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

Stem definitionDrug idCAS RN
Class I antiarrhythmics, procainamide and lidocaine derivatives 1176 54143-55-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tambocor
  • flecainide
  • flecaine
  • flecainide acetate
A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.
  • Molecular weight: 414.35
  • Formula: C17H20F6N2O3
  • CLOGP: 3.66
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 59.59
  • ALOGS: -4.11
  • ROTB: 9

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 12.07 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
S (Water solubility) 48.40 mg/mL Hosey CM, Chan R, Benet LZ
EoM (Fraction excreted unchanged in urine) 43 % Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 95 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 6.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.52 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 12 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 31, 1985 FDA

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
Electrocardiogram QRS complex prolonged 465.73 13.60 137 14530 5312 46666083
Atrial fibrillation 279.61 13.60 243 14424 103347 46568048
Electrocardiogram QT prolonged 205.78 13.60 152 14515 51173 46620222
Bradycardia 202.20 13.60 167 14500 66131 46605264
Ventricular tachycardia 178.50 13.60 93 14574 16874 46654521
Drug interaction 166.15 13.60 257 14410 202837 46468558
Arrhythmia 159.76 13.60 112 14555 34729 46636666
Cardiac arrest 147.34 13.60 161 14506 90238 46581157
Toxicity to various agents 122.75 13.60 230 14437 211536 46459859
Torsade de pointes 120.36 13.60 64 14603 12090 46659305
Atrioventricular block first degree 117.66 13.60 51 14616 6135 46665260
Bundle branch block right 82.82 13.60 37 14630 4782 46666613
Ventricular fibrillation 77.28 13.60 47 14620 11449 46659946
Device capturing issue 67.93 13.60 12 14655 37 46671358
Hypotension 64.14 13.60 189 14478 232400 46438995
Hyponatraemia 54.74 13.60 107 14560 101225 46570170
Brugada syndrome 54.03 13.60 13 14654 227 46671168
Thalamic infarction 52.27 13.60 15 14652 530 46670865
Syncope 52.22 13.60 107 14560 104696 46566699
Device pacing issue 51.64 13.60 9 14658 25 46671370
Defect conduction intraventricular 51.57 13.60 11 14656 108 46671287
Rheumatoid arthritis 49.67 13.60 8 14659 240207 46431188
Atrial flutter 48.02 13.60 32 14635 9116 46662279
Overdose 46.02 13.60 100 14567 101879 46569516
Acute kidney injury 45.59 13.60 170 14497 235685 46435710
Bifascicular block 45.52 13.60 10 14657 114 46671281
Bundle branch block left 45.17 13.60 27 14640 6372 46665023
Sinus bradycardia 44.61 13.60 36 14631 13746 46657649
Conduction disorder 41.97 13.60 16 14651 1382 46670013
Tachyarrhythmia 39.22 13.60 22 14645 4610 46666785
Cardiogenic shock 39.20 13.60 36 14631 16348 46655047
Sinoatrial block 38.27 13.60 13 14654 805 46670590
Pain 38.04 13.60 57 14610 476891 46194504
Tubulointerstitial nephritis 36.37 13.60 33 14634 14755 46656640
Cerebral venous thrombosis 35.49 13.60 16 14651 2111 46669284
Cutaneous T-cell lymphoma 35.26 13.60 14 14653 1349 46670046
Ventricular dyssynchrony 34.61 13.60 6 14661 16 46671379
Ventricular arrhythmia 33.81 13.60 18 14649 3403 46667992
Atrioventricular block 33.78 13.60 23 14644 6788 46664607
Completed suicide 33.15 13.60 111 14556 145809 46525586
