propafenone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antiarrhythmics, propafenone derivatives 2291 54063-53-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • propafenone
  • propafenone hydrochloride
  • polfenon
  • (RS)-Propafenone
  • propafenone HCl
An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.
  • Molecular weight: 341.45
  • Formula: C21H27NO3
  • CLOGP: 3.64
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 58.56
  • ALOGS: -4.65
  • ROTB: 11

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
0.30 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.09 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 12 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 16 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.04 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 27, 1989 FDA GLAXOSMITHKLINE LLC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 263.01 58.34 65 310 20969 2336741
Toxicity to various agents 225.09 58.34 63 312 32691 2325019
Atrial fibrillation 183.28 58.34 45 330 13723 2343987
Electrocardiogram QRS complex prolonged 163.53 58.34 27 348 1075 2356635
Bradycardia 144.50 58.34 35 340 9946 2347764
Cardiac arrest 130.50 58.34 35 340 14895 2342815
Drug interaction 123.99 58.34 39 336 29124 2328586
Syncope 121.63 58.34 34 341 16841 2340869
Intentional overdose 120.19 58.34 31 344 11290 2346420
Hypotension 115.81 58.34 38 337 32398 2325312
Sinus bradycardia 114.26 58.34 22 353 2094 2355616
Suicide attempt 77.62 58.34 22 353 11260 2346450
Dizziness 76.75 58.34 33 342 58632 2299078
Generalised tonic-clonic seizure 73.08 58.34 18 357 5354 2352356
Loss of consciousness 66.58 58.34 22 353 18745 2338965

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 151.12 65.61 42 250 16270 1730219
Electrocardiogram QRS complex prolonged 145.04 65.61 24 268 751 1745738
Facial asymmetry 94.25 65.61 12 280 50 1746439
Toxicity to various agents 87.71 65.61 32 260 29109 1717380
Bradycardia 73.81 65.61 22 270 10512 1735977
Atrial fibrillation 70.03 65.61 23 269 15088 1731401
Hypotension 68.84 65.61 27 265 29627 1716862

Pharmacologic Action:

SourceCodeDescription
ATC C01BC03 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class Ic
FDA EPC N0000175426 Antiarrhythmic
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D026941 Sodium Channel Blockers
CHEBI has role CHEBI:38070 anti-arrhythmia drug
MeSH PA D061567 Voltage-Gated Sodium Channel Blockers

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Atrial fibrillation indication 49436004 DOID:0060224
Paroxysmal supraventricular tachycardia indication 67198005
Paroxysmal atrial fibrillation indication 282825002
Paroxysmal atrial flutter indication 427665004
Life-Threatening Ventricular Tachycardia indication
Cardioversion of Atrial Fibrillation off-label use
Bronchospasm contraindication 4386001
Bundle branch block contraindication 6374002
Hyperkalemia contraindication 14140009
Agranulocytosis contraindication 17182001 DOID:12987
Myocardial infarction contraindication 22298006 DOID:5844
Torsades de pointes contraindication 31722008
Sick sinus syndrome contraindication 36083008 DOID:13884
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Prolonged QT interval contraindication 111975006
Structural disorder of heart contraindication 128599005
Atrioventricular block contraindication 233917008 DOID:0050820
Disease of liver contraindication 235856003 DOID:409
Severe chronic obstructive pulmonary disease contraindication 313299006
Myocardial infarction in recovery phase contraindication 418044006
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.15 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-1 adrenergic receptor GPCR ANTAGONIST Ki 6.69 DRUG MATRIX CHEMBL
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 5.48 CHEMBL CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 5.96 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.52 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 6.03 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 6.73 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 7.24 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.70 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.06 DRUG MATRIX
Beta-3 adrenergic receptor GPCR Ki 6.50 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.83 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 5.34 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 5.60 DRUG MATRIX
Cytochrome P450 1A2 Enzyme IC50 5.48 DRUG MATRIX
Solute carrier family 22 member 2 Transporter IC50 4.60 WOMBAT-PK
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Ion channel IC50 4.84 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 5.60 WOMBAT-PK
Multidrug resistance protein 1 Transporter ED50 7.06 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.10 WOMBAT-PK
Sodium channel subunit beta-4 Ion channel WOMBAT-PK
Sodium channel subunit beta-3 Ion channel WOMBAT-PK
Sodium channel subunit beta-1 Ion channel WOMBAT-PK
Solute carrier family 22 member 1 Transporter IC50 4.95 CHEMBL
Sulfonylurea receptor 2, Kir6.2 Ion channel IC50 5.66 CHEMBL
Sodium channel subunit beta-2 Ion channel WOMBAT-PK
Potassium voltage-gated channel subfamily A member 5 Ion channel BLOCKER IC50 4.40 IUPHAR
Beta-2 adrenergic receptor GPCR ANTAGONIST Ki 7.44 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 5.85 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR IC50 5.79 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 5.21 CHEMBL

