| Revision as of 13:54, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 466793557 of page Triamcinolone_acetonide for the Chem/Drugbox validation project (updated: ''). | Latest revision as of 14:16, 5 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Fluoroarenes using HotCat | ||
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| {{Short description|Medicinal chemical compound, steroid}} | |||
| {{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} | |||
| {{Use dmy dates|date=March 2024}} | |||
| {{chembox | |||
| {{Drugbox | |||
| | verifiedrevid = 434949825 | |||
| | Verifiedfields = changed | |||
| | ImageFile_Ref = {{chemboximage|correct|??}} | |||
| | Watchedfields = changed | |||
| | ImageFile=Triamcinolone acetonide.png | |||
| | verifiedrevid = 470613003 | |||
| |ImageSize=200px | |||
| | image = Triamcinolone acetonide.svg | |||
| |IUPACName= (4a''S'',4b''R'',5''S'',6a''S'',6b''S'',9a''R'',10a''S'',10b''S'')-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2''H''-naphthoindenodioxol-2-one | |||
| | width = 250 | |||
| |OtherNames= | |||
| | alt = | |||
| |Section1= {{Chembox Identifiers | |||
| | image2 = Triamcinolone acetonide (Ball-n-Stick).png | |||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| | width2 = 250 | |||
| | alt2 = | |||
| <!-- Clinical data --> | |||
| | pronounce = | |||
| | tradename = Kenalog, Nasacort, Xipere, others | |||
| | Drugs.com = {{drugs.com|monograph|triamcinolone-acetonide-topical}} | |||
| | MedlinePlus = a601124 | |||
| | DailyMedID = Triamcinolone | |||
| | pregnancy_AU = B3 | |||
| | pregnancy_AU_comment = / A | |||
| | pregnancy_category= | |||
| | routes_of_administration = ], ], ] | |||
| | class = | |||
| | ATC_prefix = A01 | |||
| | ATC_suffix = AC01 | |||
| | ATC_supplemental = {{ATC|D07|AB09}}, {{ATC|H02|AB08}} | |||
| | legal_AU = S4 | |||
| | legal_AU_comment = / S3 / S2<ref>{{cite web | title = KENALOG IN ORABASE triamcinolone acetonide | url = https://www.tga.gov.au/resources/artg/19205 | id = ARTG ID 19205 | work = Australian Register of Therapeutic Goods (ARTG) | publisher = Australian Government }}</ref><ref>{{cite web | title = KENACORT A10 triamcinolone acetonide | url = https://www.tga.gov.au/resources/artg/19204 | work = Australian Register of Therapeutic Goods (ARTG) }}</ref><ref>{{cite web | title = NASACORT AQ Triamcinolone acetonide | url = https://www.tga.gov.au/resources/annual-charge-exemptions/nasacort-aq-triamcinolone-acetonide-55-microgram-actuation-nasal-spray-bottle-2019-20 | work = Annual charge exemptions dataset | publisher = Department of Health and Aged Care, Australian Government }}</ref> | |||
| | legal_CA = Rx-only | |||
| | legal_CA_comment = / OTC<ref>{{cite web | title=Aristocort C Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=35785 | access-date=23 December 2022}}</ref><ref>{{cite web | title=Nasacort Allergy 24HR Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=90220 | access-date=23 December 2022}}</ref> | |||
| | legal_UK = POM | |||
| | legal_UK_comment = / GSL<ref>{{cite web | title=Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC) | website=(emc) | date=8 October 2021 | url=https://www.medicines.org.uk/emc/product/1410/smpc | access-date=23 December 2022}}</ref><ref>{{cite web | title=Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC) | website=(emc) | date=8 April 2022 | url=https://www.medicines.org.uk/emc/product/6748/smpc | access-date=23 December 2022}}</ref><ref>{{cite web | title=Nasacort 55 micrograms/dose, nasal spray, suspension - Summary of Product Characteristics (SmPC) | website=(emc) | date=1 November 2021 | url=https://www.medicines.org.uk/emc/product/6708/smpc | access-date=23 December 2022}}</ref><ref>{{cite web | title=Nasacort Allergy Relief for Adults 55 micrograms/dose, nasal spray, suspension - Summary of Product Characteristics (SmPC) | website=(emc) | date=1 November 2021 | url=https://www.medicines.org.uk/emc/product/6501/smpc | access-date=23 December 2022 | archive-date=23 December 2022 | archive-url=https://web.archive.org/web/20221223060559/https://www.medicines.org.uk/emc/product/6501/smpc | url-status=dead }}</ref> | |||
