Tìm theo
Quinidine
Các tên gọi khác (18 ) :
  • (+)-quinidine
  • (8R,9S)-Quinidine
  • (R)-(6-Methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanol
  • (S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol
  • (S)-(6-Methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanol
  • 6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
  • alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol
  • beta-Quinine
  • Chinidin
  • Chinidinum
  • CIN-QUIN
  • Conchinin
  • Conquinine
  • Kinidin
  • Pitayine
  • Quinidina
  • Quinidine
  • β-quinine
Thuốc chống loạn nhịp
Thuốc Gốc
Small Molecule
CAS: 56-54-2
ATC: C01BA01
ĐG : Amend
CTHH: C20H24N2O2
PTK: 324.4168
An optical isomer of quinine, extracted from the bark of the Cinchona tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular action potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C20H24N2O2
Phân tử khối
324.4168
Monoisotopic mass
324.183778022
InChI
InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1
InChI Key
InChIKey=LOUPRKONTZGTKE-LHHVKLHASA-N
IUPAC Name
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
Traditional IUPAC Name
quinidine
SMILES
[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1
Độ tan chảy
174 °C
Độ hòa tan
140 mg/L (at 25 °C)
logP
3.44
logS
-3.37
pKa (strongest acidic)
13.89
pKa (Strongest Basic)
9.05
PSA
45.59 Å2
Refractivity
94.69 m3·mol-1
Polarizability
35.82 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
4
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
caco2 Permeability
-4.69
pKa
8.56 (at 25 °C)
Dược Lực Học : Quinidine, a hydantoin anticonvulsant, is used alone or with phenobarbital or other anticonvulsants to manage tonic-clonic seizures, psychomotor seizures, neuropathic pain syndromes including diabetic neuropathy, digitalis-induced cardiac arrhythmias, and cardiac arrhythmias associated with QT-interval prolongation.
Cơ Chế Tác Dụng : An optical isomer of quinine, extracted from the bark of the Cinchona tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular action potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission. [PubChem] Quinidine 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. Quinidine may also act on the slow inward calcium current (ICa), the rapid (IKr) and slow (IKs) components of the delayed potassium rectifier current, the inward potassium rectifier current (IKI), the ATP-sensitive potassium channel (IKATP) and Ito.
Dược Động Học :

▧ Volume of Distribution :
* 2 to 3 L/kg * 0.5 L/kg [congestive heart failure] * 3 to 5 L/kg [cirrhosis of the liver]
▧ Protein binding :
80-88%
▧ Route of Elimination :
When the urine pH is less than 7, about 20% of administered quinidine appears unchanged in the urine, but this fraction drops to as little as 5% when the urine is more alkaline.
▧ Half Life :
6-8 hours
▧ Clearance :
* 3 – 5 mL/min/kg [adults]
Chỉ Định : For the treatment of ventricular pre-excitation and cardiac dysrhythmias
Tương Tác Thuốc :
  • Acenocoumarol Quinidine may increase the anticoagulant effect of acenocoumarol.
  • Alvimopan Decreases levels by P-glycoprotein (MDR-1) efflux transporter. Can significantly increase systemic exposure to P-glycoprotein substrates.
  • Amiloride Amiloride may decrease the therapeutic effect of quinidine. Monitor for changes in the therapeutic and adverse effects of quinidine if amiloride if initiated, discontinued or dose changed.
  • Amiodarone Amiodarone may increase the effect of quinidine.
  • Amitriptyline Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amitriptyline if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Amobarbital The anticonvulsant, amobarbital, decreases the effect of quinidine.
  • Anisindione Quinidine may increase the anticoagulant effect of anisindione.
  • Aprobarbital The anticonvulsant, aprobarbital, decreases the effect of quinidine.
  • Aripiprazole Quinidine increases the effect and toxicity of aripiprazole
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Atazanavir Increased risk of cardiotoxicity and arrhythmias.
  • Atomoxetine The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
  • Atracurium The quinine derivative increases the effect of the muscle relaxant
  • Bromazepam Quinidine, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if quinidine is initiated, discontinued or dose changed. Dosage adjustments may be required.
  • Butabarbital The anticonvulsant, butabarbital, decreases the effect of quinidine.
  • Butalbital The anticonvulsant, butalbital, decreases the effect of quinidine.
  • Butethal The anticonvulsant, butethal, decreases the effect of quinidine.
  • Cimetidine Cimetidine may increase the serum concentration of quinidine. Monitor for changes in the therapeutic and adverse effects of quinidine if cimetidine is initiated, discontinued or dose changed.
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Clarithromycin Increased risk of cardiotoxicity and arrhythmias
  • Clomipramine Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, clomipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of clomipramine if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Codeine Quinidine decreases the analgesic effect of codeine
  • Crizotinib Strong CYP3A4 inhibitors may increase levels of crizotinib. Consider alternative therapy.
