Triamcinolone Acetonide
Title: Triamcinolone Acetonide
CAS Registry Number: 76-25-5
CAS Name: (11b,16a)-9-Fluoro-11,21-dihydroxy-16,17-[1-methylethylidenebis(oxy)]pregna-1,4-diene-3,20-dione
Additional Names: 9a-fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone; 9a-fluoro-16a-hydroxyprednisolone acetonide; triamcinolone 16a,17-acetonide; 9a-fluoro-11b,21-dihydroxy-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione; 9a-fluoro-16a,17-isopropylidenedioxyprednisolone
Trademarks: 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)
Molecular Formula: C24H31FO6
Molecular Weight: 434.50
Percent Composition: C 66.34%, H 7.19%, F 4.37%, O 22.09%
Literature 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).
Properties: Crystals, mp 292-294°. [a]D23 +109° (c = 0.75 in chloroform). uv max (abs alc.): 238 nm (e 14600). Sparingly sol in methanol, acetone, ethyl acetate.
Melting point: mp 292-294°
Optical Rotation: [a]D23 +109° (c = 0.75 in chloroform)
Absorption maximum: uv max (abs alc.): 238 nm (e 14600)
 
Derivative Type: 21-Acetate
Properties: Crystals, mp 268-270°. [a]D23 +92° (c = 0.59 in chloroform).
Melting point: mp 268-270°
Optical Rotation: [a]D23 +92° (c = 0.59 in chloroform)
 
Derivative Type: 21-Disodium phosphate
CAS Registry Number: 1997-15-5
Trademarks: Aristosol (Lederle)
Molecular Formula: C24H30FNa2O9P
Molecular Weight: 558.44
Percent Composition: C 51.62%, H 5.41%, F 3.40%, Na 8.23%, O 25.79%, P 5.55%
 
Derivative Type: 21-Hemisuccinate
Trademarks: Solutedarol (Specia)
Molecular Formula: C28H35FO9
Molecular Weight: 534.57
Percent Composition: C 62.91%, H 6.60%, F 3.55%, O 26.94%
 
Therap-Cat: Glucocorticoid; antiasthmatic (inhalant); antiallergic (nasal).
Therap-Cat-Vet: Glucocorticoid.
Keywords: Antiallergic (Steroidal, Nasal); Antiasthmatic (Steroidal, Inhalant); Glucocorticoid.

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