QuickView for Quinine (compound)

Summary
General Info

PubChem

PubChem Compound 1065

Name:	Quinine
PubChem Compound ID:	1065
Description:	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.
Molecular formula:	C₂₀H₂₄N₂O₂
Molecular weight:	324.417 g/mol
Synonyms:	Chinine; (-)-Quinine; NSC131458; NCI60_004320; 2-Quinuclidinemethanol, .alpha.-(6-methoxy-4-quinolyl)-5-vinyl-; NSC192949; 130-95-0; Quinine; Quinidine; 6-Methoxycinchonine. show more » Chinine; (-)-Quinine; NSC131458; NCI60_004320; 2-Quinuclidinemethanol, .alpha.-(6-methoxy-4-quinolyl)-5-vinyl-; NSC192949; 130-95-0; Quinine; Quinidine; 6-Methoxycinchonine; Cinchonan-9-ol, 6'-methoxy-, (9S)-; Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-; .alpha.-(6-Methoxy-4-quinoyl)-5-vinyl-2-quinclidinemethanol; Quinine, polymers show less «

DrugBank

Identification

Name:	Quinine
Name (isomeric):	DB00468
Drug Type:	small molecule
Description:	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.
Synonyms:	6'-Methoxycinchonine; 6'-Methoxycinchonidine; Quinoline Alkaloid; Quinineanhydrous; Quinine sulfate; Quinine, Anhydrous
Brand:	Coco-Quinine, Quinine Dab, Chinine, Aflukin, None, Chinin
Brand name mixture:	Triogene for(Calcium Glycerophosphate + Gentiana Lutea + Iron + Kola + Quinine), Holis 22(Carbon Disulfide + Chenopodium Ambrosioides + Quinine Sulfate + Tobacco), Holis 73(Asafetida + Charcoal Activated + Gratiola Officinalis + Lycopodium Clavatum + Magnesium Carbonate + Potassium Carbonate + Quinine + Silver Nitrate), Holis 12 Pr(Aloe + Citrul... show more » Triogene for(Calcium Glycerophosphate + Gentiana Lutea + Iron + Kola + Quinine), Holis 22(Carbon Disulfide + Chenopodium Ambrosioides + Quinine Sulfate + Tobacco), Holis 73(Asafetida + Charcoal Activated + Gratiola Officinalis + Lycopodium Clavatum + Magnesium Carbonate + Potassium Carbonate + Quinine + Silver Nitrate), Holis 12 Pr(Aloe + Citrullus Colocynthis + Gamboge + Podophyllum + Quinine + White Hellebore Root), Holis 82(Acetic Acid + Asafetida + Charcoal Activated + Magnesium Carbonate + Potassium Carbonate + Quinine + Radish + Silver Nitrate), Thc Complex #57(Arnica Montana + Barium Carbonate + Belladonna + Carbon Disulfide + Cinchona Officinalis + Cocculus Indicus + Conium Maculatum + Ferrum Phosphoricum + Gelsemium Sempervirens + German Chamomile + Hahnemann's Causticum + Lycopodium Clavatum + Oyster Shells + Phosphorus + Pomegranate Bark + Quinine Sulfate + Salicylic Acid + Sanguinaria Canadensis + Sulfur), Holis 21(Castanea Vesca + Citrullus Colocynthis + Ipecac + Nitric Acid + Quinine + Silver Nitrate), Salzmann Product M-1 Malena(Potassium Nitrate + Potassium Phosphate Dibasic + Quinine Sulfate + Sodium Chloride + Sodium Sulfate + Sodium Sulfite), Holis 78(Aconitinum + Cedron + Citrullus Colocynthis + Hypericum Perforatum + Plantago Major + Quinine + Quinine Sulfate) show less «
Category:	Antimalarials, Analgesics, Non-Narcotic, Muscle Relaxants, Central
CAS number:	130-95-0

Pharmacology

Indication:	For the treatment of malaria and leg cramps
Pharmacology:	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 a... show more » 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. show less «
Mechanism of Action:	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.
Absorption:	76 - 88%
Protein binding:	Approximately 70%
Biotransformation:	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]
Toxicity:	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.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take with food to reduce irritation.

Drug interaction:

Vecuronium	Quinine may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Concurrent therapy should be avoided.
Artemether	Quinine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
Pancuronium	The quinine derivative increases the effect of the muscle relaxant
Digitoxin	Quinine/quinidine increases the effect of digoxin
Toremifene	May cause additive QTc-prolonging effects. Concomitant therapy is contraindicated.

Vecuronium	Quinine may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Concurrent therapy should be avoided.
Artemether	Quinine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
Pancuronium	The quinine derivative increases the effect of the muscle relaxant
Digitoxin	Quinine/quinidine increases the effect of digoxin
Toremifene	May cause additive QTc-prolonging effects. Concomitant therapy is contraindicated.
Zuclopenthixol	Additive QTc-prolonging effects increases risk of cardiac arrhythmias. Concomitant therapy should be avoided.
Succinylcholine	The quinine derivative increases the effect of the muscle relaxant
Digoxin	Quinine/quinidine increases the effect of digoxin
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.
Tramadol	Quinine may decrease the effect of Tramadol by decreasing active metabolite production.
Ziprasidone	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Dicumarol	Quinine may increase the anticoagulant effect of dicumarol.
Atracurium	The quinine derivative increases the effect of the muscle relaxant
Anisindione	Quinine may increase the anticoagulant effect of anisindione.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Atomoxetine	The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
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.
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.
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Metocurine	The quinine derivative increases the effect of the muscle relaxant
Thiothixene	May cause additive QTc-prolonging effects. Concomitant therapy should be avoided.
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.
Lumefantrine	Quinine may increase the adverse effects of lumefantrine. Combination therapy is contraindicated unless there are no other treatment options.
Acenocoumarol	Quinine, a moderate CYP2C9 inhibitor, may increase the serum concentration of acenocoumarol by decreasing its metabolism via CYP2C9.
Tamoxifen	Quinine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
Voriconazole	Additive QTc prolongation may occur. Concomitant therapy should be avoided.
Trandolapril	May cause additive hypotensive effects. Monitor for changes in blood pressure if Quinine is initiated, discontinued or dose changed.