health/cortisone-shots/MY00268 |title=Cortisone shots |publisher=MayoClinic.com |date=2010-11-16 |access-date=July 31, 2013}}</ref><ref name=mayorisk2>{{cite web|url=https://www.mayoclinic.org/steroids/art-20045692 |title=Prednisone and other corticosteroids: Balance the risks and benefits |publisher=MayoClinic.com |date=2010-06-05 |access-date=2017-12-21}}</ref> However, using cortisone only results in very mild activity, and very often more potent steroids are used instead.
			==Effects and uses==
			Cortisone itself is inactive.<ref>{{cite book |editor1-last= Martindale |editor1-first= William |editor2-last= Reynolds |editor2-first= James |date=1993 |title= Martindale, The Extra Pharmacopoeia |edition=30th|publisher= Pharmaceutical Press |page=726 |isbn= 978-0853693000}}</ref> It must be converted to cortisol by the action of ].<ref name="Cooper">{{cite journal |vauthors= Cooper MS, Stewart PM |date=2009 |title= 11Beta-hydroxysteroid dehydrogenase type 1 and its role in the hypothalamus-pituitary-adrenal axis, metabolic syndrome, and inflammation |journal= J Clin Endocrinol Metab |volume=94 |issue=12 |pages= 4645–4654 |doi=10.1210/jc.2009-1412 |pmid= 19837912|doi-access= free }}</ref> This primarily happens in the liver, the main site at which cortisone becomes cortisol after oral or systemic injection, and can thus have a pharmacological effect. After application to the skin or injection into a joint, local cells that express 11β-hydroxysteroid dehydrogenase type 1 instead convert it to active cortisol.
			A cortisone injection may provide short-term pain relief and may reduce the swelling from ] of a ], ], or ] in, for example, the joints of the ], ] and ]<ref name=mayo/> and into a broken ].<ref>{{cite web|url=http://www.coccyx.org/treatmen/inflamm.htm|title=injections and needles for coccyx pain|website=www.coccyx.org}}</ref>
			Cortisone is used by ]s to treat ]s,<ref>{{cite journal | pmid = 1582609 | year = 1992 | last1 = Zanon | first1 = E | last2 = Jungwirth | first2 = W | last3 = Anderl | first3 = H | title = Cortisone jet injection as therapy of hypertrophic keloids | volume = 24 | issue = 2 | pages = 100–2 | journal = Handchirurgie, Mikrochirurgie, Plastische Chirurgie}}</ref> relieve the symptoms of ] and ],<ref>{{cite web | url = http://www.nationaleczema.org/living-with-eczema/all-about-atopic-dermatitis | title = All About Atopic Dermatitis | publisher = National Eczema Association | access-date = 2013-05-07 | archive-date = 2012-01-30 | archive-url = https://web.archive.org/web/20120130050716/http://www.nationaleczema.org/living-with-eczema/all-about-atopic-dermatitis | url-status = dead }}</ref> and stop the development of ].<ref>{{Cite journal |url=https://www.sciencedirect.com/science/article/pii/S0096021715323463 |title=Cortisone Treatment of Sarcoidosis |year=1954 |doi=10.1378/chest.26.2.224 |last1=Bogart |first1=A.S. |last2=Daniel |first2=D.D. |last3=Poster |first3=K.G. |journal=Diseases of the Chest |volume=26 |issue=2 |pages=224–228 |pmid=13182965 }}</ref>
			==Side effects==
	'''Cortisone''' ({{IPAc-en|icon|ˈ|k|ɔr|t|ɨ|s|oʊ|n}} or {{IPAc-en|ˈ|k|ɔr|t|ɨ|z|oʊ|n}}; 17-hydroxy-11-dehydrocorticosterone) is a ]. It is one of the main hormones released by the ] in response to stress. In chemical structure, it is a ] closely related to ]. It is used to treat a variety of ailments and can be administered ]ly, ]ly, ]ly, or ]ly. Cortisone suppresses the immune system, thus reducing inflammation and attendant pain and swelling at the site of the injury. Risks exist, in particular in the long-term use of cortisone.<ref name=mayorisk1>{{cite web|url=http://www.mayoclinic.com/health/cortisone-shots/MY00268/DSECTION=risks |title=Cortisone shots: Risks |publisher=MayoClinic.com |date=2010-11-16 |accessdate=2011-09-03}}</ref><ref name=mayorisk2>{{cite web|url=http://www.mayoclinic.com/health/steroids/HQ01431 |title=Prednisone and other corticosteroids: Balance the risks and benefits |publisher=MayoClinic.com |date=2010-06-05 |accessdate=2011-09-03}}</ref>