Electrocardiogram PR prolongation 32.91 13.60 11 14656 648 46670747
Palpitations 32.72 13.60 84 14583 95175 46576220
Electrocardiogram abnormal 30.84 13.60 22 14645 6990 46664405
Cardio-respiratory arrest 29.64 13.60 61 14606 59808 46611587
Device malfunction 29.33 13.60 28 14639 13346 46658049
Intentional overdose 28.50 13.60 63 14604 64881 46606514
Cardiac failure 27.97 13.60 71 14596 79877 46591518
Medication error 26.37 13.60 40 14627 30871 46640524
Bundle branch block 26.05 13.60 10 14657 880 46670515
Hyperkalaemia 24.32 13.60 51 14616 50658 46620737
Slow response to stimuli 23.12 13.60 9 14658 823 46670572
Pulmonary alveolar haemorrhage 22.91 13.60 15 14652 4147 46667248
Sinus node dysfunction 22.50 13.60 15 14652 4274 46667121
Metabolic acidosis 22.19 13.60 42 14625 38738 46632657
Ventricular extrasystoles 22.08 13.60 22 14645 11041 46660354
Drug-device interaction 22.02 13.60 5 14662 67 46671328
Dermatitis exfoliative generalised 22.01 13.60 13 14654 3000 46668395
Intracranial haematoma 21.94 13.60 7 14660 356 46671039
Subarachnoid haemorrhage 21.93 13.60 22 14645 11131 46660264
Bradyarrhythmia 21.09 13.60 11 14656 1995 46669400
Pericardial haemorrhage 20.71 13.60 10 14657 1541 46669854
Cerebral haemorrhage 20.46 13.60 34 14633 28337 46643058
Heart rate irregular 20.19 13.60 27 14640 18564 46652831
Drug-disease interaction 19.91 13.60 6 14661 252 46671143
Tachycardia 19.34 13.60 72 14595 99550 46571845
Ischaemic stroke 19.27 13.60 25 14642 16697 46654698
Cholestasis 19.08 13.60 32 14635 26861 46644534
International normalised ratio increased 18.91 13.60 44 14623 46839 46624556
Musculoskeletal stiffness 18.65 13.60 4 14663 97989 46573406
Hepatocellular injury 18.18 13.60 33 14634 29489 46641906
Injection site discomfort 17.65 13.60 12 14655 3530 46667865
Pulseless electrical activity 17.63 13.60 16 14651 7151 46664244
Subdural haematoma 17.48 13.60 21 14646 12976 46658419
Sensitisation 17.47 13.60 7 14660 690 46670705
Orthostatic hypotension 17.04 13.60 29 14638 24629 46646766
Haemarthrosis 17.00 13.60 11 14656 2982 46668413
Phospholipidosis 16.78 13.60 4 14663 67 46671328
Corneal deposits 16.59 13.60 5 14662 210 46671185
Cardiotoxicity 16.53 13.60 15 14652 6707 46664688
Mixed liver injury 16.51 13.60 11 14656 3132 46668263
Therapeutic product effect decreased 16.50 13.60 3 14664 82598 46588797
Cardiac ablation 16.45 13.60 8 14659 1251 46670144
Rectal polyp 16.35 13.60 7 14660 816 46670579
Supraventricular extrasystoles 16.00 13.60 12 14655 4117 46667278
Congenital hypothyroidism 15.91 13.60 5 14662 242 46671153
Contraindicated product administered 15.76 13.60 3 14664 79944 46591451
Anaemia macrocytic 15.68 13.60 10 14657 2643 46668752
Drug level above therapeutic 15.41 13.60 11 14656 3498 46667897
Cardiac tamponade 15.19 13.60 12 14655 4442 46666953
Fall 15.18 13.60 164 14503 328933 46342462
Cerebral congestion 14.84 13.60 3 14664 22 46671373
Gravitational oedema 14.41 13.60 7 14660 1093 46670302
Needle issue 14.36 13.60 13 14654 5791 46665604
Extrasystoles 14.25 13.60 12 14655 4857 46666538
Rash pustular 14.24 13.60 14 14653 6915 46664480
Abdominal symptom 14.07 13.60 5 14662 354 46671041
Supraventricular tachycardia 14.00 13.60 19 14648 13251 46658144
Tachycardia foetal 13.95 13.60 4 14663 141 46671254
Haematemesis 13.84 13.60 29 14638 28777 46642618
Depression 13.82 13.60 20 14647 170084 46501311

