Triamcinolone

Triamcinolone is a glucocorticoid used to treat certain skin diseases, allergies, and rheumatic disorders among others.[1] It is also used to prevent worsening of asthma and COPD.[1] It can be taken in various ways including by mouth, injection into a muscle, and inhaled.[1]

Triamcinolone
Clinical data
Trade namesKenalog, Nasacort, others
Other names
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(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
  • US: C (Risk not ruled out)
    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
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.004.290
    Chemical and physical data
    FormulaC21H27FO6
    Molar mass394.434 g/mol g·mol−1
    3D model (JSmol)
     NY (what is this?)  (verify)

    Common side effects with long term use include osteoporosis, cataracts, thrush, and muscle weakness.[1] Serious side effects may include psychosis, increased risk of infections, adrenal suppression, and bronchospasm.[1] Use in pregnancy is generally safe.[2] It works by decreasing inflammation and immune system activity.[1]

    Triamcinolone was patented in 1956 and came into medical use in 1958.[3] It is available as a generic medication.[4] In the United States the wholesale cost is about US$0.06 per gram for the cream.[5] In 2016 it was the 122nd most prescribed medication in the United States with more than 6 million prescriptions.[6]

    Medical 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, keloids, urushiol-induced contact dermatitis, aphthous ulcers (usually as triamcinolone acetonide), central retinal vein occlusion, visualization during vitrectomy and the prevention of asthma attacks.[7][8][9]

    The derivative triamcinolone acetonide is the active ingredient in various topical skin preparations (cream, lotion, ointment, aerosol spray) designed to treat skin conditions such as rash, inflammation, redness, or intense itching due to eczema[10] and dermatitis.[11]

    Side effects

    Side effects of triamcinolone include sore throat, nosebleeds, increased coughing, headache, and runny nose. White patches in the throat or nose indicate a serious side effect. Symptoms of an allergic reaction include rash, itch, swelling, severe dizziness, trouble breathing.[12]

    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.[13][14]

    Society and culture

    In 2010, TEVA and Perrigo launched the first generic inhalable triamcinolone.[15]

    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".[16]

    Brand names

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

    See also

    References
    1. "Triamcinolone Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
    2. "Triamcinolone Use During Pregnancy". Drugs.com. Retrieved 3 March 2019.
    3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 486. ISBN 978-3-527-60749-5.
    4. Vallerand, April Hazard (2018). Davis's Drug Guide for Nurses. F.A. Davis. p. 365. ISBN 978-0-8036-7000-6.
    5. "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Retrieved 3 March 2019.
    6. "The Top 300 of 2019". clincalc.com. Retrieved 22 December 2018.
    7. Triamcinolone – Drugs.com
    8. Triamcinolone Inhalation – Drugs.com
    9. Alcon Receives FDA Approval of Triesence Injectable Triamcinolone Suspension for Use in Eye Surgery – Drugs.com
    10. 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.
    11. 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): 116–32. 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.
    12. "Drugs and Treatments – Nasacort AQ Nasl – Patient Handout". WebMD. Retrieved 2008-03-24.
    13. 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.
    14. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1054–. ISBN 978-3-88763-075-1.
    15. Perrigo Announces Launch Of Generic Version Of Nasacort AQ – CBS Detroit
    16. 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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