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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00468
rdf:type
n6:Drug
n6: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. [PubChem]
n6:dosage
n22:271B5787-363D-11E5-9242-09173F13E4C5
n6:generalReferences
# Paintaud G, Alvan G, Berninger E, Gustafsson LL, Idrizbegovic E, Karlsson KK, Wakelkamp M: The concentration-effect relationship of quinine-induced hearing impairment. Clin Pharmacol Ther. 1994 Mar;55(3):317-23. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8143397
n6:group
approved
n6:halfLife
Approximately 18 hours
n6:indication
For the treatment of malaria and leg cramps
n6:manufacturer
n7:271B5781-363D-11E5-9242-09173F13E4C5
owl:sameAs
n14:DB00468 n15:DB00468
dcterms:title
Quinine
adms:identifier
n4:C06526 n5:13310-153-07 n24:2510 n25:2510 n26:DB00468 n27:Quinine n28:50198086 n29:15854 n30:PA451213
n6:mechanismOfAction
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.
n6:packager
n7:271B577F-363D-11E5-9242-09173F13E4C5 n7:271B5780-363D-11E5-9242-09173F13E4C5 n7:271B577D-363D-11E5-9242-09173F13E4C5 n7:271B577E-363D-11E5-9242-09173F13E4C5 n7:271B5771-363D-11E5-9242-09173F13E4C5 n7:271B5772-363D-11E5-9242-09173F13E4C5 n7:271B576F-363D-11E5-9242-09173F13E4C5 n7:271B5770-363D-11E5-9242-09173F13E4C5 n7:271B5775-363D-11E5-9242-09173F13E4C5 n7:271B5776-363D-11E5-9242-09173F13E4C5 n7:271B5773-363D-11E5-9242-09173F13E4C5 n7:271B5774-363D-11E5-9242-09173F13E4C5 n7:271B576D-363D-11E5-9242-09173F13E4C5 n7:271B576E-363D-11E5-9242-09173F13E4C5 n7:271B576B-363D-11E5-9242-09173F13E4C5 n7:271B576C-363D-11E5-9242-09173F13E4C5 n7:271B5779-363D-11E5-9242-09173F13E4C5 n7:271B577A-363D-11E5-9242-09173F13E4C5 n7:271B5777-363D-11E5-9242-09173F13E4C5 n7:271B5778-363D-11E5-9242-09173F13E4C5 n7:271B577B-363D-11E5-9242-09173F13E4C5 n7:271B577C-363D-11E5-9242-09173F13E4C5
n6:routeOfElimination
Quinine is eliminated primarily via hepatic biotransformation. Approximately 20% of quinine is excreted unchanged in urine.
n6:synonym
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol Chinine Quinine Chinin Chininum (R)-(-)-Quinine 6'-Methoxycinchonidine Quinina (8S,9R)-Quinine (-)-Quinine
n6: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.
n6:volumeOfDistribution
* 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]
n10:hasAHFSCode
n12:08-30-08 n12:92-02-00%2A
n6:foodInteraction
Take with food to reduce irritation.
n6:mixture
n18:271B5762-363D-11E5-9242-09173F13E4C5 n18:271B5763-363D-11E5-9242-09173F13E4C5 n18:271B5761-363D-11E5-9242-09173F13E4C5 n18:271B576A-363D-11E5-9242-09173F13E4C5 n18:271B5768-363D-11E5-9242-09173F13E4C5 n18:271B5769-363D-11E5-9242-09173F13E4C5 n18:271B5766-363D-11E5-9242-09173F13E4C5 n18:271B5767-363D-11E5-9242-09173F13E4C5 n18:271B5764-363D-11E5-9242-09173F13E4C5 n18:271B5765-363D-11E5-9242-09173F13E4C5
n6:proteinBinding
Approximately 70%
n6:salt
n6:synthesisReference
Tong Sun, Shawn Watson, Wei Lai, Stephan D. Parent, "QUININE SULFATE/BISULFATE SOLID COMPLEX; METHODS OF MAKING; AND METHODS OF USE THEREOF." U.S. Patent US20090326005, issued December 31, 2009.
n16:hasConcept
n17:M0018346
foaf:page
n20:quinine.htm n23:quinine.html
n6:IUPAC-Name
n8:271B578C-363D-11E5-9242-09173F13E4C5
n6:InChI
n8:271B5792-363D-11E5-9242-09173F13E4C5
n6:Molecular-Formula
n8:271B5791-363D-11E5-9242-09173F13E4C5
n6:Molecular-Weight
n8:271B578E-363D-11E5-9242-09173F13E4C5
n6:Monoisotopic-Weight
n8:271B578F-363D-11E5-9242-09173F13E4C5
n6:SMILES
n8:271B5790-363D-11E5-9242-09173F13E4C5
n6:Water-Solubility
n8:271B57A2-363D-11E5-9242-09173F13E4C5 n8:271B578A-363D-11E5-9242-09173F13E4C5
n6:logP
n8:271B57A4-363D-11E5-9242-09173F13E4C5 n8:271B5788-363D-11E5-9242-09173F13E4C5 n8:271B578B-363D-11E5-9242-09173F13E4C5
n6:logS
n8:271B57A5-363D-11E5-9242-09173F13E4C5 n8:271B5789-363D-11E5-9242-09173F13E4C5
n10:hasATCCode
n11:P01BC01
n6:H-Bond-Acceptor-Count
n8:271B5798-363D-11E5-9242-09173F13E4C5
n6:H-Bond-Donor-Count
n8:271B5799-363D-11E5-9242-09173F13E4C5
n6:InChIKey
n8:271B5793-363D-11E5-9242-09173F13E4C5
n6:Polar-Surface-Area--PSA-
n8:271B5794-363D-11E5-9242-09173F13E4C5
n6:Polarizability
n8:271B5796-363D-11E5-9242-09173F13E4C5
n6:Refractivity
n8:271B5795-363D-11E5-9242-09173F13E4C5
n6:Rotatable-Bond-Count
n8:271B5797-363D-11E5-9242-09173F13E4C5
n6:absorption
76 - 88%
n6:affectedOrganism
Humans and other mammals
n6:casRegistryNumber
130-95-0
n6:category
n6: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]
n6:containedIn
n21:271B5782-363D-11E5-9242-09173F13E4C5 n21:271B5783-363D-11E5-9242-09173F13E4C5 n21:271B5786-363D-11E5-9242-09173F13E4C5 n21:271B5784-363D-11E5-9242-09173F13E4C5 n21:271B5785-363D-11E5-9242-09173F13E4C5
n6:Bioavailability
n8:271B579E-363D-11E5-9242-09173F13E4C5
n6:Ghose-Filter
n8:271B57A0-363D-11E5-9242-09173F13E4C5
n6:MDDR-Like-Rule
n8:271B57A1-363D-11E5-9242-09173F13E4C5
n6:Melting-Point
n8:271B57A3-363D-11E5-9242-09173F13E4C5
n6:Number-of-Rings
n8:271B579D-363D-11E5-9242-09173F13E4C5
n6:Physiological-Charge
n8:271B579C-363D-11E5-9242-09173F13E4C5
n6:Rule-of-Five
n8:271B579F-363D-11E5-9242-09173F13E4C5
n6:Traditional-IUPAC-Name
n8:271B578D-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-acidic-
n8:271B579A-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-basic-
n8:271B579B-363D-11E5-9242-09173F13E4C5