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
Electrocardiogram QRS complex prolonged 206.23 14.34 70 9629 4207 29938572
Atrial fibrillation 188.48 14.34 202 9497 107922 29834857
Bradycardia 177.38 14.34 156 9543 65370 29877409
Ventricular tachycardia 117.33 14.34 81 9618 23781 29918998
Atrial flutter 116.94 14.34 67 9632 14214 29928565
Brugada syndrome 96.33 14.34 25 9674 583 29942196
Electrocardiogram QT prolonged 64.00 14.34 68 9631 35767 29907012
Atrioventricular block first degree 58.41 14.34 31 9668 5657 29937122
Drug interaction 47.43 14.34 157 9542 199411 29743368
Arrhythmia 47.32 14.34 56 9643 33113 29909666
Toxicity to various agents 46.28 14.34 144 9555 177039 29765740
Syncope 45.62 14.34 91 9608 84812 29857967
Tachyarrhythmia 44.13 14.34 21 9678 3040 29939739
Cardiac arrest 40.04 14.34 91 9608 92759 29850020
Electrocardiogram abnormal 38.70 14.34 24 9675 5868 29936911
Bundle branch block right 37.17 14.34 25 9674 7017 29935762
Supraventricular tachycardia 37.16 14.34 29 9670 10243 29932536
Ventricular fibrillation 34.87 14.34 33 9666 15105 29927674
Tachycardia 34.85 14.34 75 9624 73664 29869115
Device pacing issue 32.77 14.34 6 9693 23 29942756
Electrocardiogram QRS complex shortened 32.52 14.34 8 9691 149 29942630
Cardiac flutter 32.46 14.34 14 9685 1612 29941167
Hypotension 32.00 14.34 139 9560 200426 29742353
High frequency ablation 31.62 14.34 8 9691 168 29942611
Electrocardiogram PR prolongation 31.18 14.34 11 9688 740 29942039
Amaurosis 28.43 14.34 10 9689 667 29942112
Drug level increased 27.85 14.34 32 9667 18322 29924457
Cardiogenic shock 26.60 14.34 30 9669 16831 29925948
Atrioventricular block complete 26.55 14.34 22 9677 8455 29934324
Palpitations 25.69 14.34 42 9657 33531 29909248
Pulseless electrical activity 23.54 14.34 18 9681 6169 29936610
Atrioventricular block 23.02 14.34 19 9680 7263 29935516
Intentional overdose 22.89 14.34 45 9654 41436 29901343
Atrial tachycardia 22.82 14.34 12 9687 2147 29940632
Interstitial lung disease 21.61 14.34 55 9644 60142 29882637
Overdose 21.43 14.34 68 9631 84269 29858510
International normalised ratio increased 20.77 14.34 47 9652 47692 29895087
Sinus bradycardia 20.51 14.34 22 9677 11673 29931106
Splenic rupture 20.51 14.34 10 9689 1526 29941253
Pelvic pain 20.16 14.34 11 9688 2118 29940661
Microcytic anaemia 19.93 14.34 11 9688 2167 29940612
Shock haemorrhagic 19.90 14.34 20 9679 9845 29932934
Vertigo 19.64 14.34 30 9669 22605 29920174
Hypomania 19.57 14.34 11 9688 2245 29940534
Device capturing issue 19.03 14.34 3 9696 3 29942776
Reflexes abnormal 18.46 14.34 6 9693 314 29942465
Accidental overdose 18.42 14.34 26 9673 18249 29924530
Atrial conduction time prolongation 17.81 14.34 3 9696 6 29942773
Defect conduction intraventricular 17.21 14.34 5 9694 179 29942600
Hypoglycaemic coma 16.60 14.34 10 9689 2321 29940458
Calcium ionised increased 15.91 14.34 3 9696 14 29942765
Pupillary disorder 15.86 14.34 5 9694 237 29942542
Completed suicide 15.84 14.34 69 9630 99423 29843356
Bradyarrhythmia 15.54 14.34 9 9690 1943 29940836
Eosinophilic pneumonia 15.21 14.34 10 9689 2701 29940078
Ventricular dyssynchrony 14.88 14.34 3 9696 21 29942758
Ductus arteriosus premature closure 14.85 14.34 4 9695 108 29942671
Haematoma 14.45 14.34 27 9672 23926 29918853

Pharmacologic Action:

SourceCodeDescription
ATC C01BC04 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class Ic
FDA EPC N0000175426 Antiarrhythmic
CHEBI has role CHEBI:38070 antiarrhythmic agent
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D026941 Sodium Channel Blockers
MeSH PA D061567 Voltage-Gated Sodium Channel Blockers

