Simvastatin
Simvastatin is an inhibitor of HMG-CoA reductase that exhibits anti-hyperlipidemic, anticonvulsant/antiepileptic, anti-osteoporotic, neuroprotective, cognition enhancing, antithrombotic, and anticancer chemotherapeutic activities. Clinically, simvastatin decreases levels of LDL and total cholesterol and lowers cardiovascular morbidity and mortality rates. Simvastatin decreases insulin synthesis and secretion in vitro, potentially through increasing ATP-sensitive K+ currents and inhibiting L-type Ca2+ currents. In animal models of Parkinson’s disease, simvastatin upregulates expression of M1/4 muscarinic acetylcholine receptors (mAChRs), improving long-term memory. In other animal models, simvastatin increases bone mineral density, bone volume fraction, and bone microarchitecture. Additionally, simvastatin decreases platelet activation and inhibits thrombus formation in vitro and in vivo. This compound also increases expression of p27 and decreases expression of histone methyltransferase EZH2, inhibiting cellular proliferation and tumor growth in preclinical cancer models and increasing survival rates in clinical settings.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18972678
| Cas No. |
79902-63-9 |
|---|---|
| Purity |
≥97% |
| Formula |
C25H38O5 |
| Formula Wt. |
418.57 |
| Chemical Name |
2,2-Dimethylbutanoic acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester |
| IUPAC Name |
[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate |
| Synonym |
Synvinolin; MK-733; Denan; Liponorm; Lodales; Simovil; Sinvacor; Sivastin; Zocor; Zocord |
| Melting Point |
135-138°C |
| Solubility |
Soluble in DMSO (540 mg/ml); ethanol (160 mg/ml); methanol (200 mg/ml). Insoluble in water. |
| Appearance |
Light white crystalline powder |
Zhou J, Li W, Xie Q, et al. Effects of simvastatin on glucose metabolism in mouse MIN6 cells. J Diabetes Res. 2014;2014:376570. PMID: 24995341.
Banach M, Czuczwar SJ, Borowicz KK. Statins – are they anticonvulsant? Pharmacol Rep. 2014 Aug;66(4):521-8. PMID: 24948050.
Wang Q, Wei X, Gao H, et al. Simvastatin reverses the downregulation of M1/4 receptor binding in 6-hydroxydopamine-induced parkinsonian rats: the association with improvements in long-term memory. Neuroscience. 2014 May 16;267:57-66. PMID: 24613723.
Yang N, Cui Y, Tan J, et al. Local injection of a single dose of simvastatin augments osteoporotic bone mass in ovariectomized rats. J Bone Miner Metab. 2014 May;32(3):252-60. PMID: 23934055.
Ishikawa S, Hayashi H, Kinoshita K, et al. Statins inhibit tumor progression via an enhancer of zeste homolog 2-mediated epigenetic alteration in colorectal cancer. Int J Cancer. 2013 Dec 17. [Epub ahead of print]. PMID: 24346863.
Moraes LA, Vaiyapuri S, Sasikumar P, et al. Antithrombotic actions of statins involve PECAM-1 signaling. Blood. 2013 Oct 31;122(18):3188-96. PMID: 24030383.
Liu PY, Liu YW, Lin LJ, et al. Evidence for statin pleiotropy in humans: differential effects of statins and ezetimibe on rho-associated coiled-coil containing protein kinase activity, endothelial function, and inflammation. Circulation. 2009 Jan 6;119(1):131-8. PMID: 19075102.
