Basic information
- CAS
31883-05-3- Standard SMILES
CCOC(=O)Nc1ccc2c(c1)N(C(=O)CCN1CCOCC1)c1ccccc1S2- InChIKey
FUBVWMNBEHXPSU-UHFFFAOYSA-N- Molecular formula
- C22H25N3O4S
- Average molar mass
- 427.5 g/mol
- Monoisotopic mass
- 427.15657746
Overview
Moricizine is a phenothiazine substituted on the nitrogen by a 3-(morpholin-4-yl)propanoyl group, and at position 2 by an (ethoxycarbonyl)amino group. It has a role as an anti-arrhythmia drug. It is a carbamate ester, a member of phenothiazines and a member of morpholines.
Names & identifiers
- Preferred name
- Moricizine
- IUPAC
- ethyl N-[10-(3-morpholin-4-ylpropanoyl)phenothiazin-2-yl]carbamate
- English name
- Moricizine
- Molecular formula
- C22H25N3O4S
- Molecular weight
- 427.52
Names & synonyms
MORICIZINEMoracizine31883-05-3MoracizinaMoracizinumEthyl 10-(3-morpholinopropionyl)phenothiazine-2-carbamate2GT1D0TMX1EN-313 FREE BASEethyl N-{10-[3-(morpholin-4-yl)propanoyl]-10H-phenothiazin-2-yl}carbamateCarbamic acid, (10-(3-(4-morpholinyl)-1-oxopropyl)-10H-phenothiazin-2-yl)-, ethyl esterCHEBI:6997DTXSID4023335
Show more names
MoricizinTIMTEC-BB SBB005991Ethmozin：MoricizineEthyl (10-(3-Morpholinopropanoyl)-10H-phenothiazin-2-yl)carbaMateethyl N-[10-(3-morpholin-4-ylpropanoyl)phenothiazin-2-yl]carbamate10-(3-Morpholinopropionyl)phenothiazine-2-carbamic acid ethyl esterN-[10-(3-morpholinopropanoyl)phenothiazin-2-yl]carbamic acid ethyl esterN-[10-(3-Morpholinopropionyl)-10H-phenothiazin-2-yl]carbamic acid ethyl ester10-(3-Morpholinopropionyl)-10H-phenothiazin-2-yl carbaminoic acid, ethyl ester
Moracizinethyl 10-(beta-N-morpholinylpropionyl)phenothiazine-2-carbamate[10-(3-Morpholin-4-yl-propionyl)-10H-phenothiazin-2-yl]-carbamic acid ethyl esterCARBAMIC ACID, [10-[3-(4-MORPHOLINYL)-1-OXOPROPYL]-10H-PHENOTHIAZIN-2-YL]-, ETHYL ESTERethyl N-(10-(3-(morpholin-4-yl)propanoyl)-10H-phenothiazin-2-yl)carbamate(10-(3-Morpholin-4-yl-propionyl)-10H-phenothiazin-2-yl)-carbamic acid ethyl esterN-(10-(3-(morpholin-4-yl)propanoyl)-10H-phenothiazin-2-yl)ethoxycarboximidic acidN-{10-[3-(morpholin-4-yl)propanoyl]-10H-phenothiazin-2-yl}ethoxycarboximidic acid
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 96.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 601
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP
2.3
3.1
Solubility
3.39e-02 g/L
>64.1 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
156-157 °C
156 - 157 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 156 · 156-157°
- Boiling point
- 625 · 625.0±55.0 °C(Predicted)
- Density
- 1.315 · 1.315±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly), Methanol (Very Slightly)
- form
- Solid
- pka
- 6.4 · 6.4(at 25℃)
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein BindingApproximately 95%.
Pharmacodynamics
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.
Mechanism of ActionMoricizine works by inhibiting the rapid inward sodium current across myocardial cell membranes.
Biological Half-Life2 hours (range 1.5-3.5 hours).
Metabolism/Metabolites
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).
Related reactions
1 records
Compound notes
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