Quinine

Identification

Summary

Quinine is an alkaloid used to treat uncomplicated Plasmodium falciparum malaria.

Brand Names

Qualaquin

Generic Name

Quinine

DrugBank Accession Number

DB00468

Background

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.

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 324.4168
Monoisotopic: 324.183778022
Chemical Formula: C₂₀H₂₄N₂O₂

Synonyms

(-)-Quinine
(−)-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

External IDs

WR297608

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Pharmacology

Indication

For the treatment of malaria and leg cramps

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Uncomplicated malaria caused by plasmodium falciparum		••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

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.

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.

Target	Actions	Organism
AFe(II)-protoporphyrin IX	antagonist	Plasmodium falciparum
UPlatelet glycoprotein IX	other	Humans
UIntermediate conductance calcium-activated potassium channel protein 4	inhibitor	Humans

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.

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Quinine
- 3-hydroxyquinine

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]

Adverse Effects

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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.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Glucose-6-phosphate 1-dehydrogenase	Villeurbanne	Not Available	1000_1002delACC	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Torun	Not Available	1006A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sunderland	Not Available	105_107delCAT	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Iwatsuki	Not Available	1081G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Serres	Not Available	1082C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tondela	Not Available	1084_1101delCTGAACGAGCGCAAGGCC	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Loma Linda	Not Available	1089C->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Aachen	Not Available	1089C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tenri	Not Available	1096A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Montpellier	Not Available	1132G>A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Calvo Mackenna	Not Available	1138A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Riley	Not Available	1139T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Olomouc	Not Available	1141T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tomah	Not Available	1153T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lynwood	Not Available	1154G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Madrid	Not Available	1155C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Iowa, Walter Reed, Springfield	Not Available	1156A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Beverly Hills, Genova, Iwate, Niigata, Yamaguchi	Not Available	1160G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hartford	Not Available	1162A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Praha	Not Available	1166A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Krakow	Not Available	1175T>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Wisconsin	Not Available	1177C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nashville, Anaheim, Portici	Not Available	1178G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Alhambra	Not Available	1180G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bari	Not Available	1187C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Puerto Limon	Not Available	1192G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Covao do Lobo	Not Available	1205C>A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Clinic	Not Available	1215G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Utrecht	Not Available	1225C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Suwalki	Not Available	1226C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Riverside	Not Available	1228G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Japan, Shinagawa	Not Available	1229G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kawasaki	Not Available	1229G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Munich	Not Available	1231A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Georgia	Not Available	1284C->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sumare	Not Available	1292T->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Telti/Kobe	Not Available	1318C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Santiago de Cuba, Morioka	Not Available	1339G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Harima	Not Available	1358T->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Figuera da Foz	Not Available	1366G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Amiens	Not Available	1367A>T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bangkok Noi	Not Available	1376G->T, 1502T->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Fukaya	Not Available	1462G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Campinas	Not Available	1463G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Buenos Aires	Not Available	1465C>T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Arakawa	Not Available	1466C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Brighton	Not Available	1488_1490delGAA	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kozukata	Not Available	159G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Amsterdam	Not Available	180_182delTCT	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	No name	Not Available	202G->A, 376A->G, 1264C>G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Swansea	Not Available	224T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Urayasu	Not Available	281_283delAGA	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Vancouver	Not Available	317C->G544C->T592C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mt Sinai	Not Available	376A->G, 1159C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Plymouth	Not Available	488G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Volendam	Not Available	514C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Shinshu	Not Available	527A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chikugo	Not Available	535A->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tsukui	Not Available	561_563delCTC	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Pedoplis-Ckaro	Not Available	573C>G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Santiago	Not Available	593G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Minnesota, Marion, Gastonia, LeJeune	Not Available	637G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cincinnati	Not Available	637G->T, 1037A->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Harilaou	Not Available	648T->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	North Dallas	Not Available	683_685delACA	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Asahikawa	Not Available	695G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Durham	Not Available	713A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Stonybrook	Not Available	724_729delGGCACT	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Wayne	Not Available	769C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Aveiro	Not Available	806G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cleveland Corum	Not Available	820G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lille	Not Available	821A>T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bangkok	Not Available	825G>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sugao	Not Available	826C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	La Jolla	Not Available	832T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Wexham	Not Available	833C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Piotrkow	Not Available	851T>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	West Virginia	Not Available	910G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Omiya	Not Available	921G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nara	Not