  • Dabigatran etexilate Quinidine may increase the serum concentration of dabigatran etexilate, resulting in increased bleeding. Consider modification of therapy.
  • Dantrolene Quinidine may increase the serum concentration of dantrolene by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dantrolene if quinidine is initiated, discontinued or dose changed.
  • Desipramine Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Dextromethorphan Quinidine increases the toxicity of dextromethorphan
  • Dicoumarol Quinidine may increase the anticoagulant effect of dicumarol.
  • Digitoxin Quinine/quinidine increases the effect of digoxin
  • Digoxin Quinine/quinidine increases the effect of digoxin
  • Dihydrocodeine Use of quinidine may reduce dihydrocodeine's analgesic effect.
  • Dihydroquinidine barbiturate The anticonvulsant, dihydroquinidine. barbiturate, decreases the effect of quinidine.
  • Diltiazem Diltiazem may increase the serum concentration of quinidine. Monitor for changes in the therapeutic and adverse effects of quinidine if diltiazem is initiated, discontinued or dose changed.
  • Donepezil Possible antagonism of action
  • Doxepin Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Erythromycin Increased risk of cardiotoxicity and arrhythmias
  • Etravirine Quinidine, when used concomitantly with etravirine, may experience a decrease in serum concentration. It is recommended to monitor quinidine therapy.
  • Fingolimod Pharmacodynamic synergist. Contraindicated. Increased risk of bradycardia, AV block, and torsade de pointes.
  • Fosphenytoin The anticonvulsant, fosphenytoin, decreases the effect of quinidine.
  • Galantamine Possible antagonism of action
  • Gatifloxacin Increased risk of cardiotoxicity and arrhythmias
  • Grepafloxacin Increased risk of cardiotoxicity and arrhythmias
  • Heptabarbital The anticonvulsant, heptabarbital, decreases the effect of quinidine.
  • Hexobarbital The anticonvulsant, hexobarbital, decreases the effect of quinidine.
  • Imipramine Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Itraconazole Itraconazole may increase the effect and toxicity of quinidine.
  • Ketoconazole Ketoconazole may increase the effect and toxicity of quinidine.
  • Levofloxacin Increased risk of cardiotoxicity and arrhythmias
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Magnesium Magnesium antacids may decrease the absorption of quindine.
  • Magnesium salicylate The antacid increases the effect of quinidine
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Methohexital The anticonvulsant, methohexital, decreases the effect of quinidine.
  • Methylphenobarbital The anticonvulsant, methylphenobarbital, decreases the effect of quinidine.
  • Metocurine The quinine derivative increases the effect of the muscle relaxant
  • Moxifloxacin Increased risk of cardiotoxicity and arrhythmias
  • Nelfinavir Nelfinavir increases the effect and toxicity of quinidine
  • Nifedipine Decreased quinidine effect, increased nifedipine effect
  • Nortriptyline Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Ofloxacin Increased risk of cardiotoxicity and arrhythmias
  • Pancuronium The quinine derivative increases the effect of the muscle relaxant
  • Pentobarbital The anticonvulsant, pentobarbital, decreases the effect of quinidine.
  • Phenobarbital The anticonvulsant, phenobarbital, decreases the effect of quinidine.
  • Phenytoin The anticonvulsant, phenytoin, decreases the effect of quinidine.
  • Posaconazole Contraindicated co-administration
  • Primidone The anticonvulsant, primidone, decreases the effect of quinidine.
  • Procainamide Quinidine increases the effect of procainamide
  • Propafenone Quinidine increases the effect of propafenone
  • Protriptyline Additive QTc-prolonging effects may occur. Quinidine may also increase the serum concentration of the tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of protriptyline if quinidine is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Quinidine barbiturate The anticonvulsant, quinidine. barbiturate, decreases the effect of quinidine.
  • Quinupristin This combination presents an increased risk of toxicity
  • Ranolazine Possible additive effect on QT prolongation
  • Rifampicin Rifampin decreases the effect of quinidine
  • Ritonavir Ritonavir increases the effect and toxicity of quinidine
  • Rivastigmine Possible antagonism of action
  • Secobarbital The anticonvulsant, secobarbital, decreases the effect of quinidine.
  • Sodium bicarbonate The antacid increases the effect of quinidine
  • Sparfloxacin Increased risk of cardiotoxicity and arrhythmias
  • Succinylcholine The quinine derivative increases the effect of the muscle relaxant
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. Quinidine, a strong CYP3A4 inhibitor, may also increase the serum concentration of Tacrolimus by inhibiting its metabolism and clearance.
  • Tadalafil Quinidine may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
  • Talbutal The anticonvulsant, talbutal, decreases the effect of quinidine.
  • Tamoxifen Quinidine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided.
