Cortisone: Difference between revisions
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'''Cortisone''' is a [[pregnane]] (21-carbon) [[steroid hormone]]. Cortisone is a synthetic [[corticosteroid]], which is not released by the [[adrenal gland]].<ref>https://www.arthritis-health.com/treatment/injections/what-cortisone Emmanuel Konstantakos, MD. Published by Veritas Health, LLC. Access-date 7 July 2020</ref> In chemical structure, it is closely related to [[cortisol]], a substance which is released by the adrenal gland. It is used to treat a variety of ailments and can be administered [[intravenous]]ly, [[oral administration|oral]]ly, [[intra-articular]]ly (into a joint), or [[Transdermal|transcutaneous]]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=mayo>{{cite web|url=http://www.mayoclinic.com/health/cortisone-shots/MY00268 |title=Cortisone shots |publisher=MayoClinic.com |date=2010-11-16 | |
'''Cortisone''' is a [[pregnane]] (21-carbon) [[steroid hormone]]. Cortisone is a synthetic [[corticosteroid]], which is not released by the [[adrenal gland]].<ref>https://www.arthritis-health.com/treatment/injections/what-cortisone Emmanuel Konstantakos, MD. Published by Veritas Health, LLC. Access-date 7 July 2020</ref> In chemical structure, it is closely related to [[cortisol]], a substance which is released by the adrenal gland. It is used to treat a variety of ailments and can be administered [[intravenous]]ly, [[oral administration|oral]]ly, [[intra-articular]]ly (into a joint), or [[Transdermal|transcutaneous]]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=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> |
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A cortisone injection can be used to give short-term pain relief and reduce the swelling from [[inflammation]] of a [[joint]], [[tendon]], or [[bursa (anatomy)|bursa]] in, for example, the joints of the [[knee]], [[elbow]], and [[shoulder]] <ref name=mayo/> and into a broken [[coccyx]].<ref>{{cite web|url=http://www.coccyx.org/treatmen/inflamm.htm|title=injections and needles for coccyx pain|website=www.coccyx.org}}</ref> |
A cortisone injection can be used to give short-term pain relief and reduce the swelling from [[inflammation]] of a [[joint]], [[tendon]], or [[bursa (anatomy)|bursa]] in, for example, the joints of the [[knee]], [[elbow]], and [[shoulder]] <ref name=mayo/> and into a broken [[coccyx]].<ref>{{cite web|url=http://www.coccyx.org/treatmen/inflamm.htm|title=injections and needles for coccyx pain|website=www.coccyx.org}}</ref> |
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Cortisone may also be used to deliberately suppress immune response in persons with [[autoimmune disease]]s or following an [[organ transplant]] to prevent [[transplant rejection]].{{medcn|date=October 2019}} The suppression of the immune system may also be important in the treatment of inflammatory conditions.<ref>{{cite web |first1=Catherine |last1=Driver |first2=William |last2=Shiel |title=Cortisone Injection (Corticosteroid Injection) of Soft Tissues & Joints |publisher=MedicineNet.com |url=http://www.medicinenet.com/cortisone_injection/article.htm | |
Cortisone may also be used to deliberately suppress immune response in persons with [[autoimmune disease]]s or following an [[organ transplant]] to prevent [[transplant rejection]].{{medcn|date=October 2019}} The suppression of the immune system may also be important in the treatment of inflammatory conditions.<ref>{{cite web |first1=Catherine |last1=Driver |first2=William |last2=Shiel |title=Cortisone Injection (Corticosteroid Injection) of Soft Tissues & Joints |publisher=MedicineNet.com |url=http://www.medicinenet.com/cortisone_injection/article.htm |access-date=August 7, 2013}}</ref> |
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Cortisone is also used by [[dermatologist]]s to treat [[keloid]]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 [[eczema]] and [[atopic dermatitis]],<ref>{{cite web | url = http://www.nationaleczema.org/living-with-eczema/all-about-atopic-dermatitis | title = All About Atopic Dermatitis | publisher = National Eczema Association}}</ref> and stop the development of [[sarcoidosis]].{{medcn|date=January 2014}} |
