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HomeProduct name listBetamethasone 21-acetate

Betamethasone 21-acetate

Synonym(s):9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate;Betamethasone 21-acetate

  • CAS NO.:987-24-6
  • Empirical Formula: C24H31FO6
  • Molecular Weight: 434.5
  • MDL number: MFCD00867462
  • EINECS: 213-578-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-18 17:01:59
Betamethasone 21-acetate Structural

What is Betamethasone 21-acetate?

Chemical properties

White Solid

Originator

Celestone Soluspan,Schering,US,1965

The Uses of Betamethasone 21-acetate

Betamethasone acetate (BA)

The Uses of Betamethasone 21-acetate

amino acid, nutrient

The Uses of Betamethasone 21-acetate

CORTICOSTEROID

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

Properties of Betamethasone 21-acetate

Melting point: 200-220°C (dec.)
Boiling point: 579.4±50.0 °C(Predicted)
alpha  D +140° (chloroform)
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  neat
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)
EPA Substance Registry System .beta.-Methasone acetate (987-24-6)

Safety information for Betamethasone 21-acetate

Signal word Danger
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H373:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313:IF exposed or concerned: Get medical advice/attention.
P405:Store locked up.
P501:Dispose of contents/container to..…

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