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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Simvastatin

Cayman Chemical Item Number 10010344

MK 733 (CAS 79902-63-9)

Simvastatin (CAS 79902-63-9)

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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 Simvastatin is a competitive inhibitor of HMG-CoA reductase with a Ki value of 0.12 nM for the hydrolyzed, open ring form of the molecule.2 Simvastatin is marketed under the trade name Zocor™ and is often prescribed in combination with ezetimibe (Zetia) to treat dyslipidemia. This drug combination is known commercially as Vytorin™ or Inegy™. After 18 days of treatment with simvastatin in dogs at a dose of 8 mg/kg per day, plasma cholesterol levels were reduced by 33%.3 Simvastatin also suppresses TNF-induced NF-κB activation (IC50 ~ 13 µM), which potentiates apoptosis in human myeloid leukemia cells and thus may be 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 Corsini, A., Maggi, F.M., and Catapano, A.L. Pharmacology of competitive inhibitors of HMG-CoA reductase. Pharmacol Res 31(1) 9-27 (1995).

3 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 S11-S14 (1991).

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).

Synonyms
  • MK 733
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
Molecular Formula C25H38O5
Formula Weight 418.6
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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CCC(C)​(C)​C(=O)​OC1CC(C)​C=C2C=C[C@H]​(C)​[C@H]​(CC[C@@H]​3CC(O)​CC(=O)​O3)​C12

Background Reading

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).

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

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

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 S11-S14 (1991).

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Size Price Quantity Subtotal
5 mg $18.00 $0.00
10 mg $32.00 $0.00
25 mg $72.00 $0.00
50 mg $108.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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