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Details

Stereochemistry RACEMIC
Molecular Formula C23H31NO3
Molecular Weight 369.4971
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPRAFENONE

SMILES

CCC(C)(C)NCC(O)COC1=C(C=CC=C1)C(=O)CCC2=CC=CC=C2

InChI

InChIKey=VDKMYSMWQCFYBQ-UHFFFAOYSA-N
InChI=1S/C23H31NO3/c1-4-23(2,3)24-16-19(25)17-27-22-13-9-8-12-20(22)21(26)15-14-18-10-6-5-7-11-18/h5-13,19,24-25H,4,14-17H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C23H31NO3
Molecular Weight 369.4971
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Diprafenone closely resembles propafenone in both structure and function. It is beta adrenoceptor antagonists and sodium channel antagonists. Diprafenone is highly protein bound in plasma. It has demonstrated efficacy against supraventricular and ventricular arrhythmias in clinical trials. Diprafenone produced first-degree atrioventricular block in 6/20 patients tested with coronary artery disease and sustained ventricular tachycardia. Intravenous application of diprafenone significantly increased atrioventricular nodal conduction time as well as the effective refractory periods of the right ventricle and the accessory pathway in both the antegrade and retrograde directions in 15 patients with the Wolff-Parkinson-White syndrome and symptomatic supraventricular tachycardia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
[Comment on the contribution by C. Hief, K. Frohner, A. Podczeck, W. Kaltenbrunner, M. Nürnberg and K. Steinbach: Value of a provocation test with diprafenone in patients with bifascicular block].
1992 Dec
Electrophysiological effects of diprafenone, a dimethyl congener of propafenone on guinea-pig ventricular cells.
1992 Nov
Supraventricular tachycardia and pre-excitation syndromes: pharmacological therapy.
1993 Sep
[HPLC determination of diprafenone and its active metabolite 5-hydroxydiprafenone in human plasma].
1994 Jan
Chemically modified cardiac Na+ channels and their sensitivity to antiarrhythmics: is there a hidden drug receptor?
1994 May
Single-dose interaction study of diprafenone HCl and propranolol HCl in healthy volunteers.
1995 Jul
Influence of food on the bioavailability and some pharmacokinetic parameters of diprafenone--a novel antiarrhythmic agent.
1996
Effect of diprafenone on the pharmacokinetics of digoxin.
1996
Enantioselective determination of diprafenone in human plasma.
1997 Feb
Diprafenone.
1999 Apr

Sample Use Guides

380 mg/day for at least 4 days
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:04:38 GMT 2023
Record UNII
1P35MD5C1F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPRAFENONE
INN   WHO-DD  
INN  
Official Name English
diprafenone [INN]
Common Name English
(±)-2'-(2-HYDROXY-3-(TERT-PENTYLAMINO)PROPOXY)-3-PHENYLPROPIOPHENONE
Systematic Name English
Diprafenone [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL441809
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
SMS_ID
100000082331
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
INN
5257
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
DRUG CENTRAL
923
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
WIKIPEDIA
Diprafenone
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
MESH
C047546
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
CAS
81447-80-5
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
NCI_THESAURUS
C65429
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
PUBCHEM
71249
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
FDA UNII
1P35MD5C1F
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID10868613
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
EVMPD
SUB07219MIG
Created by admin on Fri Dec 15 16:04:38 GMT 2023 , Edited by admin on Fri Dec 15 16:04:38 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY