864. Atorvastatin

Nomenclature

CAS number: 134523-00-5
(βR,δR)-2-(4-Fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid.
C33H35FN2O5; mol wt 558.64.
C 70.95%, H 6.31%, F 3.40%, N 5.01%, O 14.32%.

Description and references

HMG-CoA reductase inhibitor. Prepn: B. D. Roth, EP 409281; idem, US 5273995 (1991, 1993 both to Warner-Lambert); K. L. Baumann et al., Tetrahedron Lett. 33, 2283 (1992). Solubility and kinetic studies: A. S. Kearney et al., Pharm. Res. 10, 1461 (1993). LC/MS/MS determn in serum: M. Jemal et al., Rapid Commun. Mass Spectrom. 13, 1003 (1999). Clinical pharmacokinetics: D. D. Cilla, Jr. et al., Clin. Pharmacol. Ther. 60, 687 (1996). Review of pharmacology and clinical experience: H. S. Yee, N. T. Fong, Ann. Pharmacother. 32, 1030-1043 (1998); of efficacy in diabetic patients: K. F. Croom, G. L. Plosker, Drugs 65, 137-152 (2005).

Chemical structure

Derivative

Calcium salt trihydrate.

Nomenclature

CAS number: 344423-98-9; 134523-03-8 (anhydrous)
CI-981; Lipitor (Parke-Davis); Sortis (Pfizer); Torvast (Pfizer); Totalip (Guidotti).
C66H68CaF2N4O10.3H2O; mol wt 1209.39.
C 65.55%, H 6.17%, Ca 3.31%, F 3.14%, N 4.63%, O 17.20%.

Properties

White to off-white crystalline powder. [α]D 7.4° (c = 1 in DMSO). Freely sol in methanol; slightly sol in ethanol; very slightly sol in acetonitrile, distilled water, phosphate buffer (pH 7.4). Insol in aq solns of pH 4 and below.

Derivative

Sodium salt.

Nomenclature

CAS number: 134523-01-6
C33H34FN2NaO5; mol wt 580.62.
C 68.26%, H 5.90%, F 3.27%, N 4.82%, Na 3.96%, O 13.78%.

Properties

pKa 4.46. Soly in water (30°): 20.4 μg/ml (pH 2.1); 1.23 mg/ml (pH 6.0).

Derivative

Lactone.

Nomenclature

CAS number: 125995-03-1
5-(4-Fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1H-pyrrole-3-carboxamide.
C33H33FN2O4; mol wt 540.62.
C 73.31%, H 6.15%, F 3.51%, N 5.18%, O 11.84%.

Properties

mp 159.2-160.7°. [α]D +26.05° (c = 1 in chloroform).

Therapeutic Category

Antilipemic.

Keywords

Antilipemic; HMG CoA Reductase Inhibitors; HMG CoA Reductase Inhibitor