Prednisolone
Title: Prednisolone
CAS Registry Number: 50-24-8
CAS Name: (11b)-11,17,21-Trihydroxypregna-1,4-diene-3,20-dione
Additional Names: 1,4-pregnadiene-3,20-dione-11b,17a,21-triol; 1,4-pregnadiene-11b,17a,21-triol-3,20-dione; 3,20-dioxo-11b,17a,21-trihydroxy-1,4-pregnadiene; metacortandralone; delta F; D1-dehydrocortisol; D1-hydrocortisone; D1-dehydrohydrocortisone; hydroretrocortine
Trademarks: Codelcortone (Merck & Co.); Decaprednil (Galen); Decortin H (Merck KGaA); Deltacortril (Pfizer); Klismacort (Novartis); Meticortelone (Schering); Precortisyl (Aventis); Prednicen (Central Pharm.); Predonine (Shionogi); Solone (Abbott)
Molecular Formula: C21H28O5
Molecular Weight: 360.44
Percent Composition: C 69.98%, H 7.83%, O 22.19%
Literature References: Synthetic corticosteroid; metabolically interconvertible with prednisone, q.v. Prepn: A. Nobile et al., J. Am. Chem. Soc. 77, 4184 (1955); A. Nobile, US 2837464; US 3134718 (1958, 1964, both to Schering); Herzog et al., Tetrahedron 18, 581 (1962). HPLC determn in urine: B. M. Frey, F. J. Frey, J. Chromatogr. 229, 283 (1982). Clinical use in advanced cancer: R. G. Twycross, D. Guppy, Practitioner 229, 57 (1985); in inflammatory bowel disease: C. J. Hawkey, Neth. J. Med. 35 Suppl 1, S21-S26 (1989). Review of clinical pharmacology: W. J. Jusko, J. Q. Rose, Ther. Drug Monit. 2, 169-176 (1980); of pharmacokinetics and metabolism: B. M. Frey, F. J. Frey, Clin. Pharmacokinet. 19, 126-146 (1990). Comprehensive description: S. L. Ali, Anal. Profiles Drug Subs. Excip. 21, 415-500 (1992).
Properties: Crystals, dec 240-241°. [a]D25 +102° (dioxane). uv max (methanol): 242 nm (e 15000; A1%1cm 414). Very slightly sol in water. One gram dissolves in about 30 ml of alcohol, in about 180 ml of chloroform, in about 50 ml of acetone. Sol in methanol, dioxane.
Optical Rotation: [a]D25 +102° (dioxane)
Absorption maximum: uv max (methanol): 242 nm (e 15000; A1%1cm 414)
 
Derivative Type: 21-Acetate
CAS Registry Number: 52-21-1
Trademarks: Ak-Tate (Akorn); Deltastab (Sovereign); Inflanefran (Allergan); Pred Forte (Allergan); Pred Mild (Allergan); Scherisolon (Schering); Sterane (Pfizer)
Molecular Formula: C23H30O6
Molecular Weight: 402.48
Percent Composition: C 68.64%, H 7.51%, O 23.85%
Properties: Crystals, decomp 237-239°. [a]D25 +116° (dioxane).
Optical Rotation: [a]D25 +116° (dioxane)
 
Derivative Type: 21-tert-Butylacetate
CAS Registry Number: 7681-14-3
Additional Names: Prednisolone tebutate
Trademarks: Codelcortone-T.B.A. (Merck & Co.)
Molecular Formula: C27H38O6
Molecular Weight: 458.59
Percent Composition: C 70.71%, H 8.35%, O 20.93%
Literature References: Prepn: Sarett, US 2736734 (1956 to Merck & Co.).
Properties: Crystals from ethanol, mp 266-273°.
Melting point: mp 266-273°
 
