DEXAMETHASONE SODIUM PHOSPHATE Chemical Properties

Melting point:

154-157°C

Boiling point:

669.6±65.0 °C(Predicted)

Density 

1.45±0.1 g/cm3(Predicted)

storage temp. 

-20°C Freezer, Under Inert Atmosphere

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

1.67±0.10(Predicted)

form 

Solid

color 

White to Light Brown

Stability:

Hygroscopic, Moisture Sensitive

Safety Information

Hazard Codes 

Xn

Risk Statements 

62

HS Code 

2937220000

Toxicity

dni-rat-ipr 3 mg/kg JOENAK 62,527,74

DEXAMETHASONE SODIUM PHOSPHATE Usage And Synthesis

Originator

Decadron Phosphate,MS and D,US,1959

Uses

A pro-drug of Dexamethasone (D298800), an anti-inflammatory glucocorticoid. It was found that liposomal DXM-P inhibited both chronic inflammation and joint destruction, whereas free DXM-P failed to prevent joint destruction.

Definition

ChEBI: A steroid phosphate that is the 21-O-phospho derivative of dexamethasone.

Manufacturing Process

A solution of bis-triethylamine phosphate was prepared by slowly adding 2.36 ml of 85% phosphoric acid to 20 ml of acetonitrile containing 9.9 ml of triethylamine at 20°C. This solution was added to a stirred solution of 4.70 g of 9α-fluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,2-dione 21- methanesulfonate and 20 ml of acetonitrile. The mixture was heated under reflux for four hours and then evaporated under reduced pressure to a volume of 12 ml. This mixture was a concentrated solution of 9α-fluoro-11β,17α,21- trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione 21-phosphate triethylamine salt with some inorganic phosphate.
The mixture was cooled, 25 ml of methanol added, and the cooled mixture treated with 33 ml of 1.89 N methanolic sodium methoxide solution. The precipitated inorganic phosphates were removed by suction filtration and washed thoroughly with methanol. The combined filtrates were evaporated under reduced pressure to a volume of 12 ml and treated with 30 ml of methanol. The resulting cloudy solution was clarified by filtration through diatomaceous earth. The volume of the filtrate was brought to 40 ml by the addition of methanol, and 120 ml of ether was added with stirring. The precipitated product, which was 9α-fluoro-11β,17α,21-trihydroxy-16α-methyl1,4-pregnadiene-3,20-dione 21-phosphate sodium salt, was collected by suction filtration, and washed with acetone and then with ether. The weight of the air-dried material was 3.06 g.

brand name

Decadron (Merck); Dexacen (Cent); Dexacort (UCB); Dexair (Pharmafair); Hexadrol (Organon); Maxidex (Alcon).

Therapeutic Function

Glucocorticoid

Safety Profile

An experimental teratogen. Otherexperimental reproductive effects. Mutation data reported.When heated to decomposition it emits toxic fumes of F-and POx.

DEXAMETHASONE SODIUM PHOSPHATE(312-93-6)Related Product Information

• Desoximetasone
• Dexamethasone 21-phosphate disodium salt
• Dexamethasone palmitate
• Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-16-methyl-21-[(3-sulfobenzoyl)oxy]-, monosodium salt, (11beta,16alpha)-
• Dexamethasone dipropionate
• 9-Fluoro-11b,17,21-trihydroxy-16a-methylpregna-1,4-diene-3,20-dione 17-valerate
• Dexamethasone 9,11-epoxide
• 1,2-Dihydro DesoxyMetasone
• Dexamethasone Impurity I
• Dexamethasone EP Impurity E
• DexaMethasone β-D-Glucuronide SodiuM Salt
• Dexamethasone-d5
• Dexamethasone 21-Propionate
• PSXDNQUHAFMVPT-NWQAGDSVSA-N
• Dexamethasone-17,20 21-Aldehyde
• dexamethasone 21-pivalate
• dexamethasone 21-(3-phenylpropionate)
• Dexamethasone 17-propionate