Triamcinolone diacetate
Synonym(s):(11β,16α)-16,21-Bis(acetyloxy)-9-fluoro-11,17-dihydroxypregna-1,4-diene-3,20-dione;9α-Fluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,21-diacetate;9α-Fluoro-16α-hydroxyprednisolone 16,21-diacetate
- CAS NO.:67-78-7
- Empirical Formula: C25H31FO8
- Molecular Weight: 478.51
- MDL number: MFCD00056462
- EINECS: 200-669-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 17:34:41
What is Triamcinolone diacetate?
Chemical properties
White Solid
Originator
Aristocort,Lederle,US,1959
The Uses of Triamcinolone diacetate
A glucocorticoid that inhibits prolyl hydroxylase activity, Triamcinolone diacetate can be used as an antiasthmatic and antiallergic drug.
The Uses of Triamcinolone diacetate
antiinflammatory
The Uses of Triamcinolone diacetate
A glucocorticoid that inhibits prolyl hydroxylase activity and used as an antiasthmatic and antiallergic drug.
Definition
ChEBI: Triamcinolone diacetate is a corticosteroid hormone.
Manufacturing Process
To a solution of 16α,21-diacetoxy-11β,17α-dihydroxy-9α-fluoro-4-pregnene- 3,20-dione (1.0 g) in tertiary-butanol (160 ml) and glacial acetic acid (1.6 ml) was added 600 mg of selenium dioxide, the mixture swept with nitrogen and kept at 70°C for 24 hours, selenium dioxide (350 mg) added, and the mixture swept with nitrogen and allowed to stand for another 24 hours. The reaction mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure. The material so obtained was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, water, cold freshly prepared ammonium sulfide solution, cold dilute ammonia water, cold dilute hydrochloric acid, and finally with water. After treatment with anhydrous sodium sulfate and activated charcoal, filtration through diatomaceous earth and evaporation to dryness under reduced pressure, 850 mg of a tan glass was obtained. Paper strip chromatographic analysis showed predominantly product plus a small amount of starting material. The 850 mg was chromatographed on 320 g of diatomaceous earth containing 160 ml of stationary phase of a solvent system composed of 3,4,3,2-ethyl acetate-petroleum ether (boiling point 90°C to 100°C), methanol, and water, respectively. The column dimensions were 3.8 cm x 78 cm with 460 ml hold back volume. The fifth and sixth hold back volumes were combined and evaporated under reduced pressure to 250 mg of product which, after a single crystallization from acetone petroleum ether, gave 173 mg, melting point 150°C to 190°C. Paper strip chromatography showed a single spot having the same polarity as an authentic sample of 16α,21-diacetoxy-11β,17α-dihydroxy-9α-fluoro-1,4-pregnadiene-3,20-dione. A further crystallization from the same solvent pair gave 134 mg, melting point 185°C to 189°C, bubbles to 230°C.
Therapeutic Function
Glucocorticoid
Safety Profile
An experimental teratogen. Whenheated to decomposition it emits toxic fumes of F-.
Properties of Triamcinolone diacetate
Melting point: | 186-188 C |
Boiling point: | 608.5±55.0 °C(Predicted) |
alpha | D25 +22° (chloroform) |
Density | 1.2087 (estimate) |
storage temp. | Refrigerator |
solubility | Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly) |
form | Solid |
pka | 11.21±0.70(Predicted) |
color | White |
Water Solubility | 48mg/L(25 ºC) |
CAS DataBase Reference | 67-78-7(CAS DataBase Reference) |
NIST Chemistry Reference | Triamcinolone diacetate(67-78-7) |
EPA Substance Registry System | Triamcinolone diacetate (67-78-7) |
Safety information for Triamcinolone diacetate
Computed Descriptors for Triamcinolone diacetate
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