8270. Rosuvastatin

Nomenclature

CAS number: 287714-41-4
(3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic acid.
C22H28FN3O6S; mol wt 481.54.
C 54.87%, H 5.86%, F 3.95%, N 8.73%, O 19.94%, S 6.66%.

Description and references

HMG-CoA reductase inhibitor. Prepn: K. Hirai et al., EP 521471; eidem, US 5260440 (both 1993 to Shionogi); M. Watanabe et al., Bioorg. Med. Chem. 5, 437 (1997). Pharmacology: F. McTaggart et al., Am. J. Cardiol. 87, Suppl., 28B (2001). Comparative clinical trial with atorvastatin: M. Davidson et al., ibid. 89, 268 (2002); in metabolic syndrome: A. F. H. Stalenhoef et al., Eur. Heart J. 26, 2664 (2005); in African-American patients: K. C. Ferdinand et al., Am. J. Cardiol. 97, 229 (2006). Pharmacokinetics and pharmacogenetics in Asian and white ethnic groups: E. Lee et al., Clin. Pharmacol. Ther. 78, 330 (2005). Review of therapeutic potential: K. C. Ferdinand, Expert Opin. Pharmacother. 6, 1897-1910 (2005).

Chemical structure

Properties

Partition coefficient (octanol/water): 0.13 (pH 7.0).

Derivative

Calcium salt.

Nomenclature

CAS number: 147098-20-2
S-4522; ZD-4522; Crestor (AstraZeneca).
C44CaH54F2N6O12S2; mol wt 1001.14.
C 52.79%, Ca 4.00%, H 5.44%, F 3.80%, N 8.39%, O 19.18%, S 6.41%.

Properties

White powder from water as the monohydrate; begins to melt at 155° with no definitive mp. [α]D24 +14.8° (c = 1.012 in 50% methanol). Sparingly sol in water, methanol; slightly sol in ethanol.

Therapeutic Category

Antilipemic.

Keywords

Antilipemic; HMG CoA Reductase Inhibitors; HMG CoA Reductase Inhibitor