Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H29N3O.H3O4P |
Molecular Weight | 437.4705 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)N(CCC(c1ccccc1)(c2ccccn2)C(=N)O)C(C)C.OP(=O)(O)O
InChI
InChIKey=CGDDQFMPGMYYQP-UHFFFAOYSA-N
InChI=1S/C21H29N3O.H3O4P/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19;1-5(2,3)4/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25);(H3,1,2,3,4)
Molecular Formula | H3O4P |
Molecular Weight | 97.9952 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C21H29N3O |
Molecular Weight | 339.4753 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00280Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/pro/disopyramide.html
Sources: http://www.drugbank.ca/drugs/DB00280
Curator's Comment:: Description was created based on several sources, including
https://www.drugs.com/pro/disopyramide.html
Disopyramide is an antiarrhythmic drug indicated for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia that are life-threatening. In man, Disopyramide at therapeutic plasma levels shortens the sinus node recovery time, lengthens the effective refractory period of the atrium, and has a minimal effect on the effective refractory period of the AV node. Little effect has been shown on AV-nodal and His-Purkinje conduction times or QRS duration. However, prolongation of conduction in accessory pathways occurs. Disopyramide is a Type 1A antiarrhythmic drug (ie, similar to procainamide and quinidine). It inhibits the fast sodium channels. In animal studies Disopyramide decreases the rate of diastolic depolarization (phase 4) in cells with augmented automaticity, decreases the upstroke velocity (phase 0) and increases the action potential duration of normal cardiac cells, decreases the disparity in refractoriness between infarcted and adjacent normally perfused myocardium, and has no effect on alpha- or beta-adrenergic receptors. It is used for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, ventricular pre-excitation and cardiac dysrhythmias. It is a Class Ia antiarrhythmic drug.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00280 |
52.5 µM [IC50] | ||
Target ID: KATP channels, Mus musculus Sources: https://www.ncbi.nlm.nih.gov/pubmed/11504161 |
4.8 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DISOPYRAMIDE PHOSPHATE Approved Useindicated for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, that, in the judgment of the physician, are life-threatening. Launch Date4.7779201E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.08 mg/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DISOPYRAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059444/ |
2 mg/kg 1 times / day multiple, oral dose: 2 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
DISOPYRAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7059444/ |
2 mg/kg 1 times / day multiple, oral dose: 2 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered: |
DISOPYRAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DISOPYRAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
35% |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DISOPYRAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
432 mg 1 times / day steady, oral (median) Dose: 432 mg, 1 times / day Route: oral Route: steady Dose: 432 mg, 1 times / day Sources: |
unhealthy, 47 + 20 years n = 118 Health Status: unhealthy Condition: obstructive hypertrophic cardiomyopathy Age Group: 47 + 20 years Sex: M+F Population Size: 118 Sources: |
Disc. AE: Dry mouth, Prostatism... AEs leading to discontinuation/dose reduction: Dry mouth (7%) Sources: Prostatism (7%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dry mouth | 7% Disc. AE |
432 mg 1 times / day steady, oral (median) Dose: 432 mg, 1 times / day Route: oral Route: steady Dose: 432 mg, 1 times / day Sources: |
unhealthy, 47 + 20 years n = 118 Health Status: unhealthy Condition: obstructive hypertrophic cardiomyopathy Age Group: 47 + 20 years Sex: M+F Population Size: 118 Sources: |
Prostatism | 7% Disc. AE |
432 mg 1 times / day steady, oral (median) Dose: 432 mg, 1 times / day Route: oral Route: steady Dose: 432 mg, 1 times / day Sources: |
unhealthy, 47 + 20 years n = 118 Health Status: unhealthy Condition: obstructive hypertrophic cardiomyopathy Age Group: 47 + 20 years Sex: M+F Population Size: 118 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 4.8 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely [EC50 1.8 uM] | ||||
likely | ||||
likely | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Torsades de pointes ventricular tachycardia induced by disopyramide at therapeutic serum concentration]. | 1992 Aug 20 |
|
Acquired long QT syndrome due to antiarrhythmic drugs and bradyarrhythmias. | 1992 Jan 27 |
|
Precordial QT interval dispersion as a marker of torsade de pointes. Disparate effects of class Ia antiarrhythmic drugs and amiodarone. | 1992 Nov |
|
Use of beta-blockers in atrial fibrillation. | 2002 |
|
[Role amiodarone in sinus rhythm maintenance after successful cardioversion in patients with chronic non-valvular atrial fibrillation]. | 2002 Dec |
|
MDR1-mediated interaction of digoxin with antiarrhythmic or antianginal drugs. | 2002 Dec |
|
Effective disopyramide treatment in a boy with mid-ventricular hypertrophic obstructive cardiomyopathy. | 2002 Jul |
|
[Antiarrhythmic drugs in atrial fibrillation]. | 2002 Jun 15 |
|
What is the minimal pacing rate that prevents torsades de pointes? Insights from patients with permanent pacemakers. | 2002 Nov |
|
Development and use of a computer program to detect potentially inappropriate prescribing in older adults residing in Canadian long-term care facilities. | 2002 Oct 14 |
|
