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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

Molecular Formula C20H26N2O2
Molecular Weight 326.4326
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 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
PubMed

PubMed

TitleDatePubMed
Effect of ajmaline on action potential and ionic currents in rat ventricular myocytes.
2005 Sep
Inhibition of cardiac Kv1.5 and Kv4.3 potassium channels by the class Ia anti-arrhythmic ajmaline: mode of action.
2013 Nov
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 Fri Dec 15 14:57:54 UTC 2023
Edited
by admin
on Fri Dec 15 14:57:54 UTC 2023
Record UNII
1PON08459R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AJMALINE
MART.   MI   WHO-DD  
Common 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
NSC-15627
Code English
Classification Tree Code System Code
WHO-VATC QC01BA05
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
WHO-ATC C01BA05
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
Code System Code Type Description
EVMPD
SUB12754MIG
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
MESH
D000404
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
NSC
15627
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
DRUG CENTRAL
100
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
ECHA (EC/EINECS)
224-439-4
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
WIKIPEDIA
AJMALINE
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
CHEBI
58567
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105617
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
CAS
4360-12-7
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
CHEBI
28462
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID6045537
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
SMS_ID
100000077965
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
MERCK INDEX
m1457
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C83524
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
PUBCHEM
6100671
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
FDA UNII
1PON08459R
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
RXCUI
423
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB01426
Created by admin on Fri Dec 15 14:57:54 UTC 2023 , Edited by admin on Fri Dec 15 14:57:54 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY