DISOPYRAMIDE PHOSPHATE

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

Structure Search

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)

HIDE SMILES / InChI

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	( + / - )

Description
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: http://www.drugbank.ca/drugs/DB00280	Inhibitor 8504		52.5 µM [IC50]
KATP channels, Mus musculus 2 Target ID: KATP channels, Mus musculus Sources: https://www.ncbi.nlm.nih.gov/pubmed/11504161	Inhibitor 8504		4.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ventricular arrhythmia 50 Sources: https://www.drugs.com/pro/disopyramide.html	Primary		Approved 8583	DISOPYRAMIDE PHOSPHATE Approved Use indicated for the treatment of documented ventricular arrhythmias, such as sustained ventricular tachycardia, that, in the judgment of the physician, are life-threatening. Launch Date 1985

C_max

Value	Dose	Co-administered	Analyte	Population
3.08 mg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/3524956/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
8 h REVIEW https://pubmed.ncbi.nlm.nih.gov/3524956/	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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
35% REVIEW https://pubmed.ncbi.nlm.nih.gov/3524956/	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 Dose: 432 mg, 1 times / day Route: oral Route: steady Dose: 432 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15837258	unhealthy, 47 + 20 years Health Status: unhealthy Age Group: 47 + 20 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15837258	Disc. AE: Dry mouth, Prostatism... AEs leading to discontinuation/dose reduction: Dry mouth (7%) Prostatism (7%) Sources: https://pubmed.ncbi.nlm.nih.gov/15837258

AEs

AE	Significance	Dose	Population
Dry mouth	7% Disc. AE	432 mg 1 times / day steady, oral Dose: 432 mg, 1 times / day Route: oral Route: steady Dose: 432 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15837258	unhealthy, 47 + 20 years Health Status: unhealthy Age Group: 47 + 20 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15837258
Prostatism	7% Disc. AE	432 mg 1 times / day steady, oral Dose: 432 mg, 1 times / day Route: oral Route: steady Dose: 432 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15837258	unhealthy, 47 + 20 years Health Status: unhealthy Age Group: 47 + 20 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15837258

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
K+ channels 73 Kv1.5 27 OCT transporters 14	P-gp 2052 K+ channels 2 OCT1 393 OCT2 434 CYP 303

Drug as perpetrator

Target	Modality	Activity
K+ channels 73	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11504161/	yes [IC50 4.8 uM]
Kv1.5 42	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18818480/	yes
OCT transporters 14	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29247868/	yes

Drug as victim

Target	Modality	Activity
K+ channels 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9550298/	likely [EC50 1.8 uM]
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18027986/	likely
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15449971/	likely
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10901704/; https://pubmed.ncbi.nlm.nih.gov/15449971/	yes
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12440152/	yes
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12440152/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/16842817/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4657	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4657
ChemicalBook	CB1285468	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1285468
eMolecules	537636	https://www.emolecules.com/cgi-bin/more?vid=537636
MolPort	MolPort-003-846-985	https://www.molport.com/shop/molecule-link/MolPort-003-846-985

