Triamcinolone Hexacetonide
Title: Triamcinolone Hexacetonide
CAS Registry Number: 5611-51-8
CAS Name: (11b,16a)-21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
Additional Names: 9-fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone, 21-(3,3-dimethylbutyrate); 21-tert-butylacetate-9a-fluoro-11b-hydroxy-16a,17a-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione; 21-(3,3-dimethylbutyryloxy)-9a-fluoro-11b-hydroxy-16a,17a-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione; triamcinolone acetonide tert-butyl acetate; TATBA
Manufacturers' Codes: CL-34433
Trademarks: Aristospan (Fujisawa); Hexatrione (Lederle); Lederlon (Lederle); Lederspan (Lederle)
Molecular Formula: C30H41FO7
Molecular Weight: 532.64
Percent Composition: C 67.65%, H 7.76%, F 3.57%, O 21.03%
Literature References: The hexacetonide ester of the potent glucocorticoid, triamcinolone, q.v. Prepn of syringeable suspension: Nash, Naeger, US 3457348 (1969 to Am. Cyanamid). Anti-inflammatory activity in rabbits: I. M. Hunneyball, Agents Actions 11, 490 (1981). Early clinical studies: Bilka, Minn. Med. 50, 483 (1967); Layman, Peterson, ibid. 669. Clinical studies of intra-articular therapy in arthritis: R. C. Allen et al., Arthritis Rheum. 29, 997 (1986); M. Talke, Fortschr. Med. 104, 742 (1986). Toxicity study: Tonelli, Steroids 8, 857 (1966). Comprehensive description: V. Zbinovsky, G. P. Chrekian, Anal. Profiles Drug Subs. 6, 579-595 (1977). For structure see Triamcinolone Acetonide.
Properties: Fine, white, needle-like crystals, mp 295-296° (dec), also reported as mp 271-272° (dec). uv max (ethanol): 238 nm (e 15500). [a]D25 +90±2° (c = 1.13% in chloroform). Soly in g/100 ml at 25°: chloroform and dimethylacetamide >5; ethyl acetate 0.77, methanol 0.59, diethyl carbonate 0.50, glycerin 0.42, propylene glycol 0.13; absolute alcohol 0.03; water 0.0004.
Melting point: mp 295-296° (dec); mp 271-272° (dec)
Optical Rotation: [a]D25 +90±2° (c = 1.13% in chloroform)
Absorption maximum: uv max (ethanol): 238 nm (e 15500)
Therap-Cat: Anti-inflammatory.
Keywords: Glucocorticoid.

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