Chemical Properties
White Solid
Definition
ChEBI: A synthetic glucocorticoid that is the 16,17-acetonide of triamcinolone. Used to treat various skin infections.
Description
Triamcinolone acetonide is a synthetic corticosteroid.
1 It decreases cytokine levels, the firing rate of sensory neurons, and mechanical hypersensitivity in a rat spinal nerve ligation model when used at a dose of 1.5 mg/kg prior to and following surgery for three days. Triamcinolone acetonide also decreases outflow facility in a mouse model of steroid-induced glaucoma when 20 μl of a 40 mg/ml suspension is administered subconjunctivally.
2 Formulations containing triamcinolone acetonide are used in the treatment of diabetic macular edema.
Originator
Kenalog,Squibb,US,1958
Indications
Triamcinolone acetonide (Aristocort, Kenalog) is a synthetic fluorinated corticosteroid.
Manufacturing Process
A solution of 250 mg of 9α-fluoro-11β,16α,17α,21-tetrahydroxy-1,4-
pregnadiene-3,20-dione in 70 ml of hot acetone and 7 drops of concentrated
hydrochloric acid is boiled for 3 minutes. After standing at room temperature
for 17 hours, the reaction mixture is poured into dilute sodium bicarbonate
and extracted with ethyl acetate. The extract is washed with saturated saline
solution, dried and evaporated to a colorless glass. The residue is crystallized
from acetone-petroleum ether to afford 166 mg of the acetonide, MP 270° to
274°C, decomposition, (with previous softening and browning). Three
recrystallizations from acetone-petroleum ether give 113 mg of 9α-fluoro-
11β,21-dihydroxy-16α,17α-isopropylidenedioxy-1,4-pregnadiene-3,20-dione,
MP 274° to 279°C, decomposition, (with previous softening and browning).
Brand name
Triamcinolone acetonide was sold under the brand name Kenalog among others.
Therapeutic Function
Glucocorticoid
General Description
The three main metabolitesof triamcinolone acetonide (Azmacort, Nasacort) are 6β-hydroxytriamcinolone acetonide, 21-carboxytriamcinoloneacetonide, and 6β-hydroxy-21-carboxytriamcinolone acetonide.All are much less active than the parent compound.The 6β-hydroxyl group and the 21-carboxy group are bothstructural features that greatly reduce GC action. The increasedwater solubility of these metabolites also facilitatesmore rapid excretion.
General Description
Triamcinolone acetonide is approximately 8 times morepotent than prednisone in animal inflammation models.Topically applied triamcinolone acetonide is a potent antiinflammatoryagent, about 10 times more sothan triamcinolone. The plasma half-life is approximately 90minutes, although the plasma half-life and biological halflivesfor GCs do not correlate well. The hexacetonide isslowly converted to the acetonide in vivo and is given onlyby intra-articular injection. Only triamcinolone and the diacetateare given orally. The acetonide and diacetate may begiven by intra-articular or intrasynovial injection. In addition,the acetonide may be given by intrabursal or, sometimes,IM or subcutaneous injection. A single IM dose of thediacetate or acetonide may last up to 3 or 4 weeks. Plasmalevels with IM doses of the acetonide are significantly higherthan with triamcinolone itself. The acetonide is also used totreat asthma and allergic rhinitis.
Clinical Use
Triamcinolone acetonide frequently is used by inhalation for the treatment of lung diseases (e.g., asthma).
Side effects
The side effects of using Triamcinolone acetonide include:Skin dryness, flaking, crusting, burning, or blistering; Skin irritation; Skin soreness, itching, swelling, scaling, or severe redness; Scaling or redness near mouth; Skin thinning or bruising, especially in skin folds (like between the finger) or on the face (when directed to use it there); New or worsening pimples or acne; Skin burning and itching with tiny red blisters; Skin softening; Itching, pain, or burning sensation in hairy areas, or pus at the root of the hair; Increased hair growth on the legs, arms, back, or forehead; Lightening of skin tone; Red or purple lines on the arms, face, legs, groin, or trunk.
Veterinary Drugs and Treatments
The systemic veterinary labeled product (Vetalog? Injection) is labeled
as “indicated for the treatment of inflammation and related
disorders in dogs, cats, and horses. It is also indicated for use in
dogs and cats for the management and treatment of acute arthritis,
allergic and dermatologic disorders.”
Glucocorticoids have been used in an attempt to treat practically
every malady that afflicts man or animal, but there are three broad
uses and dosage ranges for use of these agents. 1) Replacement of
glucocorticoid activity in patients with adrenal insufficiency, 2)
as an antiinflammatory agent, and 3) as an immunosuppressive.
Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases
(e.g., rheumatoid arthritis), collagen diseases (e.g., systemic
lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic
diseases (e.g., pemphigus, allergic dermatoses), hematologic
disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias),
neoplasias, nervous system disorders (increased CSF pressure),
GI diseases (e.g., ulcerative colitis exacerbations), and renal
diseases (e.g., nephrotic syndrome). Some glucocorticoids are used
topically in the eye and skin for various conditions or are injected
intra-articularly or intra-lesionally. The above listing is certainly
not complete.
Metabolism
Triamcinolone acetonide frequently is used by inhalation for the treatment of lung diseases (e.g., asthma). After
inhalation, triamcinolone acetonide can become systemically available when the inhaled formulation is
swallowed and absorbed unchanged from the GI tract, causing undesirable systemic effects.
Triamcinolone acetonide that is swallowed is metabolized to 6β-hydroxytriamcinolone acetonide,
21-carboxytriamcinolone acetonide, and 21-carboxy-6β-hydroxytriamcinolone acetonide, all of which are more
hydrophilic than their parent drug. Only approximately 1% of the dose was recovered from the urine as
triamcinolone acetonide. Triamcinolone is not a major metabolite of triamcinolone acetonide in humans,
suggesting that acetonide is resistant to hydrolytic cleavage. Triamcinolone acetonide is approximately eight
times more potent than prednisolone.
