Ethacizine - Misplaced Pages

Chemical compound Pharmaceutical compound

Ethacizine
Clinical data

Trade names	Ethacizin
AHFS/Drugs.com	International Drug Names
ATC code	C01BC09 (WHO)
Legal status
Legal status	Prescription only (RU)
Pharmacokinetic data
Bioavailability	~40% (oral)
Protein binding	90%
Metabolism	Extensive hepatic
Elimination half-life	2.5 hours
Identifiers
IUPAC name ethyl N-phenothiazin-2-yl]carbamate
CAS Number	33414-33-4
PubChem CID	107841
ChemSpider	96982
UNII	FE5SPV1Z6G
KEGG	D10503
ChEMBL	ChEMBL1997663
CompTox Dashboard (EPA)	DTXSID50187057
Chemical and physical data
Formula	C₂₂H₂₇N₃O₃S
Molar mass	413.54 g·mol
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) Key:PQXGNJKJMFUPPM-UHFFFAOYSA-N

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:

The amide formation between Phenothiazine-2-ethylcarbamate (1) and 3-Chloropropionyl chloride (2) gives ethyl N-carbamate (3). Displacement of the remaining ω-halogen by diethylamine (4) then completes the synthesis of ethacizine (5).

References

^ "Этацизин (Ethacyzin) Prescribing Information. VIDAL Drug Compendium" (in Russian). Retrieved 5 February 2014.
Kaverina NV, Sokolov SF (April 1992). "Pharmacology and clinical use of a new group of antiarrhythmic drugs: derivatives of tricyclic nitrogen-containing systems". Pharmacological Research. 25 (3): 217–25. doi:10.1016/s1043-6618(05)80070-2. PMID 1518765.
"Этацизин—4DOKTOR.RU Drug Information Handbook" (in Russian). Retrieved 5 February 2014.
E I Chazov, et al. SE 8302120 (1984).
E I Chazov, FR 2544985 (to 1985 to INST FARMAKOLOGII AKADEMII M).
Gritsenko, A. N.; Skoldinov, A. P. (1986). "Ethacizine and its metabolites". Pharmaceutical Chemistry Journal. 20 (4): 279–282. doi:10.1007/BF00758818.
Evgeny Ivanovich Chazov, et al. GB 2139211 (1984 to NII FARMAKOL AKAD MED).

Antiarrhythmic agents (C01B)

Channel blockers

class I
(Na channel blockers)

class Ia (Phase 0→ and Phase 3→)	Ajmaline Disopyramide Hydroquinidine Lorajmine Prajmaline Procainamide Quinidine Sparteine
class Ib (Phase 3←)	IV Lidocaine enteral Aprindine Mexiletine Tocainide
class Ic (Phase 0→)	Encainide Ethacizine Flecainide Indecainide Lorcainide Moracizine Propafenone

class III
(Phase 3→, K channel blockers)

class IV
(Phase 4→, Ca channel blockers)

Receptor agonists
and antagonists

class II (Phase 4→, β blockers)	Nadolol Pindolol Propranolol cardioselective Acebutolol Atenolol Esmolol Landiolol Metoprolol
A₁ agonist	Adenosine Benzodiazepines Barbiturates
M₂	muscarinic antagonist: Atropine Disopyramide Quinidine muscarinic agonist: Digoxin
α receptors	Amiodarone Bretylium Quinidine Verapamil

Ion transporters

Na/ K-ATPase	Digitoxin Digoxin Ouabain

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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Categories:

Synthesis

See also

References