Betamethasone
Title: Betamethasone
CAS Registry Number: 378-44-9
CAS Name: (11b,16b)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
Additional Names: 9a-fluoro-16b-methylprednisolone; 16b-methyl-9a-fluoro-D1-hydrocortisone; 16b-methyl-9a-fluoroprednisolone; betadexamethasone; flubenisolone; b-methasone
Manufacturers' Codes: Sch-4831; NSC-39470
Trademarks: beta-Corlan; Becort (Rachelle); Betasolon; Betnelan (GSK); Celestene (Schering-Plough); Celestone (Schering-Plough); Dermabet (Taro); Visubeta
Molecular Formula: C22H29FO5
Molecular Weight: 392.46
Percent Composition: C 67.33%, H 7.45%, F 4.84%, O 20.38%
Literature References: Prepn: Taub et al., J. Am. Chem. Soc. 80, 4435 (1958); Oliveto et al., ibid. 6688; Taub et al., ibid. 82, 4012 (1960); US 3053865 (1962 to Merck & Co.); Amiard et al., US 3104246 (1963 to Roussel-UCLAF). Also prepared from hecogenin. Comprehensive description of the dipropionate ester: M. G. Ferrante, B. C. Rudy, Anal. Profiles Drug Subs. 6, 43-60 (1977).
Properties: Crystals from ethyl acetate, mp 231-234° (dec). [a]D +108° (acetone). uv max (methanol): 238 nm (e 15200).
Melting point: mp 231-234° (dec)
Optical Rotation: [a]D +108° (acetone)
Absorption maximum: uv max (methanol): 238 nm (e 15200)
 
Derivative Type: 21-Acetate
CAS Registry Number: 987-24-6
Trademarks: Betafluorene (Lepetit); Celestovet (Biokema)
Molecular Formula: C24H31FO6
Molecular Weight: 434.50
Percent Composition: C 66.34%, H 7.19%, F 4.37%, O 22.09%
Properties: Hexagonal prisms from acetone + ether, mp 205-208° (Taub); also reported as mp 196-201° (Oliveto). [a]D +140° (chloroform). uv max (methanol): 238 nm (e 14800).
Melting point: mp 205-208° (Taub); mp 196-201° (Oliveto)
Optical Rotation: [a]D +140° (chloroform)
Absorption maximum: uv max (methanol): 238 nm (e 14800)
 
Derivative Type: 17-Benzoate
CAS Registry Number: 22298-29-9
Manufacturers' Codes: W-5975
Trademarks: Bebate; Beben (Pfizer); Benisone (Warner-Chilcott); Euvaderm (Gecke); Flurobate (Texas Pharmacal); Uticort (Pfizer)
Molecular Formula: C29H33FO6
Molecular Weight: 496.57
Percent Composition: C 70.14%, H 6.70%, F 3.83%, O 19.33%
Properties: Crystals from acetone-ether, mp 225-228°. [a]D24 +63.5° (dioxane). Synthesis and activity: Ercoli et al., J. Med. Chem. 15, 783 (1972). See also Cullen, Curr. Ther. Res. 15, 243 (1973).
Melting point: mp 225-228°
Optical Rotation: [a]D24 +63.5° (dioxane)
 
Derivative Type: 17,21-Dipropionate
CAS Registry Number: 5593-20-4
Manufacturers' Codes: Sch-11460
Trademarks: Diproderm (Schering-Plough); Diprolene (Schering-Plough); Diprophos (Schering-Plough); Diprosis (Essex); Diprosone (Schering-Plough); Maxivate (Westwood); Rinderon-DP (Shionogi)
Molecular Formula: C28H37FO7
Molecular Weight: 504.59
Percent Composition: C 66.65%, H 7.39%, F 3.77%, O 22.20%
Properties: Powder, mp 170-179° (dec). [a]D26 +65.7° (dioxane). uv max (methanol): 238 nm (e 15700). Insol in water.
Melting point: mp 170-179° (dec)
Optical Rotation: [a]D26 +65.7° (dioxane)
Absorption maximum: uv max (methanol): 238 nm (e 15700)
 
Derivative Type: 17-Valerate
CAS Registry Number: 2152-44-5
Trademarks: Bedermin (Damor); Betnesol-V (GSK); Betneval (GSK); Betnovate (GSK); Bextasol (GSK); Celestan-V (Essex); Celestoderm-V (Schering-Plough); Dermosol (Iwaki); Dermovaleas (Valeas); Ecoval 70; Hormezon (Tobishi); Tokuderm (Nichiban); Valisone (Schering-Plough)
Molecular Formula: C27H37FO6
Molecular Weight: 476.58
Percent Composition: C 68.05%, H 7.83%, F 3.99%, O 20.14%
Properties: Needles from acetone + petr ether, mp 183-184°. [a]D +77° (dioxane). uv max: 239 nm (e 15920). NL 6406615 (1964 to Glaxo).
Melting point: mp 183-184°
Optical Rotation: [a]D +77° (dioxane)
Absorption maximum: uv max: 239 nm (e 15920)
 
Derivative Type: 21-Phosphate disodium salt
CAS Registry Number: 151-73-5
Additional Names: Betamethasone 21-(dihydrogen phosphate) disodium salt
Trademarks: Bentelan (GSK); Betnesol (GSK); Celestan (Essex); Durabetason (Durachemie); Vista-Methasone (Richard Daniel)
Molecular Formula: C22H28FNa2O8P
Molecular Weight: 516.40
Percent Composition: C 51.17%, H 5.47%, F 3.68%, Na 8.90%, O 24.79%, P 6.00%
 
Therap-Cat: Glucocorticoid.
Therap-Cat-Vet: Glucocorticoid.
Keywords: Glucocorticoid.

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