Available	953_976delCCACCAAAGGGTACCTGGAC GACC	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Manhattan	Not Available	962G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Rehevot	Not Available	964T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Honiara	Not Available	99A->G / 1360C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Tokyo, Fukushima	Not Available	1246G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chatham	Not Available	1003G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Fushan	Not Available	1004C->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Partenope	Not Available	1052G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ierapetra	Not Available	1057C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Anadia	Not Available	1193A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Abeno	Not Available	1220A->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Surabaya	Not Available	1291G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Pawnee	Not Available	1316G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	S. Antioco	Not Available	1342A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cassano	Not Available	1347G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hermoupolis	Not Available	1347G->C / 1360C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Union,Maewo, Chinese-2, Kalo	Not Available	1360C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Andalus	Not Available	1361G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Cosenza	Not Available	1376G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Canton, Taiwan- Hakka, Gifu-like, Agrigento-like	Not Available	1376G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Flores	Not Available	1387C->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kaiping, Anant, Dhon, Sapporo-like, Wosera	Not Available	1388G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kamogawa	Not Available	169C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Costanzo	Not Available	179T>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Amazonia	Not Available	185C->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Songklanagarind	Not Available	196T->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hechi	Not Available	202G->A / 871G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Namouru	Not Available	208T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bao Loc	Not Available	352T>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Crispim	Not Available	375G->T, 379G->T383T->C384C>T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Acrokorinthos	Not Available	376A->G / 463C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Santa Maria	Not Available	376A->G / 542A->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ananindeua	Not Available	376A->G / 871G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Vanua Lava	Not Available	383T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Valladolid	Not Available	406C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Belem	Not Available	409C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Liuzhou	Not Available	442G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Shenzen	Not Available	473G>A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Taipei ‚ÄúChinese- 3‚Äù	Not Available	493A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Toledo	Not Available	496C>T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Naone	Not Available	497G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nankang	Not Available	517T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Miaoli	Not Available	519C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham	Not Available	563C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Coimbra Shunde	Not Available	592C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nilgiri	Not Available	593G>A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Radlowo	Not Available	679C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Roubaix	Not Available	811G>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Haikou	Not Available	835A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chinese-1	Not Available	835A->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mizushima	Not Available	848A>G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Osaka	Not Available	853C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Viangchan, Jammu	Not Available	871G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Seoul	Not Available	916G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ludhiana	Not Available	929G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Farroupilha	Not Available	977C->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Chinese-5	Not Available	1024C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Rignano	Not Available	130G>A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Orissa	Not Available	131C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	G6PDNice	Not Available	1380G>C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kamiube, Keelung	Not Available	1387C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Neapolis	Not Available	1400C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Aures	Not Available	143T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Split	Not Available	1442C->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kambos	Not Available	148C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Palestrina	Not Available	170G>A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Metaponto	Not Available	172G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Musashino	Not Available	185C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Asahi	Not Available	202G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (202), Ferrara I	Not Available	202G->A / 376A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Murcia Oristano	Not Available	209A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ube Konan	Not Available	241C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lagosanto	Not Available	242G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Guangzhou	Not Available	274C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Hammersmith	Not Available	323T->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sinnai	Not Available	34G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (680)	Not Available	376A->G / 680G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (968), Betica,Selma, Guantanamo	Not Available	376A->G / 968T->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Salerno Pyrgos	Not Available	383T>G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Quing Yan	Not Available	392G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Lages	Not Available	40G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Ilesha	Not Available	466G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mahidol	Not Available	487G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Malaga	Not Available	542A->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Sibari	Not Available	634A->G	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Mexico City	Not Available	680G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Nanning	Not Available	703C->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Seattle, Lodi, Modena, Ferrara II, Athens-like	Not Available	844G->C	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Bajo Maumere	Not Available	844G->T	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Montalbano	Not Available	854G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Kalyan-Kerala, Jamnaga, Rohini	Not Available	949G->A	ADR Inferred	Increased risk of hemolysis.	Details
Glucose-6-phosphate 1-dehydrogenase	Gaohe	Not Available	95A->G	ADR Inferred	Increased risk of hemolysis.	Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Quinine is combined with 1,2-Benzodiazepine.
Abametapir	The serum concentration of Quinine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Quinine can be increased when combined with Abatacept.
Abciximab	The therapeutic efficacy of Abciximab can be increased when used in combination with Quinine.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Quinine.

