Triamcinolone

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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
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
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

injection into a muscle, and inhalation.[6]

Common side effects with long-term use include

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.

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]

Medical uses

Triamcinolone is used to treat a number of different medical conditions, such as

aphthous ulcers (usually as triamcinolone acetonide), central retinal vein occlusion, visualization during vitrectomy and the prevention of asthma attacks.[12][13][14]

The

eczema[15] and dermatitis.[16]

Contraindications

Contraindications for

metastasizing tumours.[17]

There are no contraindications for use in emergency medicine.[4]

Side effects

Further information: Glucocorticoid § Side effects

Side effects of triamcinolone are similar to other corticoids. In short-term treatment up to ten days, it has very few adverse effects; however, sometimes

glucose tolerance.[4]

Side effects of triamcinolone long-term treatment may include coughing (up to

allergic reaction include rash, itch, swelling, severe dizziness, trouble breathing,[18] and anaphylaxis.[17]

Overdose

No acute overdosing of triamcinolone has been described.[17]

Interactions

Drug interactions are mainly pharmacodynamic, that is, they result from other drugs either adding to triamcinolone's corticoid side effects or working against its desired effects. They include:[4][17]

Triamcinolone and other drugs can also influence each other's concentrations in the body, amounting to pharmacokinetic interactions such as:[4][17]

Pharmacology

Main article: Glucocorticoid § Pharmacology

Mechanism of action

Further information: Glucocorticoid § Mechanism of action

Triamcinolone is a glucocorticoid that is about five times as potent as cortisol, but has very little mineralocorticoid effects.[4]

Pharmacokinetics

When taken by mouth, the drug's

intracellular fluid, the total half-life is significantly longer at about 36 hours.[4][5]

A small fraction of the substance is metabolized to 6-hydroxy- and 20-dihydro-triamcinolone; most of it probably undergoes glucuronidation, and a smaller part sulfation. Three quarters are excreted via the urine, and the rest via the faeces.[4][17]

Due to corticoids' mechanism of action, the effects are delayed as compared to plasma concentrations. Depending on the route of administration and the treated condition, the onset of action can be from two hours up to one or two days after application; and the drug can act much longer than its elimination half-life would suggest.[4][5]

Chemistry

Triamcinolone is a

derivative of cortisol (hydrocortisone) and is also known as 1-dehydro-9α-fluoro-16α-hydroxyhydrocortisone or 9α-fluoro-16α-hydroxyprednisolone as well as 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione.[20][21]

The substance is a light-sensitive, white to off-white, crystalline powder, or has the form of colourless, matted crystals. It has no odour or is nearly odourless. Information on the melting point varies, partly due to the substance's

polymorphism: 260 to 263 °C (500 to 505 °F), 264 to 268 °C (507 to 514 °F), or 269 to 271 °C (516 to 520 °F) can be found in the literature.[4]

diethylether, and practically insoluble in dichloromethane. The specific rotation
is +65° to +72° cm3/dm·g (1% in dimethylformamide).[4]

Society and culture

In 2010, Teva and Perrigo launched the first generic inhalable triamcinolone.[22]

According to Chang et al. (2014), "Triamcinolone acetonide (TA) is classified as an S9 glucocorticoid in the 2014 Prohibited List published by the World Anti-Doping Agency, which caused it to be prohibited in international athletic competition when administered orally, intravenously, intramuscularly or rectally".[23]

References

  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. ^
    ISBN 978-3-7741-9846-3
    .
  5. ^ a b c d e f Triamcinolone (systemic) Professional Drug Facts. Accessed 19 August 2020.
  6. ^ a b c d e f g "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. ISBN 978-3-527-60749-5
    .
  9. 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.
  12. ^ "Triamcinolone: Uses, Dosage, Side Effects, Warnings". Drugs.com.
  13. ^ "Azmacort Inhaler: Side Effects, Dosage & Uses". Drugs.com.
  14. ^ "Alcon Receives FDA Approval of Triesence Injectable Triamcinolone Suspension for Use in Eye Surgery". Drugs.com.
  15. S2CID 44337035
    .
  16. PMID 24813302
    . Topical corticosteroids (TCS) are used in the management of AD in both adults and children and are the mainstay of anti-inflammatory therapy.
  17. ^ a b c d e f g Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Volon 4 mg-Tabletten.
  18. ^ "Drugs and Treatments – Nasacort AQ Nasl – Patient Handout". WebMD. Retrieved 24 March 2008.
  19. PMID 23143891
    .
  20. ISBN 978-1-4757-2085-3
    .
  21. ISBN 978-3-88763-075-1
    .
  22. ^ "Perrigo Announces Launch Of Generic Version Of Nasacort AQ". 15 June 2011.
  23. PMID 25126738
    .

External links
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