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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26N2O2
Molecular Weight 326.4326
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AJMALINE

SMILES

[H][C@@]12N(C)C3=C(C=CC=C3)[C@]14C[C@H]5[C@@H]([C@H]4O)[C@@]6([H])C[C@]2([H])N5[C@H](O)[C@H]6CC

InChI

InChIKey=CJDRUOGAGYHKKD-RQBLFBSQSA-N
InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16-,17-,18+,19+,20+/m0/s1

HIDE SMILES / InChI

Description

Ajmaline, (also known by trade names Gilurytmal, Ritmos, and Aritmina) is an alkaloid found in the root of Rauwolfia serpentina, among other plant sources. It is a class Ia antiarrhythmic agent that apparently acts by changing the shape and threshold of cardiac action potentials. The class I antiarrhythmic agents interfere with the sodium channel. A class IA agent lengthens the action potential (right shift) which brings about improvement in abnormal heart rhythms. This drug in particular has a high affinity for the Nav 1.5 sodium channel. Ajmaline produces potent sodium channel blocking effects and a very short half-life which makes it a very useful drug for acute intravenous treatments. The drug has been very popular in some countries for the treatment of atrial fibrillation in patients with the Wolff–Parkinson–White syndrome and in well tolerated monomorphic ventricular tachycardias. It has also been used for many years as a drug to challenge the conduction system of the heart in cases of bundle branch block and syncope. In these cases, abnormal prolongation of the HV interval has been taken as a proof for infrahisian conduction defects tributary for permanent pacemaker implantation. Ajmaline is used as an antiarrhythmic agent.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
8.2 µM [IC50]
1.7 µM [IC50]
2.66 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ajmaline
Primary
Ajmaline

AUC

ValueDoseCo-administeredAnalytePopulation
0.32 mg × h/L
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
0.36 mg × h/L
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
0.64 mg × h/L
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
0.71 mg × h/L
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
0.16 mg × h/L
50 mg single, intravenous
AJMALINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
95 min
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
99 min
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
80 min
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
90 min
50 mg single, intravenous
AJMALINE plasma
Homo sapiens
58 min
50 mg single, intravenous
AJMALINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
24%
AJMALINE plasma
Homo sapiens

Doses

PubMed

Sample Use Guides

In Vivo Use Guide
Adult: 50 mg via IV inj over at least 5 minutes. May also be given by IV infusion, IM inj and oral route.
Route of Administration: Other
In Vitro Use Guide
Clinically relevant ajmaline concentrations (1-3 uM) reduced peak I(Na) by approximately 5% but outward I(K) values were reduced by approximately 20% in amphibian skeletal muscle fibres. Peak-I(K) under maintained depolarisation was reduced to approximately 30% of control values by 100 uM ajmaline.