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Simvastatin acid

Names

[ CAS No. ]:
121009-77-6

[ Name ]:
Simvastatin acid

[Synonym ]:
simvasterol
Zocord
Rechol
[14C]-Simvastatin acid
ZOCOR
[3H]-Simvastatin
7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[[2,2-dimethyl-butanoyl]oxy]-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid
Lipex
Denan
Lipovas
simvastatin acid
Eucor
[14C]-Simvastatin
Simcor
simvastatin hydroxy acid
[3H]-Simvastatin acid

Biological Activity

[Description]:

Simvastatin acid (Tenivastatin) is an orally active HMG-CoA reductase (HMGCR) inhibitor. Simvastatin acid can reduce cholesterol synthesis and lower blood cholesterol levels[1]. Simvastatin acid shows anti-proliferation activities against cancer cells and induces apoptosis[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Research Areas >> Cardiovascular Disease
Signaling Pathways >> Metabolic Enzyme/Protease >> HMG-CoA Reductase (HMGCR)

[Target]

HMG-CoA reductase[1]


[In Vitro]

Simvastatin acid (32 and 64 μM; 24, 48, and 72 h) inhibits tumor cell growth, arrests in the G0/G1 phase[2]. Simvastatin acid (32 and 64 μM; 48 h) induces apoptosis in HepG2 and Huh7 cells[2]. Cell Proliferation Assay[2] Cell Line: HepG2 and Huh7 cells Concentration: 32 and 64 μM Incubation Time: 24, 48, and 72 hours Result: Inhibited tumor cell growth as compared to controls (ctrl, p<0.05). Apoptosis Analysis[2] Cell Line: HepG2 and Huh7 cells Concentration: 32 and 64 μM Incubation Time: 48 hours Result: Increased early apoptosis from 9.2% in non-treated ctrl cells to 18.2% (32 μM) and 19.8% (64 μM), respectively, increased late apoptosis from 35.0% in ctrl cells to 56.9% (32 μM) and 48.0% (64 μM), respectively, in HepG2 cells. Cell Cycle Analysis[2] Cell Line: HepG2 and Huh7 cells Concentration: 32 and 64 μM Incubation Time: 24, 48, and 72 hours Result: Exhibited downregulation of CDK1, CDK2, CDK4 and cyclins D1 and E as compared to ctrl tumor cells.

[In Vivo]

Simvastatin acid (oral gavage; 15 and 30 mg/kg; once daily; 14 d) treatment attenuats oxidative damage, TNF-a and IL-6 levels, and restores itochondrial enzyme complex activities[3]. Animal Model: Male wistar rats with oxidative damage by Intrastriatal 6-OHDA administration[3] Dosage: 15 and 30 mg/kg Administration: Oral gavage; once daily; 14 days Result: Attenuated oxidative damage (reduced MDA, nitrite levels and restoration of reduced GSH) , attenuated TNF-a and IL-6 levels, and restored itochondrial enzyme complex activities as compared to 6-OHDA group.

[References]

[1]. Eduardo Filipe Oliveira, et al. HMG-CoA Reductase inhibitors: an updated review of patents of novel compounds and formulations (2011-2015). Expert Opin Ther Pat. 2016 Nov;26(11):1257-1272.

[2]. Borna Relja, et al. Simvastatin inhibits cell growth and induces apoptosis and G0/G1 cell cycle arrest in hepatic cancer cells. Int J Mol Med. 2010 Nov;26(5):735-41.

[3]. Anil Kumar, et al. Neuroprotective potential of atorvastatin and simvastatin (HMG-CoA reductase inhibitors) against 6-hydroxydopamine (6-OHDA) induced Parkinson-like symptoms. Brain Res. 2012 Aug 30;1471:13-22.

Chemical & Physical Properties

[ Density]:
1.13g/cm3

[ Boiling Point ]:
607ºC at 760mmHg

[ Molecular Formula ]:
C25H40O6

[ Molecular Weight ]:
436.58200

[ Flash Point ]:
198.2ºC

[ Exact Mass ]:
436.28200

[ PSA ]:
104.06000

[ LogP ]:
4.10570

[ Vapour Pressure ]:
2.89E-17mmHg at 25°C

[ Index of Refraction ]:
1.536

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream