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Triamcinolone

From Wikipedia, the free encyclopedia
Steroid medication

Pharmaceutical compound
Triamcinolone
Clinical data
Trade namesKenalog, Nasacort, Adcortyl, others
Other names
Clickshow 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
Routes of
administration
By mouth,topical,intranasal,intramuscular,intra-articular, intra-synovial
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability>90%[4]
Protein binding68%[citation needed]
MetabolismLiver[4]
Onset of action(2–)24(–48) hours[4][5]
Eliminationhalf-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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.290Edit this at Wikidata
Chemical and physical data
FormulaC21H27FO6
Molar mass394.439 g·mol−1
3D model (JSmol)
Specific rotation[α]D20{\displaystyle [\alpha ]_{D}^{20}} +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 aglucocorticoid used to treat certainskin diseases, allergies, andrheumatic disorders among others.[6] It is also used to prevent worsening ofasthma andchronic obstructive pulmonary disease (COPD).[6] It can be taken in various ways includingby mouth,injection into a muscle, andinhalation.[6]

Common side effects with long-term use includeosteoporosis,cataracts,thrush, andmuscle weakness.[6] Serious side effects may includepsychosis, increased risk of infections,adrenal suppression, andbronchospasm.[6] Use inpregnancy is generally safe.[7] It works by decreasinginflammation andimmune system activity.[6]

Triamcinolone was patented in 1956 and came into medical use in 1958.[8] It is available as ageneric medication.[9] In 2023, it was the 108th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[10][11]

Medical uses

[edit]

Triamcinolone is used to treat various medical conditions, such aseczema,alopecia areata,lichen sclerosus,psoriasis,arthritis,allergies,ulcerative colitis,lupus,sympathetic ophthalmia,temporal arteritis,uveitis,ocularinflammation,keloids,urushiol-induced contact dermatitis,aphthous ulcers (usually astriamcinolone acetonide),central retinal vein occlusion, visualization duringvitrectomy and the prevention ofasthma attacks.[12][13][14]

Thederivativetriamcinolone acetonide is the active ingredient in various topical skin preparations (cream, lotion, ointment, aerosol spray) designed to treat such skin conditions as rash, inflammation, redness, or intense itching due toeczema[15] anddermatitis.[16]

Contraindications

[edit]

Contraindications forsystemic triamcinolone are similar to those of other corticoids. They include systemicmycoses (fungal infections) andparasitic diseases, as well as eight weeks before and two weeks after application oflive vaccines. For long-term treatment, the drug is also contraindicated in people withpeptic ulcers, severeosteoporosis, severemyopathy, certainviral infections,glaucoma, andmetastasizing tumours.[17]

There are no contraindications for use inemergency medicine.[4]

Side effects

[edit]
Further information:Glucocorticoid § Side effects

The side effects of triamcinolone are similar to other corticosteroids. In short-term treatment of up to ten days, it has very few adverse effects; however, sometimesgastrointestinal bleeding is seen, as well as acute infections (mainlyviral) and impairedglucose tolerance.[4]

Side effects of triamcinolone long-term treatment may include coughing (up tobronchospasms),sinusitis,metabolic syndrome–like symptoms such ashigh blood sugar andcholesterol,weight gain due towater retention, andelectrolyte imbalance, as well ascataract,thrush,osteoporosis,reduced muscle mass, andpsychosis.[5][6][17] Triamcinolone injections can cause bruising and joint swelling.[5] Symptoms of anallergic reaction includerash,itch,swelling, severedizziness,trouble breathing,[18] andanaphylaxis.[17]

Overdose

[edit]

No acuteoverdosing of triamcinolone has been described.[17]

Interactions

[edit]

Drug interactions are mainly pharmacodynamic, that is, they result from other drugs either adding to triamcinolone's corticosteroid 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

[edit]
Main article:Glucocorticoid § Pharmacology

Mechanism of action

[edit]
Further information:Glucocorticoid § Mechanism of action

Triamcinolone is a glucocorticoid that is about five times as potent ascortisol but has very fewmineralocorticoid effects.[4]

Pharmacokinetics

[edit]