			Oral use of cortisone has a number of potential systemic adverse effects, including ], ], ], ], ], ], ], ], ], ], ], ], and ].<ref name=mayo/><ref name=mayorisk2/> With ], it can lead to thinning of the skin, impaired ], ], ], and ]s (including ]).<ref>{{cite journal|last=Cole|first=BJ|author2=Schumacher |title=Injectable Corticosteroids in Modern Practice|journal= Journal of the American Academy of Orthopaedic Surgeons|date=Jan–Feb 2005|volume=13|issue=1|pages=37–46|doi=10.5435/00124635-200501000-00006|pmid=15712981|citeseerx=10.1.1.562.1931|s2cid=18658724}}</ref>
	==History==		==History==
	Cortisone was first identified by the American chemist ] while a researcher at the ].<ref name="urlCortisone Discovery and the Nobel Prize">{{cite web |url=http://www.mayoclinic.org/tradition-heritage/cortisone-discovery.html |title=Cortisone Discovery and the Nobel Prize |work= |accessdate=2009-07-04}}</ref> He was awarded the 1950 ] along with ] and ] for the discovery of ] hormones, their structures, and their functions. Cortisone was first produced commercially by ] On September 30, 1949, ] announced an improvement in the process of producing cortisone from ]s.{{Time fact|date=September 2011}} This eliminated the need to use ], a rare, expensive, and dangerous chemical.		Cortisone was first identified by the American chemists ] and Harold L. Mason while researching at the ].<ref name="urlCortisone Discovery and the Nobel Prize">{{cite web |url=http://www.mayoclinic.org/tradition-heritage/cortisone-discovery.html |title=Cortisone Discovery and the Nobel Prize |website=] |access-date=2009-07-04}}</ref><ref name="Ingle">"I Went to See the Elephant" autobiography of ], published by Vantage Press (1963), pg 94, 109</ref><ref name="Mason/Myers/Kendall">{{cite journal|url=http://www.jbc.org/content/114/3/613.full.pdf|journal=J. Biol. Chem.|volume=114|page=613 |title=The chemistry of crystalline substances isolated from the suprarenal gland|year=1936|doi=10.1016/S0021-9258(18)74790-X|access-date=2014-09-07|last1=Mason|first1=Harold L.|last2=Myers|first2=Charles S.|last3=Kendall|first3=Edward C.|issue=3|doi-access=free}}</ref> During the discovery process, cortisone was known as compound E (while ] was known as compound F).
			In 1949, ] and colleagues discovered that large doses of injected cortisone were effective in the treatment of patients with severe ].<ref name="LemkeWilliams2008">{{cite book|author1=Thomas L. Lemke|author2=David A. Williams|title=Foye's Principles of Medicinal Chemistry|url=https://archive.org/details/foyesprinciplesm00lemk|url-access=limited|year=2008|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6879-5|pages=–}}</ref> Kendall was awarded the 1950 ] along with ] and ] for the discovery of the structure and function of ] hormones including cortisone.<ref>{{cite web |url=https://www.nobelprize.org/prizes/medicine/1950/summary/ |title=The Nobel Prize in Physiology or Medicine 1950 |author=<!--Not stated--> |date=2021 |website=The Nobel Prize |publisher=The Nobel Foundation |access-date=2 April 2021 |quote=}}</ref><ref>{{cite journal |last1=Glyn |first1=J|date=1998 |title= The discovery and early use of cortisone|journal= J R Soc Med |volume=91 |issue=10 |pages=513–517 |doi=10.1177/014107689809101004 |pmc= 1296908 |pmid= 10070369 }}</ref> Both Reichstein and the team of O. Wintersteiner and J. Pfiffner had separately isolated the compound prior to the discovery made by Mason and Kendall, but failed to recognize its biological significance.<ref name="Ingle"/> Mason's contributions to the crystallization and characterization of the compound have generally been forgotten outside of the Mayo Clinic.<ref name="Ingle"/>
	==Production==
