Trademarks: Zocor
Molecular Formula: C25H38O5
CAS Registry Number: 79902-63-9
CAS Name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
Molecular Weight: 418.566
SMILES: [H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)C(C)(C)CC
InChI Key: RYMZZMVNJRMUDD-HGQWONQESA-N
InChI: InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
Activity: CARDIOVASCULAR DRUGS, Treatment of Lipoprotein Disorders, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, HMG-CoA Reductase Inhibitors
Status: Launched 1992
Originator: Merck
Simvastatin is an active synthetic analogue of Lovastatin. Most of the synthetic processes start with either Lovastatin or it's derivatives. Here are important ones:
Simvastatin semi-synthesis: Org Proc Res Dev 1999, 3(6), 476-479
Simvastatin semi-synthesis: Scheme 1 (J Org Chem 1991, 56(16), 4929-4932) (Not favoured as final yield is only 48%. Moreover, Lovastatin appears as major impurity with the final product)
Simvastatin semi-synthesis: Scheme 2 (J Org Chem 1991, 56(16), 4929-4932) (Yield of 91%; commerically preferred route)
References:
1. Thaper, R. K.; et. al. A Cost-Efficient Synthesis of Simvastatin via High-Conversion Methylation of an Alkoxide Ester Enolate. Org Proc Res Dev 1999, 3(6), 476-479.
2. Tang, Y.; et. al. Efficient Synthesis of Simvastatin by Use of Whole-Cell Biocatalysis. Appl Environ Microbiol 2007, 73(7), 2054-2060.
3. Askin, D.; et. al. Synthesis of synvinolin: extremely high conversion alkylation of an ester enolate. J Org Chem 1991, 56(16), 4929-4932.
4. Todd, P. A.; et. al. Simvastatin. A review of its pharmacological properties and therapeutic potential in hypercholesterolaemia. Drugs 1990, 40(4), 583-607. (activity)
5. Liu, Z.; et. al. Simvastatin Inhibits Renal Cancer Cell Growth and Metastasis via AKT/mTOR, ERK and JAK2/STAT3 Pathway. PLoS One 2013, 8(5), e62823. (antitumor activity)
