Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H29N3O |
Molecular Weight | 339.4745 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C2=CC=CC=N2)C(C)C
InChI
InChIKey=UVTNFZQICZKOEM-UHFFFAOYSA-N
InChI=1S/C21H29N3O/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/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25)
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 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 |
---|---|---|
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 |
|
Torsades de pointes ventricular tachycardia induced by clarithromycin and disopyramide in the presence of hypokalemia. | 1999 Apr |
|
Identification of CYP3A4 as the enzyme involved in the mono-N-dealkylation of disopyramide enantiomers in humans. | 2000 Aug |
|
Potentially fatal interaction between azithromycin and disopyramide. | 2000 Sep |
|
Comparative safety of the different macrolides. | 2001 |
|
Importance of QT interval determination and renal function assessment during antiarrhythmic drug therapy. | 2001 Apr |
|
The effects of flecainide on ATP-sensitive K(+) channels in pig urethral myocytes. | 2001 Jul |
|
Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. | 2001 Nov |
|
Enantioselective binding of disopyramide to alpha1-acid glycoprotein and its variants. | 2001 Oct |
|
Use of beta-blockers in atrial fibrillation. | 2002 |
|
Strategy for the management of vasovagal syncope. | 2002 |
|
Risk of mortality in a cohort of patients newly diagnosed with chronic 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 |
|
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 |
|
Maintaining stability of sinus rhythm in atrial fibrillation: antiarrhythmic drugs versus ablation. | 2002 Sep |
|
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 |
|
The effect of commonly used drugs on angiogenesis. | 2003 Jan-Feb |
|
[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 |
|
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 |
|
[Drug binding analysis of human alpha 1-acid glycoprotein using capillary electrophoresis]. | 2003 Sep |
|
Accuracy of calculated pH-dependent aqueous drug solubility. | 2004 Aug |
|
Simultaneous supraventricular tachycardias in both fetuses of a twin gestation. | 2004 Dec |
|
Repolarization abnormality in idiopathic ventricular fibrillation: assessment using 24-hour QT-RR and QaT-RR relationships. | 2004 Jan |
|
Pharmacological treatment of reflex syncope. | 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 |
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
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by
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on
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Record UNII |
GFO928U8MQ
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
C01BA03
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NCI_THESAURUS |
C47793
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NDF-RT |
N0000175426
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LIVERTOX |
NBK548693
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WHO-VATC |
QC01BA03
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NCI_THESAURUS |
C93038
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3737-09-5
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DB00280
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D004206
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DTXSID1045536
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C61730
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DISOPYRAMIDE
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4657
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CHEMBL517
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223-110-2
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Disopyramide
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M4672
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7167
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GFO928U8MQ
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
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ACTIVE MOIETY |