	Cortisone is one of several end-products of a process called ]. This process starts with the synthesis of ], which then proceeds through a series of modifications in the ] (suprarenal) to become any one of many steroid hormones. One end-product of this pathway is ]. For cortisol to be released from the adrenal gland, a cascade of signaling occurs. ] released from the ] stimulates corticotrophs in the ] to release ], which relays the signal to the adrenal cortex. Here, the ] and ], in response to ACTH, secrete glucocorticoids, in particular cortisol. In the peripheral tissues, cortisol is converted to cortisone by the ] ]. Cortisol has much greater ] 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 ] of the 11-keto-group, and cortisol is, thus, sometimes referred to as ].<ref>Samuels, Theophilus </ref>
			Cortisone was first produced commercially by ] in 1948 or 1949.<ref name="LemkeWilliams2008" /><ref name="pmid13875857">{{cite journal | vauthors = Calvert DN | title = Anti-inflammatory steroids | journal = Wis. Med. J. | volume = 61 | pages = 403–4 | year = 1962 | pmid = 13875857 }}</ref> On September 30, 1949, ] announced an improvement in the process of producing cortisone from ]s.<ref>{{cite news |last=Gibbons |first=Ray |date=1949 |title= Science gets synthetic key to rare drug; discovery is made in Chicago |work=Chicago Tribune |location=Chicago |page= 1}}</ref> This eliminated the need to use ], a rare, expensive, and dangerous chemical. In the UK in the early 1950s, ] and ] at the ] collaborated with ] to produce cortisone from ] from ] plants.<ref>{{cite journal | doi = 10.1016/j.shpsc.2005.09.001 | pmid = 16337555 | title = Making British Cortisone: Glaxo and the development of Corticosteroids in Britain in the 1950s–1960s | year = 2005 | last1 = Quirke | first1 = Viviane | journal = Studies in History and Philosophy of Science Part C | volume = 36 | issue = 4 | pages = 645–674 }}</ref>
	==Effects and uses==
	Cortisone, a ], and ] are the main hormones released by the body as a reaction to stress. They elevate blood pressure and prepare the body for a ].
			==Production==
	A cortisone injection can also be used to give short-term pain relief and reduce the swelling from ] of a ], ], or ] in, for example, the joints of the ], ], and ].<ref>{{dead link|date=September 2011}}</ref>
			Cortisone is one of several end-products of a process called ]. This process starts with the synthesis of ], which then proceeds through a series of modifications in the ] to become any one of many steroid hormones. One end-product of this pathway is ]. For cortisol to be released from the adrenal gland, a cascade of signaling occurs. ] released from the ] stimulates corticotrophs in the ] to release ], which relays the signal to the adrenal cortex. Here, the ] and ], in response to ACTH, secrete glucocorticoids, in particular cortisol. In various peripheral tissues, notably the kidneys, cortisol is inactivated to cortisone by the ] ]. This is crucial because cortisol is a potent ] and would cause havoc with electrolyte levels (raising blood sodium and lowering blood potassium levels) and raise blood pressure if it were not inactivated in the kidneys.<ref name ="Cooper"/>
			Because cortisone must be converted to cortisol before being active as a ], its activity is less than simply administering cortisol directly (80–90%).<ref>{{Cite journal|title=Corticosteroid Dose Equivalents|url=http://emedicine.medscape.com/article/2172042-overview|journal=Medscape|access-date=20 December 2016}}</ref>
	Cortisone may also be used to deliberately suppress immune response in persons with ]s or following an ] to prevent ]. The suppression of the immune system may also be important in the treatment of inflammatory conditions such as severe ]-mediated ].<ref>{{cite web|url=http://www.bio.net/bionet/mm/immuno/2000-April/015756.html |title=Cortisol vs. corticosterone |publisher=Bio.net |date= |accessdate=2011-09-03}}</ref>
			==Popular culture==
	Last, cortisone is a common treatment for a severe sore throat that occurs commonly with ]. It is important to note that cortisone does not help lessen the duration of the virus, and is used purely to increase the comfort of a patient with trouble speaking or swallowing as a result of the mononucleosis-induced swollen throat.
