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Record Information
StatusDetected and Quantified
Creation Date2006-10-16 12:25:20 UTC
Update Date2020-11-09 23:17:36 UTC
Secondary Accession Numbers
  • HMDB05006
Metabolite Identification
Common NameAtorvastatin
DescriptionAtorvastatin 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.
(R-(R*,r*))-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acidChEBI
7-[2-(4-FLUORO-phenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoIC ACIDChEBI
(R-(R*,r*))-2-(4-fluorophenyl)-b,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acidGenerator
(R-(R*,r*))-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acidGenerator
(R-(R*,r*))-2-(4-fluorophenyl)-b,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoic acidHMDB
Atorvastatin acidHMDB
Atorvastatin calciumHMDB
Anhydrous, atorvastatin calciumHMDB
Calcium hydrate, atorvastatinHMDB
Calcium trihydrate, atorvastatinHMDB
Calcium, atorvastatinHMDB
Hydrate, atorvastatin calciumHMDB
Atorvastatin calcium trihydrateHMDB
Atorvastatin, calcium saltHMDB
Trihydrate, atorvastatin calciumHMDB
Atorvastatin calcium anhydrousHMDB
Calcium anhydrous, atorvastatinHMDB
Calcium salt atorvastatinHMDB
Atorvastatin calcium hydrateHMDB
(3R,5R)-7-(2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acidMeSH
Chemical FormulaC33H35FN2O5
Average Molecular Weight558.6398
Monoisotopic Molecular Weight558.253000445
IUPAC Name(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid
Traditional Nameatorvastatin
CAS Registry Number134523-00-5
InChI Identifier
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
Sub ClassSubstituted pyrroles
Direct ParentDiphenylpyrroles
Alternative Parents
  • 2,3-diphenylpyrrole
  • Aromatic anilide
  • Medium-chain hydroxy acid
  • Pyrrole-3-carboxamide
  • Pyrrole-3-carboxylic acid or derivatives
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Fluorobenzene
  • Halobenzene
  • Halogenated fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physiological effect

Health effect:



Biological location:


Naturally occurring process:


Environmental role:

Industrial application:

Physical Properties
Experimental Properties
Melting Point159.1 - 190.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00063 g/LALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area111.79 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity158.2 m³·mol⁻¹ChemAxon
Polarizability59.45 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-5100950000-b76d194b9679e4b35417Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-082i-5320938000-c1984e6bf123460d28acSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000090000-ae5c999b091a2bc93933Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000190000-dd563e18b1f0f74aadd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfs-0007960000-cb66a18d2f0a687261baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-0059000000-0942bc1e35434cd7d0d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0093000000-f42ba46820a3cf3295c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udj-0005910000-b09ba5f3b86948c7f3cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000090000-6f297ca79ae1761aac33Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-1009300000-9479520f395dcdd585e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0092000000-9b561b8d35c3bdc5e46aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-3aad87273e7f9942a50fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01t9-1090000000-3f0efff41ebdb5320ce4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-2090000000-0227638704b90c4249d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000090000-65c729c6734f6533c431Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-1009300000-9122e4479d8c0c32bb0dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0092000000-22d639a8882509e1bcdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-30a0198165bae85fa258Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01t9-1090000000-cb3feea45f5280f05c37Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-2090000000-8db2f70b373277f143c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udj-0005910000-a63c845ca248d958068dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-1000190000-5418613834968283e5a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-3101940000-2906ea9feb05e2fc0cfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8438900000-f5abfdde8ad50c98b16eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1000290000-949ba837ddf712ee8558Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4s-6203960000-9adcd151fdfe389c7d00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9158000000-7b64ce4c34d6e9fae2b8Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Liver
  • Platelet
Normal Concentrations
BloodDetected and Quantified0.010 +/- 0.0044 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.22 +/- 0.16 uMAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
  1. Kruger PS, Freir NM, Venkatesh B, Robertson TA, Roberts MS, Jones M: A preliminary study of atorvastatin plasma concentrations in critically ill patients with sepsis. Intensive Care Med. 2009 Apr;35(4):717-21. doi: 10.1007/s00134-008-1358-3. Epub 2008 Nov 26. [PubMed:19034423 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB01076
Phenol Explorer Compound IDNot Available
FooDB IDFDB023579
KNApSAcK IDNot Available
Chemspider ID54810
KEGG Compound IDC06834
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAtorvastatin
PubChem Compound60823
PDB IDNot Available
ChEBI ID39548
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000466
Synthesis ReferenceRoth, Bruce David. Preparation of anticholesteremic (R-(R*R*))-2-(4-fluorophenyl)-b, d-dihydroxy-5-(1-methylethyl-3-phenyl-4((phenylamino)carbonyl)-1H-pyrrolyl-1-heptanoic acid, its lactone form and salts thereof. Eur. Pat. Appl. (1991), 18 pp. CODEN: EPXXDW EP 409281 A1 19910123 CAN 115:29107 AN 1991:429107
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Taylor PJ, Kubler PA, Lynch SV, Allen J, Butler M, Pillans PI: Effect of atorvastatin on cyclosporine pharmacokinetics in liver transplant recipients. Ann Pharmacother. 2004 Feb;38(2):205-8. Epub 2003 Dec 19. [PubMed:14742751 ]
  2. Funatsu T, Suzuki K, Goto M, Arai Y, Kakuta H, Tanaka H, Yasuda S, Ida M, Nishijima S, Miyata K: Prolonged inhibition of cholesterol synthesis by atorvastatin inhibits apo B-100 and triglyceride secretion from HepG2 cells. Atherosclerosis. 2001 Jul;157(1):107-15. [PubMed:11427209 ]
  3. Tannous M, Cheung R, Vignini A, Mutus B: Atorvastatin increases ecNOS levels in human platelets of hyperlipidemic subjects. Thromb Haemost. 1999 Nov;82(5):1390-4. [PubMed:10595624 ]
  4. Naoumova RP, Dunn S, Rallidis L, Abu-Muhana O, Neuwirth C, Rendell NB, Taylor GW, Thompson GR: Prolonged inhibition of cholesterol synthesis explains the efficacy of atorvastatin. J Lipid Res. 1997 Jul;38(7):1496-500. [PubMed:9254075 ]
  5. Izar MC: [Hypolipidemic treatment under special conditions: posttransplant and/or immunosuppressive therapy]. Arq Bras Cardiol. 2005 Oct;85 Suppl 5:50-7. Epub 2006 Jan 2. [PubMed:16400400 ]
  6. Hwang YS, Tsai WC, Lu YH, Lin CC, Chen YF: Effect of atorvastatin on the expression of CD40 ligand and P-selectin on platelets in patients with hypercholesterolemia. Am J Cardiol. 2004 Aug 1;94(3):364-6. [PubMed:15276107 ]
  7. Bruni F, Pasqui AL, Pastorelli M, Bova G, Cercignani M, Palazzuoli A, Sawamura T, Gioffre WR, Auteri A, Puccetti L: Different effect of statins on platelet oxidized-LDL receptor (CD36 and LOX-1) expression in hypercholesterolemic subjects. Clin Appl Thromb Hemost. 2005 Oct;11(4):417-28. [PubMed:16244767 ]
  8. Fenton JW 2nd, Brezniak DV, Ofosu FA, Shen GX, Jacobson JR, Garcia JG: Statins and thrombin. Curr Drug Targets Cardiovasc Haematol Disord. 2005 Apr;5(2):115-20. [PubMed:15853752 ]
  9. Pokrovskaia EV, Vaulin NA, Gratsianskii NA, Averkov OV, Deev AD: [Markers of inflammation and platelet aggregation in patients with non ST elevation acute coronary syndrome treated with atorvastatin or pravastatin]. Kardiologiia. 2003;43(1):7-18. [PubMed:12891281 ]
  10. Funatsu T, Kakuta H, Tanaka H, Arai Y, Suzuki K, Miyata K: [Atorvastatin (Lipitor): a review of its pharmacological and clinical profile]. Nihon Yakurigaku Zasshi. 2001 Jan;117(1):65-76. [PubMed:11233299 ]
  11. Tousoulis D, Bosinakou E, Kotsopoulou M, Antoniades C, Katsi V, Stefanadis C: Effects of early administration of atorvastatin treatment on thrombotic process in normocholesterolemic patients with unstable angina. Int J Cardiol. 2006 Jan 26;106(3):333-7. [PubMed:16337041 ]
  12. Malinowski JM: Atorvastatin: a hydroxymethylglutaryl-coenzyme A reductase inhibitor. Am J Health Syst Pharm. 1998 Nov 1;55(21):2253-67; quiz 2302-3. [PubMed:9825877 ]

