Dexamethasone-17-acetate Chemical Properties

Melting point:

238-240 °C(lit.)

alpha 

D25 +73° (chloroform) (Arth, 1958); D +77.6° (Oliveto)

Boiling point:

579.4±50.0 °C(Predicted)

Density 

1.1517 (estimate)

refractive index 

87 ° (C=1, Dioxane)

storage temp. 

2-8°C

solubility 

Soluble at 100 mg/ml in acetone

pka

12.08±0.70(Predicted)

form 

Powder

color 

White

Water Solubility 

13mg/L(25 ºC)

Merck 

2943

BRN 

2342608

CAS DataBase Reference

1177-87-3(CAS DataBase Reference)

NIST Chemistry Reference

Prednisolone, 9alpha-fluoro-16alpha-methyl-, acetate(1177-87-3)

EPA Substance Registry System

Dexamethasone-21-acetate (1177-87-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

3

RTECS 

TU4050000

TSCA 

Yes

HS Code 

29372290

MSDS

• Language:English Provider:SigmaAldrich

Dexamethasone-17-acetate Usage And Synthesis

Chemical Properties

Off-White Solid

Originator

Dexacen,Central,US,1977

Uses

Protected Dexamethasone, a glucocorticoid anti-inflammatory agent.

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.

Uses

Dexamethasone acetate is used as a pharmaceutical primary standard to quantify the analyte in pharmaceutical formulations using chromatography ttechniques.

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.]

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