An HMG-CoA reductase inhibitor
Related Products
Active Metabolite(s)
34883Simvastatin Hydroxy Acid (ammonium salt)
Alternative(s)
10010345Simvastatin (sodium salt)
Labeled Version(s)
22181Simvastatin-d6
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Simvastatin

Item No. 10010344

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,2-dimethyl-1S,2,3R,7S,8S,8aR-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, butanoic acid
CAS Number
79902-63-9
Synonyms
  • MK-733
  • SVA
Molecular Formula
C25H38O5
Formula Weight
418.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 20 mg/ml
λmax
238 nm
SMILES
C[C@H]1C=CC2=C[C@H](C)C[C@H](OC(C(C)(C)CC)=O)C2[C@H]1CC[C@@H]3C[C@@H](O)CC(O3)=O
InChi Code
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
InChi Key
RYMZZMVNJRMUDD-OVOOIQHOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    5 mg

    $28

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    25 mg

    $62

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    50 mg

    $83

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    100 mg

    $138

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Simvastatin is a competitive inhibitor of HMG-CoA reductase (Ki = 0.12 nM).1 Simvastatin reduces plasma cholesterol levels in rats and dogs when administered at doses of 1.2 and 8 mg/kg, respectively.2 Simvastatin suppresses TNF-induced NF-κB activation (IC50 = ~13 µM) and potentiates apoptosis in human myeloid leukemia cells.3 It also inhibits glutathione peroxidase 4 (GPX4) activity, increases malondialdehyde (MDA) levels, and induces ferroptosis in MDA-MB-231 and MCF-7 breast cancer cells.4 Formulations containing simvastatin have been used in the treatment of dyslipidemias.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Corsini, A., Maggi, F.M., and Catapano, A.L. Pharmacology of competitive inhibitors of HMG-CoA reductase. Pharmacol. Res. 31(1), 9-27 (1995).

    2. Chao, Y., Chen, J.S., Hunt, V.M., et al. Lowering of plasma cholesterol levels in animals by lovastatin and simvastatin. Eur. J. Clin. Pharmacol. 40(Suppl 1), S11-S14 (1991).

    3. Ahn, K.S., Sethi, G., and Aggarwal, B.B. Reversal of chemoresistance and enhancement of apoptosis by statins through down-regulation of the NF-κB pathway. Biochem. Pharmacol. 75(4), 907-913 (2008).

    4. Lu, S., Shao, N.-Y., Bi, J., et al. Abstract PS18-44: Simvastatin induces ferroptosis in breast cancer cells by inhibiting GPX4 and sensitizes chemotherapy. 2020 San Antonio Breast Cancer Virtual Symposium (2021).

    Product Citations

    Kremer, D.M., Nelson, B.S., Lin, L., et al. GOT1 inhibition primes pancreatic cancer for ferroptosis through the autophagic release of labile iron. bioRxiv (2020).

    Shiozawa, A., Yamaori, S., Kamijo, S., et al. Effects of acid and lactone forms of statins on S-warfarin 7-hydroxylation catalyzed by human liver microsomes and recombinant CYP2C9 variants (CYP2C9.1 and CYP2C9.3). Drug Metab. Pharmacokinet. 36, 100364 (2021).

    Marsh, A., Casey-Green, K., Probert, F., et al. Simvastatin sodium salt and fluvastatin interact with human gap junction gamma-3 protein. PLoS One 11(2), e0148266 (2016).

    McNeish, A.J., Jimenez-Altayo, F., Cottrell, G.S., et al. Statins and selective inhibition of Rho kinase protect small conductance calcium-activated potassium channel function (KCa2.3) in cerebral arteries. PLoS One 7(10), e46735 (2012).