117

7-[2-(4-FLUORO-PHENYL)-5-ISOPROPYL-3-PHENYL-4-PHENYLCARBAMOYL-PYRROL-1-YL]- 3,5-DIHYDROXY-HEPTANOIC ACID

Created:2001-01-17
Last modified:  2020-06-05

Find related ligands:

Chemical Details

Formal Charge0
Atom Count76
Chiral Atom Count2
Bond Count79
Aromatic Bond Count25
2D diagram of 117

Chemical Component Summary

Name7-[2-(4-FLUORO-PHENYL)-5-ISOPROPYL-3-PHENYL-4-PHENYLCARBAMOYL-PYRROL-1-YL]- 3,5-DIHYDROXY-HEPTANOIC ACID
SynonymsATORVASTATIN
Systematic Name (OpenEye OEToolkits)(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid
FormulaC33 H35 F N2 O5
Molecular Weight558.64
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(O)CC(O)CC(O)CCn2c(c(c(c2c1ccc(F)cc1)c3ccccc3)C(=O)Nc4ccccc4)C(C)C
SMILESCACTVS3.341CC(C)c1n(CC[CH](O)C[CH](O)CC(O)=O)c(c2ccc(F)cc2)c(c3ccccc3)c1C(=O)Nc4ccccc4
SMILESOpenEye OEToolkits1.5.0CC(C)c1c(c(c(n1CCC(CC(CC(=O)O)O)O)c2ccc(cc2)F)c3ccccc3)C(=O)Nc4ccccc4
Canonical SMILESCACTVS3.341 CC(C)c1n(CC[C@@H](O)C[C@@H](O)CC(O)=O)c(c2ccc(F)cc2)c(c3ccccc3)c1C(=O)Nc4ccccc4
Canonical SMILESOpenEye OEToolkits1.5.0 CC(C)c1c(c(c(n1CC[C@H](C[C@H](CC(=O)O)O)O)c2ccc(cc2)F)c3ccccc3)C(=O)Nc4ccccc4
InChIInChI1.03 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
InChIKeyInChI1.03 XUKUURHRXDUEBC-KAYWLYCHSA-N