			Abuse and addiction to cortisone was the subject of the 1956 motion picture '']'', produced by and starring ]. Though it was a box-office flop upon its initial release,{{sfn|Cossar|2011|p=273}} many modern critics hail the film as a masterpiece and brilliant indictment of contemporary attitudes toward mental illness and addiction.{{sfn|Halliwell|2013|pp=159-162}} In 1963, ] named it one of the ten greatest American sound films ever made.<ref name=godard>{{cite web |url=http://www.openculture.com/2013/12/a-young-jean-luc-godard-picks-the-best-american-films-1963.html |title=A Young Jean-Luc Godard Picks the 10 Best American Films Ever Made (1963) |publisher=Open Culture |date=December 2, 2013 |last=Marshall |first=Colin}}</ref>
			] was regularly administered ]s such as cortisone as a treatment for ].<ref name=Kennedy>{{cite web |url=https://www.nytimes.com/1992/10/06/health/the-doctor-s-world-disturbing-issue-of-kennedy-s-secret-illness.html?pagewanted=all |title=The doctor's world; Disturbing Issue of Kennedy's Secret Illness |work=] |date=October 6, 1992 |last=Altman |first=Lawrence}}</ref>
	==Side-effects==
	Oral use of cortisone has a number of potential side-effects: ], ], ], ], ], ], ], ] and ], among other problems.<ref name=mayorisk1/><ref name=mayorisk2/>{{citation needed |date=October 2009}}
	==See also==		==See also ==
			* {{Portal-inline|Biology}}
			* {{Portal-inline|Medicine}}
	* ]		* ]
	* ]		* ]
			==External links==
			* {{commonscat-inline}}
			==Notes==
			{{reflist|30em}}
	==References==		==Bibliography==
	===Notes===
	{{reflist}}
	<!---->
	===Bibliography===
	*{{cite book		*{{cite book
	| author= Bonagura J., DVM. et al.		| author= Bonagura J., DVM
	| title= Current Veterinary Therapy		| title= Current Veterinary Therapy
	| year=2000		| year=2000
	| pages=321–381		| pages=321–381
	| volume=13 }}		| volume=13 |display-authors=etal}}
			* {{cite book |last=Cossar |first=Harper |title=Letterboxed: The Evolution of Widescreen Cinema |year=2011 |publisher=] |isbn=978-0-813-12651-7 |url=https://books.google.com/books?id=ql1mQBeuPBsC}}
	* {{cite journal |author=Ingle DJ |title=The biologic properties of cortisone: a review |journal=J. Clin. Endocrinol. Metab. |volume=10 |issue=10 |pages=1312–54 |year=1950 |month=October |pmid=14794756 |doi= 10.1210/jcem-10-10-1312|url=http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=14794756}}
			* {{cite book |last=Halliwell |first=Martin |title=Therapeutic Revolutions: Medicine, Psychiatry, and American Culture, 1945-1970 |year=2013 |publisher=] |isbn=978-0-813-56066-3 |url=https://books.google.com/books?id=lXMRAAAAQBAJ}}
			* {{cite journal |author=Ingle DJ |title=The biologic properties of cortisone: a review |journal=J. Clin. Endocrinol. Metab. |volume=10 |issue=10 |pages=1312–54 |date=October 1950 |pmid=14794756 |doi=10.1210/jcem-10-10-1312 |url=http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=14794756 }}{{Dead link|date=July 2019 |bot=InternetArchiveBot |fix-attempted=yes }}
	*{{cite journal		*{{cite journal
	| author= Woodward R. B., Sondheimer F., Taub D.		|author1=Woodward R. B. |author2=Sondheimer F. |author3=Taub D. | title= The Total Synthesis of Cortisone
	| title= The Total Synthesis of Cortisone
	| journal=Journal of the American Chemical Society		| journal=Journal of the American Chemical Society
	| year=1951		| year=1951
	| pages=4057–4057		| pages=4057
	| volume=73		| volume=73
	| doi=10.1021/ja01152a551		| doi=10.1021/ja01152a551
	| issue= 8 }}		| issue= 8 |bibcode=1951JAChS..73.4057W }}
			{{Hormones}}
	==External links==
			{{Endogenous steroids}}
	*
			{{Orexigenics}}
	* 1951 article on the new drug cortisone and how it works
			{{Glucocorticoids and antiglucocorticoids}}
			{{Glucocorticoid receptor modulators}}
	{{Corticosteroids}}
			{{Authority control}}
	{{Cholesterol and steroid intermediates}}
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