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31883-05-3 molecular structure
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ethyl N-{10-[3-(morpholin-4-yl)propanoyl]-10H-phenothiazin-2-yl}carbamate

ChemBase ID: 562
Molecular Formular: C22H25N3O4S
Molecular Mass: 427.5166
Monoisotopic Mass: 427.1565773
SMILES and InChIs

SMILES:
S1c2c(N(C(=O)CCN3CCOCC3)c3c1cccc3)cc(NC(=O)OCC)cc2
Canonical SMILES:
CCOC(=O)Nc1ccc2c(c1)N(C(=O)CCN1CCOCC1)c1c(S2)cccc1
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)
InChIKey:
FUBVWMNBEHXPSU-UHFFFAOYSA-N

Cite this record

CBID:562 http://www.chembase.cn/molecule-562.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
ethyl N-{10-[3-(morpholin-4-yl)propanoyl]-10H-phenothiazin-2-yl}carbamate
IUPAC Traditional name
moricizine
Brand Name
Ethmozine
Synonyms
Moracizina [INN-Spanish]
Moracizinum [INN-Latin]
Moracizine
Moricizine
CAS Number
31883-05-3
PubChem SID
160964025
46509072
PubChem CID
34633

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00680 external link
PubChem 34633 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.896781  H Acceptors
H Donor LogD (pH = 5.5) 1.8161392 
LogD (pH = 7.4) 2.9875028  Log P 3.0723045 
Molar Refractivity 118.8787 cm3 Polarizability 45.214973 Å3
Polar Surface Area 71.11 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.04  LOG S -4.1 
Solubility (Water) 3.39e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
0.457 mg/L expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00680 external link
Item Information
Drug Groups approved
Description An antiarrhythmia agent used primarily for ventricular rhythm disturbances. [PubChem]
Indication Used to treat irregular heartbeats (arrhythmias) and maintain a normal heart rate.
Pharmacology Moricizine is used to treat irregular heartbeats (arrhythmias) and to maintain a normal heart rate. It acts on the heart muscle to improve the heart's rhythm. Moricizine has potent local anesthetic activity and membrane stabilizing effect. Decreases excitability, conduction velocity, and automaticity as a result of slowed atrioventricular (AV) nodal and His-Purkinje conduction. Decreases the action potential duration (APD) in Purkinje fibers; also decreases the effective refractory period (ERP) but to a lesser extent than the APD, so the ERP/APD ratio is increased. Decreases the maxiumum rate of Phase 0 depolarization (V max ), but does not affect action potential amplitude or maximum diastolic potential. 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). Has no effect on sinoatrial (SA) nodal or intra-atrial conduction and only minimal effect on sinus cycle length and sinus node recovery time. In the Vaughan Williams classification of antiarrhythmics, moricizine is considered to be a class I agent. It has properties of class IA, IB, and IC agents but does not clearly belong to any of the three subclasses. 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.
Toxicity Symptoms of overdose include vomiting, unconsciousness, and severe low blood pressure.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic and extensive, to at least 26 metabolites, none accounting for as much as 1% of the administered dose. Two metabolites may be pharmacologically active but are present in extremely small quantities. Moricizine induces its own metabolism (it induces hepatic cytochrome P-450 activity).
Absorption Well absorbed, absorption is complete within 2 to 3 hours. Significant first-pass metabolism results in an absolute bioavailability of approximately 38%. Administration within 30 minutes after a meal slows the rate, but does not affect the extent of absorption, although peak plasma concentrations are reduced.
Half Life 2 hours (range 1.5-3.5 hours).
Protein Binding Approximately 95%.
Elimination Less than 1% of orally administered Ethmozine? is excreted unchanged in the urine. Approximately 56% of the administered dose is excreted in the feces and 39% is excreted in the urine.
Distribution * 300 L
External Links
Wikipedia
Drugs.com

REFERENCES

REFERENCES

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PATENTS

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