Food Interactions

Take with food. Food reduces irritation.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Quinine citrate	L8D5LFU229	752-72-7	YSFIPRFOHJQXJF-VMJVVOMYSA-N
Quinine hydrochloride	711S8Y0T33	6119-47-7	MPQKYZPYCSTMEI-FLZPLBAKSA-N
Quinine phosphate	0E9UD56A3I	549-60-0	JGWCVXDJEMKYEA-INGJVHGESA-N
Quinine sulfate	M4XCR57IWG	804-63-7	RONWGALEIBILOG-VMJVVOMYSA-N

Product Images

International/Other Brands

Cinkona (Ipca) / Jasoquin (Jayson) / QSM (Leben) / Quinlup (Lupin) / Qutil (Little Greave) / Sulquin (Saga)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Qualaquin	Capsule	324 mg/1	Oral	Stat Rx USA	2005-08-12	Not applicable
Qualaquin	Capsule	324 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2005-08-12	Not applicable
Qualaquin	Capsule	324 mg/1	Oral	AR Scientific, Inc.	2005-08-12	Not applicable
Quinine - Odan	Tablet	300 mg	Oral	Odan Laboratories Ltd	2001-11-08	Not applicable
Quinine - Odan	Capsule	300 mg	Oral	Odan Laboratories Ltd	1999-05-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-quinine	Capsule	300 mg	Oral	Apotex Corporation	2004-06-08	Not applicable
Apo-quinine	Capsule	200 mg	Oral	Apotex Corporation	2004-06-08	Not applicable
Jamp-quinine	Capsule	200 mg	Oral	Jamp Pharma Corporation	2015-09-16	Not applicable
Jamp-quinine	Capsule	300 mg	Oral	Jamp Pharma Corporation	2015-09-16	Not applicable
Pro-quinine - 200	Capsule	200 mg	Oral	Pro Doc Limitee	2008-07-03	Not applicable

Chemical Identifiers

UNII: A7V27PHC7A
CAS number: 130-95-0
InChI Key: LOUPRKONTZGTKE-WZBLMQSHSA-N
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
IUPAC Name: (R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol
SMILES: [H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12

References

Synthesis Reference

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.

US20090326005

General References

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. [Article]

External Links

Human Metabolome Database: HMDB0014611
KEGG Compound: C06526
PubChem Compound: 3034034
PubChem Substance: 46507493
ChemSpider: 84989
BindingDB: 50367247
RxNav: 9071
ChEBI: 15854
ChEMBL: CHEMBL170
ZINC: ZINC000003831404
Therapeutic Targets Database: DAP000491
PharmGKB: PA451213
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: QI9
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Quinine

PDB Entries

4uil / 4uin / 4wnv / 5znc

FDA label

Download (718 KB)

MSDS

Download (72.1 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Malaria	1
4	Completed	Basic Science	Obesity	1
4	Completed	Treatment	Anemia	1
4	Completed	Treatment	Malaria	2
4	Unknown Status	Treatment	Malaria	1

Pharmacoeconomics

Manufacturers

Ar holding co inc

Packagers

Allan Pharmaceutical LLC
Amerisource Health Services Corp.
Atlantic Biologicals Corporation
Cardinal Health
Direct Dispensing Inc.
Direct Pharmaceuticals Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Heartland Repack Services LLC
J T Baker
Kaiser Foundation Hospital
Liberty Pharmaceuticals
Major Pharmaceuticals
Murfreesboro Pharmaceutical Nursing Supply
Mutual Pharmaceutical Co.
Nucare Pharmaceuticals Inc.
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
Prepackage Specialists
Qualitest
United Research Laboratories Inc.
Watson Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral	200 MG
Solution, concentrate	Intravenous
Injection, solution, concentrate	Intravenous	208.75 MG/ML
Injection, solution, concentrate	Intravenous
Tablet	Oral
Tablet, coated	Oral
Cream	Topical
Capsule	Oral	324 mg/1
Capsule	Oral	200 mg
Injection
Solution		300 mg/1ml
Injection, solution		60 mg/1ml
Tablet, film coated	Oral
Capsule	Oral	200 mg / cap
Capsule	Oral	300 mg / cap
Tablet, sugar coated	Oral
Tablet, sugar coated	Oral	300 mg
Capsule	Oral	300 mg
Tablet	Oral	300 mg
Solution		250 mg/1ml
Tablet, coated	Oral	300 mg