  • Tamsulosin Quinidine, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Quinidine is initiated, discontinued, or dose changed.
  • Telavancin Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Telithromycin Co-administration may result in altered plasma concentrations of Quinidine and/or Telithromycin. Consider alternate therapy or monitor for changes in the the therapeutic/adverse effects of both agents during concomitant therapy.
  • Temsirolimus Quinidine may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
  • Teniposide The strong CYP3A4 inhibitor, Quinidine, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Quinidine is initiated, discontinued or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Tetrabenazine Strong CYP2D6 inhibitors may increase exposure of the metabolites of tetrabenazine. Consider a reduction of dose.
  • Thiopental Thiopental may increase the metabolism and clearance of Quinidine. Monitor for decreased therapeutic effect of Quinidine if Thiopental is initiated.
  • Thioridazine Increased risk of cardiotoxicity and arrhythmias
  • Tiagabine The strong CYP3A4 inhibitor, Quinidine, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Quinidine is initiated, discontinued or dose changed.
  • Tipranavir Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Quinidine. Concomitant therapy is contraindicated.
  • Tolterodine Quinidine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
  • Topotecan The p-glycoprotein inhibitor, Quinidine, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
  • 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.
  • Tramadol Quinidine may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Quinidine may decrease the effect of Tramadol by decreasing active metabolite production.
  • Trazodone The CYP3A4 inhibitor, Quinidine, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Consider alternate therapy or monitor for changes in Trazodone efficacy/toxicity if Quinidine is initiated, discontinued or dose changed.
  • Trimipramine Additive QTc-prolonging effects may occur, increasing the risk of serious cardiac arrhythmias. Quinidine, a CYP2D6/CYP3A4 inhibitor, may also inhibit the metabolism of Trimipramine, a CYP2D6/CYP3A4 substrate. Monitor for signs of cardiac arrhythmias and for changes in Trimipramine efficacy and toxicity if Quinidine is initiated, discontinued or dose changed.
  • Vardenafil Quinidine, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
  • Vecuronium The quinine derivative increases the effect of the muscle relaxant
  • Venlafaxine Quinidine, a CYP2D6 and CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 and CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Quinidine is initiated, discontinued, or dose changed.
  • Verapamil Concurrent therapy may result in increased serum levels of both agents. Both agents are CYP3A4 inhibitors and substrates. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of the agent if the other is initiated, discontinued or dose changed.
  • Vilazodone CYP3A4 Inhibitors (Strong) may increase the serum concentration of Vilazodone. imit maximum adult vilazodone dose to 20 mg/day in patients receiving strong CYP3A4 inhibitors.
  • Vinblastine Quinidine, a strong CYP3A4 inhibitor, may decrease the metabolism of Vinblastine. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Quinidine is initiated, discontinued or dose changed.
  • Vincristine Quinidine, a strong CYP3A4 inhibitor, may increase the serum concentration of Vincristine by decreasing its metabolism. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Quinidine is initiated, discontinued or dose changed.
  • Vinorelbine Quinidine, a strong CYP3A4 inhibitor, may increase the serum concentration of Vinorelbine by decreasing its metabolism. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Quinidine is initiated, discontinued or dose changed.
  • Voriconazole Voriconazole may increase the serum concentration of quinidine likely by inhibiting its metabolism by CYP3A4. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for changes in the serum concentration and toxic effects of quinidine if voriconazole is initiated, discontinued or dose changed.
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Warfarin Quinidine may increase the anticoagulant effect of warfarin.
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.
  • Zolpidem Quinidine, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if quinidine is initiated, discontinued or dose changed.
  • Zonisamide Quinidine, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if quinidine is initiated, discontinued or dose changed.
  • Zopiclone Quinidine, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if quinidine is initiated, discontinued or dose changed.
  • 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). Quinidine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if quinidine is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng : Solution - Intramuscular
Tablet - Oral
Tablet, extended release - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Cardioquin
  • Công ty :
    Sản phẩm biệt dược : Kinidin
  • Công ty :
    Sản phẩm biệt dược : Quin-Release
  • Công ty :
    Sản phẩm biệt dược : Quinaglute
  • Công ty :
    Sản phẩm biệt dược : Quinalan
  • Công ty :
    Sản phẩm biệt dược : Quinicardine
  • Công ty :
    Sản phẩm biệt dược : Quinidex
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00908
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=441074
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505356
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06527
ChemSpider
http://www.chemspider.com/Chemical-Structure.389880.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/53489-459-02
PharmGKB
http://www.pharmgkb.org/drug/PA451209
Wikipedia
http://en.wikipedia.org/wiki/Quinidine
RxList
http://www.rxlist.com/cgi/generic/quinidine.htm
Drugs.com
http://www.drugs.com/cdi/quinidine-gluconate-controlled-release-tablets.html
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