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Literature summary extracted from

  • Bratton, L.D.; Auerbach, B.; Choi, C.; Dillon, L.; Hanselman, J.C.; Larsen, S.D.; Lu, G.; Olsen, K.; Pfefferkorn, J.A.; Robertson, A.; Sekerke, C.; Trivedi, B.K.; Unangst, P.C.
    Discovery of pyrrole-based hepatoselective ligands as potent inhibitors of HMG-CoA reductase (2007), Bioorg. Med. Chem., 15, 5576-5589.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.1.1.34 drug development inhibitors of HMG-CoA reductase for reducing low density lipoprotein cholesterol in the treatment of hypercholesterolemia Rattus norvegicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.34 (3R,5R)-7-(1-ethyl-3-(4-fluorophenyl)-4-methyl-5-[(5-methyl-pyrazin-2-ylmethyl)-carbamoyl]-1H-pyrrol-2-yl)-3,5-dihydroxy-heptanoic acid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-4-methyl-5-phenylcarbamoyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-5-(4-methoxybenzylcarbamoyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-5-(4-methoxycarbonyl-benzylcarbamoyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[3-(4-fluoro-phenyl)-1-isopropyl-5-phenylcarbamoyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[3-(4-fluorophenyl)-1-isopropyl-4-phenyl-5-phenylcarbamoyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[5-(4-carboxy-benzylcarbamoyl)-ethyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid disodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[5-benzylcarbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[5-carbamoyl-1-ethyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[5-carbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid sodium salt
-
 Rattus norvegicus
1.1.1.34 (3R,5R)-7-[5-cyano-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
-
 Rattus norvegicus
1.1.1.34 7-[5-ethylcarbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
-
 Rattus norvegicus
1.1.1.34 cerivastatin
-
 Rattus norvegicus
1.1.1.34 additional information discovery, synthesis, and optimization of substituted pyrrole-based hepatoselective ligands as potent inhibitors of HMG-CoA reductase for reducing low density lipoprotein cholesterol (LDL-c) in the treatment of hypercholesterolemia Rattus norvegicus
1.1.1.34 rosuvastatin
-
 Rattus norvegicus
1.1.1.34 simvastatin
-
 Rattus norvegicus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.1.1.34 microsome
-
 Rattus norvegicus
-
-

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.34 hydroxymethylglutaryl-CoA + NADPH + H+ Rattus norvegicus
-
 mevalonate + NADP+ + CoA
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.34 Rattus norvegicus
-
 male Charles River Sprague-Dawley rats
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.34 hepatocyte
-
 Rattus norvegicus
-
1.1.1.34 L-6 myoblast cell
-
 Rattus norvegicus
-
1.1.1.34 liver
-
 Rattus norvegicus
-
1.1.1.34 muscle
-
 Rattus norvegicus
-
1.1.1.34 myocyte
-
 Rattus norvegicus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.34 hydroxymethylglutaryl-CoA + NADPH + H+
-
 Rattus norvegicus mevalonate + NADP+ + CoA
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.1.1.34 HMG-CoA reductase
-
 Rattus norvegicus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.34 37
-
-
 Rattus norvegicus

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.34 NADPH
-
 Rattus norvegicus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.1.1.34 0.00000011
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[5-(4-carboxy-benzylcarbamoyl)-ethyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid disodium salt
1.1.1.34 0.00000015
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[5-benzylcarbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid
1.1.1.34 0.00000017
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[3-(4-fluoro-phenyl)-1-isopropyl-5-phenylcarbamoyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
1.1.1.34 0.00000023
-
 37°C, hepatocytes Rattus norvegicus rosuvastatin
1.1.1.34 0.00000024
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-5-(4-methoxybenzylcarbamoyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
1.1.1.34 0.00000028
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-5-(4-methoxycarbonyl-benzylcarbamoyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
1.1.1.34 0.00000029
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[1-ethyl-3-(4-fluorophenyl)-4-methyl-5-phenylcarbamoyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
1.1.1.34 0.00000035
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-(1-ethyl-3-(4-fluorophenyl)-4-methyl-5-[(5-methyl-pyrazin-2-ylmethyl)-carbamoyl]-1H-pyrrol-2-yl)-3,5-dihydroxy-heptanoic acid sodium salt
1.1.1.34 0.00000043
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[3-(4-fluorophenyl)-1-isopropyl-4-phenyl-5-phenylcarbamoyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt
1.1.1.34 0.0000013
-
 37°C, hepatocytes Rattus norvegicus simvastatin
1.1.1.34 0.0000017
-
 37°C, hepatocytes Rattus norvegicus cerivastatin
1.1.1.34 0.0000021
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[5-cyano-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
1.1.1.34 0.0000049
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[5-carbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxyheptanoicacid sodium salt
1.1.1.34 0.0000051
-
 37°C, hepatocytes Rattus norvegicus 7-[5-ethylcarbamoyl-3-(4-fluoro-phenyl)-1-isopropyl-4-pyridin-2-yl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoicacid sodium salt
1.1.1.34 0.000032
-
 37°C, hepatocytes Rattus norvegicus (3R,5R)-7-[5-carbamoyl-1-ethyl-3-(4-fluorophenyl)-4-methyl-1H-pyrrol-2-yl]-3,5-dihydroxy-heptanoic acid sodium salt