Ethmozine
Basic information
- CAS
29560-58-5- Standard SMILES
CCOC(=O)Nc1ccc2c(c1)N(C(=O)CCN1CCOCC1)c1ccccc1S2.Cl- InChIKey
GAQAKFHSULJNAK-UHFFFAOYSA-N- Molecular formula
- C22H26ClN3O4S
- Average molar mass
- 464 g/mol
- Monoisotopic mass
- 463.1332552
Overview
Moricizine Hydrochloride is the hydrochloride salt form of moricizine, a phenothiazine analog with class I antiarrhythmic activity. Moricizine hydrochloride blocks the rapid flow of sodium ions into the myocardial cell during phase 0 of the action potential. This decreases excitability, slows the impulse conduction through the atrioventricular (AV) node and depresses depolarization.
Names & identifiers
- Preferred name
- Ethmozine
- IUPAC
- ethyl N-[10-(3-morpholin-4-ylpropanoyl)phenothiazin-2-yl]carbamate;hydrochloride
- English name
- Moracizine hydrochloride
- Molecular formula
- C22H26ClN3O4S
- Molecular weight
- 463.98
Names & synonyms
MORICIZINE HYDROCHLORIDE29560-58-5EthmozineMoracizine hydrochlorideMoricizine HClEthmozinEtmozinDTXSID104778671OK3Z1ESPMoricizine hydrochloride (USP)Moricizine hydrochloride [USP]DTXCID1027766
Show more names
en313MORACIZINE HCLMoricizine Hydrochloride (250 mg)Moricizine Hydrochloride (1446950)ethyl10-(3-morpholinopropionyl)phenothiazine-2-carbamatehydrochloride
Ethyl 10-(3-morpholinopropionyl)phenothiazine-2-carbamate hydrochlorideEthyl 10-(beta-N-morpholinylpropionyl)phenothiazine-2-carbamate hydrochlorideCHEBI:60937RefChem:56790Hydrochloride, MoricizineCarbamic Acid,(10-(3-(4-morpholinyl)-1-oxopropyl)-10H-phenothiazin-2-yl)-, Ethyl Ester, MonohydrochlorideMoricizine (Hydrochloride)Ethmosine
Database identifiers
- CAS
29560-58-5- PubChem CID
- 34632
- DTXSID
Properties
Computed structural properties
- Topological polar surface area
- 96.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 601
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 189 ° · 189° (dec)
- form
- Solid
- color
- Off-white to light brown
- Major Application
- pharmaceutical (small molecule)
- InChI
- 1S/C22H25N3O4S.ClH/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);1H
- InChIKey
- GAQAKFHSULJNAK-UHFFFAOYSA-N
- SMILES
- S1c2c(cc(cc2)NC(=O)OCC)N(c4c1cccc4)C(=O)CC[N+H]3CCOCC3.[Cl-]
- FDA UNII
- 71 OK3Z1ESP · 71OK3Z1ESP
- EPA Substance Registry System
- Moricizine hydrochloride (29560-58-5)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Moricizine hydrochloride
Ambiguous-DILI-concern
5
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- WGK 1
- tsca
- TSCA listed
- hs_code
- 2934302700
- Toxicity
- LD50 in mice, rats (mg/kg): 36, 12 i.v.; in mice (mg/kg): 131 i.p. (Kaverina)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.
Uses & manufacturing
General Manufacturing InformationCarbamic acid, N-[10-[3-(4-morpholinyl)-1-oxopropyl]-10H-phenothiazin-2-yl]-, ethyl ester, hydrochloride (1:1): INACTIVE
Applications
DescriptionMoricizine hydrochloride is a phenothiazine derivative with antiarrhythmic activity developed by the Soviet Academy of Medical Sciences. It is licensed to Dupont-Sanko in a joint venture. Moricizine hydrochloride is the first drug licensed to a U.S. company by the Soviet Union and was introduced by Dupont in the U.S. in 1990 for specific use in Iife-threatening ventricular arrhythmias. This narrow indication reflects its proarrhythmic potential. The incidence of this adverse reaction, however, is lower than that of other antiarrhythmic agents.
UsesCardiac depressant (anti-arrhythmic).
UsesMoricizine Hydrochloride is a Phenothiazine (P318040) derivative, which It was used as an antiarrhythmic agent. It is also shown that moracizine is effective in suppressing premature ventricular contractions, couplets, and nonsustained ventricular tachycardia.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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