moracizine   Click here for help

GtoPdb Ligand ID: 7244

Synonyms: EN-313 | Ethmozine® | moricizine
Approved drug
moracizine is an approved drug (FDA (1990))
Compound class: Synthetic organic
Comment: Moracizine is a phenothiazine derivative class Ic antiarrhythmic drug. Marketing by the original manufacturer has been discontinued.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 99.9
Molecular weight 427.16
XLogP 2.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCOC(=Nc1ccc2c(c1)N(C(=O)CCN1CCOCC1)c1c(S2)cccc1)O
Isomeric SMILES CCOC(=Nc1ccc2c(c1)N(C(=O)CCN1CCOCC1)c1c(S2)cccc1)O
InChI 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 Key FUBVWMNBEHXPSU-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Moracizine is used to treat severe cardiac arrhythmias. However, this drug has been withdrawn from use in the US, but other national approval agencies may continue to grant marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug stabilises the cardiac membrane by binding to sodium channels, and decreasing permeability to Na+ ions. This blocks initiation and conductance of nerve impulses. ChEMBL report that this drug acts by blocking sodium channel α subunits. The genes and proteins SNC1A-SNC11A are listed in this database in the Voltage-gated sodium channels section. In vitro guinea-pig studies are reported in [1].
External links Click here for help
For extended ADME data see the following:

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