1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one

• ChemBase ID: 1053
• Molecular Formular: C21H27NO3
• Molecular Mass: 341.44398
• Monoisotopic Mass: 341.19909373
• SMILES: O(CC(O)CNCCC)c1c(C(=O)CCc2ccccc2)cccc1
• Canonical SMILES: CCCNCC(COc1ccccc1C(=O)CCc1ccccc1)O
• InChI: InChI=1S/C21H27NO3/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: JWHAUXFOSRPERK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one
• IUPAC Traditional name: propafenone
• Brand Name: Rythmol; Rythmol SR
• Synonyms: Propafenona [INN-Spanish]; Propafenone HCl; Propafenone hydrochloride; Propafenone-HCl; Propafenonum [INN-Latin]; Propafenone; 1-[2-(2-Hydroxy-3-[propylamino]-propoxy)phenyl]-3-phenyl-1-propanone; PROPAFENONE HYDROCHLORIDE; Rythmol SR; Rytmonorm; Propafenone (Rytmonorm)

Database IDs

• CAS Number: 54063-53-5; 34183-22-7
• EC Number: 258-955-6
• PubChem SID: 46504529; 160964516
• PubChem CID: 4932

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.085882
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.34713113
• LogD (pH = 7.4): 1.3413471
• Log P: 3.5367227
• Molar Refractivity: 100.2064 cm^3
• Polarizability: 39.38228 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.1
• LOG S: -4.65
• Solubility (Water): 7.58e-03 g/l

PROPERTIES

Physical Property

• Solubility: Slightly soluble
• Hydrophobicity(logP): 3.2

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: UC2984700

Pharmacology Properties

• Target: Sodium Channel

Product Information

• Salt Data: Free Base

DETAILS

MP Biomedicals - 02156386

Hydrochloride

DrugBank - DB01182

• Drug Groups: approved
• Description: An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity. The drug is generally well tolerated. [PubChem]
• Indication: Used to prolong the time to recurrence of paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms in patients without structural heart disease. Also used for the treatment of life-threatening documented ventricular arrhythmias, such as sustained ventricular tachycardia.
• Pharmacology: Propafenone is a Class 1C antiarrhythmic drug with local anesthetic effects, and a direct stabilizing action on myocardial membranes. It is used in the treatment of atrial and ventricular arrhythmias. It works by slowing the influx of sodium ions into the cardiac muscle cells, causing a decrease in excitablity of the cells. Propafenone has local anesthetic activity approximately equal to procaine.
• Toxicity: Symptoms of propafenone overdose (usually most severe within the first 3 hours) may include convulsions (rarely), heartbeat irregularities, low blood pressure, and sleepiness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized primarily in the liver where it is rapidly and extensively metabolized to two active metabolites, 5-hydroxypropafenone and N-depropylpropafenone. These metabolites have antiarrhythmic activity comparable to propafenone but are present in concentrations less than 25% of propafenone concentrations.
• Absorption: Nearly completely absorbed following oral administration (90%). Systemic bioavailability ranges from 5 to 50%, due to significant first-pass metabolism. This wide range in systemic bioavailability is related to two factors: presence of food (food increases bioavailability) and dosage (bioavailability is 3.4% for a 150-mg tablet compared to 10.6% for a 300-mg tablet).
• Half Life: 2-10 hours
• Protein Binding: 97%
• Elimination: Approximately 50% of propafenone metabolites are excreted in the urine following administration of immediate release tablets.
• Distribution: * 252 L
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com