Prices

Unit description	Cost	Unit
Quinine sulfate powd ultrex	25.86USD	g
Apo-Quinine 300 mg Capsule	0.39USD	capsule
Novo-Quinine 300 mg Capsule	0.39USD	capsule
Apo-Quinine 200 mg Capsule	0.25USD	capsule
Novo-Quinine 200 mg Capsule	0.25USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	57 °C	PhysProp
water solubility	500 mg/L (at 15 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	3.44	HANSCH,C ET AL. (1995)
logS	-2.76	ADME Research, USCD

Predicted Properties

Property	Value	Source
Water Solubility	0.334 mg/mL	ALOGPS
logP	2.82	ALOGPS
logP	2.51	Chemaxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.89	Chemaxon
pKa (Strongest Basic)	9.05	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	45.59 Å²	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	94.69 m³·mol^-1	Chemaxon
Polarizability	35.99 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9836
Blood Brain Barrier	+	0.9382
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Substrate	0.7863
P-glycoprotein inhibitor I	Inhibitor	0.8208
P-glycoprotein inhibitor II	Inhibitor	0.8387
Renal organic cation transporter	Inhibitor	0.762
CYP450 2C9 substrate	Non-substrate	0.7898
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.5754
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7225
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.972
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.0596 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.5884
hERG inhibition (predictor II)	Inhibitor	0.538

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4r-1901000000-8176add5a84f7ae1eb69
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0009000000-bc68328282c6154e03d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00dl-0169000000-482414433c1e7b0ca89d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0009000000-4808a6e84b0cb2d4cbc6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05fr-0519000000-2b2e0c890198ec71ca0c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-0920000000-01da964eb26702c0e20a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ab9-0910000000-a1ffa729b41cabf4fc88
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	190.5319787	predicted	DarkChem Lite v0.1.0
[M-H]-	188.8849787	predicted	DarkChem Lite v0.1.0
[M-H]-	192.1513787	predicted	DarkChem Lite v0.1.0
[M-H]-	174.37386	predicted	DeepCCS 1.0 (2019)
[M+H]+	191.1071787	predicted	DarkChem Lite v0.1.0
[M+H]+	189.1589787	predicted	DarkChem Lite v0.1.0
[M+H]+	192.2581787	predicted	DarkChem Lite v0.1.0
[M+H]+	176.76942	predicted	DeepCCS 1.0 (2019)
[M+Na]+	190.5579787	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.3449787	predicted	DarkChem Lite v0.1.0
[M+Na]+	191.9704787	predicted	DarkChem Lite v0.1.0
[M+Na]+	182.70932	predicted	DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

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Details1. Fe(II)-protoporphyrin IX

Kind

Small molecule

Organism

Plasmodium falciparum

Pharmacological action

Yes

Actions

Antagonist

References

Alumasa JN, Gorka AP, Casabianca LB, Comstock E, de Dios AC, Roepe PD: The hydroxyl functionality and a rigid proximal N are required for forming a novel non-covalent quinine-heme complex. J Inorg Biochem. 2011 Mar;105(3):467-75. doi: 10.1016/j.jinorgbio.2010.08.011. Epub 2010 Sep 22. [Article]
Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. [Article]

Details2. Platelet glycoprotein IX

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other

General Function: Not Available
Specific Function: The GPIb-V-IX complex functions as the vWF receptor and mediates vWF-dependent platelet adhesion to blood vessels. The adhesion of platelets to injured vascular surfaces in the arterial circulation...
Gene Name: GP9
Uniprot ID: P14770
Uniprot Name: Platelet glycoprotein IX
Molecular Weight: 19045.87 Da

References

Asvadi P, Ahmadi Z, Chong BH: Drug-induced thrombocytopenia: localization of the binding site of GPIX-specific quinine-dependent antibodies. Blood. 2003 Sep 1;102(5):1670-7. Epub 2003 May 8. [Article]

