AMCINONIDE

AMCINONIDE Basic information
Product Name:AMCINONIDE
Synonyms:AMCINONIDE;(11-beta,16-alpha)-fluoro-11-hydroxy;20-dione,21-(acetyloxy)-16,17-(cyclopentylidenebis(oxy))-9-pregna-4-diene-3;cl-34699;cyclocort;Amciderm;Amcinonid;Penticort
CAS:51022-69-6
MF:C28H35FO7
MW:502.57
EINECS:256-915-2
Product Categories:RELAFEN;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
Mol File:51022-69-6.mol
AMCINONIDE Structure
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
pka13.09±0.70(Predicted)
form neat
color White to Off-White
Safety Information
WGK Germany 2
RTECS TU3682500
HS Code 2937220000
MSDS Information
ProviderLanguage
SigmaAldrich English
AMCINONIDE Usage And Synthesis
OriginatorCyclocort,Lederle,US,1979
UsesGlucocorticoid.
Usesantiinflammatory
DefinitionChEBI: 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 ProcessAn 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 nameCyclocort (Astellas.
Therapeutic FunctionTopical corticosteroid, Antiinflammatory
General DescriptionAmcinonide, 21-(acetyloxy)-16α,17-[cyclopentylidenebis(oxy)]-9-fluoro-11β-hydroxypregna-1,4-diene-3,20-dione (Cyclocort).
AMCINONIDE Preparation Products And Raw materials
Raw materials11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione-->Acetic anhydride
Rimonabant (r)-budesonide Aprepitant BECLOMETHASONE Vanillin Ancitabine (S)-Glyceraldehyde acetonide Triamcinolone Descinolone 1,1-DIMETHOXYCYCLOPENTANE amcinafal Triamcinolone acetonide AMCINONIDE 2,2-Dimethyl-4-hexyl-1,3-dioxolane CYCLOPENTANONE ETHYLENE KETAL 1,3-DIMETHOXYACETONE 6(R),7-ISOPROPYLIDENE-HEPTANOL Isoflupredone Acetate

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