| Identification | More | [Name]
Betamethasone 21-acetate | [CAS]
987-24-6 | [Synonyms]
1,4-PREGNADIEN-9-ALPHA-FLUORO-16-BETA-METHYL-11-BETA, 17,21-TRIOL-3,20-DIONE 21-ACETATE
9a-fluoro-16b-methyl-11b,17a,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate
9ALPHA-FLUORO-16BETA-METHYL-11BETA,17ALPHA,21-TRIHYDROXY-1,4-PREGNADIENE-3,20-DIONE 21-ACETATE
BETAMETHASONE 21-ACETATE
BETAMETHASONE ACETATE
9-fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 21-acetate
Betamethasone acetate BP/USP/EP
BETAMETHASONE ACETATE EPB(CRM STANDARD)
BETAMETHASONE ACETATE MM(CRM STANDARD)
BETAMETHASONE ACETATE USP(CRM STANDARD)
Betamethasone21-acetatemicro
Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-fluoro-11,17-dihydroxy-16-methyl-, (11.beta.,16.beta.)-
BETAMETHASONEACETATE,MICRONIZED,USP
9alpha-Fluoro-11beta,17alpha,21-trihydroxy-16beta-methyl-1,4-pregnadiene-3,20-dione 21-Acetate
9alpha-Fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 21-acetate
(17R)-16β-Methyl-21-acetoxy-11β,17α-dihydroxy-9α-fluoropregna-1,4-diene-3,20-dione
21-Acetyloxy-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione | [EINECS(EC#)]
213-578-6 | [Molecular Formula]
C24H31FO6 | [MDL Number]
MFCD00867462 | [Molecular Weight]
434.5 | [MOL File]
987-24-6.mol |
| Chemical Properties | Back Directory | [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 ]
neat | [pka]
12.08±0.70(Predicted) | [color ]
White to Off-White | [Water Solubility ]
30mg/L(25 ºC) | [Merck ]
1180 | [CAS DataBase Reference]
987-24-6(CAS DataBase Reference) | [EPA Substance Registry System]
987-24-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
2937220000 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Originator]
Celestone Soluspan,Schering,US,1965 | [Uses]
amino acid, nutrient | [Uses]
Betamethasone acetate (BA) | [Uses]
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 |
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