Details3. Intermediate conductance calcium-activated potassium channel protein 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Protein phosphatase binding
Specific Function: Forms a voltage-independent potassium channel that is activated by intracellular calcium (PubMed:26148990). Activation is followed by membrane hyperpolarization which promotes calcium influx. Requi...
Gene Name: KCNN4
Uniprot ID: O15554
Uniprot Name: Intermediate conductance calcium-activated potassium channel protein 4
Molecular Weight: 47695.12 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Inducer

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Zhao XJ, Yokoyama H, Chiba K, Wanwimolruk S, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther. 1996 Dec;279(3):1327-34. [Article]
Allqvist A, Miura J, Bertilsson L, Mirghani RA: Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers. Eur J Clin Pharmacol. 2007 Feb;63(2):173-9. doi: 10.1007/s00228-006-0230-z. Epub 2007 Jan 3. [Article]
Mirghani RA, Hellgren U, Bertilsson L, Gustafsson LL, Ericsson O: Metabolism and elimination of quinine in healthy volunteers. Eur J Clin Pharmacol. 2003 Sep;59(5-6):423-7. doi: 10.1007/s00228-003-0637-8. Epub 2003 Aug 12. [Article]
Just JM, Weckbecker K, Just KS: Quinine induced simvastatin toxicity through cytochrome inhibition - a case report. BMC Geriatr. 2016 Oct 1;16(1):168. doi: 10.1186/s12877-016-0337-8. [Article]
Flockhart Table of Drug Interactions [Link]

Details2. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

Flockhart Table of Drug Interactions [Link]

Details3. Cytochrome P450 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Inducer

General Function: Vitamin d 24-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A1
Uniprot ID: P04798
Uniprot Name: Cytochrome P450 1A1
Molecular Weight: 58164.815 Da

References

Bapiro TE, Andersson TB, Otter C, Hasler JA, Masimirembwa CM: Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42. Epub 2002 Oct 2. [Article]
Ching MS, Blake CL, Malek NA, Angus PW, Ghabrial H: Differential inhibition of human CYP1A1 and CYP1A2 by quinidine and quinine. Xenobiotica. 2001 Nov;31(11):757-67. doi: 10.1080/00498250110065603 . [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	610	N/A	N/A	A27754
IC 50 (nM)	1800	N/A	N/A	A28284
Ki (nM)	15000	N/A	N/A	A28283
Ki (nM)	4600	N/A	N/A	A28283
Ki (nM)	5500	N/A	N/A	A28283
Ki (nM)	21000	N/A	N/A	A28283

Details4. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Kirkwood LC, Nation RL, Somogyi AA: Characterization of the human cytochrome P450 enzymes involved in the metabolism of dihydrocodeine. Br J Clin Pharmacol. 1997 Dec;44(6):549-55. [Article]
Hutzler JM, Walker GS, Wienkers LC: Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9. doi: 10.1021/tx025674x. [Article]
FDA Approved Drug Products: Qualaquin ((quinine sulfate) Capsules [Link]

Details5. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Curator comments: Evidence for this enzyme action is limited. The FDA label states a possibility of CYP1A2 as one possible enzyme responsible for the metabolism of this drug, and one paper suggests a weak inhibition of CYP1A2.

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Mirghani RA, Hellgren U, Westerberg PA, Ericsson O, Bertilsson L, Gustafsson LL: The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo. Clin Pharmacol Ther. 1999 Nov;66(5):454-60. doi: 10.1016/S0009-9236(99)70008-1. [Article]
FDA label Quinine [File]

Details6. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Ong CE, Coulter S, Birkett DJ, Bhasker CR, Miners JO: The xenobiotic inhibitor profile of cytochrome P4502C8. Br J Clin Pharmacol. 2000 Dec;50(6):573-80. doi: 10.1046/j.1365-2125.2000.00316.x. [Article]
Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
QUALAQUIN® quinine sulfate - FDA Label [Link]

Details7. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Zhao XJ, Yokoyama H, Chiba K, Wanwimolruk S, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther. 1996 Dec;279(3):1327-34. [Article]
Quinine FDA label [File]

Details8. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]
Zhao XJ, Yokoyama H, Chiba K, Wanwimolruk S, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther. 1996 Dec;279(3):1327-34. [Article]
PDR INTERACTIONS QUININE [Link]
QUALAQUIN® quinine sulfate - FDA Label [Link]

Details9. Cytochrome P450 2E1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name: CYP2E1
Uniprot ID: P05181
Uniprot Name: Cytochrome P450 2E1
Molecular Weight: 56848.42 Da

