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Identification
NameQuinine
Accession NumberDB00468  (APRD00563)
TypeSmall Molecule
GroupsApproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
(-)-QuinineNot AvailableNot Available
(8S,9R)-QuinineNot AvailableNot Available
(R)-(-)-QuinineNot AvailableNot Available
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanolNot AvailableNot Available
6'-MethoxycinchonidineNot AvailableNot Available
ChininGermanINN
ChinineNot AvailableNot Available
ChininumLatinINN
QuininaNot AvailableNot Available
QuinineFrenchINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Qualaquincapsule324 mgoralAR Scientific Inc.2005-08-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qualaquincapsule324 mgoralSTAT Rx USA LLC2005-08-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Qualaquincapsule324 mgoralCaraco Pharma, Inc.2005-08-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quinine Sulfatecapsule324 mgoralMutual Pharmaceutical Company, Inc.2012-07-23Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Quinine Sulfatecapsule324 mgoralTeva Pharmaceuticals USA Inc2012-09-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Quinine Sulfatecapsule324 mgoralMylan Pharmaceuticals Inc.2012-12-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
CinkonaIpca
JasoquinJayson
QSMLeben
QuinlupLupin
QutilLittle Greave
SulquinSaga
Brand mixtures
Brand NameIngredients
HexaquineQuinine and Thiamine
Holis 12 PrAloe + Citrullus Colocynthis + Gamboge + Podophyllum + Quinine + White Hellebore Root
Holis 21Castanea Vesca + Citrullus Colocynthis + Ipecac + Nitric Acid + Quinine + Silver Nitrate
Holis 22Carbon Disulfide + Chenopodium Ambrosioides + Quinine Sulfate + Tobacco
Holis 73Asafetida + Charcoal Activated + Gratiola Officinalis + Lycopodium Clavatum + Magnesium Carbonate + Potassium Carbonate + Quinine + Silver Nitrate
Holis 78Aconitinum + Cedron + Citrullus Colocynthis + Hypericum Perforatum + Plantago Major + Quinine + Quinine Sulfate
Holis 82Acetic Acid + Asafetida + Charcoal Activated + Magnesium Carbonate + Potassium Carbonate + Quinine + Radish + Silver Nitrate
Salzmann Product M-1 MalenaPotassium Nitrate + Potassium Phosphate Dibasic + Quinine Sulfate + Sodium Chloride + Sodium Sulfate + Sodium Sulfite
Thc Complex #57Arnica 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
Triogene forCalcium Glycerophosphate + Gentiana Lutea + Iron + Kola + Quinine
Salts
Name/CASStructureProperties
Quinine Hydrochloride
ThumbNot applicableDBSALT001044
Quinine sulfate
804-63-7
Thumb
  • InChI Key: RONWGALEIBILOG-VMJVVOMYSA-N
  • Monoisotopic Mass: 746.334935286
  • Average Mass: 746.912
DBSALT000531
Categories
CAS number130-95-0
WeightAverage: 324.4168
Monoisotopic: 324.183778022
Chemical FormulaC20H24N2O2
InChI KeyLOUPRKONTZGTKE-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCinchona alkaloids
Sub ClassNot Available
Direct ParentCinchona alkaloids
Alternative Parents
Substituents
  • Cinchonan-skeleton
  • Hydroxyquinoline
  • Quinoline
  • Quinuclidine
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Piperidine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of malaria and leg cramps
PharmacodynamicsQuinine 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 actionThe 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.
Absorption76 - 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 bindingApproximately 70%
Metabolism

Hepatic, over 80% metabolized by the liver.