| | legal_US = Rx-only | |||
| | legal_US_comment = / OTC<ref name="Xipere FDA label">{{cite web | title=Xipere- triamcinolone acetonide injection, suspension | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c55c3521-a033-4683-9a57-3207f59a4029 | access-date=19 December 2021}}</ref> | |||
| | legal_EU = Rx-only | |||
| | legal_EU_comment = <ref>{{cite web | title = Active substance(s): triamcinolone (topical and nasal formulations) | url = https://www.ema.europa.eu/en/documents/psusa/triamcinolone-topical-nasal-formulations-list-nationally-authorised-medicinal-products-psusa/00003017/201707_en.pdf | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 8 March 2018 }}</ref> | |||
| | legal_status = | |||
| <!--Pharmacokinetic data--> | |||
| | bioavailability = | |||
| | protein_bound = | |||
| | metabolism = Liver | |||
| | elimination_half-life = | |||
| | excretion = Urine (75%) and feces (25%) | |||
| <!-- Identifiers --> | |||
| | CAS_number_Ref = {{cascite|correct|CAS}} | |||
| | CAS_number = 76-25-5 | |||
| | CAS_supplemental = | |||
| | PubChem = 6436 | |||
| | IUPHAR_ligand = 2867 | |||
| | DrugBank_Ref = | |||
| | DrugBank = DBSALT000860 | |||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| | ChemSpiderID = 6196 | | ChemSpiderID = 6196 | ||
| | UNII_Ref = {{fdacite|correct|FDA}} | | UNII_Ref = {{fdacite|correct|FDA}} | ||
| | UNII = F446C597KA | | UNII = F446C597KA | ||
| | KEGG = D00983 | |||
| | ChEBI_Ref = {{ebicite|changed|EBI}} | |||
| | ChEBI = 71418 | |||
| | ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| | ChEMBL = 1504 | | ChEMBL = 1504 | ||
| | NIAID_ChemDB = | |||
| | InChI = 1/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1 | |||
| | PDB_ligand = 1TA | |||
| | InChIKey = YNDXUCZADRHECN-JNQJZLCIBL | |||
| | synonyms = | |||
| <!--Chemical data--> | |||
| | IUPAC_name = (4a''S'',4b''R'',5''S'',6a''S'',6b''S'',9a''R'',10a''S'',10b''S'')-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2''H''-naphthoindenodioxol-2-one | |||
| | C=24 | H=31 | F=1 | O=6 | |||
| | SMILES = C12C(3((1C42(OC(O4)(C)C)C(=O)CO)CCC5=CC(=O)C=C53C)F)O | |||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| | StdInChI = 1S/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1 | | StdInChI = 1S/C24H31FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h7-9,15-17,19,26,28H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1 | ||
| | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
| | StdInChIKey = YNDXUCZADRHECN-JNQJZLCISA-N | | StdInChIKey = YNDXUCZADRHECN-JNQJZLCISA-N | ||
| | CASNo=76-25-5 | |||
| <!--Physical data--> | |||
| | CASNo_Ref = {{cascite|correct|CAS}} | |||
| | melting_point = 290 | |||
| | PubChem=6436 | |||
| | melting_high = 294 | |||
| | SMILES = O=C\1\C=C5/(/C=C/1)(C)2(F)(3(C2O)(4(OC(O4C3)(C)C)C(=O)CO)C)CC5 | |||
| }} | |||
| |Section2= {{Chembox Properties | |||
| | C=24|H=31|F=1|O=6 | |||
| | Appearance= | |||
| | Density= | |||
| | MeltingPt= | |||
| | BoilingPt= | |||
| | Solubility= | |||
| }} | |||
| |Section3= {{Chembox Hazards | |||
| | MainHazards= | |||
| | FlashPt= | |||
| | Autoignition= | |||
| }} | |||
| }} | }} | ||
| '''Triamcinolone acetonide''', sold under the brand name '''Kenalog''' among others, is a ] ] medication used ] to treat various ]s,<ref>{{cite web | title=Triamcinolone Topical | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a601124.html | access-date=12 November 2020}}</ref> to relieve the discomfort of ]s, and by ] to treat various ]s. It is also injected into ] to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat ]. It is used for the treatment of ] associated with ].<ref name="Xipere FDA label" /> It is a more ] derivative of ], and is about eight times as potent as ].<ref name="Nasacort FDA label">{{cite web | title=Nasacort Allergy 24HR- triamcinolone acetonide spray, metered | website=DailyMed | date=3 February 2014 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4bff57a5-cce0-401c-a0fe-23c65c1b7ddc | access-date=12 November 2020}}</ref> | |||
