Triamcinolone hexacetonide

Triamcinolone hexacetonide
Names
Trade namesAristospan, Hexatrione, others
Other namesTriamcinolone acetonide 21-tebutate; Triamcinolone acetonide 21-(tert-butylacetate); 9α-Fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone, 21-(3,3-dimethylbutyrate); 9α-Fluoro-11β-hydroxy-16α,17α-((1-methylethylidene)bis(oxy))pregna-1,4-diene-3,20-dione 21-(3,3-dimethylbutyrate)
IUPAC name
  • 2-[(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-Fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]-2-oxoethyl 3,3-dimethylbutanoate
Clinical data
Drug classCorticosteroid; glucocorticoid
Main usesJuvenile idiopathic arthritis (JIA)[1]
Side effectsAnxiety, swelling, increased risk of infection, trouble sleeping, peptic ulcer disease[2]
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Routes of
use
Injection into a joint[1]
Chemical and physical data
FormulaC30H41FO7
Molar mass532.649 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)COC(=O)CC(C)(C)C)CCC5=CC(=O)C=C[C@@]53C)F)O
InChI
  • InChI=1S/C30H41FO7/c1-25(2,3)15-24(35)36-16-22(34)30-23(37-26(4,5)38-30)13-20-19-9-8-17-12-18(32)10-11-27(17,6)29(19,31)21(33)14-28(20,30)7/h10-12,19-21,23,33H,8-9,13-16H2,1-7H3/t19-,20-,21-,23+,27-,28-,29-,30+/m0/s1
  • Key:TZIZWYVVGLXXFV-FLRHRWPCSA-N

Triamcinolone hexacetonide, sold under the brand name Aristospan among others, is a medication used to treat juvenile idiopathic arthritis (JIA).[1] It may also be used for gout, bursitis, and tendinitis.[3] It is given by injection into a joint.[1] Effects last for up to 4 weeks.[4] Triamcinolone acetonide may be used as an alternative.[5]

Side effects may include anxiety, swelling, increased risk of infection, trouble sleeping, and peptic ulcer disease.[2] Rare side effect may include tendon rupture and central serous chorioretinopathy.[2] It is primarily a glucocorticoid with little mineralcorticoid effects.[2]

was approved for medical use in the United States in 1969.[6] It is on the World Health Organization's List of Essential Medicines.[5] In the United Kingdom a 20 mg vial costs the NHS about £12 as of 2023.[7]

References

  1. 1 2 3 4 "eEML - Electronic Essential Medicines List". list.essentialmeds.org. Archived from the original on 18 June 2022. Retrieved 8 September 2023.
  2. 1 2 3 4 "Triamcinolone hexacetonide". BNF. Archived from the original on 13 September 2023. Retrieved 12 September 2023.
  3. "Aristospan®(Triamcinolone Hexacetonide Injectable Suspension, USP)20 mg/mL PARENTERAL". FDA. Archived from the original on 13 September 2023. Retrieved 12 September 2023.
  4. Lemke, Thomas L. (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 892. ISBN 9780781768795. Archived from the original on 13 September 2023. Retrieved 12 September 2023.
  5. 1 2 World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  6. "Aristospan (Injection)". Archived from the original on 19 August 2022. Retrieved 12 September 2023.
  7. "Triamcinolone hexacetonide Medicinal forms". BNF. Archived from the original on 13 September 2023. Retrieved 12 September 2023.
Identifiers:
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