AMCINONIDE Chemical Properties

Melting point:

>216°C (dec.)

Boiling point:

635.9°C (rough estimate)

Density 

1.33±0.1 g/cm3 (20 ºC 760 Torr)

refractive index 

1.5860 (estimate)

storage temp. 

-20°C Freezer

solubility 

Acetonitrile (Slightly), Dichlomethane (Slightly), Dioxane (Slightly), Methanol

pka

13.09±0.70(Predicted)

form 

Solid

color 

White to Off-White

Safety Information

WGK Germany 

2

RTECS 

TU3682500

HS Code 

2937220000

MSDS

• Language:English Provider:SigmaAldrich

AMCINONIDE Usage And Synthesis

Originator

Cyclocort,Lederle,US,1979

Uses

antiinflammatory

Uses

Glucocorticoid.

Definition

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.

Manufacturing Process

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.

brand name

Cyclocort (Astellas.

Therapeutic Function

Topical corticosteroid, Antiinflammatory

General Description

Amcinonide, 21-(acetyloxy)-16α,17-[cyclopentylidenebis(oxy)]-9-fluoro-11β-hydroxypregna-1,4-diene-3,20-dione (Cyclocort).

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