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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:23 UTC
HMDB IDHMDB0014818
Secondary Accession Numbers
  • HMDB14818
Metabolite Identification
Common NameMoricizine
DescriptionMoricizine, also known as moracizina or ethmozin, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. Moricizine is only found in individuals that have used or taken this drug. Moricizine is a drug which is used to treat irregular heartbeats (arrhythmias) and maintain a normal heart rate. Moricizine is a very strong basic compound (based on its pKa). Moricizine induces its own metabolism (it induces hepatic cytochrome P-450 activity). It is an antiarrhythmia agent used primarily for ventricular rhythm disturbances. Does not affect atrial, AV nodal, or left ventricular refractory periods and has minimal effect on ventricular repolarization (evidenced by the overall decrease in JT interval). Two metabolites may be pharmacologically active but are present in extremely small quantities. In the Vaughan Williams classification of antiarrhythmics, moricizine is considered to be a class I agent. It has less effect on the slope of phase 0 and a greater effect on action potential duration and effective refractory period than class IC agents.
Structure
Data?1582753223
Synonyms
ValueSource
[10-(3-Morpholin-4-yl-propionyl)-10H-phenothiazin-2-yl]-carbamic acid ethyl esterChEBI
EN-313ChEBI
Ethyl 10-(3-morpholinopropionyl)phenothiazine-2-carbamateChEBI
Ethyl 10-(beta-N-morpholinylpropionyl)phenothiazine-2-carbamateChEBI
MoracizinaChEBI
MoracizineChEBI
MoracizinumChEBI
[10-(3-Morpholin-4-yl-propionyl)-10H-phenothiazin-2-yl]-carbamate ethyl esterGenerator
Ethyl 10-(3-morpholinopropionyl)phenothiazine-2-carbamic acidGenerator
Ethyl 10-(b-N-morpholinylpropionyl)phenothiazine-2-carbamateGenerator
Ethyl 10-(b-N-morpholinylpropionyl)phenothiazine-2-carbamic acidGenerator
Ethyl 10-(beta-N-morpholinylpropionyl)phenothiazine-2-carbamic acidGenerator
Ethyl 10-(β-N-morpholinylpropionyl)phenothiazine-2-carbamateGenerator
Ethyl 10-(β-N-morpholinylpropionyl)phenothiazine-2-carbamic acidGenerator
Hydrochloride, moricizineHMDB
MoracizinHMDB
EthmozinHMDB
EthmozineHMDB
EtmozinHMDB
Moricizine hydrochlorideHMDB
Chemical FormulaC22H25N3O4S
Average Molecular Weight427.517
Monoisotopic Molecular Weight427.156576993
IUPAC Nameethyl N-{10-[3-(morpholin-4-yl)propanoyl]-10H-phenothiazin-2-yl}carbamate
Traditional Namemoricizine
CAS Registry Number31883-05-3
SMILES
CCOC(=O)NC1=CC2=C(SC3=CC=CC=C3N2C(=O)CCN2CCOCC2)C=C1
InChI Identifier
InChI=1S/C22H25N3O4S/c1-2-29-22(27)23-16-7-8-20-18(15-16)25(17-5-3-4-6-19(17)30-20)21(26)9-10-24-11-13-28-14-12-24/h3-8,15H,2,9-14H2,1H3,(H,23,27)
InChI KeyFUBVWMNBEHXPSU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Beta amino acid or derivatives
  • Diarylthioether
  • Aryl thioether
  • Para-thiazine
  • Morpholine
  • Oxazinane
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Thioether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156 - 157 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.034 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP3.04ALOGPS
logP3.07ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.9ChemAxon
pKa (Strongest Basic)6.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.11 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.88 m³·mol⁻¹ChemAxon
Polarizability45.27 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0inc-3369000000-87e2c170cd925eacc845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2248900000-a5de342702a58418f8c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3549100000-266e9a246027e8b95b07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap1-4961000000-43e99c8298fe409d473eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2009200000-0195601e60bc1db3b119Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0040-4094000000-6715c6954f74a1830093Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9012000000-a2460f3acdec07cd438fSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00680 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00680 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00680
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31872
KEGG Compound IDC07743
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMoricizine
METLIN IDNot Available
PubChem Compound34633
PDB IDNot Available
ChEBI ID6997
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Ahmmed GU, Hisatome I, Kurata Y, Makita N, Tanaka Y, Tanaka H, Okamura T, Sonoyama K, Furuse Y, Kato M, Yamamoto Y, Ogura K, Shimoyama M, Miake J, Sasaki N, Ogino K, Igawa O, Yoshida A, Shigemasa C: Analysis of moricizine block of sodium current in isolated guinea-pig atrial myocytes. Atrioventricular difference of moricizine block. Vascul Pharmacol. 2002 Mar;38(3):131-41. [PubMed:12402511 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]