Tìm theo
Flecainide
Các tên gọi khác (6 ) :
  • (+-)-Flecainide
  • CCRIS 313
  • Flecaine
  • Flecainida
  • Flecainidum
  • N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
Thuốc chống loạn nhịp
Thuốc Gốc
Small Molecule
CAS: 54143-55-4
ATC: C01BC04
ĐG : 3M Health Care , http://www.3m.com
CTHH: C17H20F6N2O3
PTK: 414.3427
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]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H20F6N2O3
Phân tử khối
414.3427
Monoisotopic mass
414.137811746
InChI
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
InChIKey=DJBNUMBKLMJRSA-UHFFFAOYSA-N
IUPAC Name
N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
Traditional IUPAC Name
flecainide
SMILES
FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1
Độ tan chảy
228-229
Độ hòa tan
48.4 mg/mL at 37 °C (acetate form)
logP
3.78
logS
-4.1
pKa (strongest acidic)
13.68
pKa (Strongest Basic)
9.62
PSA
59.59 Å2
Refractivity
88.4 m3·mol-1
Polarizability
35.92 Å3
Rotatable Bond Count
9
H Bond Acceptor Count
4
H Bond Donor Count
2
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
9.3
Dược Lực Học : Flecainide has local anesthetic activity and belongs to the membrane stabilizing (Class 1) group of antiarrhythmic agents; it has electrophysiologic effects characteristic of the IC class of antiarrhythmics.
Cơ Chế Tác Dụng : 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] 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.
Dược Động Học :
▧ Absorption :
Nearly complete following oral administration.
▧ Protein binding :
40%
▧ 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).
▧ 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 μg/mL).
▧ Half Life :
20 hours (range 12-27 hours)
Độc Tính : Oral LD50 is 50-498 mg/kg in rat. 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.
Chỉ Định : 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.
Tương Tác Thuốc :
  • Amiodarone Amiodarone may increase the effect and toxicity of flecainide
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Cimetidine Cimetidine, a moderate CYP2D6 inhibitor, may decrease the metabolism of flecainide.
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Duloxetine Possible increase in the levels of this agent when used with duloxetine
  • Etravirine Flecainide, when administered concomitantly with etravirine, may experience a decrease in serum concentration. It is recommended to monitor flecainide therapy.
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Mirabegron Mirabegron is a moderate CYP2D6 inhibitor and may cause an increase in exposure of CYP2D6 substrates. Monitor concomitant therapy closely.
  • Quinupristin This combination presents an increased risk of toxicity
  • Ritonavir Ritonavir increases the toxicity of the anti-arrhythmic
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Terbinafine Terbinafine may reduce the metabolism and clearance of Flecainide. Consider alternate therapy or monitor for therapeutic/adverse effects of Flecainide if Terbinafine is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
  • Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Flecainide. Concomitant therapy is contraindicated.
  • Toremifene Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
  • Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
  • Voriconazole Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
  • Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Almarytm
  • Công ty :
    Sản phẩm biệt dược : Apocard
  • Sản phẩm biệt dược : Tambocor
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01195
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3356
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508078
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07001
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D07962
ChemSpider
http://www.chemspider.com/Chemical-Structure.3239.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50131434
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0089-0305-10
PharmGKB
http://www.pharmgkb.org/drug/PA449646
Wikipedia
http://en.wikipedia.org/wiki/Flecainide
RxList
http://www.rxlist.com/cgi/generic2/flecainide.htm
Drugs.com
http://www.drugs.com/cdi/flecainide.html
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