Triamcinolone acetonide

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Triamcinolone acetonide
Triamcinolone acetonide.png
Triamcinolone acetonide (Ball-n-Stick).png
Names
IUPAC name
(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one
Identifiers
76-25-5 YesY
ChEBI CHEBI:71418 N
ChEMBL ChEMBL1504 YesY
ChemSpider 6196 YesY
Jmol-3D images Image
PubChem 6436
UNII F446C597KA YesY
Properties
C24H31FO6
Molar mass 434.50 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Triamcinolone acetonide is a synthetic corticosteroid used to treat various skin conditions, to relieve the discomfort of mouth sores,[1] and in nasal spray form, to treat allergic rhinitis. It is a more potent derivative of triamcinolone, and is about eight times as potent as prednisone.[2]

It is also known under the brand names Kenalog (topical) and Volon A as an injection, to treat allergies, arthritis, eye diseases, intestinal problems, and skin diseases.[3] In 2014, the FDA made triamcinolone acetonide an over-the-counter drug in the USA in nasal spray form under the brand name Nasacort.[4]

Medical use[edit]

Triamcinolone acetonide as an intra-articular injectable has been used to treat a variety of musculoskeletal conditions. When applied as a topical ointment, it is used for blistering from poison ivy, oak, and sumac, applied to the skin, avoiding eyes, mouth, and genital area. It provides relatively immediate relief and is used before using oral prednisone. Oral and dental paste preparations are used for treating aphthous ulcers.

As an intravitreal injection, triamcinolone acetonide has been used to treat various eye diseases and has been found useful in reducing macular edema. Drug trials have found it to be as efficient as anti-VEGF drugs in eyes with artificial lenses over a two-year period.

Uncommonly, intramuscular injection of triamcinolone acetonide may be indicated for the control of severe or incapacitating allergic states for which conventional treatments have failed, such as asthma, atopic dermatitis, contact dermatitis, perennial or seasonal allergic rhinitis, serum sickness, and transfusion and drug hypersensitivity reactions.

Contraindications[edit]

As with all immunosuppressant drugs, triamcinolone acetonide should not be taken by persons suffering from infectious diseases, either currently or in recuperation or soon thereafter. Contact with infectious persons should be avoided during the entire course of treatment. Users who contract an infection during their regimen should contact their doctors to discuss whether to discontinue triamcinolone acetonide.

Triamcinolone acetonide should not be taken if the patient is also taking any other steroid or immunosuppressant, or if they have recently undergone any medical procedures involving the administration of steroids (e.g. nerve block).[citation needed]

Many drugs have been demonstrated to increase triamcinolone acetonide concentration in the blood to well above the intended level. Patients should inform doctors about any other drugs they are taking.[citation needed]

Triamcinolone acetonide should not be used by those with tuberculosis or untreated fungal, bacterial, systemic viral or herpes simplex infections without consulting a doctor first.

Veterinary use[edit]

Triamcinolone acetonide is also used in veterinary medicine as an ingredient in topical ointments and in topical sprays for control of pruritus in dogs.[5] A series of injections with triamcinolone acetonide or another corticosteroid may reduce keloid size and irritation. It is also used as a preinductor and/or inductor of birth in cows.

Synthesis[edit]

Triamcinolone acetonide synthesis[6]

Conversion of the 17,20 double bond to a keto alcohol is accomplished in a single step with a special combination of reagents. NMO is acronym for N-methylmorpholine N-oxide, a cooxidant. See Upjohn dihydroxylation for details. It is a sufficiently strong oxidant to oxidize the hydroxyl at 20 to a ketone.

Thus, reaction under those conditions completes the formation of the dihydroxyacetone side chain and hydrocortisone acetate. Further oxidation of the 11 hydroxyl group with, for example, Jones’ reagent gives cortisone acetate.

References[edit]

  1. ^ Triamcinolone Acetonide Drug information from MedLine Plus
  2. ^ Nasacort medication leaflet
  3. ^ [1]
  4. ^ Nasacort.com
  5. ^ GENESIS® (triamcinolone acetonide) Topical Spray Drug information
  6. ^ Bernstein, S.; Lenhard, R. H.; Allen, W. S.; Heller, M.; Littell, R.; Stolar, S. M.; Feldman, L. I.; Blank, R. H. (1959). "16-Hydroxylated Steroids. VI1The Synthesis of the 16α-Hydroxy Derivatives of 9α-Substituted Steroids". Journal of the American Chemical Society 81 (7): 1689. doi:10.1021/ja01516a043.  edit