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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:55 UTC
Update Date2017-12-07 04:29:29 UTC
HMDB IDHMDB0041918
Secondary Accession Numbers
  • HMDB41918
Metabolite Identification
Common NameLorcainide
DescriptionCardiac dysrhythmia is a heart rate disorder that manifests as an altered cardiac rhythm. It results from either abnormal pacemaker activity or a disturbance in impulse propagation, or both. Arrhythmias can be caused by various conditions including ischemia, hypoxia, pH disruptions, B adrenergic activation, drug interactions or the presence of diseased tissue. These events can trigger the development of ectopic pacemaker in the heart, which emit abnormal impulses at random times during the cardiac cycle. An arrhythmia can present itself as either bradycardia or tachycardia. Untreated arrhythmias may progress to atrial fibrillation or ventricular fibrillation. Treatment is aimed at normalizing cardiac rhythm by altering ion flow across the membrane. Antiarrhythmic agents can reduce arrhythmia related symptoms such as palpitations or syncope; however, they often have a narrow therapeutic index and can also be proarrhythmic. Lorcainide (Lorcainide hydrochloride) is a Class 1c antiarrhythmic agent that is used to help restore normal heart rhythm and conduction in patients with premature ventricular contractions, ventricular tachycardiac and Wolff-Parkinson-White syndrome. Lorcainide was developed by Janssen Pharmaceutica (Belgium) in 1968 under the commercial name Remivox and is designated by code numbers R-15889 or Ro 13-1042/001. It has a half-life of 8.9 +- 2.3 hrs which may be prolonged to 66 hrs in people with cardiac disease. Wolff-Parkinson-White syndrome (WPW) is a pre-excitation syndrome in which individuals are predisposed to supraventricular tachyarrhythmias (rapid and irregular heart beats). People with this condition have an extra or accessory atrioventricular conduction pathway that causes re-entry tachycardia. WPW is characterized by a short PR interval (<0.12 second) and a prolonged, slurred QRS complex (>0.12 seconds).
Structure
Thumb
Synonyms
ValueSource
4'-chloro-N-(1-Isopropyl-4-piperidinyl)-2-phenylacetanilideHMDB
Lorcainide hydrochlorideHMDB
4'-chloro-N-(1-Isopropyl-4-piperidyl)-2-phenylacetanilideMeSH
LorcainidMeSH
Lorcainide monohydrochlorideMeSH
Chemical FormulaC22H27ClN2O
Average Molecular Weight370.916
Monoisotopic Molecular Weight370.181191203
IUPAC NameN-(4-chlorophenyl)-2-phenyl-N-[1-(propan-2-yl)piperidin-4-yl]acetamide
Traditional Namelorcainide
CAS Registry Number59729-31-6
SMILES
CC(C)N1CCC(CC1)N(C(=O)CC1=CC=CC=C1)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C22H27ClN2O/c1-17(2)24-14-12-21(13-15-24)25(20-10-8-19(23)9-11-20)22(26)16-18-6-4-3-5-7-18/h3-11,17,21H,12-16H2,1-2H3
InChI KeyXHOJAWVAWFHGHL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • Anilide
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Piperidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point263 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.85Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0075 g/LALOGPS
logP4.59ALOGPS
logP4.31ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.18 m³·mol⁻¹ChemAxon
Polarizability40.93 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0006-9440000000-15d6038071c0a1a4e316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0139000000-ec7eb24fe97b967c6429View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9564000000-63b422a8539ceca953feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9330000000-4afb33871c22bc8594afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-924353820d8763a293e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-1397000000-3ad328a0ef23044619b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdu-5980000000-b547e89cdc5a157ff158View 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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID39116
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLorcainide
METLIN IDNot Available
PubChem Compound42884
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available