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: 2024-04-29 22:41:02
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) |
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..… |
Computed Descriptors for Betamethasone 21-acetate
Abamectin manufacturer
Varanous Labs Pvt Ltd
Horster Biotek Pvt Ltd
Stermone Chemicals Pvt Ltd
Ralington Pharma
Bhugan Lifescience Pvt Ltd
Symbiotec Pharma Lab Pvt Ltd
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