Fluvastatin

• (3R *, 5S *, 6E ) -7 - [3 - ( 4-fluorophenyl ) -1 - ( 1-methylethyl) -1H- indol- 2-yl] -3,5- dihydroxy-6 - heptenoic acid
• ( 3RS, 5SR, 6E ) -7 - [3 - ( 4-fluorophenyl) - 1 - (1 -methylethyl) -1H-indole -2-yl ] -3,5 - -dihydroxy-6 - heptenoic acid

• C24H26FNO4 ( fluvastatin )
• C24H25FNNaO4 ( fluvastatin sodium salt)

• 93957-54-1 ( fluvastatin )
• 93957-55-2 ( fluvastatin sodium salt)

C10AA04

Statins

HMG-CoA reductase inhibitor

• 411.47 g · mol -1 ( fluvastatin )
• 433.45 g.mol -1 ( fluvastatin sodium salt)

194-197 ° C ( fluvastatin sodium salt)

Template: Infobox chemical / molecular formula search available

Fluvastatin ( Lescol ® trade name (D)) is a drug from the group of statins, used for lowering elevated total cholesterol and LDL cholesterol levels.

• 2.1 stereoisomerism

Clinical information

Areas of application (indications )

Fluvastatin may be used for reduction of elevated total and LDL cholesterol levels when non- pharmacological measures, such as diet, exercise and weight loss, insufficient action show. This concerns in particular patients with primary hypercholesterolemia, with the exception of the rare homozygous familial hypercholesterolemia, as well as patients with combined hypercholesterolemia and hypertriglyceridemia, when hypercholesterolemia is in the foreground. In addition, fluvastatin is approved for the prevention of serious cardiac events after cardiac catheter therapy.

Contraindications ( contraindications)

Fluvastatin may not be used in active liver disease or with persistent, unexplained elevations of transaminases in blood serum as well as in cholestasis. Similarly, fluvastatin may not be used in patients with myopathy or a known hypersensitivity to the active substance.

For use in children under 9 years and in homozygous familial hypercholesterolemia are no adequate clinical experience.

Use during pregnancy and lactation

During pregnancy and breast-feeding Fluvastatin is contraindicated. It is reasonable to assume that fluvastatin, as well as other HMG -CoA reductase inhibitors, by inhibiting the synthesis of cholesterol and other products of cholesterol metabolism may harm the fetus. Before starting a Fluvastatintherapie therefore, pregnancy is ruled out. If pregnancy occurs during therapy, fluvastatin should be discontinued.

Chemistry

Stereoisomerism

Fluvastatin contains a asymmetrically substituted carbon-carbon double bond in the 6-position and two stereogenic centers in positions 3 and 5, it is thus the following eight stereoisomers: the (3R, 5S, 6E )-form and its enantiomer (3S, 5R, 6E )-form and the (3R, 5S, 6Z )-form, the (3S, 5R, 6Z )-form, the (3R, 5R, 6E )-form, the (3S, 5S, 6E )-form, the (3R, 5R, 6Z )-form and (3S, 5S, 6Z )-form. Of the drug in the commercial preparations is the racemate of [ 1:1 mixture ] of the (3R, 5S, 6E) - form and (3S, 5R, 6E )-form. The (3R, 5S, 6E) - enantiomer ( eutomer ) is about 30-fold more potent than the (3S, 5R, 6E )-enantiomer ( distomer ).

Trade names

Cranoc (D), Lescol (A, CH), Lescol (D), Nuvastin (A ), numerous generics (D, A, CH)