Lapaquistat

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Lapaquistat
Systematic (IUPAC) name
1-[[(3R,5S)-1-(3-hydroxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl) -2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidine-4-acetic acid
Identifiers
CAS number	189059-71-0
ATC code	?
PubChem	?
Chemical data
Formula	C31H39ClN2O8
Mol. mass	603.103 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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) Greenwood et al., 2006. It remains to be seen how effective lapaquistat will be.

On March 28, 2008, Takeda halted further development of lapaquistat.^[1]

[edit] References

• Davidson MH (Jan 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. 

v • d • e Lipid modifying agents (C10) Statins Atorvastatin • Cerivastatin‡ • Fluvastatin • Lovastatin • Mevastatin • Pitavastatin • Pravastatin • Rosuvastatin • Simvastatin Fibrates Clofibrate‡ • Bezafibrate • Aluminium clofibrate • Gemfibrozil • Fenofibrate • Simfibrate • Ronifibrate • Ciprofibrate • Etofibrate • Clofibride Bile acid sequestrants Colestyramine • Colestipol • Colextran • Colesevelam Niacin and derivatives Niceritrol • Niacin • Nicofuranose• Aluminium nicotinate• Nicotinyl alcohol • Acipimox CETP inhibitors Anacetrapib† • Torcetrapib§ Combinations Niacin/lovastatin • Niacin/simvastatin • Ezetimibe/simvastatin Other Dextrothyroxine • Probucol • Tiadenol • Benfluorex • Meglutol • Omega-3-triglycerides • Magnesium pyridoxal 5-phosphate glutamate • Policosanol • Ezetimibe • Laropiprant†, Lapaquistat§ †Undergoing clinical trials. ‡Withdrawn from market. §Development terminated.