Cortisone is also used by [[dermatologist]]s to treat [[keloid]]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 [[eczema]] and [[atopic dermatitis]],<ref>{{cite web | url = http://www.nationaleczema.org/living-with-eczema/all-about-atopic-dermatitis | title = All About Atopic Dermatitis | publisher = National Eczema Association}}</ref> and stop the development of [[sarcoidosis]].{{medcn|date=January 2014}} |
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==History== |
==History== |
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Cortisone was first identified by the American chemists [[Edward Calvin Kendall]] and [[Harold L. Mason]] while researching at the [[Mayo Clinic]].<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 | |
Cortisone was first identified by the American chemists [[Edward Calvin Kendall]] and [[Harold L. Mason]] while researching at the [[Mayo Clinic]].<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 |access-date=2009-07-04}}</ref><ref name="Ingle">"I Went to See the Elephant" autobiography of [[Dwight Ingle|Dwight J. Ingle]], 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|access-date=2014-09-07}}</ref> In 1929, [[Philip S. Hench]] and colleagues discovered that cortisone is effective in the treatment of [[rheumatoid arthritis]].<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=[https://archive.org/details/foyesprinciplesm00lemk/page/n2289 889]–}}</ref> Kendall 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 their functions. As it turns out, both Reichstein and the team of O. Wintersteiner and J. Pfiffner had separately isolated the compound prior to 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"/> |
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Cortisone was first produced commercially by [[Merck & Co.]] 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, [[Percy Lavon Julian|Percy Julian]] announced an improvement in the process of producing cortisone from [[bile acid]]s.{{Chronology citation needed|date=September 2011}} This eliminated the need to use [[osmium tetroxide]], a rare, expensive, and dangerous chemical. In the UK in the early 1950s, [[John Cornforth]] and [[Kenneth Callow]] at the [[National Institute for Medical Research]] collaborated with [[Glaxo]] to produce cortisone from [[hecogenin]] from [[sisal]] 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> |
Cortisone was first produced commercially by [[Merck & Co.]] 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, [[Percy Lavon Julian|Percy Julian]] announced an improvement in the process of producing cortisone from [[bile acid]]s.{{Chronology citation needed|date=September 2011}} This eliminated the need to use [[osmium tetroxide]], a rare, expensive, and dangerous chemical. In the UK in the early 1950s, [[John Cornforth]] and [[Kenneth Callow]] at the [[National Institute for Medical Research]] collaborated with [[Glaxo]] to produce cortisone from [[hecogenin]] from [[sisal]] 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> |
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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 fasciculata]] and [[zona reticularis]], in response to ACTH, secrete glucocorticoids, in particular cortisol. In the peripheral tissues, cortisol is converted to cortisone by the [[enzyme]] [[11-beta-steroid dehydrogenase]]. |
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 fasciculata]] and [[zona reticularis]], in response to ACTH, secrete glucocorticoids, in particular cortisol. In the peripheral tissues, cortisol is converted to cortisone by the [[enzyme]] [[11-beta-steroid dehydrogenase]]. |
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Cortisone has marginally reduced [[glucocorticoid]] activity compared to cortisol (80-90%<ref>{{Cite journal|title=Corticosteroid Dose Equivalents|url=http://emedicine.medscape.com/article/2172042-overview|journal=Medscape| |
Cortisone has marginally reduced [[glucocorticoid]] activity compared to cortisol (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>), and thus, cortisone can be considered an active metabolite of cortisol. However, 11-beta-steroid dehydrogenase can catalyze the reverse reaction as well, and, thus, cortisone is also a precursor molecule of cortisol. Cortisone is activated through [[hydrogenation]] of the 11-keto-group, and cortisol is, thus, sometimes referred to as [[hydrocortisone]].{{citation needed|date=July 2013}} |
