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Simvastatin

CAT: 0804-HY-17502-06Size: 500 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17502-06Size:500 mg
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Description
Simvastatin (MK 733) is a competitive inhibitor of HMG-CoA reductase with a Ki of 0.2 nM.
CAS Number
79902-63-9
Product Name Alternative
MK 733
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Autophagy; Ferroptosis; HMG-CoA Reductase (HMGCR) ; Mitophagy
Type
Reference compound
Related Pathways
Apoptosis; Autophagy; Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Cardiovascular Disease; Cancer
Assay Protocol
https://www.medchemexpress.com/Simvastatin.html
Concentration
10mM
Purity
99.56
Solubility
DMSO : ≥ 50 mg/mL|Ethanol : 100 mg/mL (ultrasonic)
Smiles
CCC(C)(C)C(O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H]3C[C@@H](O)CC(O3)=O)[C@@]12[H])=O
Molecular Formula
C25H38O5
Molecular Weight
418.57
Precautions
H302, H315, H319, H335
References & Citations
[1]Slater, E.E., et al. Mechanism of action and biological profile of HMG CoA reductase inhibitors. A new therapeutic alternative. Drugs, 1988. 36 Suppl 3: p. 72-82.|[2]Kureishi, Y., et al. The HMG-CoA reductase inhibitor simvastatin activates the protein kinase Akt and promotes angiogenesis in normocholesterolemic animals. Nat Med, 2000. 6 (9) : p. 1004-10.|[3]Leung BP, et al. A novel anti-inflammatory role for simvastatin in inflammatory arthritis. J Immunol. 2003 Feb 1;170 (3) :1524-30.|[4]Kobayashi M, et al. Preventive effect of MK-733 (simvastatin), an inhibitor of HMG-CoA reductase, on hypercholesterolemia and atherosclerosis induced by cholesterol feeding in rabbits. Jpn J Pharmacol. 1989 Jan;49 (1) :125-33.|[5]Ishida F, et al. Comparative effects of simvastatin (MK-733) and CS-514 on hypercholesterolemia induced by cholesterol feeding in rabbits. Biochim Biophys Acta. 1990 Feb 23;1042 (3) :365-73.|[6]Sukhova GK, et al. Statins reduce inflammation in atheroma of nonhuman primates independent of effects on serum cholesterol. Arterioscler Thromb Vasc Biol. 2002 Sep 1;22 (9) :1452-8.|[7]Weijiang Dong, et al. Differential effects of simvastatin and CS-514 on expression of Alzheimer’s disease-related genes in human astrocytes and neuronal cells. J Lipid Res. 2009 Oct; 50 (10) : 2095-2102.|[8]Liu Z, et al. Pretreatment Donors after Circulatory Death with Simvastatin Alleviates Liver Ischemia Reperfusion Injury through a KLF2-Dependent Mechanism in Rat. Oxid Med Cell Longev. 2017;2017:3861914.|[9]Ifergan I, et al. Statins reduce human blood-brain barrier permeability and restrict leukocyte migration: relevance to multiple sclerosis. Ann Neurol. 2006 Jul;60 (1) :45-55.|[10]Zhang H, et al. Advances in the discovery of exosome inhibitors in cancer. J Enzyme Inhib Med Chem. 2020;35 (1) :1322-1330.|[11]Borna Relja, et al. Simvastatin inhibits cell growth and induces apoptosis and G0/G1 cell cycle arrest in hepatic cancer cells. Int J Mol Med. 2010 Nov;26 (5) :735-41.|[12]Anil Kumar, et al. Neuroprotective potential of atorvastatin and simvastatin (HMG-CoA reductase inhibitors) against 6-hydroxydopamine (6-OHDA) induced Parkinson-like symptoms. Brain Res. 2012 Aug 30;1471:13-22.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Simvastatin

Simvastatin is a member of the class of hexahydronaphthalenes that is lovastatin in which the 2-methylbutyrate ester moiety has been replaced by a 2,2-dimethylbutyrate ester group. It is used as a cholesterol-lowering and anti-cardiovascular disease drug. It has a role as a ferroptosis inducer, a geroprotector, an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor, a prodrug and an EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor. It is a member of hexahydronaphthalenes, a delta-lactone, a fatty acid ester and a statin (semi-synthetic). It is functionally related to a lovastatin.

CAS Number79902-63-9
PubChem CID54454
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
Molecular FormulaC25H38O5
Molecular Weight418.6
XLogP4.7
Topological Polar Surface Area72.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Heavy Atom Count30
Formal Charge0
Complexity706
SMILES
CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C
InChI
InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey
RYMZZMVNJRMUDD-HGQWONQESA-N
Chemical Structure
2D Structure
2D structure of Simvastatin
CAS: 79902-63-9
CID: 54454
Formula: C25H38O5
MW: 418.6
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight418.6
XLogP34.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Exact Mass418.27192431
Monoisotopic Mass418.27192431
Topological Polar Surface Area72.8 Ų
Heavy Atom Count30
Formal Charge0
Complexity706
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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