| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-10-14 21:18:31 UTC |
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| Update Date | 2016-10-28 10:03:33 UTC |
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| Accession Number | CHEM003934 |
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| Identification |
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| Common Name | Atorvastatin |
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| Class | Small Molecule |
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| Description | Atorvastatin (Lipitor) is a member of the drug class known as statins. It is used for lowering cholesterol. Atorvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase, the rate-determining enzyme in cholesterol biosynthesis via the mevalonate pathway. HMG-CoA reductase catalyzes the conversion of HMG-CoA to mevalonate. Atorvastatin acts primarily in the liver. Decreased hepatic cholesterol levels increases hepatic uptake of cholesterol and reduces plasma cholesterol levels. |
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| Contaminant Sources | - FooDB Chemicals
- STOFF IDENT Compounds
- Suspected Compounds
- Suspected Compounds - Waste Water
- T3DB toxins
- ToxCast & Tox21 Chemicals
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| Contaminant Type | - Anticholesteremic Agent
- Drug
- Hydroxymethylglutaryl-CoA Reductase Inhibitor
- Metabolite
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C33H34FN2O5 |
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| Average Molecular Mass | 557.632 g/mol |
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| Monoisotopic Mass | 557.245 g/mol |
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| CAS Registry Number | 134523-00-5 |
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| IUPAC Name | 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate |
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| Traditional Name | 7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoate |
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| SMILES | CC(C)C1=C(C(=O)NC2=CC=CC=C2)C(=C(N1CCC(O)CC(O)CC([O-])=O)C1=CC=C(F)C=C1)C1=CC=CC=C1 |
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| InChI Identifier | 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)/p-1 |
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| InChI Key | XUKUURHRXDUEBC-UHFFFAOYSA-M |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenol ethers |
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| Sub Class | Aminophenyl ethers |
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| Direct Parent | Aminophenyl ethers |
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| Alternative Parents | |
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| Substituents | - Aminophenyl ether
- Methoxyaniline
- Phenoxy compound
- Anisole
- Aniline or substituted anilines
- Methoxybenzene
- Alkyl aryl ether
- Monocyclic benzene moiety
- Ether
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Amine
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Endogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | 159.2-160.7 °C | | Boiling Point | Not Available | | Solubility | Sodium salt soluble in water, 20.4 ug/mL (pH 2.1), 1.23 mg/mL (pH 6.0) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Toxicity Profile |
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| Route of Exposure | Atorvastatin is rapidly absorbed after oral administration with maximum plasma concentrations achieved in 1 to 2 hours. The absolute bioavailability of atorvastatin (parent drug) is approximately 14% and the systemic availability of HMG-CoA reductase inhibitory activity is approximately 30%. The low systemic bioavailability is due to presystemic clearance by gastrointestinal mucosa and first-pass metabolism in the liver. |
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| Mechanism of Toxicity | Atorvastatin selectively and competitively inhibits the hepatic enzyme HMG-CoA reductase. As HMG-CoA reductase is responsible for converting HMG-CoA to mevalonate in the cholesterol biosynthesis pathway, this results in a subsequent decrease in hepatic cholesterol levels. Decreased hepatic cholesterol levels stimulates upregulation of hepatic LDL-C receptors which increases hepatic uptake of LDL-C and reduces serum LDL-C concentrations. |
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| Metabolism | Atorvastatin is extensively metabolized to ortho- and parahydroxylated derivatives and various beta-oxidation products. In vitro inhibition of HMG-CoA reductase by ortho- and parahydroxylated metabolites is equivalent to that of atorvastatin. Approximately 70% of circulating inhibitory activity for HMG-CoA reductase is attributed to active metabolites. CYP3A4 is also involved in the metabolism of atorvastatin. |
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| Toxicity Values | Generally well-tolerated. Side effects may include myalgia, constipation, asthenia, abdominal pain, and nausea. Other possible side effects include myotoxicity (myopathy, myositis, rhabdomyolysis) and hepatotoxicity. To avoid toxicity in Asian patients, lower doses should be considered. |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | May be used as primary prevention in individuals with multiple risk factors for coronary heart disease (CHD) and as secondary prevention in individuals with CHD to reduce the risk of myocardial infarction (MI), stroke, angina, and revascularization procedures. May be used to reduce the risk of cardiovascular events in patients with acute coronary syndrome (ACS). May be used in the treatment of primary hypercholesterolemia and mixed dyslipidemia, homozygous familial hypercholesterolemia, primary dysbetalipoproteinemia, and/or hypertriglyeridemia as an adjunct to dietary therapy to decrease serum total and low-density lipoprotein cholesterol (LDL-C), apolipoprotein B (apoB), and triglyceride concentrations, while increasing high-density lipoprotein cholesterol (HDL-C) levels. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Atorvastatin |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 4636594 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Zlatko Pflaum, “Process for the preparation of amorphous atorvastatin.” U.S. Patent US20020183527, issued December 05, 2002. |
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| MSDS | Not Available |
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| General References | Not Available |
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