Pravastatin

Pravastatin
Clinical data
Trade namesPravachol, others
AHFS/Drugs.comMonograph
MedlinePlusa692025
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability18%[4]
Protein binding50%[4]
MetabolismLiver (minimal)[4]
Elimination half-life1-3 hours[4]
Identifiers
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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.216.225
Chemical and physical data
FormulaC23H36O7
Molar mass424.534 g·mol−1
3D model (JSmol)
SMILES
  • O=C(O)C[C@H](O)C[C@H](O)CC[C@H]2[C@H](/C=C\C1=C\[C@@H](O)C[C@H](OC(=O)[C@@H](C)CC)[C@@H]12)C
InChI
  • InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1 Y
  • Key:TUZYXOIXSAXUGO-PZAWKZKUSA-N Y
 NY (what is this?)  (verify)

Pravastatin, sold under the brand name Pravachol among others, is a statin medication, used for preventing cardiovascular disease in those at high risk and treating abnormal lipids.[5] It is suggested to be used together with diet changes, exercise, and weight loss.[5] It is taken by mouth.[5]

Common side effects include joint pain, diarrhea, nausea, headaches, and muscle pains.[5] Serious side effects may include rhabdomyolysis, liver problems, and diabetes.[5] Use during pregnancy may harm the fetus.[5] Like all statins, pravastatin works by inhibiting HMG-CoA reductase, an enzyme found in liver that plays a role in producing cholesterol.[5]

Pravastatin was patented in 1980 and approved for medical use in 1989.[6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication.[5] In 2022, it was the 37th most commonly prescribed medication in the United States, with more than 16 million prescriptions.[8][9]

  1. ^ Cite error: The named reference Pravastatin FDA label was invoked but never defined (see the help page).
  2. ^ "Pravachol (pravastatin sodium) Tablets Initial U.S. Approval: 1991". DailyMed. Retrieved 2 September 2024.
  3. ^ "Active substance: pravastatin" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 26 November 2020.
  4. ^ a b c d Neuvonen PJ, Backman JT, Niemi M (2008). "Pharmacokinetic comparison of the potential over-the-counter statins simvastatin, lovastatin, fluvastatin and pravastatin". Clinical Pharmacokinetics. 47 (7): 463–474. doi:10.2165/00003088-200847070-00003. PMID 18563955. S2CID 11716425.
  5. ^ a b c d e f g h "Pravastatin Sodium Monograph for Professionals". Drugs.com. AHFS. Retrieved 23 December 2018.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 472. ISBN 9783527607495.
  7. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  8. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  9. ^ "Pravastatin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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