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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

CC[C@H]1[C@@H]2C[C@H]3[C@@H]4N(C)C5=CC=CC=C5[C@]46C[C@@H]([C@H]2[C@H]6O)N3[C@@H]1O

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

Molecular Formula C20H26N2O2
Molecular Weight 326.4326
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://en.pharmacodia.com/web/drug/1_10112.html http://www.mims.com/india/drug/info/ajmaline/ajmaline?type=full&mtype=generic

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ajmaline

Approved Use

Supraventricular and ventricular arrhythmias; Differential diagnosis of Wolff-Parkinson-White syndrome
Primary
Ajmaline

Approved Use

Supraventricular and ventricular arrhythmias; Differential diagnosis of Wolff-Parkinson-White syndrome
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.32 mg × h/L
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.36 mg × h/L
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.64 mg × h/L
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.71 mg × h/L
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.16 mg × h/L
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
95 min
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
99 min
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
80 min
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
90 min
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
58 min
50 mg single, intravenous
dose: 50 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
24%
AJMALINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 3 times / day multiple, oral
Highest studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Inhibition of cardiac Kv1.5 and Kv4.3 potassium channels by the class Ia anti-arrhythmic ajmaline: mode of action.
2013-11
Effect of ajmaline on action potential and ionic currents in rat ventricular myocytes.
2005-09
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:07 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:07 GMT 2025
Record UNII
1PON08459R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AJMALINE
MART.   MI   WHO-DD  
Common Name English
NSC-15627
Preferred Name English
AJMALINE [MI]
Common Name English
(17R,21R)-AJMALAN-17,21-DIOL
Common Name English
AJMALINE [MART.]
Common Name English
AJMALAN-17,21-DIOL
Common Name English
RAUWOLFINE
Common Name English
AJMALINE [JAN]
Common Name English
Ajmaline [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01BA05
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
WHO-ATC C01BA05
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
NCI_THESAURUS C47793
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
Code System Code Type Description
EVMPD
SUB12754MIG
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
MESH
D000404
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
NSC
15627
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
DRUG CENTRAL
100
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
ECHA (EC/EINECS)
224-439-4
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
WIKIPEDIA
AJMALINE
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
CHEBI
58567
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
ChEMBL
CHEMBL2105617
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
CAS
4360-12-7
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
CHEBI
28462
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID6045537
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
SMS_ID
100000077965
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
MERCK INDEX
m1457
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C83524
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
PUBCHEM
6100671
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
FDA UNII
1PON08459R
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
RXCUI
423
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB01426
Created by admin on Mon Mar 31 17:33:07 GMT 2025 , Edited by admin on Mon Mar 31 17:33:07 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY