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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:47:12 UTC
HMDB IDHMDB0014425
Secondary Accession Numbers
  • HMDB14425
Metabolite Identification
Common NameDisopyramide
DescriptionDisopyramide, also known as rythmodan p, belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton. Disopyramide is a drug which 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. In humans, disopyramide is involved in the disopyramide action pathway. Disopyramide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Disopyramide.
Structure
Data?1582753177
Synonyms
ValueSource
alpha-(2-(Diisopropylamino)ethyl)-alpha-phenyl-2-pyridineacetamideChEBI
DisopiramidaChEBI
DisopyramidumChEBI
gamma-Diisopropylamino-alpha-phenyl-alpha-(2-pyridyl)butyramideChEBI
Rythmodan pKegg
a-(2-(Diisopropylamino)ethyl)-a-phenyl-2-pyridineacetamideGenerator
Α-(2-(diisopropylamino)ethyl)-α-phenyl-2-pyridineacetamideGenerator
g-Diisopropylamino-a-phenyl-a-(2-pyridyl)butyramideGenerator
Γ-diisopropylamino-α-phenyl-α-(2-pyridyl)butyramideGenerator
Disopyramide free baseHMDB
Disopyramide phosphateHMDB, MeSH
DiisopyramideMeSH, HMDB
Disopyramide phosphate (1:1), (S)-isomerMeSH, HMDB
Disopyramide, (+-)-isomerMeSH, HMDB
Disopyramide, L-tartrate (1:1), (R)-isomerMeSH, HMDB
Disopyramide, L-tartrate (1:1), (S)-isomerMeSH, HMDB
Searle brand OF disopyramide phosphateMeSH, HMDB
Disopyramide phosphate (1:1), (+-)-isomerMeSH, HMDB
Disopyramide phosphate (1:1), (R)-isomerMeSH, HMDB
Disopyramide, L-tartrate (1:2), (+-)-isomerMeSH, HMDB
Disopyramide, L-tartrate, (S)-isomerMeSH, HMDB
NorpaceMeSH, HMDB
PalpitinMeSH, HMDB
RythmilenMeSH, HMDB
Disopyramide phosphate (1:1)MeSH, HMDB
Disopyramide, D-tartrate (1:1), (S)-isomerMeSH, HMDB
PalpitineMeSH, HMDB
Disopyramide monohydrochlorideMeSH, HMDB
Disopyramide, (R)-isomerMeSH, HMDB
Disopyramide, (S)-isomerMeSH, HMDB
RhythmodanMeSH, HMDB
RitmilenMeSH, HMDB
Chemical FormulaC21H29N3O
Average Molecular Weight339.4745
Monoisotopic Molecular Weight339.231062565
IUPAC Name4-[bis(propan-2-yl)amino]-2-phenyl-2-(pyridin-2-yl)butanamide
Traditional Namedisopyramide
CAS Registry Number3737-09-5
SMILES
CC(C)N(CCC(C(N)=O)(C1=CC=CC=C1)C1=NC=CC=C1)C(C)C
InChI Identifier
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)
InChI KeyUVTNFZQICZKOEM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPheniramines
Direct ParentPheniramines
Alternative Parents
Substituents
  • Pheniramine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboximidic acid derivative
  • Carboximidic acid
  • Azacycle
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94.5 - 95 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.049 g/LNot Available
LogP3.5Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available179.946http://allccs.zhulab.cn/database/detail?ID=AllCCS00001003
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP10(3.21) g/LALOGPS
logP10(3.47) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)16.19ChemAxon
pKa (Strongest Basic)10.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.22 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity102.3 m³·mol⁻¹ChemAxon
Polarizability38.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.8231661259
DarkChem[M-H]-180.56631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, Positivesplash10-044m-6591000000-ade312d81f3d174aaf2d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Disopyramide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Disopyramide , positive-QTOFsplash10-0005-2920000000-e596d22799910844ad712017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 10V, Positive-QTOFsplash10-0006-0019000000-d1d8426d9efe63a8f3fd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 20V, Positive-QTOFsplash10-00dj-0295000000-27ad50b3e8f64e45b5f42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 40V, Positive-QTOFsplash10-059l-7590000000-29c623252c76f0cfe4e82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 10V, Negative-QTOFsplash10-000j-0179000000-d43460de1f53211201c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 20V, Negative-QTOFsplash10-0002-1491000000-c6005857bfdac87779c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 40V, Negative-QTOFsplash10-0uxr-7920000000-c8e9f71b29cfc8635a282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 10V, Positive-QTOFsplash10-000f-0049000000-d7931ec90cdb1287fd3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 20V, Positive-QTOFsplash10-000l-0292000000-4ce9f6848ae81d59c7e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 40V, Positive-QTOFsplash10-00kf-0900000000-ce002f8854f0666618072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 10V, Negative-QTOFsplash10-000i-0029000000-6569595ba95c091f548b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 20V, Negative-QTOFsplash10-000g-8695000000-4b18e01643972a8c92162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disopyramide 40V, Negative-QTOFsplash10-001m-9720000000-fc09dce8697633f796e92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00280 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00280 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00280