Drug Info: DrugBank

DrugBank IDDB01076?
NameAtorvastatin
Groups approved
DescriptionAtorvastatin (Lipitor?), is a lipid-lowering drug included in the statin class of medications. By inhibiting the endogenous production of cholesterol in the liver, statins lower abnormal cholesterol and lipid levels, and ultimately reduce the risk of cardiovascular disease. More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase,[A181421] which catalyzes the conversion of HMG-CoA to mevalonic acid. This conversion is a critical metabolic reaction involved in the production of several compounds involved in lipid metabolism and transport, including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as "bad cholesterol"), and very-low-density lipoprotein (VLDL). Prescribing statins is considered standard practice for patients following any cardiovascular event, and for people who are at moderate to high risk of developing cardiovascular disease. The evidence supporting statin use, coupled with minimal side effects and long term benefits, has resulted in wide use of this medication in North America.[A181087, A181406] Atorvastatin and other statins including [lovastatin], [pravastatin], [rosuvastatin], [fluvastatin], and [simvastatin] are considered first-line treatment options for dyslipidemia.[A181087, A181406] The increasing use of this class of drugs is largely attributed to the rise in cardiovascular diseases (CVD) (such as heart attack, atherosclerosis, angina, peripheral artery disease, and stroke) in many countries.[A181084] An elevated cholesterol level (elevated low-density lipoprotein (LDL) levels in particular) is a significant risk factor for the development of CVD.[A181087,A181553] Several landmark studies demonstrate that the use of statins is associated with both a reduction in LDL levels and CVD risk.[A181090,A181093,A181096,A181427,A181475,A181538] Statins were shown to reduce the incidences of all-cause mortality, including fatal and non-fatal CVD, as well as the need for surgical revascularization or angioplasty following a heart attack.[A181087, A181406] Some evidence has shown that even for low-risk individuals (with <10% risk of a major vascular event occurring within five years) statin use leads to a 20%-22% relative reduction in the number of major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks.[A181397, A181403] Atorvastatin was first synthesized in 1985 by Dr. Bruce Roth and approved by the FDA in 1996.[T568] It is a pentasubstituted pyrrole [A177415] formed by two contrasting moieties with an achiral heterocyclic core unit and a 3,5-dihydroxypentanoyl side chain identical to its parent compound.[T571] Unlike other members of the statin group, atorvastatin is an active compound and therefore does not require activation.[A177436]
Synonyms
  • atorvastatinum
  • Atorvastatin calcium trihydrate
  • atorvastatine
  • Atorvastatin
  • atorvastatina
Brand Names
  • Amlodipine and atorvastatin
  • Atorvastatin-40
  • Atorvastatin-80
  • Nra-atorvastatin
  • Priva-atorvastatin
IndicationAtorvastatin is indicated for the treatment of several types of dyslipidemias, including primary hyperlipidemia and mixed dyslipidemia in adults, hypertriglyceridemia, primary dysbetalipoproteinemia, homozygous familial hypercholesterolemia, and heterozygous familial hypercholesterolemia in adolescent patients with failed dietary modifications.[A177397] Dyslipidemia describes an elevation of plasma cholesterol, triglycerides or both as well as to the presence of low levels of high-density lipoprotein. This condition represents an increased risk for the development of atherosclerosis.[L6025] Atorvastatin is indicated, in combination with dietary modifications, to prevent cardiovascular events in patients with cardiac risk factors and/or abnormal lipid profiles.[A177397] Atorvastatin can be used as a preventive agent for myocardial infarction, stroke, revascularization, and angina, in patients without coronary heart disease but with multiple risk factors and in patients with type 2 diabetes without coronary heart disease but multiple risk factors.[A177397] Atorvastatin may be used as a preventive agent for non-fatal myocardial infarction, fatal and non-fatal stroke, revascularization procedures, hospitalization for congestive heart failure and angina in patients with coronary heart disease.[A177397] Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD. Statin-indicated conditions include diabetes mellitus, clinical atherosclerosis (including myocardial infarction, acute coronary syndromes, stable angina, documented coronary artery disease, stroke, trans ischemic attack (TIA), documented carotid disease, peripheral artery disease, and claudication), abdominal aortic aneurysm, chronic kidney disease, and severely elevated LDL-C levels.[A181087, A181406]
Categories
  • Agents Causing Muscle Toxicity
  • Anticholesteremic Agents
  • BSEP/ABCB11 Substrates
  • Cytochrome P-450 CYP2B6 Inducers
  • Cytochrome P-450 CYP2B6 Inducers (strength unknown)
ATC-Code
  • C10BA05
  • C10BX11
  • C10BX12
  • C10BX19
  • C10BX18
CAS number134523-00-5

Drug Targets

NameTarget SequencePharmacological ActionActions
3-hydroxy-3-methylglutaryl-coenzyme A reductaseMLSRLFRMHGLFVASHPWEVIVGTVTLTICMMSMNMFTGNNKICGWNYEC...unknowninhibitor
Dipeptidyl peptidase 4MKTPWKVLLGLLGAAALVTIITVPVVLLNKGTDDATADSRKTYTLTDYLK...unknowninhibitor
Aryl hydrocarbon receptorMNSSSANITYASRKRRKPVQKTVKPIPAEGIKSNPSKRHRDRLNTELDRL...unknownagonist
Histone deacetylase 2MAYSQGGGKKKVCYYYDGDIGNYYYGQGHPMKPHRIRMTHNLLLNYGLYR...unknowninhibitor
Nuclear receptor subfamily 1 group I member 3MASREDELRNCVVCGDQATGYHFNALTCEGCKGFFRRTVSKSIGPTCPFA...unknownligand
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1487
PubChem 60823
ChEMBL CHEMBL1487
ChEBI CHEBI:39548
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