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54063-53-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:1053 http://www.chembase.cn/molecule-1053.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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)
CAS Number
54063-53-5
34183-22-7
EC Number
258-955-6
PubChem SID
46504529
160964516
PubChem CID
4932

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.085882  H Acceptors
H Donor LogD (pH = 5.5) 0.34713113 
LogD (pH = 7.4) 1.3413471  Log P 3.5367227 
Molar Refractivity 100.2064 cm3 Polarizability 39.38228 Å3
Polar Surface Area 58.56 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five true 
Log P 3.1  LOG S -4.65 
Solubility (Water) 7.58e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Slightly soluble expand Show data source
Hydrophobicity(logP)
3.2 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
UC2984700 expand Show data source
MSDS Link
Download expand Show data source
Target
Sodium Channel expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank
MP Biomedicals - 02156386 external link
Hydrochloride
DrugBank - DB01182 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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