When taken by mouth, the drug'sbioavailability is over 90%. It reaches its highest concentrations in theblood plasma after one to two hours and is bound toplasma proteins to about 80%. Thebiological half-life from the plasma is 200 to 300 minutes; due to stable complexes of triamcinolone andits receptor in theintracellular 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 undergoesglucuronidation, and a smaller partsulfation. 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

[edit]

Triamcinolone is asyntheticpregnanecorticosteroid andderivative ofcortisol (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'spolymorphism: 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]

Solubility is 1:500 in water and 1:240 inethanol; it is slightly soluble inmethanol, very slightly soluble inchloroform anddiethylether, and practically insoluble indichloromethane. Thespecific rotation is[α]D20{\displaystyle [\alpha ]_{D}^{20}} +65° to +72° cm3/dm·g (1% indimethylformamide).[4]

Society and culture

[edit]

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

According to Chang et al. (2014), "Triamcinolone acetonide (TA) is classified as an S9glucocorticoid in the 2014 Prohibited List published by theWorld Anti-Doping Agency, which caused it to be prohibited in international athletic competition when administered orally, intravenously, intramuscularly or rectally".[23]

References

[edit]
  1. ^"Kenalog Intra-articular / Intramuscular Injection - Summary of Product Characteristics (SmPC)".(emc). 10 June 2020. Retrieved20 August 2020.
  2. ^"Nasacort Allergy 55 micrograms/dose Nasal Spray suspension - Summary of Product Characteristics (SmPC)".(emc). 30 August 2018. Archived fromthe original on 23 December 2022. Retrieved20 August 2020.
  3. ^"Adcortyl Intra-Articular/Intradermal Injection 10mg/ml - Summary of Product Characteristics (SmPC)".(emc). 11 December 2017. Retrieved20 August 2020.
  4. ^abcdefghijklmnDinnendahl 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. ^abcdefTriamcinolone (systemic)Professional Drug Facts. Accessed 19 August 2020.
  6. ^abcdefg"Triamcinolone Monograph for Professionals".Drugs.com. American Society of Health-System Pharmacists. Retrieved3 March 2019.
  7. ^"Triamcinolone Use During Pregnancy".Drugs.com. Retrieved3 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. ^"Top 300 of 2023".ClinCalc.Archived from the original on 12 August 2025. Retrieved12 August 2025.
  11. ^"Triamcinolone Drug Usage Statistics, United States, 2013 - 2023".ClinCalc. Retrieved18 August 2025.
  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. ^Chong M, Fonacier L (December 2016). "Treatment of Eczema: Corticosteroids and Beyond".Clinical Reviews in Allergy & Immunology.51 (3):249–262.doi:10.1007/s12016-015-8486-7.PMID 25869743.S2CID 44337035.
  16. ^Eichenfield LF, Tom WL, Berger TG, Krol A, Paller AS, Schwarzenberger K, et al. (July 2014)."Guidelines of care for the management of atopic dermatitis: section 2. Management and treatment of atopic dermatitis with topical therapies".Journal of the American Academy of Dermatology.71 (1):116–132.doi:10.1016/j.jaad.2014.03.023.PMC 4326095.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. ^abcdefgHaberfeld H, ed. (2020).Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Volon 4 mg-Tabletten.
  18. ^"Drugs and Treatments – Nasacort AQ Nasl – Patient Handout".WebMD. Retrieved24 March 2008.
  19. ^Moore CD, Roberts JK, Orton CR, Murai T, Fidler TP, Reilly CA, et al. (February 2013)."Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes".Drug Metabolism and Disposition.41 (2):379–389.doi:10.1124/dmd.112.046318.PMC 3558858.PMID 23143891.
  20. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1228–.ISBN 978-1-4757-2085-3.
  21. ^Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1054–.ISBN 978-3-88763-075-1.
  22. ^"Perrigo Announces Launch Of Generic Version Of Nasacort AQ". 15 June 2011.
  23. ^Chang CW, Huang TY, Tseng YC, Chang-Chien GP, Lin SF, Hsu MC (November 2014)."Positive doping results caused by the single-dose local injection of triamcinolone acetonide".Forensic Science International.244:1–6.doi:10.1016/j.forsciint.2014.07.024.PMID 25126738.

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