Ethacizine

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| verifiedrevid =

| IUPAC_name = ethyl N-[10-[3-(diethylamino)propanoyl]phenothiazin-2-yl]carbamate

| image = Ethacizine.svg

| width = 220

| tradename = Ethacizin

| Drugs.com = {{drugs.com|international|ethacizine}}

| pregnancy_category =

| legal_status = Prescription only (RU)

| bioavailability = ~40% (oral){{cite web|title=Этацизин (Ethacyzin) Prescribing Information. VIDAL Drug Compendium|url=http://www.vidal.ru/poisk_preparatov/ethacyzin__17943.htm|accessdate=5 February 2014|language=Russian}}

| protein_bound = 90%

| metabolism = Extensive hepatic

| elimination_half-life = 2.5 hours

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 33414-33-4

| CAS_supplemental =

| ATC_prefix = C01

| ATC_suffix = BC09

| ATC_supplemental =

| PubChem = 107841

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 96982

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = FE5SPV1Z6G

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG =D10503

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1997663

| C=22 | H=27 | N=3 | O=3 | S=1

| smiles = CCN(CC)CCC(=O)N1C2=CC=CC=C2SC3=C1C=C(C=C3)NC(=O)OCC

| StdInChI = 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)

| StdInChIKey = PQXGNJKJMFUPPM-UHFFFAOYSA-N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

Ethacizine (ethacyzine) is a class Ic antiarrhythmic agent, related to moracizine.{{cite journal | vauthors = Kaverina NV, Sokolov SF | title = Pharmacology and clinical use of a new group of antiarrhythmic drugs: derivatives of tricyclic nitrogen-containing systems | journal = Pharmacological Research | volume = 25 | issue = 3 | pages = 217–25 | date = April 1992 | pmid = 1518765 | doi = 10.1016/s1043-6618(05)80070-2 }} 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.

It is manufactured under the brand name Ethacizin (Этацизин) by Latvian pharmaceutical company Olainfarm.{{cite web|title=Этацизин—4DOKTOR.RU Drug Information Handbook|url=http://www.4doktor.ru/default.aspx?drugid=33705|accessdate=5 February 2014|language=Russian}}

Synthesis

For the treatment of heart infarction:E I Chazov, et al. {{Cite patent|SE|8302120}} (1984).E I Chazov, {{Cite patent|FR|2544985}} (to 1985 to INST FARMAKOLOGII AKADEMII M).

File:Ethacizine synthesis.svg

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).

See also

References