Chemistry:Ethacizine

Short description: Chemical compound

Ethacizine

Clinical data
Trade names	Ethacizin
AHFS/Drugs.com	International Drug Names
ATC code	C01BC09 (WHO)
Legal status
Legal status	Prescription only (Russia )
Pharmacokinetic data
Bioavailability	~40% (oral)
Protein binding	90%
Metabolism	Extensive hepatic
Elimination half-life	2.5 hours
Identifiers
IUPAC name ethyl N-[10-[3-(diethylamino)propanoyl]phenothiazin-2-yl]carbamate
CAS Number	33414-33-4 Y
PubChem CID	107841
ChemSpider	96982 Y
UNII	FE5SPV1Z6G
KEGG	D10503 Y
ChEMBL	ChEMBL1997663 N
Chemical and physical data
Formula	C22H27N3O3S
Molar mass	413.54 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCC(=O)N1C2=CC=CC=C2SC3=C1C=C(C=C3)NC(=O)OCC
InChI InChI=1S/C22H27N3O3S/c1-4-24(5-2)14-13-21(26)25-17-9-7-8-10-19(17)29-20-12-11-16(15-18(20)25)23-22(27)28-6-3/h7-12,15H,4-6,13-14H2,1-3H3,(H,23,27) Y Key:PQXGNJKJMFUPPM-UHFFFAOYSA-N Y

Ethacizine (ethacyzine) is a class Ic antiarrhythmic agent, related to moracizine. It is used in Russia and some other CIS countries for the treatment of severe and/or refractory ventricular and supraventricular arrhythmias, especially those accompanied by organic heart disease. It is also indicated as a treatment of refractory tachycardia associated with Wolff–Parkinson–White syndrome.

It is manufactured under the brand name Ethacizin (Этацизин) by Latvian pharmaceutical company Olainfarm.

Synthesis

For the treatment of heart infarction:

Synthesis: Patent:

The amide formation between Phenothiazine-2-ethylcarbamate [37711-29-8] (1) and 3-Chloropropionyl chloride [625-36-5] (2) gives ethyl N-[10-(3-chloropropanoyl)phenothiazin-2-yl]carbamate [119407-03-3] [34749-22-9] (3). Displacement of the remaining ω-halogen by diethylamine (4) then completes the synthesis of ethacizine (5).