Mevastatin

Mevastatin
Clinical data
ATC code	None;
Identifiers
	IUPAC name (1S,7S,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;
CAS Number	73573-88-3 ;
PubChem CID	64715;
IUPHAR/BPS	3031;
DrugBank	DB06693 ;
ChemSpider	58262 ;
UNII	1UQM1K0W9X;
KEGG	C13963 ;
ChEBI	CHEBI:34848 ;
ChEMBL	ChEMBL54440 ;
CompTox Dashboard (EPA)	DTXSID4040684 ;
ECHA InfoCard	100.131.541
Chemical and physical data
Formula	C23H34O5
Molar mass	390.520 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O[C@@H]1[C@H]3C(=C/CC1)\C=C/[C@@H]([C@@H]3CC[C@H]2OC(=O)C[C@H](O)C2)C)[C@@H](C)CC;
	InChI InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1 ; Key:AJLFOPYRIVGYMJ-INTXDZFKSA-N ;
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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, i.e., a statin. Mevastatin might be considered the first statin drug; clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed. The first statin drug available to the general public was lovastatin.

Mevastatin has since been derivatized to the compound pravastatin, which is a pharmaceutical used in the lowering of cholesterol and preventing cardiovascular disease.

In vitro, it has antiproliferative properties.

A British group isolated the same compound from Penicillium brevicompactum, named it compactin, and published their results in 1976. The British group mentions antifungal properties with no mention of HMG-CoA reductase inhibition.

High doses inhibit growth and proliferation of melanoma cells.

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