{{Short description|Medicinal chemical compound, steroid}} {{Use dmy dates|date=March 2024}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470613003 | image = Triamcinolone acetonide.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Triamcinolone acetonide (Ball-n-Stick).png | image_class2 = bg-transparent | 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 = Topical, joint injection, nasal | 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 }}</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 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = F446C597KA | KEGG = D00983 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 71418 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1504 | NIAID_ChemDB = | PDB_ligand = 1TA | 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''-naphtho[2',1':4,5]indeno[1,2-''d''][1,3]dioxol-2-one | C=24 | H=31 | F=1 | O=6 | SMILES = C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)CCC5=CC(=O)C=C[C@@]53C)F)O | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YNDXUCZADRHECN-JNQJZLCISA-N
<!--Physical data--> | melting_point = 290 | melting_high = 294 }}
'''Triamcinolone acetonide''', sold under the brand name '''Kenalog''' among others, is a synthetic corticosteroid medication used topically to treat various skin conditions,<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 mouth sores, and by injection into joints to treat various joint conditions. It is also injected into lesions to treat inflammation in some parts of the body, particularly the skin. In nasal spray form, it is used to treat allergic rhinitis. It is used for the treatment of macular edema associated with uveitis.<ref name="Xipere FDA label" /> It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.<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 prescription drugs. In 2014, the U.S. Food and Drug Administration (FDA) made triamcinolone acetonide an over-the-counter drug in the United States in nasal spray form under the brand name '''Nasacort'''.<ref name="Nasacort FDA label" /> It is available as a generic medication.<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. Food and Drug Administration (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | archive-url=https://web.archive.org/web/20200220015057/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | archive-date=20 February 2020 | 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 poison ivy, oak, and sumac.{{Citation needed|date=May 2016}} When combined with nystatin, 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 prednisone. Oral and dental paste preparations are used for treating aphthous ulcers.
As an intravitreal injection, triamcinolone acetonide has been used to treat various eye diseases and has been found useful in reducing macular edema.<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 | article-number = 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-VEGF 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 age-related macular degeneration.<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 | article-number = 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 hypertrophic and keloid 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 intraocular pressure 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 | article-number = 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 corticosteroid. It is specifically a glucocorticoid, or an agonist of the glucocorticoid receptor, that is about five times as potent as cortisol. It has very little mineralocorticoid 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 affinities of triamcinolone acetonide for the androgen and estrogen receptors are both <0.1% (relative to testosterone and estradiol).<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 progesterone for the progesterone receptor.<ref name="KavlockDaston2012" /> In relation to this, triamcinolone acetonide can produce endocrine side effects like ovulation inhibition and menstrual irregularities.<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 synthetic halogenated cyclic ketal pregnane corticosteroid.<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 acetonide of triamcinolone.<ref name="Elks2014" />
==Veterinary use== Triamcinolone acetonide is also used in veterinary medicine as an ingredient in topical ointments and in topical sprays for control of pruritus in dogs.<ref>[http://www.virbacvet.com/pdf/product_pdfs/GENESIS_Topical_Spray_insert.pdf Genesis (triamcinolone acetonide) Topical Spray] Drug information</ref>
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>[https://www.racingpost.com/news/news/champion-hurdle-favourite-yanworth-failed-drug-test/291782 Champion Hurdle favorite Yanworth failed drug test]</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}}
Category:Acetonides Category:Drugs developed by Bristol Myers Squibb Category:Corticosteroid cyclic ketals Category:Corticosteroids Category:Diketones Category:Diols Category:Glucocorticoids Category:Organofluorides Category:Orphan drugs Category:Pregnanes Category:Progestogens Category:Heterocyclic compounds with 5 rings