11beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-(dihydrogen phosphate) Property

Boiling point:

669.9±65.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

pka

1.67±0.10(Predicted)

Hazard and Precautionary Statements (GHS)

11beta,17,21-trihydroxypregn-4-ene-3,20-dione 21-(dihydrogen phosphate) Chemical Properties,Usage,Production

Description

Hydrocortisone phosphate (Hydrocortisone 21-phosphate), a glucocorticoid, is an orally active steroidal anti-inflammatory agent (SAID). Hydrocortisone phosphate inhibits the biological activities of IL-6 and IL-3 with IC50 values of 6.7 and 21.4 μM, respectively. Hydrocortisone phosphate can be used in the study of ulcerative colitis (UC).

Originator

Corphos,Tilden Yates,US,1959

Uses

Glucocorticoid.

Definition

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

Manufacturing Process

21-iodo-11β:17α-dihydroxypregn-4-ene-3,20-dione (5.0 g) in pure acetonitrile (125 ml) was mixed with a solution of 90% phosphoric acid (2.5 ml) and triethylamine (7.5 ml) in acetonitrile (125 ml) and boiled under reflux for 4 hours. The solvent was removed in vacuo and the residue, dissolved in ethanol (20 ml) and water (80 ml), was passed down a column of Zeo-Karb 225 (H+form) (60 g) made up in 20% alcohol. Elution was continued with 20% alcohol (50 ml), 50% alcohol (50 ml) and alcohol (150 ml). The eluate was at first cloudy, but by the end of the elution it was clear and nonacid.
The eluate was titrated to pH 7 with 0.972N NaOH (63 ml). Removal of solvent left a gum, which was boiled with methanol (400 ml) for 20 minutes. The solid insoluble inorganic phosphate was filtered off and washed with methanol (200 ml). The slightly cloudy filtrate was filtered again, and evaporated to dryness in vacuo. The residual gum dissolved readily in water (40 ml) and on addition of acetone (600 ml) to the solution a mixture of sodium salts of hydrocortisone 21-phosphate separated as a white solid. This was collected after 2 days, washed with acetone and dried at 100°C/0.l mm/2 hr to constant weight. Yield 4.45 g.

brand name

Hydrocortone (Merck).

Therapeutic Function

Glucocorticoid