ContaminantDB: Flecainide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-05 02:56:03 UTC

Update Date

2026-05-14 16:58:39 UTC

Accession Number

CHEM002083

Identification

Common Name

Flecainide

Class

Small Molecule

Description

A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial arrhythmias and tachycardias. Paradoxically, however, in myocardial infarct patients with either symptomatic or asymptomatic arrhythmia, flecainide exacerbates the arrhythmia and is not recommended for use in these patients. [PubChem]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Arrhythmia Agent
Drug
Ester
Ether
Metabolite
Organic Compound
Organofluoride
Synthetic Compound
Voltage-Gated Sodium Channel Blocker

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Flecainide	ChEBI
CCRIS 313	ChEBI
Flecaine	ChEBI
Flecainida	ChEBI
Flecainidum	ChEBI
N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide	ChEBI
Apocard	MeSH, HMDB
Flecainide monoacetate, (S)-isomer	MeSH, HMDB
Flecainide, 5-HO-N-(6-oxo)-derivative	MeSH, HMDB
Merck dura brand OF flecainide acetate	MeSH, HMDB
Alpharma brand OF flecainide acetate	MeSH, HMDB
Flecainide, 5-HO-N-(6-oxo)-derivative, (+-)-isomer	MeSH, HMDB
Flecatab	MeSH, HMDB
Tambocor	MeSH, HMDB
3m Brand OF flecainide acetate	MeSH, HMDB
Alphapharm brand OF flecainide acetate	MeSH, HMDB
Flecadura	MeSH, HMDB
Flecainid-isis	MeSH, HMDB
Flecainide acetate	MeSH, HMDB
Flecainide monoacetate, (R)-isomer	MeSH, HMDB
Flecainide, (R)-isomer	MeSH, HMDB
Flecainide, (S)-isomer	MeSH, HMDB
Riker brand OF flecainide acetate	MeSH, HMDB
Acetate, flecainide	MeSH, HMDB
Flecainid isis	MeSH, HMDB
Flecainide monoacetate	MeSH, HMDB
Flecainide monoacetate, (+-)-isomer	MeSH, HMDB
United drug brand OF flecainide acetate	MeSH, HMDB

Chemical Formula

C₁₇H₂₀F₆N₂O₃

Average Molecular Mass

414.343 g/mol

Monoisotopic Mass

414.138 g/mol

CAS Registry Number

54143-55-4

IUPAC Name

N-[(piperidin-2-yl)methyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide

Traditional Name

flecainide

SMILES

FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1

InChI Identifier

InChI=1S/C17H20F6N2O3/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)

InChI Key

DJBNUMBKLMJRSA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzamides

Alternative Parents

Substituents

Benzamide
Phenoxy compound
Benzoyl
Phenol ether
Alkyl aryl ether
Piperidine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Organohalogen compound
Alkyl halide
Alkyl fluoride
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:75984 )
organofluorine compound (CHEBI:75984 )
aromatic ether (CHEBI:75984 )
monocarboxylic acid amide (CHEBI:75984 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Flecainide Pathway	Not Available	Not Available

Applications

anti-arrhythmia drug

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Solid (1).

Experimental Properties

Property	Value
Melting Point	228-229°C
Boiling Point	Not Available
Solubility	48.4 mg/mL at 37°C (acetate form)

Predicted Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.19	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	9.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	88.4 m³·mol⁻¹	ChemAxon
Polarizability	35.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-5009000000-7b1564870deda7f2d21e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00dl-0095000000-644485d209c90776a32d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0190000000-201f2152d161a1ff83e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0790000000-928874c4b348381ad1b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0596-0940000000-ee7a94ba0d7bcfa2fe93	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-052g-1910000000-a32ac2f605f11fbbc5e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0297-1900000000-f1c49d25a6b161ff44d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-0000900000-9820e909cb01d45fa815	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00kb-2009500000-68b872fada8afdd4e580	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0f6t-5019000000-8fa5e4257c88beda0ea1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0uea-8069000000-149a79cf429446ec77c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0uei-6292000000-103ccdef98c4b6c9e408	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0pdi-8970000000-9258d139b203d6c98df0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0000900000-3df851e0ff354ab1be59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00di-0090000000-8d4a6a9978cccc816b47	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00kb-2009500000-c58556b6a88ebc0729bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0001900000-9830e722af2fab717f28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000900000-c80ce9de474de184ff13	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0f6t-5019000000-00737a572b9aa2cd61a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00dl-0095000000-43e08367bbe8d04a6a08	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-5306900000-5bc88ff27c840b41cb32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9314100000-11d4e9fa034a85ea06f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9010000000-ac2b8dd3242c0db13ae9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0004900000-9ea43375c547f2e6b28a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xu-2139400000-cddcc91db822779e66b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l2-5391000000-60f93403fdd5f22a81c3	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-b732167df77d39193144	Spectrum

Toxicity Profile

Route of Exposure

Ingestion (MSDS, A308). Nearly complete following oral administration.

Mechanism of Toxicity

Flecainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers. Flecainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole.

Metabolism

Hepatic. Flecainide does not undergo any consequential presystemic biotransformation. The two major urinary metabolites are meta-O-dealkylated flecainide (active, but about one-fifth as potent) and the meta-O-dealkylated lactam of flecainide (non-active metabolite). The absoprtion is nearly complete following oral administration. Hepatic. Flecainide does not undergo any consequential presystemic biotransformation. The two major urinary metabolites are meta-O-dealkylated flecainide (active, but about one-fifth as potent) and the meta-O-dealkylated lactam of flecainide (non-active metabolite). Route of Elimination: In healthy subjects, about 30% of a single oral dose (range, 10 to 50%) is excreted in urine as unchanged drug. Several minor metabolites (3% of the dose or less) are also found in urine; only 5% of an oral dose is excreted in feces. In patients, free (unconjugated) plasma levels of the two major metabolites are very low (less than 0.05 ug/mL). Half Life: 20 hours (range 12-27 hours)

Toxicity Values

LD50: 50-498 mg/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Flecainide is is a class Ic antiarrhythmic agent and as such, it is used for the prevention of paroxysmal supraventricular tachycardias (PSVT), including atrioventricular nodal reentrant tachycardia, atrioventricular reentrant tachycardia and other supraventricular tachycardias of unspecified mechanism associated with disablin (1).

Minimum Risk Level

Not Available

Health Effects

Signs of flecainide toxicity include marked prolongation of the PR interval and widening of the QRS duration on the surface ECG. There may be signs and symptoms attributable to overt heart failure secondary to sudden decreased myocardial contractility (7).

Symptoms

Symptoms of overdose include nausea and vomiting, convulsions, hypotension, bradycardia, syncope, extreme widening of the QRS complex, widening of the QT interval, widening of the PR interval, ventricular tachycardia, AV nodal block, asystole, bundle branch block, cardiac failure, and cardiac arrest.

Treatment

Treatment of flecainide toxicity involves increasing the excretion of flecainide, blocking its effects in the heart, and (rarely) institution of cardiovascular support to avoid impending lethal arrhythmias. Modalities that have had success include administration of a beta-sympathomimetic agent, and administration of a sodium load (often in the form of hypertonic sodium bicarbonate). Placing the individual on cardiopulmonary bypass support may be necessary in order to temporarily obviate the need for a beating heart and to increase blood flow to the liver. (7)

Concentrations

Not Available

External Links

DrugBank ID

DB01195

HMDB ID

HMDB0257376

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID