Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H36O6 |
| Molecular Weight | 408.5283 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12[C@H](CCC=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC
InChI
InChIKey=BOZILQFLQYBIIY-INTXDZFKSA-N
InChI=1S/C23H36O6/c1-4-14(2)23(28)29-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-17(24)12-18(25)13-21(26)27/h6,8-9,14-15,17-20,22,24-25H,4-5,7,10-13H2,1-3H3,(H,26,27)/t14-,15-,17+,18+,19-,20-,22-/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15531275 | https://www.ncbi.nlm.nih.gov/pubmed/28147319https://www.ncbi.nlm.nih.gov/pubmed/8121646Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27581384 | https://www.ncbi.nlm.nih.gov/pubmed/3981532
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15531275 | https://www.ncbi.nlm.nih.gov/pubmed/28147319https://www.ncbi.nlm.nih.gov/pubmed/8121646
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27581384 | https://www.ncbi.nlm.nih.gov/pubmed/3981532
Mevinic acid is reversible competitive inhibitors of HMG-CoA reductase (Ki in the range of 0.2-1 nM). Mevinic acid is a precursor of a Mevastatin (mevinic acid lactone) -- a hypolipidemic agent that belongs to the statins class. Mevastatin inactive until metabolized in the liver to the open-ring hydroxy acid (Mevinic acid). 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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1010803Tetrahedron Volume42 Issue18 Pages 4909-51
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P04035 Gene ID: 3156.0 Gene Symbol: HMGCR Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL402 |
1.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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PubMed
| Title | Date | PubMed |
|---|---|---|
| Competitive inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase by ML-236A and ML-236B fungal metabolites, having hypocholesterolemic activity. | 1976 Dec 31 |
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| [Mevastatin induced apoptosis in U266 human myeloma cell line]. | 2004 |
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| Isolation and characterization of a novel trans-factor for luteinizing hormone receptor mRNA from ovary. | 2004 Apr 9 |
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| Chronic mevastatin modulates receptor-dependent vascular contraction in eNOS-deficient mice. | 2004 Aug |
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| Antioxidant effects of statins via S-nitrosylation and activation of thioredoxin in endothelial cells: a novel vasculoprotective function of statins. | 2004 Aug 17 |
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| Statins prevent bisphosphonate-induced gamma,delta-T-cell proliferation and activation in vitro. | 2004 Feb |
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| Statins potentiate caspase-3 activity in immortalized murine neurons. | 2004 Jan 23 |
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| Depletion of membrane cholesterol causes ligand-independent activation of Fas and apoptosis. | 2004 Jul 16 |
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| [In vitro effects of mevastatin on the proliferation and apoptosis in human multiple myeloma cell line U266]. | 2004 Jun |
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| De novo biosynthesis and radiolabeling of mammalian digitalis-like factors. | 2004 Mar |
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| Statins inhibit osteoblast migration by inhibiting Rac-Akt signaling. | 2004 Mar 12 |
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| Mevastatin-induced apoptosis and growth suppression in U266 myeloma cells. | 2004 May-Jun |
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| Inhibition of geranylgeranylation mediates the effects of 3-hydroxy-3-methylglutaryl (HMG)-CoA reductase inhibitors on microglia. | 2004 Nov 12 |
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| Mevastatin inhibits ovarian theca-interstitial cell proliferation and steroidogenesis. | 2004 Oct |
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| Statins inhibit reoxygenation-induced cardiomyocyte apoptosis: role for glycogen synthase kinase 3beta and transcription factor beta-catenin. | 2004 Sep |
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| Disruption of lipid rafts causes apoptotic cell death in HaCaT keratinocytes. | 2005 Apr |
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| Effector gammadelta T cells and tumor cells as immune targets of zoledronic acid in multiple myeloma. | 2005 Apr |
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| Statins potentiate the IFN-gamma-induced upregulation of group IIA phospholipase A2 in human aortic smooth muscle cells and HepG2 hepatoma cells. | 2005 Apr 15 |
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| Induction of de novo volatile terpene biosynthesis via cytosolic and plastidial pathways by methyl jasmonate in foliage of Vitis vinifera L. | 2005 Apr 6 |
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| Genomic effect of vitamin 'C' and statins within human mononuclear cells involved in atherogenic process. | 2005 Aug |
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| Kruppel-like factor 2 as a novel mediator of statin effects in endothelial cells. | 2005 Aug 2 |
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| Fast analysis of pravastatin in production media. | 2005 Aug 5 |
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| Statins prevent beta-amyloid inhibition of sympathetic alpha7-nAChR-mediated nitrergic neurogenic dilation in porcine basilar arteries. | 2005 Dec |
