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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
6'-MethoxycinchonidineNot AvailableNot Available
ChininGermanINN
ChininumLatinINN
QuinineFrenchINN
Salts
Name/CAS Structure Properties
Quinine Hydrochloride
Thumb Not applicable DBSALT001044
Quinine sulfate
804-63-7
Thumb
  • InChI Key: RONWGALEIBILOG-VMJVVOMYSA-N
  • Monoisotopic Mass: 746.334935286
  • Average Mass: 746.912
DBSALT000531
Brand names
NameCompany
CinkonaIpca
JasoquinJayson
QSMLeben
QUALAQUINNot Available
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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassCinchona Alkaloids
SubclassNot Available
Direct parentCinchona Alkaloids
Alternative parentsHydroxyquinolines; Anisoles; Quinuclidines; Alkyl Aryl Ethers; Pyridines and Derivatives; Piperidines; Tertiary Amines; Secondary Alcohols; Polyamines
Substituentshydroxyquinoline; quinoline; quinuclidine; anisole; phenol ether; alkyl aryl ether; piperidine; benzene; pyridine; tertiary amine; secondary alcohol; polyamine; ether; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
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
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8931
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Ar holding co inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
LiquidOral
Solution / dropsOral
TabletOral
Prices
Unit descriptionCostUnit
Quinine sulfate powd ultrex25.86USDg
Apo-Quinine 300 mg Capsule0.39USDcapsule
Novo-Quinine 300 mg Capsule0.39USDcapsule
Apo-Quinine 200 mg Capsule0.25USDcapsule
Novo-Quinine 200 mg Capsule0.25USDcapsule
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 solubility3.34e-01 g/lALOGPS
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 area45.59ChemAxon
rotatable bond count4ChemAxon
refractivity94.69ChemAxon
polarizability35.96ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG CompoundC06526
BindingDB50198086
ChEBI15854
ChEMBLCHEMBL387326
Therapeutic Targets DatabaseDAP000491
PharmGKBPA451213
IUPHAR2510
Guide to Pharmacology2510
Drug Product Database2254522
RxListhttp://www.rxlist.com/cgi/generic3/quinine.htm
Drugs.comhttp://www.drugs.com/cdi/quinine.html
WikipediaQuinine
ATC CodesM09AA01P01BC01
AHFS Codes
  • 08:30.08
  • 92:02.00*
PDB EntriesNot Available
FDA labelshow(718 KB)
MSDSshow(72.1 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolQuinine, a moderate CYP2C9 inhibitor, may increase the serum concentration of acenocoumarol by decreasing its metabolism via CYP2C9.
AnisindioneQuinine may increase the anticoagulant effect of anisindione.
ArtemetherQuinine may increase the adverse effects of artemether. Combination therapy is contraindicated unless there are no other treatment options.
AstemizoleIncreased risk of cardiotoxicity and arrhythmias
AtomoxetineThe CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine
AtracuriumThe quinine derivative increases the effect of the muscle relaxant
DicoumarolQuinine may increase the anticoagulant effect of dicumarol.
DigitoxinQuinine/quinidine increases the effect of digoxin
DigoxinQuinine/quinidine increases the effect of digoxin
LumefantrineQuinine may increase the adverse effects of lumefantrine. Combination therapy is contraindicated unless there are no other treatment options.
MesoridazineIncreased risk of cardiotoxicity and arrhythmias
MetocurineThe quinine derivative increases the effect of the muscle relaxant
PancuroniumThe quinine derivative increases the effect of the muscle relaxant
SuccinylcholineThe quinine derivative increases the effect of the muscle relaxant
TamoxifenQuinine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
TamsulosinQuinine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Quinine is initiated, discontinued, or dose changed.
TelithromycinTelithromycin may reduce clearance of Quinine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Quinine if Telithromycin is initiated, discontinued or dose changed.
TerfenadineIncreased risk of cardiotoxicity and arrhythmias
ThioridazineIncreased risk of cardiotoxicity and arrhythmias
ThiothixeneMay cause additive QTc-prolonging effects. Concomitant therapy should be avoided.
ToremifeneMay cause additive QTc-prolonging effects. Concomitant therapy is contraindicated.
TramadolQuinine may decrease the effect of Tramadol by decreasing active metabolite production.
TrandolaprilMay cause additive hypotensive effects. Monitor for changes in blood pressure if Quinine is initiated, discontinued or dose changed.
TretinoinThe moderate CYP2C8 inhibitor, Quinine, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Quinine is initiated, discontinued to dose changed.
VecuroniumQuinine may increase the neuromuscular blocking action of Vecuronium. Risk of respiratory depression and apnea. Concurrent therapy should be avoided.
VoriconazoleAdditive QTc prolongation may occur. Concomitant therapy should be avoided.
VorinostatAdditive QTc prolongation may occur. Concomitant therapy should be avoided.
WarfarinQuinine, a moderate CYP2C9 inhibitor, may increase the serum concentration of S-warfarin by decreasing its metabolism via CYP2C9.
ZiprasidoneAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
ZuclopenthixolAdditive QTc-prolonging effects increases risk of cardiac arrhythmias. Concomitant therapy should be avoided.
Zuclopenthixol acetateAdditive QTc-prolonging effects increases risk of cardiac arrhythmias. Concomitant therapy should be avoided.
Zuclopenthixol decanoateAdditive QTc-prolonging effects increases risk of cardiac arrhythmias. Concomitant therapy should be avoided.
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 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.

2. 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

3. 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

4. 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

5. 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

6. 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.

7. 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.

8. 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

9. 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

10. 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

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