Ethacizine
- C01BC09 (WHO)
- Prescription only (RU)
- ethyl N-[10-[3-(diethylamino)propanoyl]phenothiazin-2-yl]carbamate
- 33414-33-4 Y
- 107841
- 96982 Y
- FE5SPV1Z6G
- D10503 Y
- ChEMBL1997663 N
- DTXSID50187057
- Interactive image
- CCN(CC)CCC(=O)N1C2=CC=CC=C2SC3=C1C=C(C=C3)NC(=O)OCC
- 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.[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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class I (Na+ channel blockers) |
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class III (Phase 3→, K+ channel blockers) | |||||||
class IV (Phase 4→, Ca2+ channel blockers) |
and antagonists
class II (Phase 4→, β blockers) |
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A1 agonist | |
M2 | |
α receptors |
Na+/ K+-ATPase |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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