| Most forms of triamcinolone acetonide are ]. In 2014, the U.S. ] (FDA) made triamcinolone acetonide an ] drug in the United States in ] form under the brand name '''Nasacort'''.<ref name="Nasacort FDA label" /> It is available as a ].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=6 March 2023}}</ref> | |||
| ==Medical uses== | |||
| Triamcinolone acetonide as an intra-articular injectable has been used to treat a variety of musculoskeletal conditions. When applied to the skin as a topical ointment, it is used to mitigate blistering from ], oak, and sumac.{{Citation needed|date=May 2016}} When combined with ], it is used to treat skin infections with discomfort from fungus, though it should not be used on the eyes.<ref>{{cite web|title=Nystatin And Triamcinolone (Topical Route)|url=http://www.mayoclinic.org/drugs-supplements/nystatin-and-triamcinolone-topical-route/description/drg-20062448|website=mayoclinic.org|publisher=Mayo Foundation for Medical Education and Research|access-date=18 May 2016}}</ref> It provides relatively immediate relief and is used before using oral ]. Oral and dental paste preparations are used for treating ]s. | |||
| As an intravitreal injection, triamcinolone acetonide has been used to treat various eye diseases and has been found useful in reducing ].<ref>{{cite journal | vauthors = Rittiphairoj T, Mir TA, Li T, Virgili G | title = Intravitreal steroids for macular edema in diabetes | journal = The Cochrane Database of Systematic Reviews | volume = 2020 | issue = 11 | pages = CD005656 | date = November 2020 | pmid = 33206392 | pmc = 8095060 | doi = 10.1002/14651858.CD005656.pub3 }}</ref> Drug trials have found it to be as efficient as anti-] drugs in eyes with artificial lenses over a two-year period. A systematic review did not find any evidence of any benefit in preventing vision loss in eyes treated with triamcinolone acetonide over placebo, for patients with ].<ref name="Geltzer">{{cite journal | vauthors = Geltzer A, Turalba A, Vedula SS | title = Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age-related macular degeneration | journal = The Cochrane Database of Systematic Reviews | volume = 1 | issue = 1 | pages = CD005022 | date = January 2013 | pmid = 23440797 | pmc = 4269233 | doi = 10.1002/14651858.CD005022.pub3 }}</ref> | |||
| Triamcinolone acetonide is also administered via intralesional injection in the treatment of ] and ] scars.<ref>{{Cite web|url=http://www.bad.org.uk/patient-information-leaflets/intralesional-steroid-therapy/?showmore=1&returnlink=http%3a%2f%2fwww.bad.org.uk%2ffor-the-public%2fpatient-information-leaflets%3fl%3d0%26q%3dkeloid%26range%3dkeloid#.Xm4_9iWnyEc|title=Intralesional Steroid Therapy (Patient Information Leaflets)|website=British Association of Dermatologists|year=2008|url-status=live|archive-url=https://web.archive.org/web/20200315144900/http://www.bad.org.uk/patient-information-leaflets/intralesional-steroid-therapy/?showmore=1&returnlink=http%3A%2F%2Fwww.bad.org.uk%2Ffor-the-public%2Fpatient-information-leaflets%3Fl%3D0%26q%3Dkeloid%26range%3Dkeloid%23.Xm4_9iWnyEc|archive-date=15 March 2020|access-date=15 March 2020}}</ref><ref>{{cite journal | vauthors = Griffith BH | title = The treatment of keloids with triamcinolone acetonide | journal = Plastic and Reconstructive Surgery | volume = 38 | issue = 3 | pages = 202–208 | date = September 1966 | pmid = 5919603 | doi = 10.1097/00006534-196609000-00004 }}</ref> | |||
| ==Contraindications== | |||