Derivative Type: 21-Disodium Phosphate
CAS Registry Number: 125-02-0
Additional Names: Prednisolone sodium phosphate
Trademarks: Codelsol (Merck & Co.); Colicort (Merck & Co.); Hefasolon i.v. (Sanavita); Inflamase (Novartis); Orapred (BioMarin); Predsol (UCB); Solucort (Merck & Co.)
Molecular Formula: C21H27Na2O8P
Molecular Weight: 484.39
Percent Composition: C 52.07%, H 5.62%, Na 9.49%, O 26.42%, P 6.39%
Literature References: Prepn: Sarett, US 2789117 (1957 to Merck & Co.). Alternate synthesis: Poos et al., Chem. Ind. (London) 1958, 1260; Elks, Phillips, US 2936313 (1960 to Glaxo).
Properties: White powder. Slightly hygroscopic. Stable at room temp. [a]D25 +102.5°. uv max (methanol): 243 nm (A1%1cm 308). Sol in water, methanol, ethanol. pH of 1% aq soln 7.5 to 8.5.
Optical Rotation: [a]D25 +102.5°
Absorption maximum: uv max (methanol): 243 nm (A1%1cm 308)
 
Derivative Type: 21-Succinate sodium salt
CAS Registry Number: 1715-33-9
Additional Names: Prednisolone sodium succinate
Trademarks: Meticortelone Soluble (Schering); Solu-Decortin-H (Merck KGaA)
Molecular Formula: C25H31NaO8
Molecular Weight: 482.50
Percent Composition: C 62.23%, H 6.48%, Na 4.76%, O 26.53%
Literature References: Prepn: Shull, Kita, DE 1045400 (1958 to Pfizer), C.A. 55, 2746f (1961).
 
Derivative Type: 21-Stearoylglycolate
CAS Registry Number: 5060-55-9
Additional Names: Prednisolone steaglate
Trademarks: Sintisone (Pharmacia)
Molecular Formula: C41H64O8
Molecular Weight: 684.94
Percent Composition: C 71.90%, H 9.42%, O 18.69%
Literature References: Prepn: Giraldi, Nannini, US 3171846 (1965 to Carlo Erba); Giraldi et al., Arzneim.-Forsch. 16, 162 (1966).
Properties: Crystals from dilute alcohol or butyl ether, mp 105-107°. uv max (methanol): 242 nm (E1%1cm 212 ±10). [a]D20 +57-63°.
Melting point: mp 105-107°
Optical Rotation: [a]D20 +57-63°
Absorption maximum: uv max (methanol): 242 nm (E1%1cm 212 ±10)
 
Derivative Type: 21-m-Sulfobenzoate sodium salt
CAS Registry Number: 630-67-1
CAS Name: (11b)-11,17-Dihydroxy-21-[(3-sulfobenzoyl)oxy]pregna-1,4-diene-3,20-dione monosodium salt
Additional Names: prednisolone sodium metasulfobenzoate
Trademarks: Predenema (Forest); Predfoam (Pharmax); Solupred (Aventis)
Molecular Formula: C28H31NaO9S
Molecular Weight: 566.60
Percent Composition: C 59.35%, H 5.51%, Na 4.06%, O 25.41%, S 5.66%
Literature References: Prepn: Allais, Girault, US 3032568; Joly, Warnant, US 3037034 (both 1962 to Roussel-UCLAF).
Properties: Crystals from water, dec 293-295°. [a]D20 +170° (water).
Optical Rotation: [a]D20 +170° (water)
 
Derivative Type: 21-Trimethylacetate
CAS Registry Number: 1107-99-9
Additional Names: Prednisolone 21-pivalate
Trademarks: Ultracortenol (Novartis)
Molecular Formula: C26H36O6
Molecular Weight: 444.56
Percent Composition: C 70.24%, H 8.16%, O 21.59%
Literature References: Prepn: Vischer et al., Helv. Chim. Acta 38, 1502 (1955); Joly, Warnant, US 3037034 (1962 to Roussel-UCLAF).
Properties: Crystals from acetone, mp 233-236°. [a]D26 +103° (c = 1.208 in chloroform); [a]D20 +97.5° (c = 1 in chloroform). uv max: 244 nm (e 14700).
Melting point: mp 233-236°
Optical Rotation: [a]D26 +103° (c = 1.208 in chloroform); [a]D20 +97.5° (c = 1 in chloroform)
Absorption maximum: uv max: 244 nm (e 14700)
 
Therap-Cat: Glucocorticoid.
Therap-Cat-Vet: Glucocorticoid.
Keywords: Glucocorticoid.

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