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Triamcinolone acetonide

November 30, 2023

Triamcinolone acetonide, sold under the brand name Kenalog among others, is a synthetic corticosteroid medication used topically to treat various skin conditions,[12] 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.[10] It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.[13]

Triamcinolone acetonide
Clinical data
Trade namesKenalog, Nasacort, Xipere, others
AHFS/Drugs.comMonograph
MedlinePlusa601124
License data
Pregnancy
category
  • AU: B3/ A
Routes of
administration		Topical, joint injection, nasal
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
ExcretionUrine (75%) and feces (25%)
Identifiers
  • (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
CAS Number
  • 76-25-5 Y
PubChem CID
  • 6436
IUPHAR/BPS
  • 2867
DrugBank
  • DBSALT000860
ChemSpider
  • 6196 Y
UNII
  • F446C597KA
KEGG
  • D00983
ChEBI
  • CHEBI:71418 N
ChEMBL
  • ChEMBL1504 Y
PDB ligand
  • 1TA (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID6021371
ECHA InfoCard100.000.863
Chemical and physical data
FormulaC24H31FO6
Molar mass434.504 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point290 to 294 °C (554 to 561 °F)
  • 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
  • InChI=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 Y
  • Key:YNDXUCZADRHECN-JNQJZLCISA-N Y
 NY (what is this?)  (verify)

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.[13] It is available as a generic medication.[14]

Medical uses edit

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] When combined with nystatin, it is used to treat skin infections with discomfort from fungus, though it should not be used on the eyes.[15] 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.[16] 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.[17]

Triamcinolone acetonide is also administered via intralesional injection in the treatment of hypertrophic and keloid scars.[18][19]

Contraindications edit

Evidence suggests that usage of triamcinolone acetonide or other steroids to treat macular edema increases the risk of increasing intraocular pressure in patients.[20]

Triamcinolone acetonide should not be used by those with tuberculosis or untreated fungal, bacterial, systemic viral or herpes simplex infections without consulting a doctor first.

Pharmacology edit

Pharmacodynamics edit

Further information: 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.[21] The affinities of triamcinolone acetonide for the androgen and estrogen receptors are both <0.1% (relative to testosterone and estradiol).[22] However, triamcinolone acetonide has 15% of the affinity of progesterone for the progesterone receptor.[22] In relation to this, triamcinolone acetonide can produce endocrine side effects like ovulation inhibition and menstrual irregularities.[23][24][25]

Chemistry edit

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.[26] It is the C16α,17α acetonide of triamcinolone.[26]

Veterinary use edit

Triamcinolone acetonide is also used in veterinary medicine as an ingredient in topical ointments and in topical sprays for control of pruritus in dogs.[27]

A series of injections with triamcinolone acetonide or another corticosteroid may reduce keloid size and irritation. 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.[28]

References edit

  1. ^ "KENALOG IN ORABASE triamcinolone acetonide". Australian Register of Therapeutic Goods (ARTG). Australian Government. ARTG ID 19205.
  2. ^ "KENACORT A10 triamcinolone acetonide". Australian Register of Therapeutic Goods (ARTG).
  3. ^ "NASACORT AQ Triamcinolone acetonide". Annual charge exemptions dataset. Department of Health and Aged Care, Australian Government.
  4. ^ "Aristocort C Product information". Health Canada. 25 April 2012. Retrieved 23 December 2022.
  5. ^ "Nasacort Allergy 24HR Product information". Health Canada. 25 April 2012. Retrieved 23 December 2022.
  6. ^ "Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC)". (emc). 8 October 2021. Retrieved 23 December 2022.
  7. ^ "Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC)". (emc). 8 April 2022. Retrieved 23 December 2022.
  8. ^ "Nasacort 55 micrograms/dose, nasal spray, suspension - Summary of Product Characteristics (SmPC)". (emc). 1 November 2021. Retrieved 23 December 2022.
  9. ^ "Nasacort Allergy Relief for Adults 55 micrograms/dose, nasal spray, suspension - Summary of Product Characteristics (SmPC)". (emc). 1 November 2021. Retrieved 23 December 2022.
  10. ^ a b "Xipere- triamcinolone acetonide injection, suspension". DailyMed. Retrieved 19 December 2021.
  11. ^ "Active substance(s): triamcinolone (topical and nasal formulations)" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 8 March 2018.
  12. ^ "Triamcinolone Topical". MedlinePlus. Retrieved 12 November 2020.
  13. ^ a b "Nasacort Allergy 24HR- triamcinolone acetonide spray, metered". DailyMed. 3 February 2014. Retrieved 12 November 2020.
  14. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Retrieved 6 March 2023.
  15. ^ "Nystatin And Triamcinolone (Topical Route)". mayoclinic.org. Mayo Foundation for Medical Education and Research. Retrieved 18 May 2016.
  16. ^ Rittiphairoj T, Mir TA, Li T, Virgili G (November 2020). "Intravitreal steroids for macular edema in diabetes". The Cochrane Database of Systematic Reviews. 2020 (11): CD005656. doi:10.1002/14651858.CD005656.pub3. PMC 8095060. PMID 33206392.
  17. ^ Geltzer A, Turalba A, Vedula SS (January 2013). "Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age-related macular degeneration". The Cochrane Database of Systematic Reviews. 1 (1): CD005022. doi:10.1002/14651858.CD005022.pub3. PMC 4269233. PMID 23440797.
  18. ^ "Intralesional Steroid Therapy (Patient Information Leaflets)". British Association of Dermatologists. 2008. from the original on 15 March 2020. Retrieved 15 March 2020.
  19. ^ Griffith BH (September 1966). "The treatment of keloids with triamcinolone acetonide". Plastic and Reconstructive Surgery. 38 (3): 202–208. doi:10.1097/00006534-196609000-00004. PMID 5919603.
  20. ^ Gewaily D, Muthuswamy K, Greenberg PB (September 2015). "Intravitreal steroids versus observation for macular edema secondary to central retinal vein occlusion". The Cochrane Database of Systematic Reviews. 2015 (9): CD007324. doi:10.1002/14651858.CD007324.pub3. PMC 4733851. PMID 26352007.
  21. ^ Dinnendahl V, Fricke U, eds. (2004). Arzneistoff-Profile (in German). Vol. 10 (19 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Triamcinolon. ISBN 978-3-7741-9846-3.
  22. ^ a b Kavlock RJ, Daston GP (6 December 2012). Drug Toxicity in Embryonic Development II: Advances in Understanding Mechanisms of Birth Defects: Mechanistics Understanding of Human Development Toxicants. Springer Science & Business Media. pp. 437–. ISBN 978-3-642-60447-8.
  23. ^ Brook EM, Hu CH, Kingston KA, Matzkin EG (March 2017). "Corticosteroid Injections: A Review of Sex-Related Side Effects". Orthopedics. 40 (2): e211–e215. doi:10.3928/01477447-20161116-07. PMID 27874912.
  24. ^ Cunningham GR, Goldzieher JW, de la Pena A, Oliver M (January 1978). "The mechanism of ovulation inhibition by triamcinolone acetonide". The Journal of Clinical Endocrinology and Metabolism. 46 (1): 8–14. doi:10.1210/jcem-46-1-8. PMID 376542.
  25. ^ Luzzani F, Gallico L, Glässer A (1982). "In vitro and ex vivo binding to uterine progestin receptors of the rat as a tool to assay progestational activity of glucocorticoids". Methods and Findings in Experimental and Clinical Pharmacology. 4 (4): 237–242. PMID 7121132.
  26. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1228–. ISBN 978-1-4757-2085-3.
  27. ^ Genesis (triamcinolone acetonide) Topical Spray Drug information
  28. ^ Champion Hurdle favorite Yanworth failed drug test

External links edit

  • "Triamcinolone acetonide". Drug Information Portal. U.S. National Library of Medicine.
  • "Triamcinolone". MedlinePlus.
  • "Triamcinolone Nasal Spray". MedlinePlus.