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3002
KEGG Compound IDC06965
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDisopyramide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID4657
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Echizen H, Tanizaki M, Tatsuno J, Chiba K, Berwick T, Tani M, Gonzalez FJ, Ishizaki T: Identification of CYP3A4 as the enzyme involved in the mono-N-dealkylation of disopyramide enantiomers in humans. Drug Metab Dispos. 2000 Aug;28(8):937-44. [PubMed:10901704 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Zhang L, Fitzloff JF, Engel LC, Cook CS: Species difference in stereoselective involvement of CYP3A in the mono-N-dealkylation of disopyramide. Xenobiotica. 2001 Feb;31(2):73-83. [PubMed:11407536 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Sugao M, Fujiki A, Nishida K, Sakabe M, Tsuneda T, Iwamoto J, Mizumaki K, Inoue H: Repolarization dynamics in patients with idiopathic ventricular fibrillation: pharmacological therapy with bepridil and disopyramide. J Cardiovasc Pharmacol. 2005 Jun;45(6):545-9. [PubMed:15897781 ]
  2. Fujiki A, Sugao M, Nishida K, Sakabe M, Tsuneda T, Mizumaki K, Inoue H: Repolarization abnormality in idiopathic ventricular fibrillation: assessment using 24-hour QT-RR and QaT-RR relationships. J Cardiovasc Electrophysiol. 2004 Jan;15(1):59-63. [PubMed:15028073 ]
  3. Shimizu W, Antzelevitch C, Suyama K, Kurita T, Taguchi A, Aihara N, Takaki H, Sunagawa K, Kamakura S: Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9. [PubMed:11196553 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T: A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. [PubMed:10413067 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T: A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. [PubMed:10413067 ]
  2. Ishida Y, Mizukami M, Taniguchi T, Satake N, Fujiwara M, Shibata S: Anticholinergic action of disopyramide in intestinal smooth muscle of the guinea pig: inhibition of muscarinic receptors (M1 and M2). Jpn J Pharmacol. 1990 Feb;52(2):363-70. [PubMed:1690310 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T: A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. [PubMed:10413067 ]
  2. Ishida Y, Mizukami M, Taniguchi T, Satake N, Fujiwara M, Shibata S: Anticholinergic action of disopyramide in intestinal smooth muscle of the guinea pig: inhibition of muscarinic receptors (M1 and M2). Jpn J Pharmacol. 1990 Feb;52(2):363-70. [PubMed:1690310 ]
General function:
Involved in protein binding
Specific function:
Pore-forming (alpha) subunit of voltage-gated rapidly inactivating A-type potassium channels. May contribute to I(To) current in heart and I(Sa) current in neurons. Channel properties are modulated by interactions with other alpha subunits and with regulatory subunits
Gene Name:
KCND2
Uniprot ID:
Q9NZV8
Molecular weight:
70535.8
References
  1. Casis O, Sanchez-Chapula JA: Disopyramide, imipramine, and amitriptyline bind to a common site on the transient outward K+ channel. J Cardiovasc Pharmacol. 1998 Oct;32(4):521-6. [PubMed:9781919 ]
General function:
Involved in protein binding
Specific function:
Pore-forming (alpha) subunit of voltage-gated rapidly inactivating A-type potassium channels. May contribute to I(To) current in heart and I(Sa) current in neurons. Channel properties are modulated by interactions with other alpha subunits and with regulatory subunits
Gene Name:
KCND3
Uniprot ID:
Q9UK17
Molecular weight:
73450.5
References
  1. Casis O, Sanchez-Chapula JA: Disopyramide, imipramine, and amitriptyline bind to a common site on the transient outward K+ channel. J Cardiovasc Pharmacol. 1998 Oct;32(4):521-6. [PubMed:9781919 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
  2. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular weight:
62564.0
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]