SubstrateEnzymesProduct
Quinine
3-hydroxyquinineDetails
Route of eliminationQuinine is eliminated primarily via hepatic biotransformation. Approximately 20% of quinine is excreted unchanged in urine.
Half lifeApproximately 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]
ToxicityQuinine 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9836
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7863
P-glycoprotein inhibitor IInhibitor0.8208
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterInhibitor0.762
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5754
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8931
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7225
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.972
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0596 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5884
hERG inhibition (predictor II)Inhibitor0.538
Pharmacoeconomics
Manufacturers
  • Ar holding co inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral324 mg
Prices
Unit descriptionCostUnit
Quinine sulfate powd ultrex25.86USD g
Apo-Quinine 300 mg Capsule0.39USD capsule
Novo-Quinine 300 mg Capsule0.39USD capsule
Apo-Quinine 200 mg Capsule0.25USD capsule
Novo-Quinine 200 mg Capsule0.25USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point57 °CPhysProp
water solubility500 mg/L (at 15 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.44HANSCH,C ET AL. (1995)
logS-2.76ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.334 mg/mLALOGPS
logP2.82ALOGPS
logP2.51ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.59 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity94.69 m3·mol-1ChemAxon
Polarizability35.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 Reference
  1. 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
External Links
ATC CodesP01BC01
AHFS Codes
  • 08:30.08
  • 92:02.00*
PDB EntriesNot Available
FDA labelDownload (718 KB)
MSDSDownload (72.1 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolMay enhance the anticoagulant effect of Vitamin K Antagonists.
AcetohexamideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Acetylsalicylic acidMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents.
AfatinibP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Afatinib.
AlogliptinMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Aluminum hydroxideMay decrease the serum concentration of QuiNINE. Exceptions: Calcium Carbonate; Sodium Bicarbonate.
AminophyllineMay increase the serum concentration of Theophylline Derivatives.
AprepitantMay increase the serum concentration of CYP3A4 Substrates.
ArtemetherMay enhance the adverse/toxic effect of Antimalarial Agents.
AtorvastatinMay increase the serum concentration of HMG-CoA Reductase Inhibitors.
AtracuriumMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
BiotinTetracycline may increase the serum concentration of QuiNINE.
BosentanMay decrease the serum concentration of CYP3A4 Substrates.
BosutinibP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Bosutinib.
Brentuximab vedotinP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Brentuximab Vedotin. Specifically, concentrations of the active monomethyl auristatin E (MMAE) component may be increased.
BuforminMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Calcium carbonateMay decrease the serum concentration of QuiNINE. Exceptions: Calcium Carbonate; Sodium Bicarbonate.
CanagliflozinMay enhance the hypoglycemic effect of Hypoglycemic Agents.
CarbamazepineMay decrease the serum concentration of QuiNINE. QuiNINE may increase the serum concentration of CarBAMazepine.
CarvedilolCYP2C9 Inhibitors (Moderate) may increase the serum concentration of Carvedilol. Specifically, concentrations of the S-carvedilol enantiomer may be increased.
ChlorpropamideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
CimetidineMay increase the serum concentration of QuiNINE.
Cisatracurium BesylateMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
ClarithromycinMacrolide Antibiotics may increase the serum concentration of QuiNINE.
CodeineCYP2D6 Inhibitors (Moderate) may diminish the therapeutic effect of Codeine. These CYP2D6 inhibitors may prevent the metabolic conversion of codeine to its active metabolite morphine.
ColchicineP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Colchicine. Colchicine distribution into certain tissues (e.g., brain) may also be increased.
ConivaptanMay increase the serum concentration of CYP3A4 Substrates.
Dabigatran etexilateP-glycoprotein/ABCB1 Inhibitors may increase serum concentrations of the active metabolite(s) of Dabigatran Etexilate.
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DigoxinMay increase the serum concentration of Digoxin.
DihydrotestosteroneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
DronabinolCYP2C9 Inhibitors (Moderate) may increase the serum concentration of Dronabinol.
EverolimusP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Everolimus.
ExenatideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
FesoterodineCYP2D6 Inhibitors may increase serum concentrations of the active metabolite(s) of Fesoterodine.
FosaprepitantMay increase the serum concentration of CYP3A4 Substrates.
FosphenytoinMay decrease the serum concentration of QuiNINE.
GliclazideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
GlimepirideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
GlipizideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
GliquidoneMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Glucagon recombinantMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
GlyburideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
HalofantrineQuiNINE may enhance the adverse/toxic effect of Halofantrine. QuiNINE may increase the serum concentration of Halofantrine.
HydrocodoneCYP3A4 Inhibitors (Weak) may increase the serum concentration of Hydrocodone.
Insulin AspartMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin DetemirMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin GlargineMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin GlulisineMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin LisproMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin RegularMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin, isophaneMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin, porcineMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
IvacaftorMay increase the serum concentration of CYP3A4 Substrates.
LedipasvirP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Ledipasvir.
LinagliptinMay enhance the hypoglycemic effect of Hypoglycemic Agents.
LomitapideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Lomitapide.
LopinavirMay decrease the serum concentration of QuiNINE. This effect has been seen with lopinavir/ritonavir. The individual contributions of lopinavir and ritonavir to this effect are unclear.
LovastatinMay increase the serum concentration of HMG-CoA Reductase Inhibitors.
LULICONAZOLEMay increase the serum concentration of CYP3A4 Substrates.
LumefantrineAntimalarial Agents may enhance the adverse/toxic effect of Lumefantrine.
Magnesium oxideMay decrease the serum concentration of QuiNINE. Exceptions: Calcium Carbonate; Sodium Bicarbonate.
MefloquineMay enhance the adverse/toxic effect of Mefloquine. Specifically, the risk for QTc-prolongation and the risk for convulsions may be increased. Mefloquine may increase the serum concentration of QuiNINE.
MetforminMay enhance the hypoglycemic effect of Hypoglycemic Agents.
MetoprololCYP2D6 Inhibitors may increase the serum concentration of Metoprolol.
MifepristoneMay enhance the QTc-prolonging effect of Highest Risk QTc-Prolonging Agents.
MitiglinideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
NateglinideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
NebivololCYP2D6 Inhibitors (Moderate) may increase the serum concentration of Nebivolol.
Nitric OxideMay enhance the adverse/toxic effect of Methemoglobinemia Associated Agents. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
OxandroloneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PancuroniumMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
PazopanibP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of PAZOPanib.
PegvisomantMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents.
PhenforminMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
PhenobarbitalMay decrease the serum concentration of QuiNINE. QuiNINE may increase the serum concentration of PHENobarbital.
PhenytoinPhenytoin may decrease the serum concentration of QuiNINE.
PimozideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Pimozide.
PioglitazoneMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
PrilocaineMethemoglobinemia Associated Agents may enhance the adverse/toxic effect of Prilocaine. Combinations of these agents may increase the likelihood of significant methemoglobinemia.
prucaloprideP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Prucalopride.
RepaglinideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
RifampicinRifampin may decrease the serum concentration of QuiNINE.
RifaximinP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Rifaximin.
RitonavirQuiNINE may increase the serum concentration of Ritonavir. Ritonavir may decrease the serum concentration of QuiNINE. This effect has been seen with lopinavir/ritonavir. The individual contributions of lopinavir and ritonavir to this effect are unclear. Ritonavir may increase the serum concentration of QuiNINE.
RivaroxabanP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Rivaroxaban.
RocuroniumMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
Salicylate-sodiumMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents.
SaxagliptinMay enhance the hypoglycemic effect of Hypoglycemic Agents.
SilodosinP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Silodosin.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SimeprevirMay increase the serum concentration of CYP3A4 Substrates.
SimvastatinMay increase the serum concentration of HMG-CoA Reductase Inhibitors.
Sodium bicarbonateAlkalinizing Agents may increase the serum concentration of QuiNINE.
SpiramycinMacrolide Antibiotics may increase the serum concentration of QuiNINE.
SuccinylcholineMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
SulfisoxazoleMacrolide Antibiotics may increase the serum concentration of QuiNINE.
SulodexideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
TamoxifenCYP2D6 Inhibitors (Moderate) may decrease serum concentrations of the active metabolite(s) of Tamoxifen. Specifically, CYP2D6 inhibitors may decrease the metabolic formation of highly potent active metabolites.
TelithromycinMacrolide Antibiotics may increase the serum concentration of QuiNINE.
TestosteroneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
TetracyclineMay increase the serum concentration of QuiNINE.
TheophyllineMay increase the serum concentration of Theophylline Derivatives.
ThioridazineCYP2D6 Inhibitors may increase the serum concentration of Thioridazine.
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
TolbutamideMay enhance the hypoglycemic effect of Hypoglycemic Agents.
TopotecanP-glycoprotein/ABCB1 Inhibitors may increase the serum concentration of Topotecan.
TramadolCYP2D6 Inhibitors (Moderate) may diminish the therapeutic effect of TraMADol. These CYP2D6 inhibitors may prevent the metabolic conversion of tramadol to its active metabolite that accounts for much of its opioid-like effects.
VecuroniumMay enhance the neuromuscular-blocking effect of Neuromuscular-Blocking Agents.
VildagliptinMay enhance the hypoglycemic effect of Hypoglycemic Agents.
Food Interactions
  • Take with food to reduce irritation.

