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
Identifiers
CAS Number	73573-88-3 N
ATC code	none
PubChem	CID: 64715
IUPHAR/BPS	3031
DrugBank	DB06693 Y
ChemSpider	58262 Y
UNII	1UQM1K0W9X Y
KEGG	C13963 Y
ChEBI	CHEBI:34848 N
ChEMBL	CHEMBL54440 Y
Chemical data
Formula	C23H34O5
Molecular mass	390.513 g/mol
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 Y Key:AJLFOPYRIVGYMJ-INTXDZFKSA-N Y
NY (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, 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.

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.

See also

• Medicinal molds