Jump to content

Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

(Top) 1 Synthesis 2 References

Ethacizine

●Latviešu ●Русский ●Српски / srpski ●Srpskohrvatski / српскохрватски ●Українська ●Tiếng Việt Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version Appearance From Wikipedia, the free encyclopedia

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)^[1]
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
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)^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[edit]

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

Synthesis:^[6] Patent:^[7]

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).

Antiarrhythmic agents (C01B)

Channel blockers

class I
(Na⁺ channel blockers)

class Ia (Phase 0→ and Phase 3→)

class Ib (Phase 3←)

IV
- Lidocaine^#
enteral

class Ic (Phase 0→)

class III
(Phase 3→, K⁺ channel blockers)

class IV
(Phase 4→, Ca²⁺ channel blockers)

Diltiazem
Verapamil^#

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

^#WHO-EM

^‡Withdrawn from market

Clinical trials:

^†Phase III
^§Never to phase III

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Ethacizine&oldid=1134006973" Categories: ●Antiarrhythmic agents ●Carbamates ●Sodium channel blockers ●Phenothiazines ●Diethylamino compounds ●Drugs in the Soviet Union ●Cardiovascular system drug stubs Hidden categories: ●CS1 Russian-language sources (ru) ●Articles with short description ●Short description matches Wikidata ●Drugs with non-standard legal status ●Articles with changed EBI identifier ●Chemical pages without DrugBank identifier ●Articles containing unverified chemical infoboxes ●All stub articles ●This page was last edited on 16 January 2023, at 15:21 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view