Simvastatin

Simvastatin

Cayman Chemical Item Number 10010344

MK 733 (CAS 79902-63-9)

Simvastatin (CAS 79902-63-9)

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 K_i 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%

λ_max

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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Simvastatin (CAS 79902-63-9)

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Simvastatin

Simvastatin (CAS 79902-63-9)

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