Lapaquistat

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Lapaquistat
Lapaquistat.svg
Systematic (IUPAC) name
(1-{[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl}piperidin-4-yl)acetic acid
Clinical data
Legal status ?
Identifiers
CAS number 189059-71-0 N
ATC code None
PubChem CID 9960389
ChemSpider 8135996 YesY
UNII PEZ79BV72X YesY
ChEMBL CHEMBL341976 YesY
Chemical data
Formula C31H39ClN2O8 
Mol. mass 603.103 g/mol
 N (what is this?)  (verify)

Lapaquistat (TAK-475) is a cholesterol-lowering drug. Unlike statins, which inhibit HMG-CoA reductase, lapaquistat metabolites inhibit squalene synthase, which is further downstream in the synthesis of cholesterol. It is hoped that side effects can be reduced by not disturbing the mevalonate pathway, which is important for other biochemical molecules besides cholesterol. However, there is increasing evidence that statins (which inhibit the mevalonate pathway) may be clinically useful because they affect these other molecules (including protein prenylation).[1]

On March 28, 2008, Takeda halted further development of lapaquistat.[2]

References[edit]

  1. ^ Greenwood J, Steinman L, Zamvil SS (May 2006). "Statin therapy and autoimmune disease: from protein prenylation to immunomodulation". Nat. Rev. Immunol. 6 (5): 358–70. doi:10.1038/nri1839. PMID 16639429. 
  2. ^ Takeda Pharmaceutical Company Limited press release - Discontinuation of Development of TAK-475, A Compound for Treatment of Hypercholesterolemia
  • Davidson MH (January 2007). "Squalene synthase inhibition: a novel target for the management of dyslipidemia". Curr Atheroscler Rep 9 (1): 78–80. doi:10.1007/BF02693932. PMID 17169251.