Targets

1. Fe(II)-protoporphyrin IX

Kind: small molecule

Organism: Plasmodium falciparum

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details

References:

  1. 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. 2010 Sep 21. Pubmed
  2. Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. Pubmed

2. Platelet glycoprotein IX

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: other

Components

Name UniProt ID Details
Platelet glycoprotein IX P14770 Details

References:

  1. 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. Pubmed

3. Intermediate conductance calcium-activated potassium channel protein 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Intermediate conductance calcium-activated potassium channel protein 4 O15554 Details

References:

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

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.
  2. 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. Pubmed
  3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  5. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed

2. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

3. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.
  2. 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. Pubmed
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed

9. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. AR Scientific, Inc. Qualaquin® (quinine sulfate) capsules prescribing information. Philadelphia, PA; 2008 Jun.

10. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

Transporters

1. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed

2. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. Pubmed
  2. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed
  6. 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. Pubmed
  7. Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. Pubmed
  8. 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. Pubmed
  9. 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. Pubmed
  10. 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. Pubmed

3. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

References:

  1. 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. Pubmed

4. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. 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. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed

5. Solute carrier organic anion transporter family member 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. 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. Pubmed
  2. Kullak-Ublick, G.A. et al. Organic anion-transporting polypeptide B (OATP- B) and its functional comparison with three other OATPs of human liver. Gastroenterology 120, 525-533 (2001).Pubmed

6. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

References:

  1. 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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10