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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:51:58 UTC
Update Date2017-12-07 04:30:05 UTC
HMDB IDHMDB0041991
Secondary Accession Numbers
  • HMDB41991
Metabolite Identification
Common NamePitavastatin
DescriptionMost statins are metabolised in part by one or more hepatic cytochrome P450 enzymes, leading to an increased potential for drug interactions and problems with certain foods (such as grapefruit juice). Pitavastatin appears to be a substrate of CYP2C9, and not CYP3A4 (which is a common source of interactions in other statins). As a result, pitavastatin is less likely to interact with drugs that are metabolized via CYP3A4, which might be important for elderly patients who need to take multiple medicines. Pitavastatin (usually as a calcium salt) is a member of the medication class of statins, marketed in the United States under the trade name Livalo. Like other statins, it is an inhibitor of HMG-CoA reductase, the enzyme that catalyses the first step of cholesterol synthesis. It has been available in Japan since 2003, and is being marketed under licence in South Korea and in India. It is likely that pitavastatin will be approved for use in hypercholesterolaemia (elevated levels of cholesterol in the blood) and for the prevention of cardiovascular disease outside South and Southeast Asia as well.
Structure
Thumb
Synonyms
ValueSource
NK 104ChEBI
NK-104ChEBI
PitavastatiaChEBI
PitavastatineChEBI
PitavastatinumChEBI
Pitavastatin calciumHMDB
ItavastatinMeSH
NisvastatinMeSH
Chemical FormulaC25H24FNO4
Average Molecular Weight421.4608
Monoisotopic Molecular Weight421.168936466
IUPAC Name(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoic acid
Traditional Namepitavastatin
CAS Registry Number147511-69-1
SMILES
O[C@H](C[C@H](O)\C=C\C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N=C1C1CC1)CC(O)=O
InChI Identifier
InChI=1S/C25H24FNO4/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-18(28)13-19(29)14-23(30)31/h1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31)/b12-11+/t18-,19-/m1/s1
InChI KeyVGYFMXBACGZSIL-MCBHFWOFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassPhenylquinolines
Direct ParentPhenylquinolines
Alternative Parents
Substituents
  • Phenylquinoline
  • 4-phenylpyridine
  • Medium-chain hydroxy acid
  • 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
  • Pyridine
  • Unsaturated fatty acid
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP3.75ALOGPS
logP2.92ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)4.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.74 m³·mol⁻¹ChemAxon
Polarizability43.76 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-8149500000-7a528b44f7ab848deb48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fr-9313086000-f40b861f3306cfd0bb1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0006-0095000000-052cbc222b6600555667View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uki-0017900000-2273fa72cf719982fbb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-3039200000-1c1e957b8189d1f5d719View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-9166000000-2131d127f06f3bf43554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2006900000-04f6a2452db80a3d1aa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-7109200000-ca0e31aa0813197a4a1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9123000000-3e730deb6619e525d76bView in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08860
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445604
KEGG Compound IDC13334
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPitavastatin
METLIN IDNot Available
PubChem Compound5282452
PDB IDNot Available
ChEBI ID32020
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available