Tìm theo
Quinine
Các tên gọi khác (10 ) :
  • (-)-Quinine
  • (8S,9R)-Quinine
  • (R)-(-)-Quinine
  • (R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol
  • 6'-Methoxycinchonidine
  • Chinin
  • Chinine
  • Chininum
  • Quinina
  • Quinine
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 130-95-0
ATC: M09AA01, P01BC01
ĐG : Allan Pharmaceutical LLC
CTHH: C20H24N2O2
PTK: 324.4168
An alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood. [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-WZBLMQSHSA-N
IUPAC Name
(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
Traditional IUPAC Name
(-)-quinine
SMILES
Độ tan chảy
57 °C
Độ hòa tan
500 mg/L (at 15 °C)
logP
3.44
logS
-2.76
pKa (strongest acidic)
13.89
pKa (Strongest Basic)
9.05
PSA
45.59 Å2
Refractivity
94.69 m3·mol-1
Polarizability
35.96 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
Dược Lực Học : Quinine is used parenterally to treat life-threatening infections caused by chloroquine-resistant Plasmodium falciparum malaria. Quinine acts as a blood schizonticide although it also has gametocytocidal activity against P. vivax and P. malariae. Because it is a weak base, it is concentrated in the food vacuoles of P. falciparum. It is thought to act by inhibiting heme polymerase, thereby allowing accumulation of its cytotoxic substrate, heme. As a schizonticidal drug, it is less effective and more toxic than chloroquine. However, it has a special place in the management of severe falciparum malaria in areas with known resistance to chloroquine.
Cơ Chế Tác Dụng : An alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood. [PubChem] The theorized mechanism of action for quinine and related anti-malarial drugs is that these drugs are toxic to the malaria parasite. Specifically, the drugs interfere with the parasite's ability to break down and digest hemoglobin. Consequently, the parasite starves and/or builds up toxic levels of partially degraded hemoglobin in itself.
Dược Động Học :
▧ Absorption :
76 - 88%
▧ Volume of Distribution :
* 1.43 ± 0.18 L/kg [Healthy Pediatric Controls] * 0.87 ± 0.12 L/kg [P. falciparum Malaria Pediatric Patients] * 2.5 to 7.1 L/kg [healthy subjects who received a single oral 600 mg dose]
▧ Protein binding :
Approximately 70%
▧ Metabolism :
Hepatic, over 80% metabolized by the liver.
▧ Route of Elimination :
Quinine is eliminated primarily via hepatic biotransformation. Approximately 20% of quinine is excreted unchanged in urine.
▧ Half Life :
Approximately 18 hours
▧ Clearance :
* 0.17 L/h/kg [healthy] * 0.09 L/h/kg [patients with uncomplicated malaria] * 18.4 L/h [healthy adult subjects with administration of multiple-dose activated charcoal] * 11.8 L/h [healthy adult subjects without administration of multiple-dose activated charcoal] * Oral cl=0.06 L/h/kg [elderly subjects]
Độc Tính : Quinine is a documented causative agent of drug induced thrombocytopenia (DIT). Thrombocytopenia is a low amount of platelets in the blood. Quinine induces production of antibodies against glycoprotein (GP) Ib-IX complex in the majority of cases of DIT, or more rarely, the platelet-glycoprotein complex GPIIb-IIIa. Increased antibodies against these complexes increases platelet clearance, leading to the observed thrombocytopenia.
Chỉ Định : For the treatment of malaria and leg cramps
Tương Tác Thuốc :
  • Acenocoumarol Quinine, a moderate CYP2C9 inhibitor, may increase the serum concentration of acenocoumarol by decreasing its metabolism via CYP2C9.
  • Anisindione Quinine may increase the anticoagulant effect of anisindione.
  • Artemether Quinine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
  • Astemizole 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
  • Dicoumarol Quinine may increase the anticoagulant effect of dicumarol.
  • Digitoxin Quinine/quinidine increases the effect of digoxin
  • Digoxin Quinine/quinidine increases the effect of digoxin
  • Lumefantrine Quinine may increase the adverse effects of lumefantrine. Combination therapy is contraindicated unless there are no other treatment options.
  • Mesoridazine Increased risk of cardiotoxicity and arrhythmias
  • Metocurine The quinine derivative increases the effect of the muscle relaxant
  • Pancuronium The quinine derivative increases the effect of the muscle relaxant
  • Succinylcholine The quinine derivative increases the effect of the muscle relaxant
  • Tamoxifen Quinine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
  • Tamsulosin Quinine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Quinine is initiated, discontinued, or dose changed.
  • Telithromycin Telithromycin may reduce clearance of Quinine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Quinine if Telithromycin 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. Concomitant therapy should be avoided.
  • Toremifene May cause additive QTc-prolonging effects. Concomitant therapy is contraindicated.
  • Tramadol Quinine may decrease the effect of Tramadol by decreasing active metabolite production.
  • Trandolapril May cause additive hypotensive effects. Monitor for changes in blood pressure if Quinine is initiated, discontinued or dose changed.
  • Tretinoin The moderate CYP2C8 inhibitor, Quinine, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Quinine is initiated, discontinued to dose changed.
  • Vecuronium Quinine may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Concurrent therapy should be avoided.
  • Voriconazole Additive QTc prolongation may occur. Concomitant therapy should be avoided.
  • Vorinostat Additive QTc prolongation may occur. Concomitant therapy should be avoided.
  • Warfarin Quinine, a moderate CYP2C9 inhibitor, may increase the serum concentration of S-warfarin by decreasing its metabolism via CYP2C9.
  • Ziprasidone Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Zuclopenthixol Additive QTc-prolonging effects increases risk of cardiac arrhythmias. Concomitant therapy should be avoided.
Liều Lượng & Cách Dùng : Capsule - Oral
Liquid - Oral
Solution / drops - Oral
Tablet - Oral
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