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==Popular culture== |
==Popular culture== |
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Revision as of 17:55, 6 January 2021
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| Names | |
|---|---|
| Pronunciation | /ˈkɔːrtɪsoʊn/, /ˈkɔːrtɪzoʊn/ |
| 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
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| Other names
17α,21-Dihydroxypregn-4-ene-3,11,20-trione; 17α,21-Dihydroxy-11-ketoprogesterone; 17α-Hydroxy-11-dehydrocorticosterone
| |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.000.149 |
| KEGG | |
| MeSH | Cortisone |
PubChem CID
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|
| UNII | |
CompTox Dashboard (EPA)
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| |
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| Properties | |
| C21H28O5 | |
| Molar mass | 360.450 g·mol−1 |
| Melting point | 220 to 224 °C (428 to 435 °F; 493 to 497 K) |
| Pharmacology | |
| H02AB10 (WHO) S01BA03 (WHO) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Cortisone is a pregnane (21-carbon) steroid hormone. Cortisone is a synthetic corticosteroid, which is not released by the adrenal gland.[1] In chemical structure, it is closely related to cortisol, a substance which is released by the adrenal gland. It is used to treat a variety of ailments and can be administered intravenously, orally, intra-articularly (into a joint), or transcutaneously. 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.[2][3]
It was first described in 1949.[4]
Effects and uses
Cortisol, a glucocorticoid, and epinephrine (adrenaline) are the main substances released by the body as a reaction to stress. They elevate blood pressure and prepare the body for a fight or flight response.
A cortisone injection can be used to give short-term pain relief and reduce the swelling from inflammation of a joint, tendon, or bursa in, for example, the joints of the knee, elbow, and shoulder [2] and into a broken coccyx.[5]
Cortisone may also be used to deliberately suppress immune response in persons with autoimmune diseases or following an organ transplant to prevent transplant rejection.[medical citation needed] The suppression of the immune system may also be important in the treatment of inflammatory conditions.[6]
Cortisone is also used by dermatologists to treat keloids,[7] relieve the symptoms of eczema and atopic dermatitis,[8] and stop the development of sarcoidosis.[medical citation needed]
Side effects
Oral use of cortisone has a number of potential systemic side-effects: Asthma, hyperglycemia, insulin resistance, diabetes mellitus, osteoporosis, anxiety, depression, amenorrhoea, cataracts, Cushing's syndrome and glaucoma, among other problems.[2][3]
Local side effects are rare but can include: pain, infection, skin pigment changes, loss of fatty tissue, and tendon rupture.[9]
History
Cortisone was first identified by the American chemists Edward Calvin Kendall and Harold L. Mason while researching at the Mayo Clinic.[10][11][12] In 1929, Philip S. Hench and colleagues discovered that cortisone is effective in the treatment of rheumatoid arthritis.[13] Kendall 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 their functions. As it turns out, both Reichstein and the team of O. Wintersteiner and J. Pfiffner had separately isolated the compound prior to Mason and Kendall, but failed to recognize its biological significance.[11] Mason's contributions to the crystallization and characterization of the compound have generally been forgotten outside of the Mayo Clinic.[11]
Cortisone was first produced commercially by Merck & Co. in 1948 or 1949.[13][14] On September 30, 1949, Percy Julian announced an improvement in the process of producing cortisone from bile acids.[chronology citation needed] This eliminated the need to use osmium tetroxide, a rare, expensive, and dangerous chemical. In the UK in the early 1950s, John Cornforth and Kenneth Callow at the National Institute for Medical Research collaborated with Glaxo to produce cortisone from hecogenin from sisal plants.[15]
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 fasciculata and zona reticularis, in response to ACTH, secrete glucocorticoids, in particular cortisol. In the peripheral tissues, cortisol is converted to cortisone by the enzyme 11-beta-steroid dehydrogenase.
