Moracizine

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Moracizine
Moricizin.svg
Systematic (IUPAC) name
ethyl [10-(3-morpholin-4-ylpropanoyl)-10H-phenothiazin-2-yl]carbamate
Clinical data
Trade names Ethmozine
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a601214
Pregnancy cat.
Legal status
?
Pharmacokinetic data
Bioavailability 34–38%
Protein binding 95%
Half-life 3–4 hours (healthy volunteers), 6–13 hours (cardiac disease)
Identifiers
CAS number 31883-05-3 YesY
ATC code C01BG01
PubChem CID 34633
DrugBank DB00680
ChemSpider 31872 YesY
UNII 2GT1D0TMX1 YesY
KEGG D05077 YesY
ChEBI CHEBI:6997 YesY
ChEMBL CHEMBL1075 YesY
Chemical data
Formula C22H25N3O4S 
Mol. mass 427.518 g/mol
 N (what is this?)  (verify)

Moracizine (INN,[1] or moricizine, trade name Ethmozine) is an antiarrhythmic of class IC.[2] It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias,[3] but was withdrawn in 2007 for commercial reasons.[4]

Pharmacology[edit]

Moracizine, a phenothiazine derivative, undergoes extensive first-pass metabolism and is also extensively metabolized after it has entered the circulation. It may have pharmacologically active metabolites. A clinical study has shown that moracizine is slightly less effective than encainide or flecainide in suppressing ventricular premature depolarizations.[citation needed] Compared with disopyramide and quinidine, moracizine was equally or more effective in suppressing premature ventricular contractions, couplets, and nonsustained ventricular tachycardia.[citation needed]

In the Cardiac Arrhythmia Suppression Trial (CAST), a large study testing the influence of antiarrhythmics on mortality, showed a non-significant increase of mortality from 5.4 to 7.2% under moracizine. This is in line with other class IC antiarrhythmics.[5]

Synthesis[edit]

Moricizine synthesis: A Gritsenko, J Vikhlyaev, Z Senova, O Ulyanova, S Zhuravlev, N Kaverina; U.S. Patent 3,740,395

References[edit]

  1. ^ "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances". World Health Organization. 2009. p. 103. 
  2. ^ Ahmmed, G. U.; Hisatome, I.; Kurata, Y.; Makita, N.; Tanaka, Y.; Tanaka, H.; Okamura, T.; Sonoyama, K.; Furuse, Y.; Kato, M.; Yamamoto, Y.; Ogura, K.; Shimoyama, M.; Miake, J.; Sasaki, N.; Ogino, K.; Igawa, O.; Yoshida, A.; Shigemasa, C. (2002). "Analysis of moricizine block of sodium current in isolated guinea-pig atrial myocytes. Atrioventricular difference of moricizine block". Vascular pharmacology 38 (3): 131–141. doi:10.1016/S1537-1891(02)00213-6. PMID 12402511.  edit
  3. ^ British National Formulary (59th ed.). British Medical Journal Publishing Group, Pharmaceutical Press. 2010. 
  4. ^ "Shire Announces Ethmozine will be Available until December 31, 2007". Heart Rhythm Society. 
  5. ^ "Effect of the Antiarrhythmic Agent Moricizine on Survival after Myocardial Infarction". New England Journal of Medicine 327 (4): 227–233. 1992. doi:10.1056/NEJM199207233270403. PMID 1377359.  edit