Propafenone Hydrochloride
PROPAFENONE HCL · Pronon · Rythmol · rytmonorm · SA-79 (hydrochloride) · 1-Propanone, 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-, hydrochloride (9CI) · sa79 · wz884
Identifiers & Physical Properties
| CAS No. | 34183-22-7 |
|---|---|
| Molecular formula | C21H28ClNO3 |
| Average molar mass | 377.9 g/mol |
| Monoisotopic mass | 377.17577144 g/mol |
| SMILES | CCCNCC(O)COc1ccccc1C(=O)CCc1ccccc1.Cl |
| InChIKey | XWIHRGFIPXWGEF-UHFFFAOYSA-N |
| PubChem CID | 36708 |
| ChEMBL | CHEMBL1201063 |
| ChEBI | CHEBI:8466 |
| EC No. | 251-867-9 |
| DTXSID | DTXSID101017233 |
Chemical & Physical Properties
| Topological polar surface area | 58.6 |
|---|---|
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 11 |
| Heavy atoms | 26 |
| Formal charge | 0 |
| Complexity | 368 |
| Solubility | >56.7 [ug/mL] (The mean of the results at pH 7.4)Slightly soluble in cold water, soluble in methanol and in hot water, practically insoluble in ethanol (96 per cent). |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Collision Cross Section | 177.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Melting point | 165-1670C |
| Storage conditions | 2-8°C |
| Physical state | Solid |
| Color | White to Off-White |
| λmax | 303nm(MeOH)(lit.) |
| Merck | 14,7794 |
| Major applications | clinical testing |
| InChI | InChI=1S/C21H27NO3.ClH/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3 |
| InChIKey | XWIHRGFIPXWGEF-UHFFFAOYSA-N |
| SMILES | C1(=CC=CC=C1C(=O)CCC1C=CC=CC=1)OCC(O)CNCCC.Cl |
| CAS DataBase Reference | 34183-22-7(CAS DataBase Reference) |
| FDA UNII | 33XCH0HOCD |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| Protein binding | >95% |
| Excreted unchanged in urine | <1% |
| Volume of distribution | 1.9-3(L/kg) |
| Biological half-life | 2-10 (10-32 hours in slow metabolisers) / Unchanged |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P301+P312+P330 |
| Target organs | Eyes |
| Hazard symbols | T,Xn |
| Risk statements (R) | 46-22 |
| Safety statements (S) | 53-36/37/39-45 |
| Water hazard class (WGK) | 3 |
| RTECS number | UH2833000 |
| Customs code | 2922504500 |
| Storage class | 3 - Flammable liquids |
| Hazard class | Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1 |
| Toxicity | LD50 in rats (mg/kg): 18.8 i.v.700 orally (Hapke, Prigge) |
Safety & Regulations
| GHS classification | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 154 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Propafenone hydrochloridevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Water hazard class (WGK) | 3 |
| RTECS number | UH2833000 |
| Customs code | 2922504500 |
| Toxicity | LD50 in rats (mg/kg): 18.8 i.v.700 orally (Hapke, Prigge) |
| Risk statements (R) | 46-22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | T,Xn |
| Safety statements (S) | 53-36/37/39-45 |
| Storage class | 3 - Flammable liquids |
| Target organs | Eyes |
| GHS hazard statements | H302 |
| Hazard class | Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1 |
| GHS precautionary statements | P301+P312+P330 |
Applications & Uses
Description
Propafenone hydrochloride is a class I anti-arrhythmic agent with basic local anaesthetic and membrane-stabilizing properties. Some P-adrenergic blocking action has also been described. Propafenone decreases the depolarization velocity and slows conduction in the His-Purkinje system with resultant increase in the PR interval and the QRS complex. Propafenone is used in the treatment of paroxysmal supraventricular tachycardias and ventricular arrhythmias.Propafenone should not be used in uncontrolled cardiac failure, severe obstructive pulmonary disease or marked hypotension. Propafenone may worsen myasthenia gravis.
Uses
Propafenone hydrochloride is a class IC antiarrhythmic agent used for the management of severe ventricular and supraventricular arrhythmias. It has beta-blocking and weak calcium channel blocking properties, as well as some negative inotropic activity. Propafenone is in a class of medications called antiarrhythmics. It works by acting on the heart muscle to improve the heart's rhythm.
Uses
Sodium channel blocker. Antiarrhythmic (class IC)