Prajmaline

Prajmaline
Clinical data
ATC code	C01BA08 (WHO) ;
Identifiers
	IUPAC name (4α,16R,17R,21α)-4-propylajmalan-4-ium-17,21-diol;
CAS Number	35080-11-6 ;
PubChem CID	37042;
ChemSpider	16735977 ;
UNII	75934UD4GJ;
CompTox Dashboard (EPA)	DTXSID6023494 ;
Chemical and physical data
Formula	C23H33N2O2+
Molar mass	369.529 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@@H]6C4[C@@H]2C[C@]65c1ccccc1N(C)[C@H]5[C@@H]3C[C@H]4[C@H](CC)[C@@H](O)[N+]23CCC;
	InChI InChI=1S/C23H33N2O2/c1-4-10-25-17-11-14(13(5-2)22(25)27)19-18(25)12-23(21(19)26)15-8-6-7-9-16(15)24(3)20(17)23/h6-9,13-14,17-22,26-27H,4-5,10-12H2,1-3H3/q+1/t13-,14-,17-,18-,19?,20-,21+,22+,23+,25?/m0/s1 ; Key:UAUHEPXILIZYCU-UUEXUKNBSA-N ;
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Prajmaline (Neo-gilurythmal)^[1] is a class Ia antiarrhythmic agent^[2] which has been available since the 1970s.^[3] Class Ia drugs increase the time one action potential lasts in the heart.^[4] Prajmaline is a semi-synthetic propyl derivative of ajmaline, with a higher bioavailability than its predecessor.^[5] It acts to stop arrhythmias of the heart through a frequency-dependent block of cardiac sodium channels.^[2]

^ Janicki K, Orski J, Kakol J (1995). "[Antiarrhythmic effects of prajmaline (Neo-Gilurythmal) in stable angina pectoris in light of Holter electrocardiographic monitoring]". Przegląd Lekarski (in Polish). 52 (10): 485–491. PMID 8834838.
^ ^a ^b Weirich J, Antoni H (June 1990). "Differential analysis of the frequency-dependent effects of class 1 antiarrhythmic drugs according to periodical ligand binding: implications for antiarrhythmic and proarrhythmic efficacy". Journal of Cardiovascular Pharmacology. 15 (6): 998–1009. doi:10.1097/00005344-199006000-00019. PMID 1694924.
^ Köppel C, Oberdisse U, Heinemeyer G (1990). "Clinical course and outcome in class IC antiarrhythmic overdose". Clinical Toxicology. 28 (4): 433–44. doi:10.3109/15563659009038586. PMID 2176700.
^ Milne JR, Hellestrand KJ, Bexton RS, Burnett PJ, Debbas NM, Camm AJ (February 1984). "Class 1 antiarrhythmic drugs--characteristic electrocardiographic differences when assessed by atrial and ventricular pacing". European Heart Journal. 5 (2): 99–107. doi:10.1093/oxfordjournals.eurheartj.a061633. PMID 6723689.
^ Hinse C, Stöckigt J (July 2000). "The structure of the ring-opened N beta-propyl-ajmaline (Neo-Gilurytmal) at physiological pH is obviously responsible for its better absorption and bioavailability when compared with ajmaline (Gilurytmal)". Die Pharmazie. 55 (7): 531–2. PMID 10944783.

[Jan-1] Janicki K, Orski J, Kakol J (1995). "[Antiarrhythmic effects of prajmaline (Neo-Gilurythmal) in stable angina pectoris in light of Holter electrocardiographic monitoring]". Przegląd Lekarski (in Polish). 52 (10): 485–491. PMID 8834838.

[Weir-2] Weirich J, Antoni H (June 1990). "Differential analysis of the frequency-dependent effects of class 1 antiarrhythmic drugs according to periodical ligand binding: implications for antiarrhythmic and proarrhythmic efficacy". Journal of Cardiovascular Pharmacology. 15 (6): 998–1009. doi:10.1097/00005344-199006000-00019. PMID 1694924.

[Kopp-3] Köppel C, Oberdisse U, Heinemeyer G (1990). "Clinical course and outcome in class IC antiarrhythmic overdose". Clinical Toxicology. 28 (4): 433–44. doi:10.3109/15563659009038586. PMID 2176700.

[4] Milne JR, Hellestrand KJ, Bexton RS, Burnett PJ, Debbas NM, Camm AJ (February 1984). "Class 1 antiarrhythmic drugs--characteristic electrocardiographic differences when assessed by atrial and ventricular pacing". European Heart Journal. 5 (2): 99–107. doi:10.1093/oxfordjournals.eurheartj.a061633. PMID 6723689.

[5] Hinse C, Stöckigt J (July 2000). "The structure of the ring-opened N beta-propyl-ajmaline (Neo-Gilurytmal) at physiological pH is obviously responsible for its better absorption and bioavailability when compared with ajmaline (Gilurytmal)". Die Pharmazie. 55 (7): 531–2. PMID 10944783.

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