Ethacizine
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Trade names | Ethacizin |
AHFS/Drugs.com | International Drug Names |
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Pharmacokinetic data | |
Bioavailability | ~40% (oral)[1] |
Protein binding | 90% |
Metabolism | Extensive hepatic |
Elimination half-life | 2.5 hours |
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Chemical and physical data | |
Formula | C22H27N3O3S |
Molar mass | 413.54 g·mol−1 |
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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
[edit]For the treatment of heart infarction:[4][5]
![](http://upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Ethacizine_synthesis.svg/501px-Ethacizine_synthesis.svg.png)
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
[edit]- ^ 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).