Moracizine

Moracizine
Clinical data
Trade names	Ethmozine
Synonyms	Moricizine (USAN US)
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a601214
Pregnancy; category	B (U.S.);
ATC code	C01BG01 (WHO) ;
Pharmacokinetic data
Bioavailability	34–38%
Protein binding	95%
Elimination half-life	3–4 hours (healthy volunteers), 6–13 hours (cardiac disease)
Identifiers
	IUPAC name ethyl [10-(3-morpholin-4-ylpropanoyl)-10H-phenothiazin-2-yl]carbamate;
CAS Number	31883-05-3 ;
PubChem CID	34633;
IUPHAR/BPS	7244;
DrugBank	DB00680 ;
ChemSpider	31872 ;
UNII	2GT1D0TMX1;
KEGG	D05077 ;
ChEBI	CHEBI:6997 ;
ChEMBL	CHEMBL1075 ;
ECHA InfoCard	100.046.216
Chemical and physical data
Formula	C22H25N3O4S
Molar mass	427.518 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(OCC)Nc2cc1N(c3c(Sc1cc2)cccc3)C(=O)CCN4CCOCC4;
	InChI InChI=1S/C22H25N3O4S/c1-2-29-22(27)23-16-7-8-20-18(15-16)25(17-5-3-4-6-19(17)30-20)21(26)9-10-24-11-13-28-14-12-24/h3-8,15H,2,9-14H2,1H3,(H,23,27) ; Key:FUBVWMNBEHXPSU-UHFFFAOYSA-N ;
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Moracizine^[1] or moricizine and sold under the 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It was used for the prophylaxis and treatment of serious and life-threatening ventricular arrhythmias,^[3] but was withdrawn in 2007 for commercial reasons.^[4]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

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. Compared with disopyramide and quinidine, moracizine was equally or more effective in suppressing premature ventricular contractions, couplets, and nonsustained ventricular tachycardia.

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

References

↑ "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). World Health Organization. 2009. p. 103.
↑ 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.
↑ British National Formulary (59th ed.). British Medical Journal Publishing Group, Pharmaceutical Press. 2010.
↑ "Shire Announces Ethmozine will be Available until December 31, 2007". Heart Rhythm Society.
↑ Cardiac Arrhythmia Suppression Trial II Investigators (1992). "Effect of the Antiarrhythmic Agent Moricizine on Survival after Myocardial Infarction". New England Journal of Medicine. 327 (4): 227–233. doi:10.1056/NEJM199207233270403. PMID 1377359.

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[1] "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). 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.

[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] Cardiac Arrhythmia Suppression Trial II Investigators (1992). "Effect of the Antiarrhythmic Agent Moricizine on Survival after Myocardial Infarction". New England Journal of Medicine. 327 (4): 227–233. doi:10.1056/NEJM199207233270403. PMID 1377359.