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Identification
NamePrimaquine
Accession NumberDB01087  (APRD00604)
TypeSmall Molecule
GroupsApproved
DescriptionAn aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)
Structure
Thumb
Synonyms
6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline
Neo-quipenyl
Primachin
Primachinum
Primaquin
Primaquina
Primaquinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Primaquinetablet26.3 mgoralSanofi Aventis Canada Inc1945-12-31Not applicableCanada
Primaquine Phosphatetablet, film coated15 mg/1oralSanofi Aventis U.S. Llc2011-04-15Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Primaquine Phosphatetablet26.3 mg/1oralPd Rx Pharmaceuticals, Inc.2010-01-01Not applicableUs
Primaquine Phosphatetablet, film coated26.3 mg/1oralAlvogen, Inc.2011-12-08Not applicableUs
Primaquine Phosphatetablet, film coated15 mg/1oralGolden State Medical Supply, Inc.2014-05-08Not applicableUs
Primaquine Phosphatetablet15 mg/1oralBayshore Pharmaceuticals, LLC2014-08-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Neo-QuipenylNot Available
PrimachinNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Primaquine phosphate
ThumbNot applicableDBSALT001188
Categories
UNIIMVR3634GX1
CAS number90-34-6
WeightAverage: 259.3467
Monoisotopic: 259.168462309
Chemical FormulaC15H21N3O
InChI KeyInChIKey=INDBQLZJXZLFIT-UHFFFAOYSA-N
InChI
InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
IUPAC Name
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
SMILES
COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyquinolines. These are compounds containing a quinoline moiety bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHydroxyquinolines
Direct ParentHydroxyquinolines
Alternative Parents
Substituents
  • Hydroxyquinoline
  • Methoxyaniline
  • Anisole
  • Secondary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Ether
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of malaria.
PharmacodynamicsPrimaquine is an antimalarial agent and is the essential co-drug with chloroquine in treating all cases of malaria. In the blood, malaria parasites break down a part of the red blood cells known as haemoglobin. When this happens haemoglobin is divided into two parts; haem and globin. Haem is toxic to the malaria parasite. To prevent it from being damaged, the malaria parasite produces an chemical which converts the toxic haem into a non-toxic product. Primaquine acts by interfering with a part of the parasite (mitochondria) that is responsible for supplying it with energy. Without energy the parasite dies. This stops the infection from continuing and allows the person to recover. Primaquine kills the intrahepatic form of Plasmodium vivax and Plasmodium ovale, and thereby prevents the development of the erythrocytic forms that are responsible for relapses (it also kills gametocytes). Primaquine is not used in the prevention of malaria, only in the treatment. It has insignificant activity against the asexual blood forms of the parasite and therefore it is always used in conjunction with a blood schizonticide and never as a single agent. Primaquine has gametocytocidal activity against all plasmodia, including P. falciparum.
Mechanism of actionPrimaquine's mechanism of action is not well understood. It may be acting by generating reactive oxygen species or by interfering with the electron transport in the parasite. Also, although its mechanism of action is unclear, primaquine may bind to and alter the properties of protozoal DNA.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life3.7-7.4 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Plasmodium
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9776
Blood Brain Barrier+0.9787
Caco-2 permeable-0.5622
P-glycoprotein substrateSubstrate0.8018
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.7681
Renal organic cation transporterInhibitor0.5501
CYP450 2C9 substrateNon-substrate0.8703
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5723
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.93
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5057
Ames testAMES toxic0.9106
CarcinogenicityNon-carcinogens0.9283
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4474 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7858
hERG inhibition (predictor II)Inhibitor0.8162
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral26.3 mg
Tabletoral15 mg/1
Tabletoral26.3 mg/1
Tablet, film coatedoral15 mg/1
Tablet, film coatedoral26.3 mg/1
Prices
Unit descriptionCostUnit
Primaquin phosphate powder18.2USD g
Primaquine 26.3 mg tablet1.51USD tablet
Primaquine Phosphate 15 mg Tablet0.43USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point177 °C at 2.00E-01 mm HgPhysProp
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0564 mg/mLALOGPS
logP2.76ALOGPS
logP1.64ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.17 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.51 m3·mol-1ChemAxon
Polarizability29.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. [PubMed:4027117 ]
  2. ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. [PubMed:13242948 ]
  3. Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. [PubMed:16968913 ]
  4. Cohen RJ, Sachs JR, Wicker DJ, Conrad ME: Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med. 1968 Nov 21;279(21):1127-31. [PubMed:5686480 ]
  5. Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. [PubMed:8828017 ]
External Links
ATC CodesP01BA03
AHFS Codes
  • 08:30.08
PDB Entries
FDA labelDownload (105 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Primaquine can be increased when it is combined with Abiraterone.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Primaquine.
