9596. Triamcinolone Acetonide

Nomenclature

CAS number: 76-25-5
(11β,16α)-9-Fluoro-11,21-dihydroxy-16,17-[1-methylethylidenebis(oxy)]pregna-1,4-diene-3,20-dione; 9α-fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone; 9α-fluoro-16α-hydroxyprednisolone acetonide; triamcinolone 16α,17-acetonide; 9α-fluoro-11β,21-dihydroxy-16α,17α-isopropylidenedioxy-1,4-pregnadiene-3,20-dione; 9α-fluoro-16α,17-isopropylidenedioxyprednisolone; Adcortyl (BMS); Azmacort (Aventis); Delphicort (Lederle); Extracort (Basotherm); Ftorocort (Gedeon Richter); Kenacort-A (BMS); Kenalog (Apothecon); Ledercort Cream (Lederle); Nasacort (Aventis); Respicort (Mundipharma); Rineton (Sanwa); Solodelf (Cyanamid); Tramacin (J & J); Triam (Lichtenstein); Tricinolon (Kaken); Vetalog (Solvay); Volon A (BMS); Volonimat (BMS).
C24H31FO6; mol wt 434.50.
C 66.34%, H 7.19%, F 4.37%, O 22.09%.

Description and references

Prepd by stirring a suspension of triamcinolone in acetone in the presence of a trace of perchloric acid: Fried et al., J. Am. Chem. Soc. 80, 2338 (1958); Bernstein et al., ibid. 81, 1689 (1959); Bernstein, Allen, US 2990401 (1961 to Am. Cyanamid). Alternate synthesis using 2,3-dibromo-5,6-dicyanoquinone: Hydorn, US 3035050 (1962 to Olin Mathieson). Clinical trial in chronic asthma: I. L. Bernstein et al., Chest 81, 20 (1982). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 1, 397-421 (1972); D. H. Sieh, ibid. 11, 615-649 (1982).

Chemical structure

Properties

Crystals, mp 292-294°. [α]D23 +109° (c = 0.75 in chloroform). uv max (abs alc.): 238 nm (ε 14600). Sparingly sol in methanol, acetone, ethyl acetate.

Derivative

21-Acetate.

Properties

Crystals, mp 268-270°. [α]D23 +92° (c = 0.59 in chloroform).

Derivative

21-Disodium phosphate.

Nomenclature

CAS number: 1997-15-5
Aristosol (Lederle).
C24H30FNa2O9P; mol wt 558.44.
C 51.62%, H 5.41%, F 3.40%, Na 8.23%, O 25.79%, P 5.55%.

Derivative

21-Hemisuccinate.

Nomenclature

Solutedarol (Specia).
C28H35FO9; mol wt 534.57.
C 62.91%, H 6.60%, F 3.55%, O 26.94%.

Therapeutic Category

Glucocorticoid; antiasthmatic (inhalant); antiallergic (nasal).

Therapeutic Category (Veterinary)

Glucocorticoid.

Keywords

Antiallergic (Steroidal, Nasal); Antiasthmatic (Steroidal, Inhalant); Glucocorticoid