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Triamcinolone

Triamcinolone
Clinical data
Trade namesKenalog, Nasacort, Adcortyl, others
Other names
Click show to see
(8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one; (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
AHFS/Drugs.comMonograph
MedlinePlusa601122
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, topical, intranasal, intramuscular, intra-articular, intra-synovial
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) / S3
  • UK: POM (Prescription only) / P[1][2][3]
  • US: ℞-only / OTC (Nasacort, intranasal)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability>90%[4]
Protein binding68%[citation needed]
MetabolismLiver[4]
Onset of action(2–)24(–48) hours[4][5]
Elimination half-life200–300 minutes (plasma), up to 36 hours (total)[4]
ExcretionUrine (75%) and faeces (25%)[5]
Identifiers
  • (11β,16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.290 Edit this at Wikidata
Chemical and physical data
FormulaC21H27FO6
Molar mass394.439 g·mol−1
3D model (JSmol)
Specific rotation +65° to +72°
Melting point260 to 271 °C (500 to 520 °F)
Solubility in water2
  • O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@H]3O)C)C
  • InChI=1S/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1 checkY
  • Key:GFNANZIMVAIWHM-OBYCQNJPSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others.[6] It is also used to prevent worsening of asthma and COPD.[6] It can be taken in various ways including by mouth, injection into a muscle, and inhalation.[6]

Common side effects with long-term use include osteoporosis, cataracts, thrush, and muscle weakness.[6] Serious side effects may include psychosis, increased risk of infections, adrenal suppression, and bronchospasm.[6] Use in pregnancy is generally safe.[7] It works by decreasing inflammation and immune system activity.[6]

Triamcinolone was patented in 1956 and came into medical use in 1958.[8] It is available as a generic medication.[9] In 2021, it was the 104th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[10][11]

  1. ^ "Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC)". (emc). 10 June 2020. Retrieved 20 August 2020.
  2. ^ "Nasacort Allergy 55 micrograms/dose Nasal Spray suspension - Summary of Product Characteristics (SmPC)". (emc). 30 August 2018. Retrieved 20 August 2020.
  3. ^ "Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC)". (emc). 11 December 2017. Retrieved 20 August 2020.
  4. ^ a b c d 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.
  5. ^ a b Cite error: The named reference PPA was invoked but never defined (see the help page).
  6. ^ a b c d e f "Triamcinolone Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  7. ^ "Triamcinolone Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 486. ISBN 978-3-527-60749-5.
  9. ^ Vallerand AH (2018). Davis's Drug Guide for Nurses. F.A. Davis. p. 365. ISBN 978-0-8036-7000-6.
  10. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  11. ^ "Triamcinolone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
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