An internal standard for the quantification of lovastatin
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Unlabeled Version(s)
10010338Lovastatin
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Lovastatin-d9

Item No. 26461

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-(methyl-d3)-butanoic acid-2,3,3,4,4,4-d6, 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
Molecular Formula
C24H27D9O5
Formula Weight
413.6
Purity
≥99% deuterated forms (d1-d9)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: slightly soluble
SMILES
C[C@@H]1C[C@H](OC(C(C([2H])([2H])[2H])([2H])C([2H])([2H])C([2H])([2H])[2H])=O)[C@@]2([H])C(C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(O3)=O)=C1
InChi Code
InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1/i1D3,3D3,5D2,15D
InChi Key
PCZOHLXUXFIOCF-LPWHJBMXSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $303

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Lovastatin-d9 is intended for use as an internal standard for the quantification of lovastatin (Item No. 10010338) by GC- or LC-MS. Lovastatin is a fungal metabolite that has been found in A. terreus and an inhibitor of HMG-CoA reductase (Ki = 1.4 nM).1,2 It is also a prodrug form of the HMG-CoA reductase inhibitor lovastatin hydroxy acid (Item No. 10010339).2 Lovastatin (8 mg/kg per day) reduces plasma cholesterol levels in dogs. It suppresses TNF-induced NF-κB activation (IC50 = ~15 µM) and potentiates apoptosis in human myeloid leukemia cells.3 Lovastatin also increases cellular lipid peroxidation and decreases glutathione peroxidase 4 (GPX4) levels in cancer cells.4 Formulations containing lovastatin have been used in the treatment of hypercholesterolemia.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Endo, A. The discovery and development of HMG-CoA reductase inhibitors. J. Lipid Res. 33(11), 1569-1582 (1992).

    2. Alberts, A.W., Chen, J., Kuron, G., et al. Mevinolin: A highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent. Proc. Natl. Acad. Sci. USA 77(7), 3957-3961 (1980).

    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. Viswanathan, V.S., Ryan, M.J., Dhruv, H.D., et al. Dependency of a therapy-resistant state of cancer cells on a lipid peroxidase pathway. Nature 547(7664), 453-457 (2017).