Details10. Cytochrome P450 3A7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A7
Uniprot ID: P24462
Uniprot Name: Cytochrome P450 3A7
Molecular Weight: 57525.03 Da

References

Flockhart Table of Drug Interactions [Link]

Transporters

Details1. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Sweet DH, Miller DS, Pritchard JB: Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9. Epub 2001 Sep 11. [Article]
Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [Article]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [Article]
Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [Article]
Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [Article]
Sweet DH, Pritchard JB: rOCT2 is a basolateral potential-driven carrier, not an organic cation/proton exchanger. Am J Physiol. 1999 Dec;277(6 Pt 2):F890-8. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	51600	N/A	N/A	A16058

Details2. Solute carrier family 22 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Secondary active organic cation transmembrane transporter activity
Specific Function: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name: SLC22A1
Uniprot ID: O15245
Uniprot Name: Solute carrier family 22 member 1
Molecular Weight: 61153.345 Da

References

Martel F, Vetter T, Russ H, Grundemann D, Azevedo I, Koepsell H, Schomig E: Transport of small organic cations in the rat liver. The role of the organic cation transporter OCT1. Naunyn Schmiedebergs Arch Pharmacol. 1996 Aug-Sep;354(3):320-6. [Article]
Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [Article]
Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [Article]
Herraez E, Lozano E, Macias RI, Vaquero J, Bujanda L, Banales JM, Marin JJ, Briz O: Expression of SLC22A1 variants may affect the response of hepatocellular carcinoma and cholangiocarcinoma to sorafenib. Hepatology. 2013 Sep;58(3):1065-73. doi: 10.1002/hep.26425. Epub 2013 Jul 30. [Article]
Hubeny A, Keiser M, Oswald S, Jedlitschky G, Kroemer HK, Siegmund W, Grube M: Expression of Organic Anion Transporting Polypeptide 1A2 in Red Blood Cells and Its Potential Impact on Antimalarial Therapy. Drug Metab Dispos. 2016 Oct;44(10):1562-8. doi: 10.1124/dmd.116.069807. Epub 2016 Aug 8. [Article]

Details3. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	159300	N/A	N/A	A15813
IC 50 (nM)	112400	N/A	N/A	A15813
IC 50 (nM)	184900	N/A	N/A	A15813
IC 50 (nM)	74400	N/A	N/A	A15813
IC 50 (nM)	87600	N/A	N/A	A15813
IC 50 (nM)	167800	N/A	N/A	A15813
IC 50 (nM)	22600	N/A	N/A	A15813
IC 50 (nM)	430000	N/A	N/A	A27451
Ki (nM)	12000	N/A	N/A	A27451

Details4. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
van der Sandt IC, Blom-Roosemalen MC, de Boer AG, Breimer DD: Specificity of doxorubicin versus rhodamine-123 in assessing P-glycoprotein functionality in the LLC-PK1, LLC-PK1:MDR1 and Caco-2 cell lines. Eur J Pharm Sci. 2000 Sep;11(3):207-14. [Article]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [Article]

Details5. Solute carrier organic anion transporter family member 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name: SLCO1A2
Uniprot ID: P46721
Uniprot Name: Solute carrier organic anion transporter family member 1A2
Molecular Weight: 74144.105 Da

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [Article]
Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [Article]

Details6. Solute carrier family 22 member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name: SLC22A4
Uniprot ID: Q9H015
Uniprot Name: Solute carrier family 22 member 4
Molecular Weight: 62154.48 Da

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]

Details7. Solute carrier organic anion transporter family member 1B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Sodium-independent organic anion transmembrane transporter activity
Specific Function: Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name: SLCO1B1
Uniprot ID: Q9Y6L6
Uniprot Name: Solute carrier organic anion transporter family member 1B1
Molecular Weight: 76447.99 Da

References

Karlgren M, Ahlin G, Bergstrom CA, Svensson R, Palm J, Artursson P: In vitro and in silico strategies to identify OATP1B1 inhibitors and predict clinical drug-drug interactions. Pharm Res. 2012 Feb;29(2):411-26. doi: 10.1007/s11095-011-0564-9. Epub 2011 Aug 23. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Quinine

Identification

Structure for Quinine (DB00468)

Pharmacology

Interactions

Products

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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Transporters

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