November 30, 2023
triamcinolone, acetonide, sold, under, brand, name, kenalog, among, others, synthetic, corticosteroid, medication, used, topically, treat, various, skin, conditions, relieve, discomfort, mouth, sores, injection, into, joints, treat, various, joint, conditions,. Triamcinolone acetonide sold under the brand name Kenalog among others is a synthetic corticosteroid medication used topically to treat various skin conditions 12 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 10 It is a more potent derivative of triamcinolone and is about eight times as potent as prednisone 13 Triamcinolone acetonideClinical dataTrade namesKenalog Nasacort Xipere othersAHFS Drugs comMonographMedlinePlusa601124License dataUS DailyMed TriamcinolonePregnancycategoryAU B3 ARoutes ofadministrationTopical joint injection nasalATC codeA01AC01 WHO D07AB09 WHO H02AB08 WHO Legal statusLegal statusAU S4 Prescription only S3 S2 1 2 3 CA only OTC 4 5 UK POM Prescription only GSL 6 7 8 9 US only OTC 10 EU Rx only 11 Pharmacokinetic dataMetabolismLiverExcretionUrine 75 and feces 25 IdentifiersIUPAC name 4aS 4bR 5S 6aS 6bS 9aR 10aS 10bS 4b fluoro 6b glycoloyl 5 hydroxy 4a 6a 8 8 tetramethyl 4a 4b 5 6 6a 6b 9a 10 10a 10b 11 12 dodecahydro 2H naphtho 2 1 4 5 indeno 1 2 d 1 3 dioxol 2 oneCAS Number76 25 5 YPubChem CID6436IUPHAR BPS2867DrugBankDBSALT000860ChemSpider6196 YUNIIF446C597KAKEGGD00983ChEBICHEBI 71418 NChEMBLChEMBL1504 YPDB ligand1TA PDBe RCSB PDB CompTox Dashboard EPA DTXSID6021371ECHA InfoCard100 000 863Chemical and physical dataFormulaC 24H 31F O 6Molar mass434 504 g mol 13D model JSmol Interactive imageMelting point290 to 294 C 554 to 561 F 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 OInChI InChI 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 YKey YNDXUCZADRHECN JNQJZLCISA N Y N Y what is this verify 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 13 It is available as a generic medication 14 Contents 1 Medical uses 2 Contraindications 3 Pharmacology 3 1 Pharmacodynamics 4 Chemistry 5 Veterinary use 6 References 7 External linksMedical uses editTriamcinolone 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 When combined with nystatin it is used to treat skin infections with discomfort from fungus though it should not be used on the eyes 15 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 16 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 17 Triamcinolone acetonide is also administered via intralesional injection in the treatment of hypertrophic and keloid scars 18 19 Contraindications editEvidence suggests that usage of triamcinolone acetonide or other steroids to treat macular edema increases the risk of increasing intraocular pressure in patients 20 Triamcinolone acetonide should not be used by those with tuberculosis or untreated fungal bacterial systemic viral or herpes simplex infections without consulting a doctor first Pharmacology editPharmacodynamics edit Further information 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 21 The affinities of triamcinolone acetonide for the androgen and estrogen receptors are both lt 0 1 relative to testosterone and estradiol 22 However triamcinolone acetonide has 15 of the affinity of progesterone for the progesterone receptor 22 In relation to this triamcinolone acetonide can produce endocrine side effects like ovulation inhibition and menstrual irregularities 23 24 25 Chemistry editSee also List of corticosteroids Triamcinolone acetonide also known as 9a fluoro 16a hydroxyprednisolone 16a 17a acetonide or as 9a fluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16 17 acetal with acetone is a synthetic halogenated cyclic ketal pregnane corticosteroid 26 It is the C16a 17a acetonide of triamcinolone 26 Veterinary use editTriamcinolone acetonide is also used in veterinary medicine as an ingredient in topical ointments and in topical sprays for control of pruritus in dogs 27 A series of injections with triamcinolone acetonide or another corticosteroid may reduce keloid size and irritation 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 28 References edit KENALOG IN ORABASE triamcinolone acetonide Australian Register of Therapeutic Goods ARTG Australian Government ARTG ID 19205 KENACORT A10 triamcinolone acetonide Australian Register of