HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Disopyramid
h3292 · H 3292 · sc7031 · H. 3292 · Lispine · SC 7031 · Isorythm · Ritmodan
Identifikatoren & physikalische Daten
| CAS No. | 22059-60-5 |
|---|---|
| Summenformel | C21H29N3O |
| Durchschnittliche Molmasse | 339,5 g/mol |
| Monoisotopische Masse | 339,23106256 g/mol |
| SMILES | CC(C)N(CCC(C(N)=O)(c1ccccc1)c1ccccn1)C(C)C |
| InChIKey | UVTNFZQICZKOEM-UHFFFAOYSA-N |
| PubChem CID | 3114 |
| ChEMBL | CHEMBL517 |
| ChEBI | CHEBI:4657 |
| EC No. | 223-110-2 |
| DTXSID | DTXSID1045536 |
| Lokaler Name | Disopyramid |
Chemische & physikalische Eigenschaften
| XLogP | 3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 59,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 25 |
| Formalladung | 0 |
| Komplexität | 409 |
| LogP (Verteilungskoeffizient) | 3.52.71 |
| Löslichkeit | 4.93e-02 g/LSoluble in DMSO (25 mg/ml) and Ethanol (>35 mg/mL)6.17mg/L(22.5 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAntiarrhythmicsPharmaceuticals |
| Schmelzpunkt | 94.5-95 °C94.5 - 95 °C94.5-950C |
| Physical Description | Solid |
| Dissociation Constants | 10.32 |
| Collision Cross Section | 183.45 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 475.43°C (rough estimate) |
| Dichte | 1.0779 (rough estimate) |
| Brechungsindex | 1.6300 (estimate) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | 10.2also reported as 10.45(at 25℃) |
| Farbe | White |
| Merck | 14,3360 |
| Stabilität | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| Hauptanwendungen | pharmaceutical (small molecule) |
| 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) |
| InChIKey | UVTNFZQICZKOEM-UHFFFAOYSA-N |
| SMILES | CC(C)N(CCC(C(N)=O)(c1ccccc1)c2ccccn2)C(C)C |
| CAS Datenbank | 3737-09-5(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | REACH registered substance: Disopyramide (EC: 223-110-2)Disopyramide: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Pyridineacetamide, .alpha.-[2-[bis(1-methylethyl)amino]ethyl]-.alpha.-phenyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Hepatotoxicity | In clinical trials, disopyramide was associated with a low rate of serum aminotransferase and alkaline phosphatase elevations. Despite wide scale use, disopyramide has only rarely been linked to cases of clinically apparent liver injury. Two types of hepatic injury have been described. The first is an acute hepatocellular injury that arises within 1 to 3 days of starting disopyramide and resembles acute hepatic ischemia with marked early rises in serum aminotransferase levels (and LDH), with minimal increase in alkaline phosphatase and subsequent rise in serum bilirubin. The prothrombin time may be abnormal initially. The injury resolves rapidly and may relate to sudden worsening of congestive heart failure due to the myocardial depressant effects of disopyramide. |
| Unerwünschte Wirkungen | The most serious adverse reactions identified include hypotension and congestive heart failure. Common adverse reactions, which may be dose-dependent, are linked to the drug's anticholinergic properties. Although these effects can be transitory, they may also persist or become severe. |
| Toxizitätsübersicht | Signs and Symptoms of Overdose |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)disopyramideDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| EPA Human Health Benchmarks for Pharmaceuticals | Disopyramide14.059.2The recommended dosage for most adults is 600 mg/day given in divided doses (150 mg every 6 hours). For patients whose body weight is less than 110 pounds (50 kg), the recommended dosage is 400 mg/day given in divided doses (100 mg every 6 hours).Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 600 mg/day, Lowest Therapeutic Dose (LTD): 7.5 mg/kg-day, and Screening Dose: 0.003 mg/kg-day.31-Aug-15 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2933.39.4100 |
| RTECS-Nr. | UR8432000 |
| R-Sätze (R) | 22-36/37/38-39/23/24/25-23/24/25-11 |
| Toxizität | LD50 i.p. in mice: 517 mmol/kg (Ruenitz, Mokler) |
| Gefahrensymbole | Xn,Xi,T,F |
| Sicherheitshinweise (S) | 36-26-45-36/37-16-7 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralRepr. 2 |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
Disopyramide is used for preventing and restoring atrial and ventricular extrasystole and tachycardia in order to prevent atrial flutter and arrhythmia.