| Evidence suggests that usage of triamcinolone acetonide or other steroids to treat macular edema increases the risk of increasing ] in patients.<ref name="Gewaily">{{cite journal | vauthors = Gewaily D, Muthuswamy K, Greenberg PB | title = Intravitreal steroids versus observation for macular edema secondary to central retinal vein occlusion | journal = The Cochrane Database of Systematic Reviews | volume = 2015 | issue = 9 | pages = CD007324 | date = September 2015 | pmid = 26352007 | pmc = 4733851 | doi = 10.1002/14651858.CD007324.pub3 }}</ref> | |||
| ==Pharmacology== | |||
| ===Pharmacodynamics=== | |||
| {{see|Glucocorticoid#Mechanism of action}} | |||
| Triamcinolone acetonide is a ]. It is specifically a ], or an ] of the ], that is about five times as potent as ]. It has very little ] effects.<ref name="Dinnendahl">{{cite book|title=Arzneistoff-Profile| veditors = Dinnendahl V, Fricke U |publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany|date=2004|edition=19|volume=10|at=Triamcinolon|isbn=978-3-7741-9846-3|language=de}}</ref> The ] of triamcinolone acetonide for the ] and ]s are both <0.1% (relative to ] and ]).<ref name="KavlockDaston2012">{{cite book| vauthors = Kavlock RJ, Daston GP |title=Drug Toxicity in Embryonic Development II: Advances in Understanding Mechanisms of Birth Defects: Mechanistics Understanding of Human Development Toxicants|url=https://books.google.com/books?id=vcHsCAAAQBAJ&pg=PA437|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60447-8|pages=437–}}</ref> However, triamcinolone acetonide has 15% of the affinity of ] for the ].<ref name="KavlockDaston2012" /> In relation to this, triamcinolone acetonide can produce endocrine side effects like ] and ].<ref name="pmid27874912">{{cite journal | vauthors = Brook EM, Hu CH, Kingston KA, Matzkin EG | title = Corticosteroid Injections: A Review of Sex-Related Side Effects | journal = Orthopedics | volume = 40 | issue = 2 | pages = e211–e215 | date = March 2017 | pmid = 27874912 | doi = 10.3928/01477447-20161116-07 }}</ref><ref name="pmid376542">{{cite journal | vauthors = Cunningham GR, Goldzieher JW, de la Pena A, Oliver M | title = The mechanism of ovulation inhibition by triamcinolone acetonide | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 46 | issue = 1 | pages = 8–14 | date = January 1978 | pmid = 376542 | doi = 10.1210/jcem-46-1-8 }}</ref><ref name="pmid7121132">{{cite journal | vauthors = Luzzani F, Gallico L, Glässer A | title = In vitro and ex vivo binding to uterine progestin receptors of the rat as a tool to assay progestational activity of glucocorticoids | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 4 | issue = 4 | pages = 237–242 | date = 1982 | pmid = 7121132 }}</ref> | |||
| ==Chemistry== | |||
| {{See also|List of corticosteroids}} | |||
| Triamcinolone acetonide, also known as ''9α-fluoro-16α-hydroxyprednisolone 16α,17α-acetonide'' or as ''9α-fluoro-11β,16α-17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone'', is a ] ]ated ] ] ].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1228|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1228–}}</ref> It is the C16α,17α ] of ].<ref name="Elks2014" /> | |||
| ==Veterinary use== | |||
| Triamcinolone acetonide is also used in ] as an ] in ] ]s and in topical sprays for control of ] in dogs.<ref> Drug information</ref> | |||
| A series of ]s with triamcinolone acetonide or another ] may reduce ] size and ]. It is used as a preinductor and/or inductor of birth in cows. It was also used in the horse racing industry, but it is now a banned substance if found in a horse's system on race day.<ref></ref>{{clear}} | |||
| == References == | |||
| {{Reflist}} | |||
| == External links == | |||
| * {{cite web | title=Triamcinolone | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a601122.html }} | |||
| * {{cite web | title=Triamcinolone Nasal Spray | website=MedlinePlus | url=https://medlineplus.gov/druginfo/meds/a682791.html }} | |||
| {{Glucocorticoids and antiglucocorticoids}} | |||
| {{Glucocorticoid receptor modulators}} | |||
| {{Progesterone receptor modulators}} | |||
| {{Portal bar | Medicine}} | |||
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