Pilsicainide (CHEM019141)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:51:14 UTC
Update Date2016-11-09 01:15:56 UTC
Accession NumberCHEM019141
Identification
Common NamePilsicainide
ClassSmall Molecule
DescriptionA secondary carboxamide resulting from the formal condensation of the amino group of 2,6-dimethylaniline with the carboxy group of (tetrahydro-1H-pyrrolizin-7a(5H)-yl)acetic acid. It is a sodium channel blocker which is used as an antiarrhythmic drug for the management of atrial tachyarrhythmias in Japan.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PilsicainidaChEBI
PilsicainidumChEBI
PilzicainideChEBI
Pilsicainide HCLChEMBL
N-(2,6-Dimethylphenyl)-8-pyrrolizidineacetamide hydrochlorideMeSH
PilsicainideMeSH
1H-Pyrrolizine-7a(5H)-acetamide, N-(2,6-dimethylphenyl)tetrahydro-, hydrochloride (1:1)MeSH
1H-Pyrrolizine-7a(5H)-acetamide, N-(2,6-dimethylphenyl)tetrahydro-, hydrochloride hemihydrateMeSH
Pilsicainide hydrochlorideMeSH
Pilsicainide hydrochloride hemihydrateMeSH
Pilsicainide hydrochloride hydrateMeSH
Tetrahydro-1H-pyrrolizine-7a(5H)-aceto-2',6'-xylidideMeSH
Chemical FormulaC17H24N2O
Average Molecular Mass272.392 g/mol
Monoisotopic Mass272.189 g/mol
CAS Registry Number88069-67-4
IUPAC NameN-(2,6-dimethylphenyl)-2-(hexahydro-1H-pyrrolizin-7a-yl)ethanimidic acid
Traditional NameN-(2,6-dimethylphenyl)-2-(hexahydropyrrolizin-7a-yl)ethanimidic acid
SMILESCC1=CC=CC(C)=C1N=C(O)CC12CCCN1CCC2
InChI IdentifierInChI=1S/C17H24N2O/c1-13-6-3-7-14(2)16(13)18-15(20)12-17-8-4-10-19(17)11-5-9-17/h3,6-7H,4-5,8-12H2,1-2H3,(H,18,20)
InChI KeyBCQTVJKBTWGHCX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Anilide
  • M-xylene
  • Xylene
  • Pyrrolizidine
  • N-arylamide
  • Monocyclic benzene moiety
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.09 g/LALOGPS
logP2.75ALOGPS
logP1.16ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)10.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.53 m³·mol⁻¹ChemAxon
Polarizability30.22 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02hc-6920000000-506478b6320963870fd4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0970000000-1f370142e6fba5527e66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-87b0c1a7e27fee9716b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-7900000000-4faca1ba67e2081250e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0290000000-803be3bfcd2c4d57948fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0940000000-59ae0aeffc201389864eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-1900000000-db411616dfcdf51344ccSpectrum
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 IDDB12712
HMDB IDHMDB0256549
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPilsicainide
Chemspider ID4654
ChEBI ID135127
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15988120
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16723783
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17112301
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18642016
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20205487
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20590641
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21869589
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22333385
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22466963
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24480637
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24653743
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27920831
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28364267
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=28607619
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=28765762
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30028738
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=6089001