Mevastatin

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Mevastatin
Mevastatin2DCSD.svg
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
Legal status ?
Identifiers
CAS number 73573-88-3 N
ATC code None
PubChem CID 64715
DrugBank DB06693
ChemSpider 58262 YesY
UNII 1UQM1K0W9X YesY
KEGG C13963 YesY
ChEBI CHEBI:34848 N
ChEMBL CHEMBL54440 YesY
Chemical data
Formula C23H34O5 
Mol. mass 390.513 g/mol
 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]

A British group isolated the same compound from Penicillium brevicompactum, named it compactin and also published it in 1976.[5] The British group mentions anti-fungal properties with no mention of HMG-CoA Reductase inhibition.

High doses inhibit growth and proliferation of melanoma cells.[6]

See also[edit]

References[edit]

Ajaz Ahmad, M Mujeeb, Bibhu Prasad Panda (2010) An HPTLC Method for the Simultaneous Analysis of Compactin and Citrinin in Penicillium citrinum Fermentation Broth. Journal of Planar Chromatography-Modern TLC, 23 (4), 282–285 [1]

  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. doi:10.7164/antibiotics.29.1346. 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. ^ Brown, Allan G.; Smale, Terry C.; King, Trevor J.; Hasenkamp, Rainer; Thompson, Ronald H. (1976). "Crystal and molecular structure of compactin, a new antifungal metabolite from Penicillium brevicompactum.". J. Chem. Soc., Perkin Trans. 1 (11): 1165–1170. doi:10.1039/P19760001165. PMID 945291. 
  6. ^ 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