4130. Fludrocortisone

Nomenclature

CAS number: 127-31-1
(11β)-9-Fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione; 9α-fluorohydrocortisone; 9α-fluoro-17-hydroxycorticosterone; 9α-fluorocortisol; fluodrocortisone; fluohydrisone; fluohydrocortisone; Astonin H (Merck KGaA).
C21H29FO5; mol wt 380.45.
C 66.30%, H 7.68%, F 4.99%, O 21.03%.

Description and references

Prepn: J. Fried, E. F. Sabo, J. Am. Chem. Soc. 76, 1455 (1954); GB 792224; J. Fried, US 2852511 (both 1958 to Olin Mathieson). Series of articles on pharmacology and metabolism: Arzneim.-Forsch. 21, 1103-1158 (1971). Comprehensive description of the acetate: K. Florey, Anal. Profiles Drug Subs. 3 281-306 (1974).

Chemical structure

Properties

Crystals, dec 260-262°. [α]D23 +139° (c = 0.55 in 95% ethanol). uv max (ethanol): 239 nm (ε 17600). Soly in water: 0.14 mg/ml.

Derivative

21-Acetate.

Nomenclature

CAS number: 514-36-3
Florinef (BMS).
C23H31FO6; mol wt 422.49.
C 65.39%, H 7.40%, F 4.50%, O 22.72%.

Properties

Crystals, polymorphic, mp 233-234° (occasionally mp 205-208°, resolidifying on further heating, then mp 226-228°). Crystallizing procedure: R. P. Graber, C. S. Snoddy, US 2957013 (1960 to Merck & Co.). [α]D23 +123° (c = 0.64 in chloroform). uv max (ethanol): 238 nm (ε 16800). Soly (mg/ml): water 0.04; acetone 56; alc 20; chloroform 20; ether 4.

Therapeutic Category

Mineralocorticoid.

Therapeutic Category (Veterinary)

Mineralocorticoid.

Keywords

Mineralocorticoid