Mevastatin

Mevastatin
Mevastatin
Systematic (IUPAC) name
(1S,7R,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 73573-88-3 YesY
ATC code None
PubChem CID 64715
DrugBank DB06693
ChemSpider 58262 YesY
UNII 1UQM1K0W9X N
KEGG C13963 N
ChEMBL CHEMBL54440 YesY
Chemical data
Formula C23H34O5 
Mol. mass 390.513 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Mevastatin, compactin, ML-236B is a hypolipidemic agent that belongs to the statins class.

It was isolated from the mold Penicillium citrinum by Akira Endo in the 1970s and he identified it as a HMG-CoA reductase inhibitor,[1] i.e.; a statin. Mevastatin might be considered the first statin drug,[2] but, although clinical trials on mevastatin were performed in the late 1970s in Japan, it was never marketed.[3]The first statin drug available to the general public was lovastatin. In vitro it has antiproliferative properties.[4]

High doses inhibit growth and proliferation of melanoma cells.[5]

References

  1. ^ Endo, Akira; Kuroda M., Tsujita Y. (December 1976). "ML-236A, ML-236B, and ML-236C, new inhibitors of cholesterogenesis produced by Penicillium citrinium". Journal of Antibiotics (Tokyo) 29 (12): 1346–8. PMID 1010803. 
  2. ^ http://www.world-of-fungi.org/Mostly_Medical/Mark_Gilson/Mark_Gilson.htm "the story of statins"
  3. ^ Endo, Akira (Oct 2004). "The origin of the statins". Atheroscler Suppl. 5 (3): 125–30. doi:10.1016/j.atherosclerosissup.2004.08.033. PMID 15531285. 
  4. ^ http://carcin.oxfordjournals.org/cgi/content/abstract/22/7/1061 "HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2" 2001
  5. ^ http://www.biomedcentral.com/1471-2407/8/9/abstract "The 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors, simvastatin, lovastatin and mevastatin inhibit proliferation and invasion of melanoma cells" 2008


v · d · eLipid modifying agents (C10)
GI tract
Ezetimibe • SCH-48461
Liver
Simvastatin# • Atorvastatin • Fluvastatin • Lovastatin • Mevastatin • Pitavastatin • Pravastatin • Rosuvastatin • Cerivastatin‡
Niacin and derivatives (HDL and LDL)
Blood vessels
CETP inhibitors (HDL)
Anacetrapib† • Dalcetrapib • Evacetrapib • Torcetrapib§
Combinations
Other
Dextrothyroxine • Probucol • Tiadenol • Benfluorex • Meglutol • Omega-3-triglycerides • Magnesium pyridoxal 5-phosphate glutamate • Policosanol • Lapaquistat§ • Alipogene tiparvovec

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)


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