Effects of disopyramide and mexiletine on the terminal repolarization process of the in situ heart assessed using the halothane-anesthetized in vivo canine model. | 2002 Sep |
|
[Anti-arrhythmic therapy: diagnostic possibilities of signal-averaged electrocardiography and heart rate variability]. | 2003 |
|
[Comparison of the efficacies of disopyramide, cibenzoline and aprindine for the termination of paroxysmal and persistent atrial fibrillation in elderly and non-elderly patients]. | 2003 Apr |
|
Capillary electrophoretic study on pH dependence of enantioselective disopyramide binding to genetic variants of human alpha1-acid glycoprotein. | 2003 Aug |
|
Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods. | 2003 Aug 18 |
|
Ropivacaine combined with various anti-arrhythmic drugs results in mild alterations in myocardial contractility in pigs. | 2003 Dec |
|
Management of atrial fibrillation: review of the evidence for the role of pharmacologic therapy, electrical cardioversion, and echocardiography. | 2003 Dec 16 |
|
Hypertrophic obstructive cardiomyopathy: mechanism of obstruction and response to therapy. | 2003 Fall |
|
Abnormal response to sodium channel blockers in patients with Brugada syndrome: augmented localised wall motion abnormalities in the right ventricular outflow tract region detected by electron beam computed tomography. | 2003 Feb |
|
The effect of commonly used drugs on angiogenesis. | 2003 Jan-Feb |
|
Inhibitory effect of erythromycin on potassium currents in rat ventricular myocytes in comparison with disopyramide. | 2003 Jul |
|
Multivariate analysis of risk factors for QT prolongation following subarachnoid hemorrhage. | 2003 Jun |
|
Characterisation of recombinant HERG K+ channel blockade by the Class Ia antiarrhythmic drug procainamide. | 2003 Jun 27 |
|
Comparison of the effect of class IA antiarrhythmic drugs on transmembrane potassium currents in rabbit ventricular myocytes. | 2003 Mar |
|
[Relationship between duration of arrhythmia and subsequent preventive effect of disopyramide after cardioversion in patients with symptomatic paroxysmal and persistent atrial fibrillation]. | 2003 Sep |
|
[Drug binding analysis of human alpha 1-acid glycoprotein using capillary electrophoresis]. | 2003 Sep |
|
Randomized clinical trials of neurally mediated syncope. | 2003 Sep |
|
Interactions between grapefruit juice and cardiovascular drugs. | 2004 |
|
Atrial fibrillation: rate control often better than rhythm control. | 2004 Apr |
|
Recurrent syncopic episodes as a consequence of combined Brugada syndrome and paroxysmal atrial fibrillation. Which is the therapy of choice? | 2004 Apr |
|
Rate control vs rhythm control in patients with nonvalvular persistent atrial fibrillation: the results of the Polish How to Treat Chronic Atrial Fibrillation (HOT CAFE) Study. | 2004 Aug |
|
Accuracy of calculated pH-dependent aqueous drug solubility. | 2004 Aug |
|
Simultaneous supraventricular tachycardias in both fetuses of a twin gestation. | 2004 Dec |
|
Two cases of ventricular tachycardia with congenital left ventricular malformation in an adult. | 2004 Feb |
|
Antiarrhythmic drug therapy of atrial fibrillation. | 2004 Feb |
|
Repolarization abnormality in idiopathic ventricular fibrillation: assessment using 24-hour QT-RR and QaT-RR relationships. | 2004 Jan |
|
Theoretical possibilities for the development of novel antiarrhythmic drugs. | 2004 Jan |
|
Effects of class I antiarrhythmic drugs on the digitalis-induced triggered activity arrhythmia model: a rationale for the short-term use of class I drugs against triggered arrhythmias. | 2004 Jan |
|
Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels. | 2004 Jul |
|
Is this form of syncope to blame? | 2004 Jun |
|
Effects of antiarrhythmic agents on left ventricular function during exercise in patients with chronic left ventricular dysfunction. | 2004 May |
|
Failure of disopyramide to improve right ventricular outflow tract obstruction after living-donor lobar lung transplantation. | 2004 Nov |
|
Pharmacological treatment of reflex syncope. | 2004 Oct |
|
Acute ventricular rate control in atrial fibrillation and atrial flutter. | 2004 Oct |
|
Myocardial bundles with slow conduction properties are present on the left interventricular septal surface of normal human hearts. | 2004 Sep |
|
Human organic cation transporter 3 mediates the transport of antiarrhythmic drugs. | 2004 Sep 19 |
|
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring. | 2005 Feb |
|
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
Toxic interactions between fluconazole and disopyramide in chick embryos. | 2005 Jan |
|
Pilsicainide in breast milk from a mother: comparison with disopyramide and propafenone. | 2005 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/disopyramide.html
Usual Adult Dose for Arrhythmias
400-800 mg/day. The recommended dose for most adults is 600 mg/day. Patients < 50 kg may be given 400 mg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12906757
Disopyramide (10-100 uM) led to increases in the action potential duration (APD) at 90% repolarization level in rat ventricular myocytes.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:04:56 UTC 2021
by
admin
on
Fri Jun 25 21:04:56 UTC 2021
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Record UNII |
N6BOM1935W
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C93038
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NCI_THESAURUS |
C47793
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31758-86-8
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M4672
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C47497
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