Item № 10010338
CAS № 75330-75-5
Purity ≥98%
5 mg $20.00 $0.00
10 mg $30.00 $0.00
50 mg $70.00 $0.00

Pricing updated 2016-05-03. Prices are subject to change without notice.

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Hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase is the rate-limiting enzyme in the cholesterol biosynthetic pathway and the target of the “statin” class of cholesterol-lowering drugs.1 Lovastatin is an HMG-CoA reductase inhibitor that was initially isolated from Aspergillus terreus.2 Marketed as Mevinolin™, Mevacor™, and under several other trade names, Lovastatin was the first HMG-CoA reductase inhibitor to be used in the treatment of hypercholesterolemia. It is a competitive inhibitor of HMG-CoA reductase with a Ki value of 0.6 nM for the open ring, hydroxy acid form of the molecule.3 During a three week study in dogs, a dose of 8 mg/kg per day resulted in a 29% reduction in plasma cholesterol.3 Lovastatin also suppresses TNF-induced NF-κB activation (IC50 ~ 15 µM), which potentiates apoptosis in human myeloid leukemia cells and thus, maybe useful in treating cancer.4

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Technical Information
Formal Name 2-methyl-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 75330-75-5
Molecular Formula C24H36O5
Formula Weight 404.5
Purity ≥98%
Formulation A crystalline solid
λmax 238 nm
SMILES C[C@@H]1C[C@H](OC([C@@H](C)CC)=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 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

WARNING - This product is not for human or veterinary use.

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Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
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References & Background Reading
Product Description References

1. Tobert, J.A. Lovastatin and beyond: The history of the HMG-CoA reductase inhibitors. Nat Rev Drug Discov 2 517-526 (2003).

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

3. 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).

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

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