Ethacizine

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-[10-[3-(diethylamino)propanoyl]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−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) ; Key:PQXGNJKJMFUPPM-UHFFFAOYSA-N ;

Ethacizine (ethacyzine) is a class Ic antiarrhythmic agent, related to moracizine.^[2] 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.^[1]

It is manufactured under the brand name Ethacizin (Этацизин) by Latvian pharmaceutical company Olainfarm.^[3]

Synthesis

For the treatment of heart infarction:^[4]^[5]

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).

References

^ ^a ^b "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).

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[PI-1] "Этацизин (Ethacyzin) Prescribing Information. VIDAL Drug Compendium" (in Russian). Retrieved 5 February 2014.

[pmid1518765-2] 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.

[3] "Этацизин—4DOKTOR.RU Drug Information Handbook" (in Russian). Retrieved 5 February 2014.

[4] E I Chazov, et al. SE 8302120 (1984).

[5] E I Chazov, FR 2544985 (to 1985 to INST FARMAKOLOGII AKADEMII M).

[6] Gritsenko, A. N.; Skoldinov, A. P. (1986). "Ethacizine and its metabolites". Pharmaceutical Chemistry Journal. 20 (4): 279–282. doi:10.1007/BF00758818.

[7] Evgeny Ivanovich Chazov, et al. GB 2139211 (1984 to NII FARMAKOL AKAD MED).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Synthesis

See also

References