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Atrial fibrillation indication 49436004 DOID:0060224
Paroxysmal atrial fibrillation indication 282825002
Paroxysmal atrial flutter indication 427665004
Prevention of Paroxysmal Supraventricular Tachycardia indication
Life-Threatening Ventricular Tachycardia indication
Cardioversion of Atrial Fibrillation off-label use
Hyperkalemia contraindication 14140009
Myocardial infarction contraindication 22298006 DOID:5844
Complete atrioventricular block contraindication 27885002
Sick sinus syndrome contraindication 36083008 DOID:13884
Hypokalemia contraindication 43339004
Chronic heart failure contraindication 48447003
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Second degree atrioventricular block contraindication 195042002
Disease of liver contraindication 235856003 DOID:409
Smokes tobacco daily contraindication 449868002
Right Bundle Branch Block with Left Hemiblock contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.78 acidic
pKa2 8.94 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
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 5.19 CHEMBL CHEMBL
Potassium voltage-gated channel subfamily A member 5 Ion channel BLOCKER Kd 4 IUPHAR
Sodium channel protein type 4 subunit alpha Ion channel Ki 4.74 WOMBAT-PK
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Ion channel IC50 2.77 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.41 CHEMBL
Potassium voltage-gated channel subfamily A member 7 Ion channel BLOCKER Kd 5.10 IUPHAR
Potassium voltage-gated channel subfamily D member 2 Unclassified IC50 5 CHEMBL
Potassium voltage-gated channel subfamily C member 1 Unclassified BLOCKER IC50 4 IUPHAR

External reference:

IDSource
D00638 KEGG_DRUG
54143-56-5 SECONDARY_CAS_RN
4018822 VANDF
4019757 VANDF
C0016229 UMLSCUI
CHEBI:75984 CHEBI
K4D PDB_CHEM_ID
CHEMBL652 ChEMBL_ID
CHEMBL398673 ChEMBL_ID
CHEMBL1200822 ChEMBL_ID
DB01195 DRUGBANK_ID
D005424 MESH_DESCRIPTOR_UI
2560 IUPHAR_LIGAND_ID
4096 INN_ID
K94FTS1806 UNII
3356 PUBCHEM_CID
152403 RXNORM
2279 MMSL
43018 MMSL
4730 MMSL
d00234 MMSL
000628 NDDF
004483 NDDF
372751001 SNOMEDCT_US
46576005 SNOMEDCT_US
8886003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0010 TABLET 50 mg ORAL ANDA 18 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0011 TABLET 100 mg ORAL ANDA 18 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 0054-0012 TABLET 150 mg ORAL ANDA 18 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 50090-1132 TABLET 50 mg ORAL ANDA 18 sections
Flecainide Acetate Human Prescription Drug Label 1 50090-2233 TABLET 100 mg ORAL ANDA 18 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 50090-2968 TABLET 100 mg ORAL ANDA 19 sections
Flecainide Acetate Human Prescription Drug Label 1 50090-5267 TABLET 100 mg ORAL ANDA 18 sections
Flecainide Acetate Human Prescription Drug Label 1 50090-5306 TABLET 50 mg ORAL ANDA 18 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 50268-320 TABLET 50 mg ORAL ANDA 12 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 50268-321 TABLET 100 mg ORAL ANDA 12 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 50268-322 TABLET 150 mg ORAL ANDA 12 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 51407-018 TABLET 50 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 51407-019 TABLET 100 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 51407-020 TABLET 150 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 53746-641 TABLET 50 mg ORAL ANDA 12 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 53746-642 TABLET 100 mg ORAL ANDA 12 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 53746-643 TABLET 150 mg ORAL ANDA 12 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 54868-5074 TABLET 50 mg ORAL ANDA 17 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 54868-5405 TABLET 100 mg ORAL ANDA 17 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 54868-5586 TABLET 150 mg ORAL ANDA 17 sections
Flecainide Acetate Human Prescription Drug Label 1 57237-063 TABLET 50 mg ORAL ANDA 18 sections
Flecainide Acetate Human Prescription Drug Label 1 57237-064 TABLET 100 mg ORAL ANDA 18 sections
Flecainide Acetate Human Prescription Drug Label 1 57237-065 TABLET 150 mg ORAL ANDA 18 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 62559-380 TABLET 50 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 62559-381 TABLET 100 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 62559-382 TABLET 150 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 63304-794 TABLET 50 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 63304-795 TABLET 100 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 63304-796 TABLET 150 mg ORAL ANDA 19 sections
Flecainide Acetate HUMAN PRESCRIPTION DRUG LABEL 1 63629-1945 TABLET 100 mg ORAL ANDA 19 sections