Simvastatin

IUPAC: (1S, 3R, 7S, 8S, 8aR ) -8 - {2 - [( 2R, 4R )-4- hydroxy-6- oxooxan -2-yl ] ethyl} - 3,7- dimethyl-1, 2, 3,7,8,8 a- hexahydronaphthalen -1-yl -2 ,2- dimethylbutanoat

• C10AA01
• C10BA02

Statins

HMG-CoA reductase inhibitor

127-132 ° C

4438 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Simvastatin is the generic name of a drug from the group of statins, used as a cholesterol-lowering drug.

Structurally, Simvastatin is derived from the naturally-occurring monacolin K ( lovastatin ).

Mechanism of Action

Simvastatin is an HMG -CoA reductase inhibitors. The HMG -CoA reductase acts as a catalyst in the reduction of 3-hydroxy -3-methylglutaryl -coenzyme A to mevalonate, which is a limiting step in hepatic cholesterol synthesis. By lowering the cholesterol synthesis, the liver cells increase the number of LDL - receptors on the cell surface, so that the increased LDL uptake into the liver cell and thus reduce the LDL levels in the blood.

Uptake and distribution in the body

After absorption of the drug is mainly metabolized by cytochrome P450 3A4, CYP 3A4 inhibitors, therefore, such as ketoconazole, itraconazole and clarithromycin or grapefruit juice should not be taken with simvastatin.

Side effects

Simvastatin has the usual side effects of this drug group, such as rhabdomyolysis.

Production

The preparation takes some synthetically from lovastatin, with its 2- Methylbutanoylseitenkette is transesterified to give 2,2 - Dimethylbutanoylrest.

A multi-step synthesis of simvastatin is described in the literature.

Commercial forms

Simvastatin was in Germany in 1990 by MSD Sharp & Dohme as Zocor on the market. In May 2003, the patent ran out on the drug. Since simvastatin is produced and distributed by several generic manufacturers. Tablets are available in the dosages 5, 10, 20, 40, 60 and 80 mg.

Zocor (D, CH), Zocord (A ), numerous generics (D, A, CH)

Vytorin (D, A, CH)