PubMed

Title	Date	PubMed
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.	2005-02	15658999
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.	2005-02	15342952
Toxic interactions between fluconazole and disopyramide in chick embryos.	2005-01	15635181
Pilsicainide in breast milk from a mother: comparison with disopyramide and propafenone.	2005-01	15606453
Simultaneous supraventricular tachycardias in both fetuses of a twin gestation.	2004-12	14745562
Failure of disopyramide to improve right ventricular outflow tract obstruction after living-donor lobar lung transplantation.	2004-11	15502393
Pharmacological treatment of reflex syncope.	2004-10	15480933
Acute ventricular rate control in atrial fibrillation and atrial flutter.	2004-10	15336799
Human organic cation transporter 3 mediates the transport of antiarrhythmic drugs.	2004-09-19	15363950
Myocardial bundles with slow conduction properties are present on the left interventricular septal surface of normal human hearts.	2004-09	15363072
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.	2004-08	15302734
Accuracy of calculated pH-dependent aqueous drug solubility.	2004-08	15265508
Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels.	2004-07	15272206
Is this form of syncope to blame?	2004-06	15317281
Effects of antiarrhythmic agents on left ventricular function during exercise in patients with chronic left ventricular dysfunction.	2004-05	15233282
Atrial fibrillation: rate control often better than rhythm control.	2004-04	15148984
Recurrent syncopic episodes as a consequence of combined Brugada syndrome and paroxysmal atrial fibrillation. Which is the therapy of choice?	2004-04	15094000
Two cases of ventricular tachycardia with congenital left ventricular malformation in an adult.	2004-02	15008699
Antiarrhythmic drug therapy of atrial fibrillation.	2004-02	14994845
Repolarization abnormality in idiopathic ventricular fibrillation: assessment using 24-hour QT-RR and QaT-RR relationships.	2004-01	15028073
Theoretical possibilities for the development of novel antiarrhythmic drugs.	2004-01	14754422
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.	2004-01	14685755
Interactions between grapefruit juice and cardiovascular drugs.	2004	15449971
Management of atrial fibrillation: review of the evidence for the role of pharmacologic therapy, electrical cardioversion, and echocardiography.	2003-12-16	14678922
Management of newly detected atrial fibrillation: a clinical practice guideline from the American Academy of Family Physicians and the American College of Physicians.	2003-12-16	14678921
Ropivacaine combined with various anti-arrhythmic drugs results in mild alterations in myocardial contractility in pigs.	2003-12	14656782
Differential binding of disopyramide and warfarin enantiomers to human alpha(1)-acid glycoprotein variants.	2003-12	14616427
QT prolongation and fatal arrhythmias: a review of clinical implications and effects of drugs.	2003-11-19	14624285
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.	2003-11-17	14612892
[An approach to complete the manual for determination of serum pirmenol levels].	2003-11	14631760
[Relationship between duration of arrhythmia and subsequent preventive effect of disopyramide after cardioversion in patients with symptomatic paroxysmal and persistent atrial fibrillation].	2003-09	14526660
[Drug binding analysis of human alpha 1-acid glycoprotein using capillary electrophoresis].	2003-09	14513769
Randomized clinical trials of neurally mediated syncope.	2003-09	12950522
Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods.	2003-08-18	12873512
Capillary electrophoretic study on pH dependence of enantioselective disopyramide binding to genetic variants of human alpha1-acid glycoprotein.	2003-08	12964601
Inhibitory effect of erythromycin on potassium currents in rat ventricular myocytes in comparison with disopyramide.	2003-07	12906757
Interaction of quinidine, disopyramide and metoprolol with melanin in vitro in relation to drug-induced ocular toxicity.	2003-07	12889538
Characterisation of recombinant HERG K+ channel blockade by the Class Ia antiarrhythmic drug procainamide.	2003-06-27	12804575
[Drug therapy of atrial fibrillation].	2003-06-15	12866149
Safety and feasibility of a clinical pathway for the outpatient initiation of antiarrhythmic medications in patients with atrial fibrillation or atrial flutter.	2003-06-15	12804730
Multivariate analysis of risk factors for QT prolongation following subarachnoid hemorrhage.	2003-06	12793884
[Comparison of the efficacies of disopyramide, cibenzoline and aprindine for the termination of paroxysmal and persistent atrial fibrillation in elderly and non-elderly patients].	2003-04	12728540
Effects of orthostatic self-training on head-up tilt testing for the prevention of tilt-induced neurocardiogenic syncope: comparison of pharmacological therapy.	2003-04	12716081
Hypertrophic obstructive cardiomyopathy: mechanism of obstruction and response to therapy.	2003	14668688
[Anti-arrhythmic therapy: diagnostic possibilities of signal-averaged electrocardiography and heart rate variability].	2003	12891276
[Role amiodarone in sinus rhythm maintenance after successful cardioversion in patients with chronic non-valvular atrial fibrillation].	2002-12	12687927
Use of beta-blockers in atrial fibrillation.	2002	14727997
Precordial QT interval dispersion as a marker of torsade de pointes. Disparate effects of class Ia antiarrhythmic drugs and amiodarone.	1992-11	1423949
[Torsades de pointes ventricular tachycardia induced by disopyramide at therapeutic serum concentration].	1992-08-20	1412257
Acquired long QT syndrome due to antiarrhythmic drugs and bradyarrhythmias.	1992-01-27	1562120

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 18:50:32 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:32 GMT 2025`
Record UNII	N6BOM1935W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DISOPYRAMIDE PHOSPHATE

Official Name

English

DIRYTHMIN SA

Preferred Name

English

DISOPYRAMIDE PHOSPHATE [ORANGE BOOK]

Common Name

English

DISOPYRAMIDE PHOSPHATE [USAN]

Common Name

English

RYTHMODAN

Brand Name

English

DISOPYRAMIDE PHOSPHATE [USP MONOGRAPH]

Common Name

English

DISOPYRAMIDE PHOSPHATE [EP MONOGRAPH]

Common Name

English

DISOPYRAMIDE PHOSPHATE [MART.]

Common Name

English

SC-7031 PHOSPHATE

Code

English

Disopyramide phosphate [WHO-DD]

Common Name

English

DISOPYRAMIDE PHOSPHATE [VANDF]

Common Name

English

NORPACE

Brand Name

English

2-PYRIDINEACETAMIDE, .ALPHA.-(2-(BIS(1-METHYLETHYL)AMINO)ETHYL)-.ALPHA.-PHENYL-, (±)-, PHOSPHATE (1:1)

Systematic Name

English

4-DIISOPROPYLAMINO-2-PHENYL-2-(2-PYRIDYL)BUTYRAMIDE PHOSPHATE

Systematic Name

English

DISOPYRAMIDE PHOSPHATE [USP-RS]

Common Name

English

SC-13957

Code

English

DISO-DURILES

Brand Name

English

NSC-756744

Code

English

DISOPYRAMIDE PHOSPHATE [JAN]

Common Name

English

(±)-.ALPHA.-(2-(DIISOPROPYLAMINO)ETHYL)-.ALPHA.-PHENYL-2-PYRIDINEACETAMIDE PHOSPHATE (1:1)

Systematic Name

English

DISOPYRAMIDE PHOSPHATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C93038