Cortisone has marginally reduced glucocorticoid activity compared to cortisol (80-90%[16]), and thus, cortisone can be considered an active metabolite of cortisol. However, 11-beta-steroid dehydrogenase can catalyze the reverse reaction as well, and, thus, cortisone is also a precursor molecule of cortisol. Cortisone is activated through hydrogenation of the 11-keto-group, and cortisol is, thus, sometimes referred to as hydrocortisone.[citation needed]
Popular culture
Addiction to cortisone was the subject of the 1956 motion picture, Bigger Than Life, produced by and starring James Mason. Though it was a box-office flop upon its initial release,[17] many modern critics hail it as a masterpiece and brilliant indictment of contemporary attitudes towards mental illness and addiction.[18] In 1963, Jean-Luc Godard named it one of the ten best American sound films ever made.[19]
John F. Kennedy needed to regularly use corticosteroids such as cortisone as a treatment for Addison's disease.[20]
See also
Notes
- ^ https://www.arthritis-health.com/treatment/injections/what-cortisone Emmanuel Konstantakos, MD. Published by Veritas Health, LLC. Access-date 7 July 2020
- ^ a b c "Cortisone shots". MayoClinic.com. 2010-11-16. Retrieved July 31, 2013.
- ^ a b "Prednisone and other corticosteroids: Balance the risks and benefits". MayoClinic.com. 2010-06-05. Retrieved 2017-12-21.
- ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 484. ISBN 9783527607495.
- ^ "injections and needles for coccyx pain". www.coccyx.org.
- ^ Driver, Catherine; Shiel, William. "Cortisone Injection (Corticosteroid Injection) of Soft Tissues & Joints". MedicineNet.com. Retrieved August 7, 2013.
- ^ Zanon, E; Jungwirth, W; Anderl, H (1992). "Cortisone jet injection as therapy of hypertrophic keloids". Handchirurgie, Mikrochirurgie, Plastische Chirurgie. 24 (2): 100–2. PMID 1582609.
- ^ "All About Atopic Dermatitis". National Eczema Association.
- ^ Cole, BJ; Schumacher (Jan–Feb 2005). "Injectable Corticosteroids in Modern Practice". Journal of the American Academy of Orthopaedic Surgeons. 13 (1): 37–46. CiteSeerX 10.1.1.562.1931. doi:10.5435/00124635-200501000-00006. PMID 15712981. S2CID 18658724.
- ^ "Cortisone Discovery and the Nobel Prize". Retrieved 2009-07-04.
- ^ a b c "I Went to See the Elephant" autobiography of Dwight J. Ingle, published by Vantage Press (1963), pg 94, 109
- ^ "The chemistry of crystalline substances isolated from the suprarenal gland" (PDF). J. Biol. Chem. 114: 613. Retrieved 2014-09-07.
- ^ a b Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 889–. ISBN 978-0-7817-6879-5.
- ^ Calvert DN (1962). "Anti-inflammatory steroids". Wis. Med. J. 61: 403–4. PMID 13875857.
- ^ Quirke, Viviane (2005). "Making British Cortisone: Glaxo and the development of Corticosteroids in Britain in the 1950s–1960s". Studies in History and Philosophy of Science Part C. 36 (4): 645–674. doi:10.1016/j.shpsc.2005.09.001. PMID 16337555.
- ^ "Corticosteroid Dose Equivalents". Medscape. Retrieved 20 December 2016.
- ^ Cossar 2011, p. 273.
- ^ Halliwell 2013, pp. 159–162.
- ^ Marshall, Colin (December 2, 2013). "A Young Jean-Luc Godard Picks the 10 Best American Films Ever Made (1963)". Open Culture.
- ^ Altman, Lawrence (October 6, 1992). "The doctor's world; Disturbing Issue of Kennedy's Secret Illness". New York Times.
Bibliography
- Bonagura J., DVM; et al. (2000). Current Veterinary Therapy. Vol. 13. pp. 321–381.
- Ingle DJ (October 1950). "The biologic properties of cortisone: a review". J. Clin. Endocrinol. Metab. 10 (10): 1312–54. doi:10.1210/jcem-10-10-1312. PMID 14794756.[permanent dead link]
- Woodward R. B.; Sondheimer F.; Taub D. (1951). "The Total Synthesis of Cortisone". Journal of the American Chemical Society. 73 (8): 4057. doi:10.1021/ja01152a551.