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. {{cite web}}: More than one of |archivedate= and |archive-date= specified (help); More than one of |archiveurl= and |archive-url= specified (help)
  2. 1 2 3 4 "Triamcinolone hexacetonide". BNF. Archived from the original on 13 September 2023. Retrieved 12 September 2023. {{cite web}}: More than one of |archivedate= and |archive-date= specified (help); More than one of |archiveurl= and |archive-url= specified (help)
  3. ↑ "Aristospan®(Triamcinolone Hexacetonide Injectable Suspension, USP)20 mg/mL PARENTERAL". FDA. Archived from the original on 13 September 2023. Retrieved 12 September 2023. {{cite web}}: More than one of |archivedate= and |archive-date= specified (help); More than one of |archiveurl= and |archive-url= specified (help)
  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. {{cite book}}: More than one of |archivedate= and |archive-date= specified (help); More than one of |archiveurl= and |archive-url= specified (help)
  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. {{cite web}}: More than one of |archivedate= and |archive-date= specified (help); More than one of |archiveurl= and |archive-url= specified (help)
  7. ↑ "Triamcinolone hexacetonide Medicinal forms". BNF. Archived from the original on 13 September 2023. Retrieved 12 September 2023. {{cite web}}: More than one of |archivedate= and |archive-date= specified (help); More than one of |archiveurl= and |archive-url= specified (help)
Identifiers:
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