9595. Triamcinolone

Nomenclature

CAS number: 124-94-7
(11β, 16α)-9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione; Δ1-9α-fluoro-16α-hydroxyhydrocortisone; 9α-fluoro-16α-hydroxyprednisolone; Δ1-16α-hydroxy-9α-fluorohydrocortisone; 16α-hydroxy-9α-fluoroprednisolone; CL-19823; Aristocort (Lederle); Kenacort (BMS); Ledercort (tabl.) (Lederle); Omcilon (BMS); Tricortale (Bergamon); Volon (BMS).
C21H27FO6; mol wt 394.43.
C 63.95%, H 6.90%, F 4.82%, O 24.34%.

Description and references

Prepn: Bernstein et al., J. Am. Chem. Soc. 78, 5693 (1956); 81, 1689 (1959); Thoma et al., ibid. 79, 4818 (1957); Bernstein et al., Allen et al., US 2789118; US 3021347 (1957, 1962, both to Am. Cyanamid). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 1, 367-396, 423-442 (1972); D. H. Sieh, ibid. 11, 593-614, 651-661 (1982).

Chemical structure

Properties

Crystals, mp 269-271°. mp also reported as 260-262.5°. [α]D25 +75° (acetone). uv max: 238 nm (ε 15800).

Derivative

16,21-Diacetate.

Nomenclature

CAS number: 67-78-7
(11β,16α)-16,21-Bis(acetyloxy)-9-fluoro-11,17-dihydroxypregna-1,4-diene-3,20-dione; 16α,21-diacetoxy-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione; Cenocort (Central Pharm.); CINO-40 (Tutag); Tracilon (Savage).
C25H31FO8; mol wt 478.51.
C 62.75%, H 6.53%, F 3.97%, O 26.75%.

Properties

Solvated crystals, mp 186-188° (with effervescence, mp 235° after drying). [α]D25 +22° (chloroform). uv max: 239 nm (ε 15200).

Therapeutic Category

Glucocorticoid.

Therapeutic Category (Veterinary)

Glucocorticoid.

Keywords

Glucocorticoid