1.0 2011-09-21 00:31:53 UTC 2015-07-21 06:57:46 UTC FDB023579 Atorvastatin Atorvastatin (INN) is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol; Atorvastatin is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol; As with other statins, atorvastatin is a competitive inhibitor of HMG-CoA reductase. Unlike most others, however, it is a completely synthetic compound. HMG-CoA reductase catalyzes the reduction of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) to mevalonate, which is the rate-limiting step in hepatic cholesterol biosynthesis. Inhibition of the enzyme decreases de novo cholesterol synthesis, increasing expression of low-density lipoprotein receptors (LDL receptors) on hepatocytes. This increases the LDL uptake by the hepatocytes, decreasing the amount of LDL in the blood. [HMDB] (R-(R*,r*))-2-(4-fluorophenyl)-b,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoate (R-(R*,r*))-2-(4-fluorophenyl)-b,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acid (R-(R*,r*))-2-(4-fluorophenyl)-b,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoate (R-(R*,r*))-2-(4-fluorophenyl)-b,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acid (R-(R*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoate (R-(R*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acid (R-(R*,r*))-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoate (R-(R*,r*))-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acid 7-[2-(4-FLUORO-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoate 7-[2-(4-FLUORO-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoIC ACID Atorlip Atorpic Atorvastatin acid Atorvastatin calcium Atorvastatina Atorvastatine Atorvastatinum Cardyl Lipitor Liprimar C33H35FN2O5 558.6398 558.253000445 (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid atorvastatin 134523-00-5 CC(C)C1=C(C(=O)NC2=CC=CC=C2)C(=C(N1CC[C@@H](O)C[C@@H](O)CC(O)=O)C1=CC=C(F)C=C1)C1=CC=CC=C1 InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1 XUKUURHRXDUEBC-KAYWLYCHSA-N belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups. Diphenylpyrroles Organic compounds Organoheterocyclic compounds Pyrroles Substituted pyrroles Aromatic heteromonocyclic compounds Aromatic anilides Aryl fluorides Azacyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Fluorobenzenes Halogenated fatty acids Heteroaromatic compounds Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monocarboxylic acids and derivatives Organic oxides Organofluorides Organonitrogen compounds Organopnictogen compounds Pyrrole carboxamides Secondary alcohols Secondary carboxylic acid amides Vinylogous amides 2,3-diphenylpyrrole Alcohol Aromatic anilide Aromatic heteromonocyclic compound Aryl fluoride Aryl halide Azacycle Benzenoid Beta-hydroxy acid Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Fluorobenzene Halobenzene Halogenated fatty acid Heteroaromatic compound Heterocyclic fatty acid Hydrocarbon derivative Hydroxy acid Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organofluoride Organohalogen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Pyrrole-3-carboxamide Pyrrole-3-carboxylic acid or derivatives Secondary alcohol Secondary carboxylic acid amide Vinylogous amide aromatic amide dihydroxy monocarboxylic acid monofluorobenzenes pyrroles statin (synthetic) Solid logp 4.24 ALOGPS logs -5.95 ALOGPS solubility 6.30e-04 g/l ALOGPS logp 5.39 ChemAxon pka_strongest_acidic 4.33 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid ChemAxon average_mass 558.6398 ChemAxon mono_mass 558.253000445 ChemAxon smiles CC(C)C1=C(C(=O)NC2=CC=CC=C2)C(=C(N1CC[C@@H](O)C[C@@H](O)CC(O)=O)C1=CC=C(F)C=C1)C1=CC=CC=C1 ChemAxon formula C33H35FN2O5 ChemAxon inchi InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1 ChemAxon inchikey XUKUURHRXDUEBC-KAYWLYCHSA-N ChemAxon polar_surface_area 111.79 ChemAxon refractivity 158.2 ChemAxon polarizability 59.45 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18638 Specdb::CMs 38833 Specdb::CMs 281959 Specdb::CMs 342868 Specdb::CMs 342869 Specdb::CMs 342870 Specdb::CMs 342871 Specdb::CMs 342872 Specdb::CMs 342873 Specdb::CMs 342874 Specdb::CMs 342875 Specdb::CMs 342876 Specdb::CMs 342877 Specdb::CMs 342878 Specdb::CMs 342879 Specdb::CMs 342880 Specdb::CMs 342881 Specdb::CMs 342882 Specdb::CMs 342883 Specdb::CMs 342884 Specdb::CMs 342885 Specdb::CMs 342886 Specdb::CMs 342887 Specdb::CMs 342888 Specdb::CMs 342889 Specdb::MsMs 261873 Specdb::MsMs 261874 Specdb::MsMs 261875 Specdb::MsMs 281805 Specdb::MsMs 281806 Specdb::MsMs 281807 Specdb::MsMs 435396 Specdb::MsMs 435397 Specdb::MsMs 435398 Specdb::MsMs 435399 Specdb::MsMs 435400 Specdb::MsMs 436103 Specdb::MsMs 436104 Specdb::MsMs 436105 Specdb::MsMs 436106 Specdb::MsMs 436107 Specdb::MsMs 436108 Specdb::MsMs 436109 Specdb::MsMs 436110 Specdb::MsMs 436111 Specdb::MsMs 436112 Specdb::MsMs 436113 Specdb::MsMs 436114 Specdb::MsMs 436115 Specdb::MsMs 436116 HMDB05006 2910 117 #<Reference:0x000055ce32acfe30> #<Reference:0x000055ce32acfc78> #<Reference:0x000055ce32acfac0> #<Reference:0x000055ce32acf908> #<Reference:0x000055ce32acf750> #<Reference:0x000055ce32acf598> #<Reference:0x000055ce32acf3e0> #<Reference:0x000055ce32acf228> #<Reference:0x000055ce32acf070> #<Reference:0x000055ce32aceeb8> #<Reference:0x000055ce32aced00> #<Reference:0x000055ce32aceb48> 3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMGCR Angiotensinogen P01019 AGT Apolipoprotein B-100 P04114 APOB C-C motif chemokine 2 P13500 CCL2 CD40 ligand P29965 CD40LG Collagen alpha-1(XIII) chain Q5TAT6 COL13A1 Peroxisome proliferator-activated receptor alpha Q07869 PPARA Peroxisome proliferator-activated receptor gamma P37231 PPARG Plasminogen activator inhibitor 1 P05121 SERPINE1 Serum paraoxonase/arylesterase 1 P27169 PON1 Tumor necrosis factor P01375 TNF Vascular endothelial growth factor A P15692 VEGFA