Simvastatin ammonium salt

Names

[ Name ]:
Simvastatin ammonium salt

[Synonym ]:
Simvastatin hydroxy acid ammonium salt
Simvastatin ammonium salt
Ammonium (3R,5R)-7-{(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-1-naphthalenyl}-3,5-dihydroxyheptanoate
Simvastatin carboxylic acid ammonium salt
Tenivastatin ammonium salt
azanium,(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
1-Naphthaleneheptanoate, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-β,δ-dihydroxy-2,6-dimethyl-, ammonium salt, (βR,δR,1S,2S,6R,8S,8aR)- (1:1)

Biological Activity

[Description]:

Simvastatin ammonium is an active metabolite of simvastatin lactone mediated by CYP3A4/5 in the intestinal wall and liver (pKa=5.5). Simvastatin ammonium reduces indoxyl sulfate-mediated reactive oxygen species and modulates OATP3A1 expression in cardiomyocytes and HEK293 cells transfected with the OATP3A1 gene[1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

There is a pH-dependent effect on organic anion transporting polypeptide 3A1 (OATP3A1) uptake, with more efficient simvastatin acid uptake at pH5.5 in HEK293 cells transfected with the OATP3A1 gene. The Michaelis-Menten constant (Km) for simvastatin acid uptake by OATP3A1 was 0.017 μM and the Vmax was 0.995 fmol/min/105 cells[1].

[References]

[1]. Atilano-Roque A, et al. Characterization of simvastatin acid uptake by organic anion transporting polypeptide 3A1 (OATP3A1) and influence of drug-drug interaction. Toxicol In Vitro. 2017 Dec;45(Pt 1):158-165.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₅H₄₃NO₆

[ Molecular Weight ]:
453.612

[ Exact Mass ]:
453.309052

[ PSA ]:
107.30000

[ LogP ]:
4.42960

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H351-H360-H412

[ Precautionary Statements ]:
P201-P273-P281-P308 + P313

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

Articles

Simvastatin decreases steroid production in the H295R cell line and decreases steroids and FSH in female rats.

Reprod. Toxicol. 58 , 174-83, (2015)

Endocrine modulating effects of Simvastatin (SV) and its metabolite, Simvastatin β-hydroxy acid (SVA), were investigated in H295R cells and in female Sprague-Dawley (SPRD) rats. H295R cells were expos...