Lorajmine

Lorajmine
Systematic (IUPAC) name

(17R,21β)-ajmalan-17,21-diol 17-chloroacetate OR (1R,9R,10S,13R,14R,16S,18S)-13-ethyl-8-methyl-14-hydroxy-8,15-diazahexacyclo [14.2.1.0^1,9.0^2,7.0^10,15.0^12,17]nonadeca-2(7),3,5-triene-18-yl chloroacetate
Identifiers
CAS Number	47562-08-3
ATC code	C01BA12
PubChem	CID 76957773
ChemSpider	16735878^Y
UNII	F96VX65849^Y
ChEMBL	CHEMBL2111031
Chemical data
Formula	C₂₂H₂₇ClN₂O₃
Molar mass	402.914 g/mol
SMILES CCC1C2CC3C4C5(CC(C2C5C(=O)OCCl)N3C1O)C6=CC=CC=C6N4C
InChI InChI=1S/C22H27ClN2O3/c1-3-11-12-8-15-19-22(13-6-4-5-7-14(13)24(19)2)9-16(25(15)21(11)27)18(12)20(22)28-17(26)10-23/h4-7,11-12,15-16,18-21,27H,3,8-10H2,1-2H3/t11-,12-,15-,16-,18?,19-,20+,21+,22+/m0/s1^Y Key:LAHDERDHXJFFJU-KBFYUGGWSA-N^Y
(verify)

Lorajmine (17-monochloroacetylajmaline) is a drug that is a potent sodium channel blocker (more specifically, a class Ia antiarrhythmic agent) that was used for treating arrhythmia.^[1]^[2] It is derived from ajmaline, an alkaloid from the roots of Rauwolfia serpentina, by synthetically adding a chloroacetate residue.

References

Antiarrhythmic agents (C01B)

Channel blockers

class I
(Na⁺ channel blockers)

class Ia (Phase 0→ and Phase 3→)	Ajmaline Disopyramide Lorajmine Prajmaline Procainamide^# Quinidine^# Sparteine

class Ib (Phase 3←)	IV (Lidocaine^#) enteral (Aprindine Mexiletine Tocainide)

class Ic (Phase 0→)	Encainide^‡ Ethacizine Flecainide Indecainide^‡ Lorcainide Moracizine^‡ Propafenone

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 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	Digoxin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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