Cyclocort,Lederle,US,1979
ChEBI: Amcinonide is a corticosteroid, an 11beta-hydroxy steroid, a fluorinated steroid, a 20-oxo steroid, an acetate ester, a spiroketal and a 3-oxo-Delta(1),Delta(4)-steroid. It has a role as an anti-inflammatory drug. It derives from a hydride of a pregnane.
An 11.1 g (24.1 mmol) portion of the compound 16α,17α-
cyclopentylidenedioxy-9α-fluoro-11β,21-dihydroxy-1,4-pregnadiene-3,20-dione
is placed in a 250 ml round-bottom flask. A 100 ml portion of pyridine is
added and the mixture is stirred to a complete solution. A 5.5 ml (54.6 mmol)
portion of acetic anhydride is added dropwise and the mixture is stirred for
2% hours. An 11 ml portion of methanol is added and the mixture is stirred
an additional hour. This mixture is concentrated under reduced pressure to
about 10 to 15 ml and then poured slowly into a mixture of ice, water and
dilute hydrochloric acid. This mixture is stirred and the solid which forms is
collected by filtration, washed with water to a neutral pH and air dried yielding
11.5 g. This solid is taken up in hot acetone, treated with activated charcoal
and filtered while hot through diatomaceous earth. The filtrate is concentrated
on a steam bath while adding n-hexane to the point of incipient crystallization.
This mixture is allowed to cool to room temperature. The solid which forms is collected by filtration, washed with acetone-n-hexane (1:14) and air dried
yielding 7.0 g of the desired product.
Topical corticosteroid, Antiinflammatory
Amcinonide, 21-(acetyloxy)-16α,17-[cyclopentylidenebis(oxy)]-9-fluoro-11β-hydroxypregna-1,4-diene-3,20-dione (Cyclocort).
