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Betamethasone 21-acetate

CAS No.987-24-6
Chemical Name:Betamethasone 21-acetate
CBNumber:CB1337284
Molecular Formula:C24H31FO6
Formula Weight:434.5
MOL File:987-24-6.mol

Betamethasone 21-acetate Property

Melting point 200-220°C (dec.)
alpha D +140° (chloroform)
Boiling point 579.4±50.0 °C(Predicted)
Density 1.0932 (rough estimate)
refractive index 1.5980 (estimate)
storage temp. Refrigerator
solubility Practically insoluble in water, freely soluble in acetone, soluble in ethanol (96 per cent) and in methylene chloride. It shows polymorphism (5.9).
form Solid
pka 12.08±0.70(Predicted)
color White to Off-White
Water Solubility 30mg/L(25 ºC)
Merck 14,1180
CAS DataBase Reference 987-24-6(CAS DataBase Reference)
FDA UNII TI05AO53L7
EPA Substance Registry System .beta.-Methasone acetate (987-24-6)

Safety

Hazard Codes :Xn
Risk Statements :40
Safety Statements :22-36
WGK Germany :3
HS Code :2937220000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H360FD-H373
Precautionary statements P202-P260-P280-P308+P313-P405-P501

Betamethasone 21-acetate Price More Price(1)

Brand: Sigma-Aldrich(India)
Product number: PHR1779
Product name : Betamethasone Acetate
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹24085.63
Updated: 2022/06/14
Buy: Buy

Betamethasone 21-acetate Chemical Properties,Usage,Production

Chemical Properties White Solid
Originator Celestone Soluspan,Schering,US,1965
Uses CORTICOSTEROID
Uses amino acid, nutrient
Uses Betamethasone acetate (BA)
Definition ChEBI: Betamethasone acetate is an acetate ester, a steroid ester, a fluorinated steroid, a 17alpha-hydroxy steroid, a 20-oxo steroid, an 11beta-hydroxy steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a tertiary alpha-hydroxy ketone. It is functionally related to a betamethasone.
Manufacturing Process The synthesis is long and complex. For brevity, only the last steps are given here. Refer to the patents cited below for full details.
Preparation of 9α-Bromo-11β,17α,21-Trihydroxy-16β-Methyl-4-Pregnene-3,20- Dione 21-Acetate: To a mixture of 620 mg of 17α,21-dihydroxy-16β-methyl- 4,9(11)-pregnadiene-3,20-dione 21-acetate and 330 mg of Nbromosuccinimide in 10 ml of dioxane and 3.2 ml of water cooled to 10°C was added 1.8 ml of cold 1 M aqueous perchloric acid. The mixture was stirred at 15°C for 3 hours. Excess N-bromosuccinimide was destroyed by addition of aqueous sodium thiosulfate and most of the dioxane was removed in vacuo. About 30 ml of water was added and crystalline bromohydrin, 9α-bromo- 11β,17α,21-trihydroxy-16β-methyl-4-pregnene-3,20-dione 21-acetate, was filtered, washed with water, and dried in air. Preparation of 9β,11β-Epoxy-17α-21-Dihydroxy-16β-Methyl-4-Pregnene-3,20- Dione 21-Acetate: To a stirred solution of 100 mg of the 9α-bromo- 11β,17α,21-trihydroxy-16β-methyl-4-pregnene-3,20-dione 21-acetate in 3 ml of tetrahydrofuran and 1 ml of methanol under nitrogen was added 1.02 ml of 0.215N methanolic sodium methoxide. After 10 minutes at 25°C, 0.2 ml of acetic acid was added and the methanol removed in vacuo. The residue was acetylated with 1.00 ml of pyridine and 0.5 ml of acetic anhydride at 60°C for 70 minutes. The mixture was taken to dryness in vacuo, water added, and the product extracted into chloroform. The residue was crystallized from etheracetone to give pure 9β,11β-epoxy-17α,21-dihydroxy-16β-methyl-4-pregnene- 3,20-dione 21-acetate.
Preparation of 9α-Fluoro-11β,17α,21-Trihydroxy-16β-Methyl-4-Pregnene-3,20- Dione 21-Acetate: To a solution of 200 mg of 9β,11β-epoxy-17α,21-dihydroxy- 16β-methyl-4-pregnene-3,20-dione 21-acetate in 2 ml of chloroform and 2 ml of tetrahydrofuran in a polyethylene bottle at -60°C was added 2 ml of a 2:1 (by weight) mixture of anhydrous hydrogen fluoride and tetrahydrofuran. After 4 hours at -10°C the mixture was cooled to -60°C and cautiously added to a stirred mixture of 30 ml or 25% aqueous potassium carbonate and 25 ml of chloroform kept at -5°C. The aqueous phase was further extracted with chloroform and the latter phase washed with water and dried over magnesium sulfate. The residue on crystallization from acetone-ether gave pure 9α-fluoro- 11β,17α,21-trihydroxy-16β-methyl-4-pregnene-3,20-dione 21-acetate.
Preparation of 9α-Fluoro-11β,17α,21-Trihydroxy-16β-Methyl-4-Pregnadiene- 3,20-Dione 21-Acetate 100 mg of 9α-fluoro-11β,17α,21-trihydroxy-16β- methyl-4-pregnene-3,20-dione 21-acetate was treated with selenium dioxide to produce the corresponding 9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-4- pregnadiene-3,20-dione 21-acetate. Alternately, Bacillus sphaericus may be utilized.
Therapeutic Function Glucocorticoid