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
ATC code	None
PubChem	CID 64715
DrugBank	DB06693
ChemSpider	58262
UNII	1UQM1K0W9X
KEGG	C13963
ChEMBL	CHEMBL54440
Chemical data
Formula	C23H34O5
Mol. mass	390.513 g/mol
SMILES	eMolecules & PubChem
	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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メバスタチン

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/02/22 09:53:06」(JST)

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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,^[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

^ 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.
^ http://www.world-of-fungi.org/Mostly_Medical/Mark_Gilson/Mark_Gilson.htm "the story of statins"
^ 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.
^ 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
^ 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

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

English Journal

Differential roles of the mevalonate pathway in the development and survival of mouse purkinje cells in culture.

Barszczyk A1, Sun HS, Quan Y, Zheng W, Charlton MP, Feng ZP.
Molecular neurobiology.Mol Neurobiol.2015 Jun;51(3):1116-29. doi: 10.1007/s12035-014-8778-6. Epub 2014 Jun 29.
The cerebellum is an important locus for motor learning and higher cognitive functions, and Purkinje cells constitute a key component of its circuit. Biochemically, significant turnover of cholesterol occurs in Purkinje cells, causing the activation of the mevalonate pathway. The mevalonate pathway
PMID 24973985

Sterol liganding of OSBP-related proteins (ORPs) regulates the subcellular distribution of ORP-VAPA complexes and their impacts on organelle structure.

Kentala H1, Pfisterer SG2, Olkkonen VM3, Weber-Boyvat M4.
Steroids.Steroids.2015 Feb 11. pii: S0039-128X(15)00056-2. doi: 10.1016/j.steroids.2015.01.027. [Epub ahead of print]
Oxysterol-binding protein (OSBP) and its homologues (ORPs) are lipid-binding/transfer proteins with affinity for oxysterols, cholesterol and glycerophospholipids. In addition to a ligand-binding domain, a majority of the ORPs carry a pleckstrin homology domain that targets organelle membranes via ph
PMID 25681634

[Overexpression of LaeA enhances mevastatin production and reduces sporulation of Penicillium citrinum].

Zheng Y, Cao S, Huang Y, Liao G, Hu C.
Wei sheng wu xue bao = Acta microbiologica Sinica.Wei Sheng Wu Xue Bao.2014 Dec 4;54(12):1438-45.
OBJECTIVE: To study the regulation of laeA overexpression on mevastatin production and sporulation in Penicillium citrinum.METHODS: We cloned the laeA gene from Penicillium citrinum and constructed the vector pGiHTGi-laeA. The plasmid pGiHTGi-laeA was transformed in Penicillium citrinum by agrobacte
PMID 25876329

Japanese Journal

Development of natural anti-tumor drugs by microorganisms

Chang Chia-Che,Chen Wei-Chuan,Ho Tsing-Fen,Wu Ho-Shing,Wei Yu-Hong
Journal of bioscience and bioengineering 111(5), 501-511, 2011-05
… The great biodiversity of microorganisms raises the possibility of producing secondary metabolites (e.g., mevastatin, lovastatin, epothilone, salinosporamide A) to cope with adverse environments. …
NAID 110008661194

Pharmacological Topics of Bone Metabolism : Antiresorptive Microbial Compounds That Inhibit Osteoclast Differentiation, Function, and Survival

WOO Je-Tae,YONEZAWA Takayuki,CHA Byung-Yoon,TERUYA Toshiaki,NAGAI Kazuo
Journal of pharmacological sciences 106(4), 547-554, 2008-04-20
… As a result, we identified reveromycin A, destruxins, mevastatin, FK506, cyclosporin A, prodigiosins, concanamycins, and symbioimine among microbial natural compounds. …
NAID 10024319737

ジャスモン酸とそのアミド誘導体によってイヌタデ葉から放出される揮発性セスキテルペン

田母神繁,成田泰洋,鈴木成治,西澤知之,花井秀俊,野間正名
Journal of pesticide science = 日本農薬学会誌 32(3), 264-269, 2007-08-20
セスキテルペンの,ジンギベレン,β-エレメン,α-ベルガモテン,β-カリオフイレン, (E,E)-α-ファルネセンなどを,ジャスモン酸で処理されたイヌタデ葉が放出する植物揮発性物質として同定した.これらのセスキテルペンは1μMの濃度で放出され,相対的な放出量は濃度によって変化した.チオ硫酸銀を使った実験から放出にはエチレンが関与することが示唆された.また,チオ硫酸銀の効果はセスキテルペン間で異なっ …
NAID 110006379898

Related Pictures

[0] 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.

[1] ttp://www.world-of-fungi.org/Mostly_Medical/Mark_Gilson/Mark_Gilson.htm "the story of statins"

[2] 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.

[3] ttp://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

[4] ttp://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

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