Cerivastatin (CHEM043960)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:29:11 UTC
Update Date2016-11-09 01:23:01 UTC
Accession NumberCHEM043960
Identification
Common NameCerivastatin
ClassSmall Molecule
DescriptionOn August 8, 2001 the U.S. Food and Drug Administration (FDA) announced that Bayer Pharmaceutical Division voluntarily withdrew Baycol from the U.S. market, due to reports of fatal Rhabdomyolysis, a severe adverse reaction from this cholesterol-lowering (lipid-lowering) product. It has also been withdrawn from the Canadian market.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoic acidChEBI
(3R,5S,6E)-7-(4-(p-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoic acidChEBI
(3R,5S,e)-7-(4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoic acidChEBI
Cerivastatin acidChEBI
(3R,5S,6E)-7-(4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-bis(1-methylethyl)-3-pyridinyl)-3,5-dihydroxy-6-heptenoateGenerator
(3R,5S,6E)-7-(4-(p-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)-3-pyridyl)-3,5-dihydroxy-6-heptenoateGenerator
(3R,5S,e)-7-(4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl)-3,5-dihydroxyhept-6-enoateGenerator
7-(4-(4-Fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyrid-3-yl)-3,5-dihydroxy-6-heptenoate sodium saltMeSH
Bay W 6228MeSH
BaycolMeSH
CertaMeSH
Cerivastatin sodiumMeSH
KazakMeSH
LipobayMeSH
RivastatinMeSH
Chemical FormulaC26H34FNO5
Average Molecular Mass459.550 g/mol
Monoisotopic Mass459.242 g/mol
CAS Registry Number145599-86-6
IUPAC Name(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
Traditional Namecerivastatin
SMILESCOCC1=C(C2=CC=C(F)C=C2)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(C(C)C)N=C1C(C)C
InChI IdentifierInChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1
InChI KeySEERZIQQUAZTOL-ANMDKAQQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPhenylpyridines
Direct ParentPhenylpyridines
Alternative Parents
Substituents
  • 4-phenylpyridine
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Heterocyclic fatty acid
  • Beta-hydroxy acid
  • Fluorobenzene
  • Halogenated fatty acid
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Benzenoid
  • Fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP4.15ALOGPS
logP2.67ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)5.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.88 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity126.82 m³·mol⁻¹ChemAxon
Polarizability50.23 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-4109800000-c584ff51808361730735Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01vo-0002900000-102e1abb000304d4bb3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022c-2009800000-ef796d571fa6ceb33110Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gm-3029200000-2ca13e234834bdc3e4cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1002900000-7c1796303bd5582434c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-7109400000-9c6452e8723677df671bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9106000000-77096145e3ccba82192dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00439
HMDB IDHMDB0061389
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCerivastatin
Chemspider IDNot Available
ChEBI ID3558
PubChem Compound ID446156
Kegg Compound IDC07966
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17560788
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18155906