7721. Prednisolone

Nomenclature

CAS number: 50-24-8
(11β)-11,17,21-Trihydroxypregna-1,4-diene-3,20-dione; 1,4-pregnadiene-3,20-dione-11β,17α,21-triol; 1,4-pregnadiene-11β,17α,21-triol-3,20-dione; 3,20-dioxo-11β,17α,21-trihydroxy-1,4-pregnadiene; metacortandralone; delta F; Δ1-dehydrocortisol; Δ1-hydrocortisone; Δ1-dehydrohydrocortisone; hydroretrocortine; Codelcortone (Merck & Co.); Decaprednil (Galen); Decortin H (Merck KGaA); Deltacortril (Pfizer); Klismacort (Novartis); Meticortelone (Schering); Precortisyl (Aventis); Prednicen (Central Pharm.); Predonine (Shionogi); Solone (Abbott).
C21H28O5; mol wt 360.44.
C 69.98%, H 7.83%, O 22.19%.

Description and 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).

Chemical structure

Properties

Crystals, dec 240-241°. [α]D25 +102° (dioxane). uv max (methanol): 242 nm (ε 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.

Derivative

21-Acetate.

Nomenclature

CAS number: 52-21-1
Ak-Tate (Akorn); Deltastab (Sovereign); Inflanefran (Allergan); Pred Forte (Allergan); Pred Mild (Allergan); Scherisolon (Schering); Sterane (Pfizer).
C23H30O6; mol wt 402.48.
C 68.64%, H 7.51%, O 23.85%.

Properties

Crystals, decomp 237-239°. [α]D25 +116° (dioxane).

Derivative

21-tert-Butylacetate.

Nomenclature

CAS number: 7681-14-3
Prednisolone tebutate; Codelcortone-T.B.A. (Merck & Co.).
C27H38O6; mol wt 458.59.
C 70.71%, H 8.35%, O 20.93%.

Description and references

Prepn: Sarett, US 2736734 (1956 to Merck & Co.).

Properties

Crystals from ethanol, mp 266-273°.

Derivative

21-Disodium Phosphate.

Nomenclature

CAS number: 125-02-0
Prednisolone sodium phosphate; Codelsol (Merck & Co.); Colicort (Merck & Co.); Hefasolon i.v. (Sanavita); Inflamase (Novartis); Orapred (BioMarin); Predsol (UCB); Solucort (Merck & Co.).
C21H27Na2O8P; mol wt 484.39.
C 52.07%, H 5.62%, Na 9.49%, O 26.42%, P 6.39%.

Description and 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. [α]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.

Derivative

21-Succinate sodium salt.

Nomenclature

CAS number: 1715-33-9
Prednisolone sodium succinate; Meticortelone Soluble (Schering); Solu-Decortin-H (Merck KGaA).
C25H31NaO8; mol wt 482.50.
C 62.23%, H 6.48%, Na 4.76%, O 26.53%.

Description and references

Prepn: Shull, Kita, DE 1045400 (1958 to Pfizer), C.A. 55, 2746f (1961).

Derivative

21-Stearoylglycolate.

Nomenclature

CAS number: 5060-55-9
Prednisolone steaglate; Sintisone (Pharmacia).
C41H64O8; mol wt 684.94.
C 71.90%, H 9.42%, O 18.69%.

Description and 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). [α]D20 +57-63°.

Derivative

21-m-Sulfobenzoate sodium salt.

Nomenclature

CAS number: 630-67-1
(11β)-11,17-Dihydroxy-21-[(3-sulfobenzoyl)oxy]pregna-1,4-diene-3,20-dione monosodium salt; prednisolone sodium metasulfobenzoate; Predenema (Forest); Predfoam (Pharmax); Solupred (Aventis).
C28H31NaO9S; mol wt 566.60.
C 59.35%, H 5.51%, Na 4.06%, O 25.41%, S 5.66%.

Description and references

Prepn: Allais, Girault, US 3032568; Joly, Warnant, US 3037034 (both 1962 to Roussel-UCLAF).

Properties

Crystals from water, dec 293-295°. [α]D20 +170° (water).

Derivative

21-Trimethylacetate.

Nomenclature

CAS number: 1107-99-9
Prednisolone 21-pivalate; Ultracortenol (Novartis).
C26H36O6; mol wt 444.56.
C 70.24%, H 8.16%, O 21.59%.

Description and 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°. [α]D26 +103° (c = 1.208 in chloroform); [α]D20 +97.5° (c = 1 in chloroform). uv max: 244 nm (ε 14700).

Therapeutic Category

Glucocorticoid.

Therapeutic Category (Veterinary)

Glucocorticoid.

Keywords

Glucocorticoid