Disopyramide

Base Information

• Chemical Name: Disopyramide
• CAS No.: 3737-09-5
• Molecular Formula: C₂₁H₂₉N₃O
• Molecular Weight: 339.481
• European Community (EC) Number: 223-110-2
• UNII: GFO928U8MQ
• DSSTox Substance ID: DTXSID1045536
• Nikkaji Number: J3.408H
• Wikipedia: Disopyramide
• Wikidata: Q425120
• NCI Thesaurus Code: C61730
• RXCUI: 3541
• Pharos Ligand ID: L68HUP8VBMHC
• Metabolomics Workbench ID: 42672
• ChEMBL ID: CHEMBL517
• Mol file: 3737-09-5.mol

Synonyms:Diisopyramide;Disopyramide;Disopyramide Monohydrochloride;Disopyramide Phosphate;Disopyramide Phosphate (1:1);Disopyramide Phosphate (1:1), (+-)-Isomer;Disopyramide Phosphate (1:1), (R)-Isomer;Disopyramide Phosphate (1:1), (S)-Isomer;Disopyramide, (+-)-Isomer;Disopyramide, (R)-Isomer;Disopyramide, (S)-Isomer;Disopyramide, D-Tartrate (1:1), (S)-Isomer;Disopyramide, L-Tartrate (1:1), (R)-Isomer;Disopyramide, L-Tartrate (1:1), (S)-Isomer;Disopyramide, L-Tartrate (1:2), (+-)-Isomer;Disopyramide, L-Tartrate, (S)-isomer;Norpace;Palpitin;Palpitine;Rhythmodan;Ritmilen;Rythmilen;SC 13957;SC-13957;SC13957

Chemical Property of Disopyramide

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Melting Point: 94.5-950C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 505.2°Cat760mmHg
• PKA: 10.2; also reported as 10.45(at 25℃)
• Flash Point: 259.4°C
• PSA: 59.22000
• Density: 1.059g/cm³
• LogP: 4.06220
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (25 mg/ml) and Ethanol (>35 mg/mL)
• Water Solubility.: 6.17mg/L(22.5 oC)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 339.231062557
• Heavy Atom Count: 25
• Complexity: 409

Purity/Quality:

99.9% ^*data from raw suppliers

Disopyramide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi,T,F
• Statements: 22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 36-26-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiarrhythmic Agents
• Canonical SMILES: CC(C)N(CCC(C1=CC=CC=C1)(C2=CC=CC=N2)C(=O)N)C(C)C
• Recent ClinicalTrials: Catheter Ablation Compared With Pharmacological Therapy for Atrial Fibrillation (CAPTAF Trial)
• Recent EU Clinical Trials: CRioablation vs Antiarrhythmic Drugs for Persistent Atrial Fibrillation Trial (CRAFT)
• Description: Structurally, disopyramide does not belong to any of the known classes of antiarrhythmics; however, being a drug of the class IA sodium channel blockers, it exhibits membranestabilizing action and increases the effective refractory period and duration of an action potential in the atrium and ventricles. It causes a decrease in contractability and excitability of the myocardium, slowing of conductivity, and suppression of sinoatride automatism.
• Uses: Disopyramide is used for preventing and restoring atrial and ventricular extrasystole and tachycardia in order to prevent atrial flutter and arrhythmia.
• Therapeutic Function: Antiarrhythmic
• Clinical Use: Disopyramide (Norpace) can suppress atrial and ventricular arrhythmias and is longer acting than other drugs in its class. The indications for use of disopyramide are similar to those for quinidine, except that it is not approved for use in the prophylaxis of atrial flutter or atrial fibrillation after DC conversion.The indications are as follows: unifocal premature (ectopic) ventricular contractions, premature (ectopic) ventricular contractions of multifocal origin, paired premature ventricular contractions (couplets), and episodes of ventricular tachycardia. Persistent ventricular tachycardia is usually treated with DC conversion.
• Drug interactions: In the presence of phenytoin, the metabolism of disopyramide is increased (reducing its effective concentration) and the accumulation of its metabolites is also increased, thereby increasing the probability of anticholinergic adverse effects. Rifampin also stimulates the hepatic metabolism of disopyramide, reducing its plasma concentration. Unlike quinidine, disopyramide does not increase the plasma concentration of digoxin in patients receiving a maintenance dose of the cardiac glycoside. Hypoglycemia has been reported with the use of disopyramide, particularly in conjunction with moderate or excessive alcohol intake.

Technology Process of Disopyramide

There total 2 articles about Disopyramide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.7%

disopyramide phosphate (22059-60-5) → disopyramide (74427-45-5,74464-83-8,74464-84-9,3737-09-5)

Guidance literature:

disopyramide phosphate; With sodium hydroxide; In n-heptane; water; toluene; at 23 - 27 ℃; for 0.833333h; pH=12.65;

at 20 - 46 ℃; for 4h;

at 60 ℃; for 7h; under 22.5023 Torr; Purification / work up;

Reference yield:

→ disopyramide (74427-45-5,74464-83-8,74464-84-9,3737-09-5)

Guidance literature:

Reference yield: 78.0%

disopyramide (74427-45-5,74464-83-8,74464-84-9,3737-09-5) → α-[2-[bis(1-methylethyl)amino]ethyl]-α-phenyl-2-piperidineacetamide (107256-81-5)

Guidance literature:

With sulfuric acid; hydrogen; PtO₂/C; In water; at 75 ℃; for 4h; under 3102.9 Torr;

DOI:10.1021/jm00147a029

upstream raw materials:

disopyramide phosphate

Downstream raw materials:

α-[2-[bis(1-methylethyl)amino]ethyl]-α-phenyl-2-piperidineacetamide

(-)-Disopyramide

(+)-Disopyramide

(+/-)-trans-4-<2-ethyl>octahydro-2-methyl-4-phenyl-3H-pyrido<1,2-c>-pyrimidin-3-one

Refernces

• 1、 -. "(-)-α-{2-[Bis(1-methylethyl)amino]ethyl}-α-phenyl-2-pyridineacetamide and pharmacologically acceptable salts thereof". . . Retrieved 2008/06/13.