7714. Pravastatin Sodium

Nomenclature

CAS number: 81131-70-6
(βR,δR,1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β,δ,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic acid monosodium salt; sodium (+)-(3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(S)-2-methylbutyryloxy]-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoate; eptastatin sodium; 3β-hydroxycompactin sodium salt; CS-514; SQ-31000; Elisor (BMS); Lipostat (BMS); Liprevil (Schwarz); Mevalotin (Sankyo); Oliprevin (BMS); Pravachol (BMS); Pravaselect (Menarini); Pravasin (BMS); Selectin (BMS); Selipran (BMS); Vasten (Specia).
C23H35NaO7; mol wt 446.51.
C 61.87%, H 7.90%, Na 5.15%, O 25.08%.

Description and references

HMG-CoA reductase inhibitor; bioactive metabolite of mevastatin, q.v. Prepn by microbial hydroxylation: A. Terahara, M. Tanaka, DE 3122499; eidem, US 4346227 (1981, 1982 both to Sankyo); N. Serizawa et al., J. Antibiot. 36, 604 (1983). Structure elucidation: H. Haruyama et al., Chem. Pharm. Bull. 34, 1459 (1986). HPLC determn in biological fluids: S. Bauer et al., J. Chromatogr. B 818, 257 (2005). Effect on serum lipid concentration: N. Nakaya et al., Atherosclerosis 61, 125 (1986); on hepatic metabolism of cholesterol: E. Reihnér et al., N. Engl. J. Med. 323, 224 (1990). Clinical comparison with probucol, q.v.: G. Yoshino et al., Lancet 2, 740 (1986). Clinical reduction of risk of major cardiovascular events in patients with coronary heart disease: LIPID Study Group, N. Engl. J. Med. 339, 1349 (1998). Clinical effect on risk of stroke: H. D. White et al., ibid. 343, 317 (2000).

Chemical structure

Properties

Odorless, white to off-white, fine or crystalline powder. uv max (methanol): 230, 237, 245 nm. Sol in methanol, water; slightly sol in isopropanol. Practically insol in acetone, acetonitrile, chloroform, ether.

Derivative

Lactone.
C23H34O6; mol wt 406.51.
C 67.96%, H 8.43%, O 23.61%.

Properties

Colorless plate crystals, mp 138-142°. [α]D22 +194.0° (c = 0.51 in methanol). uv max (methanol): 230, 237, 245 nm.

Therapeutic Category

Antilipemic.

Keywords

Antilipemic; HMG CoA Reductase Inhibitors; HMG CoA Reductase Inhibitor