Tìm theo
Propafenone
Các tên gọi khác (4 ) :
  • 1-(2-(2-Hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-1-propanone
  • 2-(2'-Hydroxy-3'-propylaminopropoxy)-omega-phenylpropiophenone
  • Propafenona
  • Propafenonum
Thuốc chống loạn nhịp
Thuốc Gốc
Small Molecule
CAS: 54063-53-5
ATC: C01BC03
ĐG : Abbott Laboratories Ltd. , http://www.abbott.com
CTHH: C21H27NO3
PTK: 341.444
An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity. The drug is generally well tolerated. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C21H27NO3
Phân tử khối
341.444
Monoisotopic mass
341.199093735
InChI
InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3
InChI Key
InChIKey=JWHAUXFOSRPERK-UHFFFAOYSA-N
IUPAC Name
1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one
Traditional IUPAC Name
propafenone
SMILES
CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1
Độ hòa tan
Slightly soluble
logP
3.2
logS
-4.7
pKa (strongest acidic)
14.09
pKa (Strongest Basic)
9.63
PSA
58.56 Å2
Refractivity
100.21 m3·mol-1
Polarizability
39.75 Å3
Rotatable Bond Count
11
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
Dược Lực Học : Propafenone is a Class 1C antiarrhythmic drug with local anesthetic effects, and a direct stabilizing action on myocardial membranes. It is used in the treatment of atrial and ventricular arrhythmias. It works by slowing the influx of sodium ions into the cardiac muscle cells, causing a decrease in excitablity of the cells. Propafenone has local anesthetic activity approximately equal to procaine.
Cơ Chế Tác Dụng : An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity. The drug is generally well tolerated. [PubChem] The electrophysiological effect of propafenone manifests itself in a reduction of upstroke velocity (Phase 0) of the monophasic action potential. In Purkinje fibers, and to a lesser extent myocardial fibers, propafenone reduces the fast inward current carried by sodium ions, which is responsible for the drugs antiarrhythmic actions. Diastolic excitability threshold is increased and effective refractory period prolonged. Propafenone reduces spontaneous automaticity and depresses triggered activity. At very high concentrations in vitro, propafenone can inhibit the slow inward current carried by calcium but this calcium antagonist effect probably does not contribute to antiarrhythmic efficacy.
Dược Động Học :
▧ Absorption :
Nearly completely absorbed following oral administration (90%). Systemic bioavailability ranges from 5 to 50%, due to significant first-pass metabolism. This wide range in systemic bioavailability is related to two factors: presence of food (food increases bioavailability) and dosage (bioavailability is 3.4% for a 150-mg tablet compared to 10.6% for a 300-mg tablet).
▧ Volume of Distribution :
* 252 L
▧ Protein binding :
97%
▧ Metabolism :
Metabolized primarily in the liver where it is rapidly and extensively metabolized to two active metabolites, 5-hydroxypropafenone and N-depropylpropafenone. These metabolites have antiarrhythmic activity comparable to propafenone but are present in concentrations less than 25% of propafenone concentrations.
▧ Route of Elimination :
Approximately 50% of propafenone metabolites are excreted in the urine following administration of immediate release tablets.
▧ Half Life :
2-10 hours
Độc Tính : Symptoms of propafenone overdose (usually most severe within the first 3 hours) may include convulsions (rarely), heartbeat irregularities, low blood pressure, and sleepiness.
Chỉ Định : Used to prolong the time to recurrence of paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms in patients without structural heart disease. Also used for the treatment of life-threatening documented ventricular arrhythmias, such as sustained ventricular tachycardia.
Tương Tác Thuốc :
  • Acenocoumarol Propafenone may increase the anticoagulant effect of acenocoumarol.
  • Aminophylline Propafenone increases the effect of theophylline
  • Anisindione Propafenone may increase the anticoagulant effect of anisindione.
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Cyclosporine Propafenone increases the effect and toxicity of cyclosporine
  • Dicoumarol Propafenone may increase the anticoagulant effect of dicumarol.
  • Digoxin Propafenone increases the effect of digoxin
  • Dihydroquinidine barbiturate Quinidine increases the effect of propafenone
  • Duloxetine Possible increase in the levels of this agent when used with duloxetine
  • Dyphylline Propafenone increases the effect of theophylline
  • Etravirine Propafenone, when used concomitantly with Etravirine, may experience a decrease in serum concentration. It is recommended to monitor for continued efficacy of propafenone therapy.
  • Fluoxetine Additive QTc-prolongation may occur increasing the risk of serious life-threatening arrhythmias. Fluoxetine may also increase the serum concentration of propafenone. Use caution during concomitant therapy and monitor for QTc-prolongation.
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias.
  • Metoprolol Propafenone may increase the effect of beta-blocker, metoprolol.
  • Mexiletine Propafenone may increase the effect and toxicity of mexilitine.
  • Mirabegron Mirabegron is a moderate CYP2D6 inhibitor and may cause an increase in exposure of CYP2D6 substrates. Monitor concomitant therapy closely.
  • Oxtriphylline Propafenone increases the effect of theophylline
  • Paroxetine Paroxetine may increase the effect and toxicity of propafenone.
  • Propranolol Propafenone may increase the effect of the beta-blocker, propranolol.
  • Quinidine Quinidine increases the effect of propafenone
  • Quinidine barbiturate Quinidine increases the effect of propafenone
  • Rifabutin Rifampin decreases the effect of propafenone
  • Rifampicin Rifampin decreases the effect of propafenone
  • Ritonavir Ritonavir increases the effect and toxicity of propafenone
  • Sertraline Fluoxetine increases the effect and toxicity of propafenone
  • 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 Propafenone. Consider alternate therapy or monitor for therapeutic/adverse effects of Propafenone if Terbinafine is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias.
  • Theophylline Propafenone increases the effect of theophylline
  • Thiopental Thiopental may increase the metabolism and clearance of Propafenone. Monitor for decreased therapeutic effect of Propafenone if Thiopental is initiated.
  • 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 Propafenone. Concomitant therapy is contraindicated.
  • Tizanidine Propafenone may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
  • 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.
  • Venlafaxine Propafenone increases the effect and toxicity of venlafaxine
  • 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).
  • Warfarin Propafenone may increase the anticoagulant effect of warfarin.
  • 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 : Rythmol
  • Công ty :
    Sản phẩm biệt dược : Rythmol SR
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01182
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4932
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46504529
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07381
ChemSpider
http://www.chemspider.com/Chemical-Structure.4763.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50067133
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0173-0786-01
PharmGKB
http://www.pharmgkb.org/drug/PA451131
Wikipedia
http://en.wikipedia.org/wiki/Propafenone
RxList
http://www.rxlist.com/cgi/generic3/propafen.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ryt1392.shtml
Drugs.com
http://www.drugs.com/cdi/propafenone.html
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