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Mevastatin information


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 ☒N
PubChem CID
  • 64715
IUPHAR/BPS
  • 3031
DrugBank
  • DB06693 checkY
ChemSpider
  • 58262 checkY
UNII
  • 1UQM1K0W9X
KEGG
  • C13963 checkY
ChEBI
  • CHEBI:34848 ☒N
ChEMBL
  • ChEMBL54440 checkY
CompTox Dashboard (EPA)
  • DTXSID4040684 Edit this at Wikidata
ECHA InfoCard100.131.541 Edit this at Wikidata
Chemical and physical data
FormulaC23H34O5
Molar mass390.520 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 checkY
  • Key:AJLFOPYRIVGYMJ-INTXDZFKSA-N checkY
 ☒NcheckY (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] clinical trials on mevastatin were performed in the late 1970s in Japan, but it was never marketed.[3] 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.[4]

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

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

  1. ^ Endo A, Kuroda M, Tsujita Y (December 1976). "ML-236A, ML-236B, and ML-236C, new inhibitors of cholesterogenesis produced by Penicillium citrinium". The Journal of Antibiotics. 29 (12): 1346–8. doi:10.7164/antibiotics.29.1346. PMID 1010803.
  2. ^ "The story of statins". Archived from the original on December 21, 2008.
  3. ^ Endo A (October 2004). "The origin of the statins. 2004". Atherosclerosis. Supplements. 5 (3): 125–30. doi:10.1016/j.atherosclerosissup.2004.08.033. PMID 15531285.
  4. ^ Wächtershäuser A, Akoglu B, Stein J (July 2001). "HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2". Carcinogenesis. 22 (7): 1061–7. doi:10.1093/carcin/22.7.1061. PMID 11408350.
  5. ^ Brown AG, Smale TC, King TJ, Hasenkamp R, Thompson RH (1976). "Crystal and molecular structure of compactin, a new antifungal metabolite from Penicillium brevicompactum". Journal of the Chemical Society, Perkin Transactions 1 (11): 1165–70. doi:10.1039/P19760001165. PMID 945291.
  6. ^ Glynn SA, O'Sullivan D, Eustace AJ, Clynes M, O'Donovan N (January 2008). "The 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors, simvastatin, lovastatin and mevastatin inhibit proliferation and invasion of melanoma cells". BMC Cancer. 8: 9. doi:10.1186/1471-2407-8-9. PMC 2253545. PMID 18199328.

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Mevastatin

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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...

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Penicillium citrinum

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species of the genus of Penicillium which produces tanzawaic acid A-D, ACC, Mevastatin, Quinocitrinine A, Quinocitrinine B, and nephrotoxic citrinin. Penicillium...

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Medicinal uses of fungi

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red yeast rice fungus, Monascus purpureus, can synthesize lovastatin, mevastatin, and the simvastatin precursor monacolin J. Nicotinamide riboside, a cholesterol...

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Fungus

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inhibit cholesterol synthesis. Examples of statins found in fungi include mevastatin from Penicillium citrinum and lovastatin from Aspergillus terreus and...

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Pharmaceutical industry

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toxic effects at higher doses and as a result mevastatin was believed to be too toxic for human use. Mevastatin was never marketed, because of its adverse...

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Erythromycin

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Tetrahydrocannabinol

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Fenbendazole

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Flucloxacillin

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Nicotine

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Levothyroxine

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Fentanyl

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Progesterone

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Omeprazole

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Clotrimazole

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Loratadine

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Permethrin

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Tetracycline

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Hypericum perforatum

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Statin

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walls or cytoskeleton (isoprenoids). The first agent they identified was mevastatin (ML-236B), a molecule produced by the fungus Penicillium citrinum.[citation...

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Tolnaftate

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Dehydroepiandrosterone

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Valproate

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Simvastatin

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of this enzyme. By 1976, Akira Endo had isolated the first inhibitor, mevastatin, from the fungus Penicillium citrinium while working at Daiichi Sankyo...

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Prednisolone

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Spironolactone

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Dexamethasone

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Testosterone isocaproate

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Tacrolimus

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