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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26N2O2.C2H6O
Molecular Weight 372.5011
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AJMALINE MONOETHANOLATE

SMILES

CCO.[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=ASXHFVPFQMMNNZ-LCJCZRDQSA-N
InChI=1S/C20H26N2O2.C2H6O/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;1-2-3/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3;3H,2H2,1H3/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

Molecular Formula C2H6O
Molecular Weight 46.0684
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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 Sat Dec 16 08:37:21 GMT 2023
Edited
by admin
on Sat Dec 16 08:37:21 GMT 2023
Record UNII
QT1U5T329Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AJMALINE MONOETHANOLATE
WHO-DD  
Common Name English
ETHANOL, COMPD. WITH (17R,21.ALPHA.)-AJMALAN-17,21-DIOL (1:1)
Common Name English
Ajmaline monoethanolate [WHO-DD]
Common Name English
AJMALAN-17,21-DIOL, (17R,21.ALPHA.)-, COMPD. WITH ETHANOL (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
100000077966
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
EVMPD
SUB12756MIG
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID30976466
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
PUBCHEM
90479366
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
FDA UNII
QT1U5T329Q
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
CAS
60991-48-2
Created by admin on Sat Dec 16 08:37:21 GMT 2023 , Edited by admin on Sat Dec 16 08:37:21 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY