7508. Pitavastatin

Nomenclature

CAS number: 147511-69-1
(3R,5S,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid; itavastatin; nisvastatin.
C25H24FNO4; mol wt 421.46.
C 71.24%, H 5.74%, F 4.51%, N 3.32%, O 15.18%.

Description and references

HMG CoA reductase inhibitor. Prepn: Y. Fujikawa et al., EP 304063; eidem, US 5011930 (1989, 1991 both to Nissan Chem. Ind.). Prepn of lactone: S. Takano et al., Tetrahedron: Asymmetry 4, 201 (1993). Chiral synthesis: M. Suzuki et al., Bioorg. Med. Chem. Lett. 9, 2977 (1999). Structure-activity study: idem et al., Bioorg. Med. Chem. 9, 2727 (2001). Pharmacology: T. Aoki et al., Arzneim.-Forsch. 47, 904 (1997). HPLC determn in plasma: J. Kojima et al., J. Chromatogr. B 724, 173 (1999). Metabolism: I. Yamada et al., Xenobiotica 33, 789 (2003). Clinical comparison with pravastatin: Y. Saito et al., Atherosclerosis 162, 373 (2002). Clinical evaluation in hypercholesterolemia: S. Park et al., Clin. Ther. 27, 1074 (2005). Review of pharmacokinetics and clinical experience: K. Kajinami et al., Cardiovasc. Drug Rev. 21, 199-215 (2003); R. Y. A. Mukhtar et al., Int. J. Clin. Pract. 59, 239-252 (2005).

Chemical structure

Derivative

Calcium salt.

Nomenclature

CAS number: 147526-32-7
Monocalcium bis[(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoate]; NK-104; Livalo (Kowa).
C50H46CaF2N2O8; mol wt 880.98.
C 68.17%, H 5.26%, Ca 4.55%, F 4.31%, N 3.18%, O 14.53%.

Properties

Lipophilic. [α]D20 +23.1° (c = 1.00 in acetonitrile/water).

Derivative

Lactone.

Nomenclature

CAS number: 141750-63-2
(4R,6S)-6-[(1E)-2-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-one.
C25H22FNO3; mol wt 403.45.
C 74.42%, H 5.50%, F 4.71%, N 3.47%, O 11.90%.

Properties

mp 138-139°. [α]D32 +8.84° (c = 0.92 in chloroform).

Therapeutic Category

Antilipemic.

Keywords

Antilipemic; HMG CoA Reductase Inhibitors; HMG CoA Reductase Inhibitor