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| Three-dimensional quantitative structure (3-D QSAR) activity relationship studies on imidazolyl and N-pyrrolyl heptenoates as 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitors by comparative molecular similarity indices analysis (CoMSIA). | 2005 Feb 15 |
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| Mevastatin induces apoptosis in HL60 cells dependently on decrease in phosphorylated ERK. | 2005 Jan |
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| High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line. | 2005 Jan |
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| Inhibitory effects of mevastatin and a geranylgeranyl transferase I inhibitor (GGTI-2166) on mononuclear osteoclast formation induced by receptor activator of NF kappa B ligand (RANKL) or tumor necrosis factor-alpha (TNF-alpha). | 2005 Jan 1 |
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| In vivo and in vitro effects of statins on lymphocytes in patients with Hashimoto's thyroiditis. | 2005 Jul |
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| Statins prevent oxidized LDL-induced injury of glomerular podocytes by activating the phosphatidylinositol 3-kinase/AKT-signaling pathway. | 2005 Jul |
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| Induction of macrophage elastase (MMP-12) gene expression by statins. | 2005 Jul |
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| 4,8-Dimethyldecanal, the aggregation pheromone of Tribolium castaneum, is biosynthesized through the fatty acid pathway. | 2005 Jun |
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| FOXO-dependent expression of the proapoptotic protein Bim: pivotal role for apoptosis signaling in endothelial progenitor cells. | 2005 Jun |
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| Regulation of HMG-CoA reductase in MCF-7 cells by genistein, EPA, and DHA, alone and in combination with mevastatin. | 2005 Jun 28 |
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| Chlamydophila pneumoniae induces expression of toll-like receptor 4 and release of TNF-alpha and MIP-2 via an NF-kappaB pathway in rat type II pneumocytes. | 2005 Jun 3 |
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| Cholesterol modulation of the expression of mitochondrial aconitase in human prostatic carcinoma cells. | 2005 Jun 30 |
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| Progesterone-receptor antagonists and statins decrease de novo cholesterol synthesis and increase apoptosis in rat and human periovulatory granulosa cells in vitro. | 2005 Mar |
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| Interleukin-6 and mevastatin regulate plasminogen activator inhibitor-1 through CCAAT/enhancer-binding protein-delta. | 2005 May |
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| Novel and simple high-performance liquid chromatographic method for determination of 3-hydroxy-3-methylglutaryl-coenzyme A reductase activity. | 2005 May 25 |
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| HMG CoA reductase inhibitors (statins) to treat Epstein-Barr virus-driven lymphoma. | 2005 May 9 |
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| Cholesterol biosynthesis and the pro-apoptotic effects of the p75 nerve growth factor receptor in PC12 pheochromocytoma cells. | 2005 Oct 3 |
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| Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. | 2005 Sep 9 |
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| Statins decrease serotonin-induced contractions in coronary arteries of swine in vitro. | 2006 |
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| Involvement of Rho signaling in PAR2-mediated regulation of neutrophil adhesion to lung epithelial cells. | 2006 Apr 24 |
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| Activators of the energy sensing kinase AMPK inhibit random cell movement and chemotaxis in U937 cells. | 2006 Feb |
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| Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: 2H labeling studies. | 2006 Feb 22 |
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| HMG-CoA reductase inhibitors upregulate heme oxygenase-1 expression in murine RAW264.7 macrophages via ERK, p38 MAPK and protein kinase G pathways. | 2006 Jan |
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| Alkylamines cause Vgamma9Vdelta2 T-cell activation and proliferation by inhibiting the mevalonate pathway. | 2006 Jan 15 |
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| Statins inhibit growth of human endometrial stromal cells independently of cholesterol availability. | 2006 Jul |
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| Statins revert doxorubicin resistance via nitric oxide in malignant mesothelioma. | 2006 Jul 1 |
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| HMG-CoA reductase inhibitors induce apoptosis in pericytes. | 2006 Mar |
Sample Use Guides
Mevastatin induced a profound concentration-dependent inhibition of DNA synthesis. At the highest concentration (30 microM), mevastatin inhibited DNA synthesis by 92%. Similarly, in the MTT proliferation assay, mevastatin induced a concentration-dependent decrease in cell number. Mevastatin decreased production of P (by up to 49%) and T (by up to 52%); these effects remained significant when the effect on cell culture protein content was accounted for.
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39508
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84064-38-0
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1R89KK61YI
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446154
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DTXSID40875476
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
