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Substance Name: Flecainide acetate [USAN:USP:JAN]
RN: 54143-56-5
UNII: M8U465Q1WQ
InChIKey: RKXNZRPQSOPPRN-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C17-H20-F6-N2-O3.C2-H4-O2

Molecular Weight

  • 474.3956
 

Classification Codes

  • Cardiac Depressant (Anti-Arrhythmic)
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Flecainide acetate [USAN:USP:JAN]

MeSH Heading

  • Flecainide

Synonyms

  • 2,5-Bis-(2,2,2-trifluoroethoxy)-N-(2-piperidinylmethyl)benzamide acetate
  • EINECS 258-997-5
  • Flecainide acetate
  • Flecainide monoacetate
  • N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide monoacetate
  • N-(2-Piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide monoacetate
  • R 818
  • R-818
  • Tambocor
  • UNII-M8U465Q1WQ

Systematic Names

  • Benzamide, N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-, monoacetate
  • N-(Piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide monoacetate

Registry Numbers

CAS Registry Number

  • 54143-56-5

FDA UNII

  • M8U465Q1WQ

Related Registry Number

  • 54143-55-4 (Parent)

System Generated Number

  • 0054143565

Molecular Formulas

Molecular Formula

  • C17-H20-F6-N2-O3.C2-H4-O2

Molecular Formula Fragments

  • C17-H20-F6-N2-O3
  • C2-H4-O2

Structure Descriptors

InChI

1S/C17H20F6N2O3.C2H4O2/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;1-2(3)4/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26);1H3,(H,3,4)

InChIKey

RKXNZRPQSOPPRN-UHFFFAOYSA-N

Smiles

CC(=O)O.c1cc(c(cc1OCC(F)(F)F)C(=O)NCC2CCCCN2)OCC(F)(F)F

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 50mg/kg (50mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 33, Pg. 2427, 1991.
dog LDLo unreported 15mg/kg (15mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 1714, 1999.
man LDLo multiple routes 25mg/kg/1W-I (25mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Journal of Cardiology. Vol. 53, Pg. 329, 1984.
man LDLo oral 22989ug/kg (22.989mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Forensic Science International. Vol. 106, Pg. 115, 1999.
man TDLo intravenous 1714ug/kg/4M- (1.714mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Heart Journal. Vol. 107, Pg. 222, 1984.
man TDLo multiple routes 26mg/kg/89H-I (26mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Postgraduate Medical Journal. Vol. 62, Pg. 61, 1986.
man TDLo oral 40mg/kg/2W-I (40mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Annals of Internal Medicine. Vol. 111, Pg. 107, 1989.
mouse LD50 intravenous 23800ug/kg (23.8mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
mouse LD50 oral 170mg/kg (170mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
mouse LD50 subcutaneous 188mg/kg (188mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
rat LD50 intravenous 16200ug/kg (16.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
rat LD50 oral 1346mg/kg (1346mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
rat LD50 subcutaneous 215mg/kg (215mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991.
women TDLo oral 20mg/kg (20mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
American Journal of Emergency Medicine. Vol. 16, Pg. 534, 1998.
women TDLo oral 28mg/kg/1W-I (28mg/kg) SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE British Medical Journal. Vol. 291, Pg. 450, 1985.
women TDLo oral 40mg/kg (40mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
British Journal of Clinical Practice. Vol. 49, Pg. 218, 1995.
women TDLo oral 50mg/kg (50mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE Connectical Medicine. Vol. 54, Pg. 183, 1990.
women TDLo oral 56mg/kg/1W-I (56mg/kg) CARDIAC: OTHER CHANGES American Journal of Cardiology. Vol. 55, Pg. 1643, 1985.
women TDLo oral 76mg/kg (76mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Annals of Internal Medicine. Vol. 106, Pg. 807, 1987.
women TDLo oral 160mg/kg (160mg/kg) CARDIAC: CHANGE IN RATE

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Medical Journal of Australia. Vol. 155, Pg. 349, 1991.