4243. Formocortal

Nomenclature

CAS number: 2825-60-7
(11β,16α)-21-(Acetyloxy)-3-(2-chloroethoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-20-oxopregna-3,5-diene-6-carboxaldehyde; 3-(2-chloroethoxy)-9-fluoro-11β,16α,17,21-tetrahydroxy-20-oxopregna-3,5-diene-6-carboxaldehyde, cyclic 16,17-acetal with acetone, 21-acetate; 3-(2-chloroethoxy)-6-formyl-9α-fluoropregna-3,5-diene-11β,16α,17,21-tetrol-20-one 21-acetate 16α,17α-acetonide; 3-(2-chloroethoxy)-9α-fluoro-6-formyl-11β,21-dihydroxy-16α,17α-isopropylidenedioxypregna-3,5-dien-20-one; fluoroformylon; FI-6341; Cortocin-F (Eisai); Cutisterol (Farmitalia); Deflamene (Farmitalia); Fluderma (Farmitalia).
C29H38ClFO8; mol wt 569.06.
C 61.21%, H 6.73%, Cl 6.23%, F 3.34%, O 22.49%.

Description and references

Prepn: Camerino et al., FR 1396602 C.A. 63, 5713c (1965); NL 6508458; US 3314945 (1965, 1966, 1967 all to Farmitalia); Baldratti et al., Experientia 22, 468 (1966). Pharmacology: Suchowsky, Baldratti, Proc. 2nd Int. Congr. Horm. Steroids 1966, L. Martini, F. Fraschini, M. Motta, Eds. (Excerpta Medica Found., Amsterdam, 1967) pp 536-540; Tajima, Otsu, Jpn. J. Pharmacol. 62, 115 (1966), C.A. 67, 72329v (1967); Baldratti et al., Arzneim.-Forsch. 21, 1533 (1971). Toxicity studies: Bertazzoli et al., J. Eur. Toxicol. 4, 88 (1971).

Chemical structure

Properties

White crystalline powder from ether-petroleum ether, mp 180-182°. [α]D20 +26° (chloroform). uv max (ethanol): 216, 324 nm (ε 12,100, 17,100). LD50 in mice: >2000 mg/kg orally; 490 mg/kg s.c.; 537 mg/kg i.p. (Bertazzoli).

Therapeutic Category

Glucocorticoid.

Keywords

Glucocorticoid