Chemical Properties
Off-White Solid
Originator
Dexacen,Central,US,1977
Uses
Protected Dexamethasone, a glucocorticoid anti-inflammatory agent.
Uses
Dexamethasone acetate is used as a pharmaceutical primary standard to quantify the analyte in pharmaceutical formulations using chromatography ttechniques.
Uses
Dexamethasone has many uses in the treatment of cancer. Dexamethasone relieves inflammation in various parts of the body. To treat or prevent allergic reactions. As treatment of certain kinds of autoimmune diseases, skin conditions, asthma and other lung conditions. As treatment for a variety of cancers, such as leukemia, lymphoma, and multiple myeloma. It is also used for replacement therapy in adrenal insufficiency and in a screening test for the diagnosis of cushing's syndrome. Dexamethasone Acetate has also been determined to markedly decrease the number of activated macrophages. In addition, Dexamethasone Acetate has been observed to significantly decrease mRNA levels of TPH2 (tryptophan hydroxylase-2) in the raphe nuclei of C57/Bl6 mice.
Definition
ChEBI: Dexamethasone acetate is a corticosteroid hormone.
Manufacturing Process
The preparation of dexamethasone acetate is described in US Patent
3,007,923 as follows. 1.5 cc of dimethylformamide and 1.5 cc of anhydrous
hydrofluoric acid are admixed and treated with 480 mg of 9β,11β-epoxy-17αhydroxy-21-acetoxy-16α-methyl-?1,4-pregnadiene-3,20-dione (prepared
according to E.P. Oliveto et al, J. Am. Chem. Soc., 80, 44331, 1958). The
steroid dissolves in about 15 minutes. The reaction mixture is shaken for two
hours at a temperature between 0 and +5°C, and then poured into 75 cc of
water containing in suspension, 7.5 grams of sodium bicarbonate. The mixture
is vacuum filtered, the filter cake washed and then dried at 100°C, yielding
460 mg of crude hexadecadrol contaminated with a small amount of the
starting material. A single recrystallization from methylene chloride yields 370
mg of the pure product having a melting point of 170°C and 229°C. The
mother liquor yields 62 mg of the starting material, and a remainder
constituting a mixture of starting and final materials with little other
contamination.
brand name
Decadron (Merck).
Therapeutic Function
9-Fluoro-11β,17-dihydroxy-21-acetoxy-16α-methylpregna1,4-diene-3,20-dione
Safety Profile
Experimental
teratogenic and reproductive effects. A
steroid. When heated to decomposition it
emits toxic fumes of F-.
Purification Methods
Dexamethasone 21-acetate is purified on neutral Al2O3 using CHCl3 as eluent, the fractions are evaporated, and the residue is recrystallised from CHCl3. It has max at 239nm. [Oliveto et al. J Am Chem Soc 8 0 4431 1958]. [Beilstein 8 IV 3501.]
