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Dexamethasone-17-acetate

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Dexamethasone-17-acetate Basic information

Product Name:
Dexamethasone-17-acetate
Synonyms:
  • 20-dione,9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methyl-pregna-4-diene-3
  • 9alpha-Fluoro-16alpha-methylprednisolone acetate
  • 9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione21-acetate
  • 9-Fluoro-11,17-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-yl acetate
  • 9-fluoro-11-beta,17,21-trihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione
  • 9-Fluoro-11beta,17,21-trihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate
  • 9-Fluoro-11-beta,17,21-trihydroxy-16-alpha-methylpregna-1,4-diene-3,20-dione acetate
  • Dalalone D.P.
CAS:
1177-87-3
MF:
C24H31FO6
MW:
434.5
EINECS:
214-646-8
Product Categories:
  • Hormone Drugs
  • DECADRON
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Pharmaceutical intermediate
  • API
  • Biochemistry
  • Hydroxyketosteroids
  • Steroids
Mol File:
1177-87-3.mol
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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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
43
Safety Statements 
36/37
WGK Germany 
3
RTECS 
TU4050000
TSCA 
Yes
HS Code 
29372290

MSDS

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Dexamethasone-17-acetate Usage And Synthesis

Chemical Properties

Off-White Solid

Originator

Dexacen,Central,US,1977

Uses

Protected Dexamethasone, a glucocorticoid anti-inflammatory agent.

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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