Therapeutic Goods ARTG NASACORT AQ Triamcinolone acetonide Annual charge exemptions dataset Department of Health and Aged Care Australian Government Aristocort C Product information Health Canada 25 April 2012 Retrieved 23 December 2022 Nasacort Allergy 24HR Product information Health Canada 25 April 2012 Retrieved 23 December 2022 Adcortyl Intra Articular Intradermal Injection 10mg ml Summary of Product Characteristics SmPC emc 8 October 2021 Retrieved 23 December 2022 Kenalog Intra articular Intramuscular Injection Summary of Product Characteristics SmPC emc 8 April 2022 Retrieved 23 December 2022 Nasacort 55 micrograms dose nasal spray suspension Summary of Product Characteristics SmPC emc 1 November 2021 Retrieved 23 December 2022 Nasacort Allergy Relief for Adults 55 micrograms dose nasal spray suspension Summary of Product Characteristics SmPC emc 1 November 2021 Retrieved 23 December 2022 a b Xipere triamcinolone acetonide injection suspension DailyMed Retrieved 19 December 2021 Active substance s triamcinolone topical and nasal formulations PDF List of nationally authorised medicinal products European Medicines Agency 8 March 2018 Triamcinolone Topical MedlinePlus Retrieved 12 November 2020 a b Nasacort Allergy 24HR triamcinolone acetonide spray metered DailyMed 3 February 2014 Retrieved 12 November 2020 Competitive Generic Therapy Approvals U S Food and Drug Administration FDA 3 March 2023 Retrieved 6 March 2023 Nystatin And Triamcinolone Topical Route mayoclinic org Mayo Foundation for Medical Education and Research Retrieved 18 May 2016 Rittiphairoj T Mir TA Li T Virgili G November 2020 Intravitreal steroids for macular edema in diabetes The Cochrane Database of Systematic Reviews 2020 11 CD005656 doi 10 1002 14651858 CD005656 pub3 PMC 8095060 PMID 33206392 Geltzer A Turalba A Vedula SS January 2013 Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age related macular degeneration The Cochrane Database of Systematic Reviews 1 1 CD005022 doi 10 1002 14651858 CD005022 pub3 PMC 4269233 PMID 23440797 Intralesional Steroid Therapy Patient Information Leaflets British Association of Dermatologists 2008 Archived from the original on 15 March 2020 Retrieved 15 March 2020 Griffith BH September 1966 The treatment of keloids with triamcinolone acetonide Plastic and Reconstructive Surgery 38 3 202 208 doi 10 1097 00006534 196609000 00004 PMID 5919603 Gewaily D Muthuswamy K Greenberg PB September 2015 Intravitreal steroids versus observation for macular edema secondary to central retinal vein occlusion The Cochrane Database of Systematic Reviews 2015 9 CD007324 doi 10 1002 14651858 CD007324 pub3 PMC 4733851 PMID 26352007 Dinnendahl V Fricke U eds 2004 Arzneistoff Profile in German Vol 10 19 ed Eschborn Germany Govi Pharmazeutischer Verlag Triamcinolon ISBN 978 3 7741 9846 3 a b Kavlock RJ Daston GP 6 December 2012 Drug Toxicity in Embryonic Development II Advances in Understanding Mechanisms of Birth Defects Mechanistics Understanding of Human Development Toxicants Springer Science amp Business Media pp 437 ISBN 978 3 642 60447 8 Brook EM Hu CH Kingston KA Matzkin EG March 2017 Corticosteroid Injections A Review of Sex Related Side Effects Orthopedics 40 2 e211 e215 doi 10 3928 01477447 20161116 07 PMID 27874912 Cunningham GR Goldzieher JW de la Pena A Oliver M January 1978 The mechanism of ovulation inhibition by triamcinolone acetonide The Journal of Clinical Endocrinology and Metabolism 46 1 8 14 doi 10 1210 jcem 46 1 8 PMID 376542 Luzzani F Gallico L Glasser A 1982 In vitro and ex vivo binding to uterine progestin receptors of the rat as a tool to assay progestational activity of glucocorticoids Methods and Findings in Experimental and Clinical Pharmacology 4 4 237 242 PMID 7121132 a b Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 1228 ISBN 978 1 4757 2085 3 Genesis triamcinolone acetonide Topical Spray Drug information Champion Hurdle favorite Yanworth failed drug testExternal links edit Triamcinolone acetonide Drug Information Portal U S National Library of Medicine Triamcinolone MedlinePlus Triamcinolone Nasal Spray MedlinePlus Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Triamcinolone acetonide amp oldid 1143350825, wikipedia, wiki, book, books, library,

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