Only showing the first 10 proteins. There are 17 proteins in total.


General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in serine-type endopeptidase inhibitor activity
Specific function:
This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, and protein C. Its rapid interaction with TPA may function as a major control point in the regulation of fibrinolysis
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in chemokine activity
Specific function:
Chemotactic factor that attracts monocytes and basophils but not neutrophils or eosinophils. Augments monocyte anti-tumor activity. Has been implicated in the pathogenesis of diseases characterized by monocytic infiltrates, like psoriasis, rheumatoid arthritis or atherosclerosis. May be involved in the recruitment of monocytes into the arterial wall during the disease process of atherosclerosis
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in GTP binding
Specific function:
Regulates a signal transduction pathway linking plasma membrane receptors to the assembly of focal adhesions and actin stress fibers. Serves as a target for the yopT cysteine peptidase from Yersinia pestis, vector of the plague, and Yersinia pseudotuberculosis, which causes gastrointestinal disorders. May be an activator of PLCE1. Activated by ARHGEF2, which promotes the exchange of GDP for GTP
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in tumor necrosis factor receptor binding
Specific function:
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:
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Molecular weight:
General function:
Involved in choline binding
Specific function:
Displays several functions associated with host defense:it promotes agglutination, bacterial capsular swelling, phagocytosis and complement fixation through its calcium-dependent binding to phosphorylcholine. Can interact with DNA and histones and may scavenge nuclear material released from damaged circulating cells
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in lipid transporter activity
Specific function:
Apolipoprotein B is a major protein constituent of chylomicrons (apo B-48), LDL (apo B-100) and VLDL (apo B-100). Apo B-100 functions as a recognition signal for the cellular binding and internalization of LDL particles by the apoB/E receptor
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in growth factor activity
Specific function:
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of blood vessels. Binds to the FLT1/VEGFR1 and KDR/VEGFR2 receptors, heparan sulfate and heparin. NRP1/Neuropilin-1 binds isoforms VEGF-165 and VEGF-145. Isoform VEGF165B binds to KDR but does not activate downstream signaling pathways, does not activate angiogenesis and inhibits tumor growth
Gene Name:
Uniprot ID:
Molecular weight:

Only showing the first 10 proteins. There are 17 proteins in total.