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Triamcinolone

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Triamcinolone
Clinical data
Trade namesKenalog Nasacort
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
Pregnancy
category
  • AU: A
Routes of
administration		Oral, topical, IM, intra-articular, intrasynovial
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding68%
MetabolismHepatic
Elimination half-life88 minutes
ExcretionFecal and renal
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 mass394.434 g/mol g·mol−1
3D model (JSmol)
  • 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 an intermediate-acting synthetic glucocorticoid given orally, by injection, by inhalation, or as a topical ointment or cream.[1]

Uses

Triamcinolone is used to treat a number of different medical conditions, such as eczema, Lichen sclerosus, psoriasis, arthritis, allergies, ulcerative colitis, lupus, sympathetic ophthalmia, temporal arteritis, uveitis, ocular inflammation, Urushiol-induced contact dermatitis, aphthous ulcers (usually as triamcinolone acetonide), visualization during vitrectomy and the prevention of asthma attacks. It will not treat an asthma attack once it has already begun.[2][3][4] It has also been used off-label for macular degeneration.[5]

Prior to 2007 it was sold under the name Azmacort as a corticosteroid inhaler for asthma long-term care.

In 2010, TEVA and Perrigo launched the first generic inhalable triamcinolone.[6]

Triamcinolone is used to alleviate infection-induced eczema in fungal skin infections in the combination drug of econazole/triamcinolone.

The derivative triamcinolone acetonide is one of the ingredients of Ledermix, an endodontic (tooth's root canal) lotion used between sessions, and Sanofi sold it under the brand name Nasacort. Triamcinolone acetonide is also used as intra lesional steroid injection to treat keloids and hypertrophic scars.

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-competition when administered orally, intravenously, intramuscularly or rectally".[7]

Forms

Different triamcinolone derivatives are available, including acetonide, benetonide, furetonide, hexacetonide and diacetate.

Triamcinolone acetonide is a more potent type of triamcinolone, being about eight times as effective as prednisone.

Side effects

Side effects of triamcinolone include sore throat, nosebleeds, increased coughing, headache, and runny nose.[citation needed] White patches in the throat or nose indicate a serious side effect.[clarification needed] Symptoms of an allergic reaction include rash, itch, swelling, severe dizziness, trouble breathing.[8] An additional side effect for women is a prolonged menstrual cycle.

Chemistry

Triamcinolone is a synthetic pregnane corticosteroid and 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.[9][10]

Society and culture

Brand names

Trade names for triamcinolone include Aristocort (Sandoz, now Novartis), Kenacort (Bristol-Myers Squibb), Kenalog (Bristol-Myers Squibb), Tricort (Cadila), Triaderm (Schering-Plough), Azmacort (KOS), Trilone, Volon A, Tristoject, Tricortone, Ratio-Triacomb, and Trianex.

See also

References

Aristocort (triamcinolone) topical cream
Kenalog (triamcinolone) IM injection
  1. ^ Chrousos G, Pavlaki AN, Magiakou MA (2011). "Glucocorticoid Therapy and Adrenal Suppression". PMID 25905379. {{cite journal}}: Cite journal requires |journal= (help)
  2. ^ Triamcinolone - Drugs.com
  3. ^ Triamcinolone Inhalation - Drugs.com
  4. ^ Alcon Receives FDA Approval of Triesence Injectable Triamcinolone Suspension for Use in Eye Surgery - Drugs.com
  5. ^ Age-Related Macular Degeneration (AMD) Treatment
  6. ^ Perrigo Announces Launch Of Generic Version Of Nasacort AQ - CBS Detroit
  7. ^ Chang, Chih-Wei; Huang, Tai-Yuan; Tseng, Yi-Chun; Chang-Chien, Guo-Ping; Lin, Su-Fan; Hsu, Mei-Chich (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. {{cite journal}}: Cite has empty unknown parameter: |1= (help)
  8. ^ "Drugs and Treatments - Nasacort AQ Nasl - Patient Handout". WebMD. Retrieved 2008-03-24.
  9. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1228–. ISBN 978-1-4757-2085-3.
  10. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1054–. ISBN 978-3-88763-075-1.
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