Lovastatin

Cayman Chemical Item Number 10010338

(CAS 75330-75-5)

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Description

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

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-κB pathway. Biochem Pharmacol 75 907-913 (2008).

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
Formulation A crystalline solid
Purity ≥98%
λmax 238 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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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
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​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
InCHI Key
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PCZOHLXUXFIOCF-BXMDZJJMSA-N

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Size Price Quantity Subtotal
5 mg $20.00 $0.00
10 mg $30.00 $0.00
50 mg $70.00 $0.00
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Pricing updated 2015-03-27. Prices are subject to change without notice.

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