External reference:

IDSource
4019911 VUID
N0000147996 NUI
C0033429 UMLSCUI
D00640 KEGG_DRUG
33XCH0HOCD UNII
34183-22-7 SECONDARY_CAS_RN
3312 INN_ID
96300001 SNOMEDCT_US
4019911 VANDF
40681 MMSL
8754 RXNORM
372910007 SNOMEDCT_US
d00358 MMSL
004487 NDDF
CHEMBL631 ChEMBL_ID
DB01182 DRUGBANK_ID
CHEBI:63619 CHEBI
CHEMBL1201063 ChEMBL_ID
D011405 MESH_DESCRIPTOR_UI
4932 PUBCHEM_CID
2561 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
RYTHMOL HUMAN PRESCRIPTION DRUG LABEL 1 0173-0823 CAPSULE, EXTENDED RELEASE 225 mg ORAL NDA 18 sections
RYTHMOL HUMAN PRESCRIPTION DRUG LABEL 1 0173-0824 CAPSULE, EXTENDED RELEASE 325 mg ORAL NDA 18 sections
RYTHMOL HUMAN PRESCRIPTION DRUG LABEL 1 0173-0826 CAPSULE, EXTENDED RELEASE 425 mg ORAL NDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1258 CAPSULE, EXTENDED RELEASE 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1259 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1261 CAPSULE, EXTENDED RELEASE 425 mg ORAL ANDA 18 sections
Propafenone HCl HUMAN PRESCRIPTION DRUG LABEL 1 0591-0582 TABLET, FILM COATED 150 mg ORAL ANDA 18 sections
Propafenone HCl HUMAN PRESCRIPTION DRUG LABEL 1 0591-0583 TABLET, FILM COATED 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-2285 CAPSULE, EXTENDED RELEASE 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-2286 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-2287 CAPSULE, EXTENDED RELEASE 425 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-5448 TABLET, FILM COATED 150 mg ORAL ANDA 19 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-5449 TABLET, FILM COATED 225 mg ORAL ANDA 19 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-5450 TABLET, FILM COATED 300 mg ORAL ANDA 19 sections
propafenone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-825 CAPSULE, EXTENDED RELEASE 225 mg ORAL ANDA 18 sections
propafenone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-826 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 18 sections
propafenone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-827 CAPSULE, EXTENDED RELEASE 425 mg ORAL ANDA 18 sections
Propafenone HUMAN PRESCRIPTION DRUG LABEL 1 21695-814 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 11 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-545 CAPSULE, EXTENDED RELEASE 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-546 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42291-547 CAPSULE, EXTENDED RELEASE 425 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-113 CAPSULE, EXTENDED RELEASE 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-210 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 49884-211 CAPSULE, EXTENDED RELEASE 425 mg ORAL ANDA 18 sections
Propafenone HCl HUMAN PRESCRIPTION DRUG LABEL 1 50090-2975 TABLET, FILM COATED 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-4227 TABLET, COATED 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51407-016 TABLET, COATED 225 mg ORAL ANDA 18 sections
Propafenone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51407-017 TABLET, COATED 300 mg ORAL ANDA 18 sections
PROPAFENONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 52536-730 CAPSULE, EXTENDED RELEASE 225 mg ORAL ANDA 19 sections
PROPAFENONE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 52536-733 CAPSULE, EXTENDED RELEASE 325 mg ORAL ANDA 19 sections