Basic information
- CAS
22059-60-5- Standard SMILES
CC(C)N(CCC(C(N)=O)(c1ccccc1)c1ccccn1)C(C)C.O=P(O)(O)O- InChIKey
CGDDQFMPGMYYQP-UHFFFAOYSA-N- Molecular formula
- C21H32N3O5P
- Average molar mass
- 437.5 g/mol
- Monoisotopic mass
- 437.20795813
Overview
Disopyramide phosphate is an organoammonium phosphate. It is functionally related to a disopyramide.
Names & identifiers
- Preferred name
- Disopyramide Phosphate
- IUPAC
- 4-[di(propan-2-yl)amino]-2-phenyl-2-pyridin-2-ylbutanamide;phosphoric acid
- English name
- Disopyramid phosphate
- Molecular formula
- C21H32N3O5P
- Molecular weight
- 437.47
Names & synonyms
DISOPYRAMIDE PHOSPHATE22059-60-5NorpaceRythmodanNorpace CrDirythmin saDiso-durilesSC-7031 PHOSPHATENSC-756744N6BOM1935WSC-13957CHEBI:4658
Show more names
sc13957disopyramid phosphateDisopyramide phosphate CRSDISOPYRAMIDE PHOSPHATE SALTDisopyramid phosphate USP/EP/BPDisopyramide Phosphate (200 mg)
DTXSID309446852-(1-(Ammoniocarbonyl)-3-(diisopropylammonio)-1-phenylpropyl)pyridinium phosphate4-(diisopropylamino)-2-phenyl-2-(2-pyridyl)butanamide;phosphoric acidDirythminRythmodan retDirythmin-saIsomide crRefChem:56639
Database identifiers
- CAS
22059-60-5- PubChem CID
- 30928
- DTXSID
DTXSID30944685- ChEMBL
CHEMBL1201020- ChEBI
CHEBI:4658- UNII
- N6BOM1935W
- EC Number
- 244-756-1
Properties
Computed structural properties
- Topological polar surface area
- 137 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 8
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 459
Experimental & physicochemical properties
Solubility>65.6 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section179.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 202 · 202-204°C
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly, Heated, Sonicated), Methanol (Slightly), Water (Slightly)
- form
- solid
- color
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- 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)
- InChIKey
- CGDDQFMPGMYYQP-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationDisopyramide phosphate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2-Pyridineacetamide, .alpha.-[2-[bis(1-methylethyl)amino]ethyl]-.alpha.-phenyl-, phosphate (1:1): Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Disopyramide phosphate
vLess-DILI-concern
2
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- rtecs
- UR8440000
- hs_code
- 2933399090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
DISOPYRAMIDE PHOSPHATE
Antiarrhythmic [EPC]
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.
Applications
UsesDisopyramide Phosphate is an antiarrhythmic (class IA). Sodium channel blocker.
UsesDisopyramide phosphate salt has been used as an internal standard for plasma sample analysis by mass spectrometry. It might be used as a test compound in a teratogenicity study.
UsesCardiac depressant (anti-arrhythmic).
General DescriptionDisopyramide phosphate, -[2(diisopropylamino)ethyl]- -phenyl-2-pyridineacetamidephosphate (Norpace), is an oral and intravenousclass IA antiarrhythmic agent. It is quite similar to quinidineand procainamide in its electrophysiological properties, inthat it decreases phase 4 diastolic depolarization, decreasesconduction velocity, and has vagolytic properties.31 It is usedclinically in the treatment of refractory, life-threatening ventriculartachyarrhythmias. Oral administration of the drugproduces peak plasma levels within 2 hours. The drug isbound approximately 50% to plasma protein and has a halflifeof 6.7 hours in humans. More than 50% is excretedunchanged in the urine. Therefore, patients with renal insufficiencyshould be monitored carefully for evidence ofoverdose. Disopyramide phosphate commonly exhibits sideeffects of dry mouth, constipation, urinary retention, andother cholinergic blocking actions because of its structuralsimilarity to anticholinergic drugs.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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