Triamcinolone acetonide

Triamcinolone acetonide is a synthetic corticosteroid medication used topically to treat various skin conditions,[2] 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.[1] It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.[3]

Triamcinolone acetonide
Clinical data
Trade namesKenalog, Volon A, Nasacort, others
AHFS/Drugs.comMonograph
MedlinePlusa601124
License data
Pregnancy
category
  • AU: B3(topical)
Routes of
administration		Topical, joint injection, suprachoroidal
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S3 / S2
  • US: ℞-only / OTC[1]
Pharmacokinetic data
MetabolismLiver
ExcretionUrine (75%) and faeces (25%)
Identifiers
IUPAC 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-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.863
Chemical and physical data
FormulaC24H31FO6
Molar mass434.504 g·mol−1
3D model (JSmol)
Melting 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)O
InChI
  • 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)

It is also known under the brand names Kenalog (topical) and Volon A as an injection, to treat allergies, arthritis, eye diseases, intestinal problems, and skin diseases.

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.[3]

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. When combined with nystatin, it is used to treat skin infections with discomfort from fungus, though it should not be used on the eyes.[4] 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.[5] 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.[6]

Triamcinolone acetonide is also administered via intralesional injection in the treatment of hypertrophic and keloid scars.[7][8]

Uncommonly, intramuscular injection of triamcinolone acetonide may be indicated for the control of severe or incapacitating allergic states for which conventional treatments have failed, such as asthma, atopic dermatitis, contact dermatitis, perennial or seasonal allergic rhinitis, serum sickness, and transfusion and drug hypersensitivity reactions.

Contraindications

Evidence suggests that usage of triamcinolone acetonide or other steroids to treat macular edema increases the risk of increasing intraocular pressure in patients.[9]

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.

Doping

Triamcinolone acetonide, when given orally, rectally, intramuscularly or intravenously, is a banned substance in competitive sports, as it reduces weight and increases strength and endurance. Several Kenyan marathon runners have been found to have taken the drug, including 2021 Boston Marathon winner Diana Kipyokei.[10]

Pharmacology

Pharmacodynamics
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.[11] The affinities of triamcinolone acetonide for the androgen and estrogen receptors are both <0.1% (relative to testosterone and estradiol).[12] However, triamcinolone acetonide has 15% of the affinity of progesterone for the progesterone receptor.[12] In relation to this, triamcinolone acetonide can produce endocrine side effects like ovulation inhibition and menstrual irregularities.[13][14][15]

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.[16] It is the C16α,17α acetonide of triamcinolone.[16]

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.[17] 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.[18]

See also

References
  1. "Xipere- triamcinolone acetonide injection, suspension". DailyMed. Retrieved 19 December 2021.
  2. "Triamcinolone Topical". MedlinePlus. Retrieved 12 November 2020.
  3. "Nasacort Allergy 24HR- triamcinolone acetonide spray, metered". DailyMed. 3 February 2014. Retrieved 12 November 2020.
  4. "Nystatin And Triamcinolone (Topical Route)". mayoclinic.org. Mayo Foundation for Medical Education and Research. Retrieved 18 May 2016.
  5. Rittiphairoj, Thanitsara; Mir, Tahreem A.; Li, Tianjing; Virgili, Gianni (17 November 2020). "Intravitreal steroids for macular edema in diabetes". The Cochrane Database of Systematic Reviews. 2020 (11): CD005656. doi:10.1002/14651858.CD005656.pub3. ISSN 1469-493X. PMC 8095060. PMID 33206392.
  6. Geltzer A, Turalba A, Vedula SS (2013). "Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age-related macular degeneration". Cochrane Database Syst Rev (1): CD005022. doi:10.1002/14651858.CD005022.pub3. PMC 4269233. PMID 23440797.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. "Intralesional Steroid Therapy (Patient Information Leaflets)". British Association of Dermatologists. 2008. Archived from the original on 15 March 2020. Retrieved 15 March 2020.
  8. Griffith, B.H. (1966). "The treatment of keloids with triamcinolone acetonide". Plastic and Reconstructive Surgery. 38 (3): 202–208. doi:10.1097/00006534-196609000-00004. PMID 5919603.
  9. Gewaily D, Muthuswamy K, Greenberg PB (2015). "Intravitreal steroids versus observation for macular edema secondary to central retinal vein occlusion". Cochrane Database Syst Rev. 2021 (9): CD007324. doi:10.1002/14651858.CD007324.pub3. PMC 4733851. PMID 26352007.
  10. Reuters (14 October 2022). "Kenyans Kipyokei, Lempus provisionally suspended for doping". Reuters. Retrieved 19 October 2022.
  11. 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.
  12. Robert J. Kavlock; George P. Daston (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.
  13. 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.
  14. Cunningham GR, Goldzieher JW, de la Pena A, Oliver M (January 1978). "The mechanism of ovulation inhibition by triamcinolone acetonide". J Clin Endocrinol Metab. 46 (1): 8–14. doi:10.1210/jcem-46-1-8. PMID 376542.
  15. 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 Find Exp Clin Pharmacol. 4 (4): 237–42. PMID 7121132.
  16. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1228–. ISBN 978-1-4757-2085-3.
  17. Genesis (triamcinolone acetonide) Topical Spray Drug information
  18. Champion Hurdle favourite Yanworth failed drug test
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