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Substrate Report for: Simvastatin

Simvastatin is a lipid-lowering agent derived synthetically from a fermentation product of the fungus Aspergillus terreus. Hydrolyzed in vivo to an active metabolite, simvastatin competitively inhibits hepatic hydroxymethyl-glutaryl coenzyme A (HMG-CoA) reductase, the enzyme which catalyzes the conversion of HMG-CoA to mevalonate, a key step in cholesterol synthesis. This agent lowers plasma cholesterol and lipoprotein levels, and modulates immune responses by suppressing MHC II (major histocompatibility complex II) on interferon gamma-stimulated, antigen-presenting cells such as human vascular endothelial cells. Simvastatin is a prodrug hydrolysed by carboxylesterases. Simvastatin is a substrate of PON1, CES1b, PON3 and CES1c



General
Type: Drug, Not A/B H target, Naphthalen
Chemical_Nomenclature: [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
Canonical SMILES: CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)C
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
InChIKey: RYMZZMVNJRMUDD-HGQWONQESA-N
Other name(s): Zocor ; Synvinolin ; Sinvacor ; Denan
MW: 418.57
Formula: C25H38O5
CAS_number: 79902-63-9
PubChem: 54454
IUPHAR:
Wikipedia:

Target families
Simvastatin ligand of proteins in family: Carb_B_Chordata
No structure

Protein target

References
Search PubMed for references concerning: Simvastatin
    Title: Role of esterase mediated hydrolysis of simvastatin in human and rat blood and its impact on pharmacokinetic profiles of simvastatin and its active metabolite in rat
    Li Z, Zhang J, Zhang Y, Zuo Z
    Ref: J Pharm Biomed Anal, 168:13, 2019 : PubMed

            

    Title: Simvastatin requires activation in accessory cells to modulate T-cell responses in asthma and COPD
    Knobloch J, Yakin Y, Korber S, Grensemann B, Bendella Z, Boyaci N, Gallert WJ, Yanik SD, Jungck D, Koch A
    Ref: European Journal of Pharmacology, 788:294, 2016 : PubMed

            

    Title: Carboxylesterase 1-Mediated Drug-Drug Interactions between Clopidogrel and Simvastatin
    Wang X, Zhu HJ, Markowitz JS
    Ref: Biol Pharm Bull, 38:292, 2015 : PubMed