| Identification | Back Directory | [Name]
MORACIZINE HYDROCHLORIDE | [CAS]
29560-58-5 | [Synonyms]
en313
etmozin
ethmosine
ethmozine
MORACIZINE HCL
MORACIZINE HYDROCHLORIDE
Moricizine hydrochloride
Moricizine Hydrochloride (250 mg)
Moricizine Hydrochloride (1446950)
ethyl10-(3-morpholinopropionyl)phenothiazine-2-carbamatehydrochloride
ethyletherof10-(beta-morpholylpropionyl)phenthiazinecarbaminoacidhydroch
[10-[3-(4-morpholinyl)-1-oxopropyl]-10h-phenothiazin-2-yl]-carbamicacieth
phenothiazine-2-carbamicacid,10-(3-morpholinopropionyl)-,ethylester,hydroc
10-(3-Morpholinopropionyl)-10H-phenothiazin-2-yl carbaminoic acid, ethyl esterhydrochloride | [Molecular Formula]
C22H26ClN3O4S | [MDL Number]
MFCD00329917 | [MOL File]
29560-58-5.mol | [Molecular Weight]
463.98 |
| Chemical Properties | Back Directory | [Melting point ]
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-] | [EPA Substance Registry System]
Moricizine hydrochloride (29560-58-5) |
| Safety Data | Back Directory | [WGK Germany ]
WGK 1 | [TSCA ]
TSCA listed | [HS Code ]
2934302700 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 in mice, rats (mg/kg): 36, 12 i.v.; in mice (mg/kg): 131 i.p. (Kaverina) |
| Hazard Information | Back Directory | [Description]
Moricizine 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. | [Originator]
Acad. Med. Sci. (USSR) | [Uses]
Cardiac depressant (anti-arrhythmic). | [Uses]
Moricizine 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. | [Definition]
ChEBI: A hydrochloride salt obtained from equimola amounts of moricizine and hydrogen chloride. | [Manufacturing Process]
To a solution of 10 g (0.035 mole) of ethyl phenthiazine-2-carbamate in 30 ml
of anhydrous toluene is added dropwise 5.3 g (0.042 mole) of 3-
chloropropionyl chloride, and the mixture is refluxed at 110-120°C for 4
hours, followed by clarifying the mixture with activated carbon and cooling it
to room temperature. A precipitate of ethyl 10-(3-chloropropionyl)-
phenthiazine-2-carbamate is removed by filtration. The yield is 10.2 g (77.5%
of the theoretical amount), M.P. 169-170°C.
10.2 g of ethyl 10-(3-chloropropionyl)-phenthiazine-2-carbamate ester is
dissolved in 50 ml of toluene, 4.72 g of morpholine is added thereto, and the
mixture is refluxed at 110-120°C for a period of 3 hours. A precipitate of
morpholine hydrochloride is removed by filtration, and the filtrate is washed
with water in order to remove excess morpholine, followed by acidulating with
dilute hydrochloric acid to adjust the pH of the filtrate is adjusted at 3. The
acidic aqueous layer is separated, clarified by treatment with activated carbon
and made alkaline until the pH equals 8-9. This procedure yields the free base
of ethyl 10-(β-morpholylpropionyl)-phenthiazine-2-carbamate, M.P. 156-
157°C.
The free base thus obtained is extracted with toluene, the extract is dried over
magnesium sulphate and to the anhydrous toluene solution is added an
anhydrous ethereal solution of hydrogen chloride until the precipitation of the
target compound is complete. This procedure yields 9.53 g (76.2% of the
theoretical amount) of ethyl 10-(β-morpholylpropionyl)-phenthiazine-2-
carbamate hydrochloride. After recrystallization from dichloroethane, the
target compound melts at 189°C. (decomp.). | [Brand name]
Ethmozine (Shire). | [Therapeutic Function]
Antiarrhythmic |
|
| Company Name: |
Energy Chemical
|
| Telephone: |
021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
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