| Systematic (IUPAC) name | |
|---|---|
| (3R,5R)-3,5-dihydroxy-7-((1R,2S,6S,8R,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-heptanoic acid | |
| Clinical data | |
| Trade names | Pravachol |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a692025 |
| Pregnancy cat. | X |
| Legal status | ℞ Prescription only |
| Routes | oral |
| Pharmacokinetic data | |
| Bioavailability | 17% |
| Protein binding | 50% |
| Metabolism | renal and hepatic |
| Half-life | 1.5-2 hours |
| Identifiers | |
| CAS number | 81093-37-0 |
| ATC code | C10AA03 |
| PubChem | CID 54687 |
| DrugBank | APRD00328 |
| ChemSpider | 49398 |
| UNII | KXO2KT9N0G |
| ChEMBL | CHEMBL1144 |
| Chemical data | |
| Formula | C23H36O7 |
| Mol. mass | 424.528 g/mol |
| SMILES | eMolecules & PubChem |
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Pravastatin (marketed as Pravachol or Selektine) is a member of the drug class of statins, used for lowering cholesterol and preventing cardiovascular disease.
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The primary uses of prevastatin is for the treatment of dyslipidemia and the prevention of cardiovascular disease.[1] It is recommended to be used only after other measures such as diet, exercise, and weight reduction have not improved cholesterol levels.[1]
Pravastatin has undergone over 112,000 patient-years of double-blind randomized trials utilizing the 40mg once daily dose and placebos. These trials indicate that pravastatin is well tolerated and displays few non-cardiovascular abnormalities in patients.[2]
However, side effects may occur. A doctor should be consulted if symptoms such as heartburn or headache are severe and do not go away. The following is a list of uncommon side effects that may require attention:[3]
Pravastatin acts as a lipoprotein-lowering drug through two pathways. In the major pathway, pravastatin inhibits the function of hydroxymethylglutaryl-CoA (HMG-CoA) reductase. As a reversible competitive inhibitor, pravastatin sterically hinders the action of HMG-CoA reductase by occupying the active site of the enzyme. Taking place primarily in the liver, this enzyme is responsible for the conversion of HMG-CoA to mevalonate in the rate-limiting step of the biosynthetic pathway for cholesterol. Pravastatin also inhibits the synthesis of very-low-density lipoproteins, which are the precursor to low-density lipoproteins (LDL). These reductions increase the number of cellular LDL receptors and, thus, LDL uptake increases, removing it from the bloodstream.[4] Overall, the result is a reduction in circulating cholesterol and LDL. A minor reduction in triglycerides and an increase in high-density lipoproteins (HDL) are common.
Initially known as CS-514, it was originally identified in a bacterium called Nocardia autotrophica by researchers of the Sankyo Pharma Inc..[5] It is presently being marketed outside Japan by the pharmaceutical company Bristol-Myers Squibb. In 2005, Pravachol was the 22nd highest-selling brand-name drug in the United States, with sales totaling $1.3 billion.[6]
The U.S. Food and Drug Administration approved generic pravastatin for sale in the United States for the first time on April 24, 2006. Generic pravastatin sodium tablets are manufactured by TEVA Pharmaceuticals in Kfar Sava, Israel.[6]
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