Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C21H29N3O.H3O4P |
| Molecular Weight | 437.4696 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C2=CC=CC=N2)C(C)C
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 | 339.4745 |
| 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 |
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 |
|
| 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 |
|
| Age- and gender-related differences in carbohydrate concentrations of alpha1-acid glycoprotein variants and the effects of glycoforms on their drug-binding capacities. | 2002 Dec |
|
| What is the minimal pacing rate that prevents torsades de pointes? Insights from patients with permanent pacemakers. | 2002 Nov |
|
| Atrial fibrillation threshold predicted long-term efficacy of pharmacological treatment of patients without structural heart disease. | 2002 Oct |
|
| 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 |
|
| [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 |
|
| Effects of orthostatic self-training on head-up tilt testing for the prevention of tilt-induced neurocardiogenic syncope: comparison of pharmacological therapy. | 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 |
|
| Differential binding of disopyramide and warfarin enantiomers to human alpha(1)-acid glycoprotein variants. | 2003 Dec |
|
| Management of atrial fibrillation: review of the evidence for the role of pharmacologic therapy, electrical cardioversion, and echocardiography. | 2003 Dec 16 |
|
| Management of newly detected atrial fibrillation: a clinical practice guideline from the American Academy of Family Physicians and the American College of Physicians. | 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 |
|
| Interaction of quinidine, disopyramide and metoprolol with melanin in vitro in relation to drug-induced ocular toxicity. | 2003 Jul |
|
| Multivariate analysis of risk factors for QT prolongation following subarachnoid hemorrhage. | 2003 Jun |
|
| [Drug therapy of atrial fibrillation]. | 2003 Jun 15 |
|
| Safety and feasibility of a clinical pathway for the outpatient initiation of antiarrhythmic medications in patients with atrial fibrillation or atrial flutter. | 2003 Jun 15 |
|
| 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 |
|
| [An approach to complete the manual for determination of serum pirmenol levels]. | 2003 Nov |
|
| Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia. | 2003 Nov 17 |
|
| QT prolongation and fatal arrhythmias: a review of clinical implications and effects of drugs. | 2003 Nov-Dec |
|
| [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 |
|
| 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 |
|
| 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 |
|
| 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 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
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on
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by
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on
Fri Dec 16 22:45:09 UTC 2022
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| Record UNII |
N6BOM1935W
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| Record Status |
Validated (UNII)
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C47497
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