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with Primaquine.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Primaquine.
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Primaquine.
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Primaquine.
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with Primaquine.
AlprenololThe metabolism of Alprenolol can be decreased when combined with Primaquine.
AmantadineAmantadine may increase the QTc-prolonging activities of Primaquine.
AmiodaronePrimaquine may increase the QTc-prolonging activities of Amiodarone.
AmiodaroneThe metabolism of Primaquine can be decreased when combined with Amiodarone.
AmitriptylineAmitriptyline may increase the QTc-prolonging activities of Primaquine.
AmoxapineAmoxapine may increase the QTc-prolonging activities of Primaquine.
AnagrelidePrimaquine may increase the QTc-prolonging activities of Anagrelide.
ApomorphineApomorphine may increase the QTc-prolonging activities of Primaquine.
AprepitantThe serum concentration of Primaquine can be increased when it is combined with Aprepitant.
ArformoterolArformoterol may increase the QTc-prolonging activities of Primaquine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Primaquine.
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Primaquine.
ArotinololThe metabolism of Arotinolol can be decreased when combined with Primaquine.
ArsenamideThe serum concentration of Arsenamide can be decreased when it is combined with Primaquine.
Arsenic trioxidePrimaquine may increase the QTc-prolonging activities of Arsenic trioxide.
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Primaquine.
ArtemetherPrimaquine may increase the QTc-prolonging activities of Artemether.
AsenapinePrimaquine may increase the QTc-prolonging activities of Asenapine.
AtazanavirAtazanavir may increase the QTc-prolonging activities of Primaquine.
AtenololThe metabolism of Atenolol can be decreased when combined with Primaquine.
AtomoxetineAtomoxetine may increase the QTc-prolonging activities of Primaquine.
AzithromycinPrimaquine may increase the QTc-prolonging activities of Azithromycin.
AzithromycinThe metabolism of Primaquine can be decreased when combined with Azithromycin.
BedaquilinePrimaquine may increase the QTc-prolonging activities of Bedaquiline.
BefunololThe metabolism of Befunolol can be decreased when combined with Primaquine.
BenzimidazoleThe serum concentration of Benzimidazole can be decreased when it is combined with Primaquine.
BetaxololThe metabolism of Betaxolol can be decreased when combined with Primaquine.
BevantololThe metabolism of Bevantolol can be decreased when combined with Primaquine.
BexaroteneThe serum concentration of Primaquine can be decreased when it is combined with Bexarotene.
BisoprololThe metabolism of Bisoprolol can be decreased when combined with Primaquine.
BithionolThe serum concentration of Bithionol can be decreased when it is combined with Primaquine.
BoceprevirThe metabolism of Primaquine can be decreased when combined with Boceprevir.
BopindololThe metabolism of Bopindolol can be decreased when combined with Primaquine.
BortezomibBortezomib may increase the QTc-prolonging activities of Primaquine.
BosentanThe serum concentration of Primaquine can be decreased when it is combined with Bosentan.
BufuralolThe metabolism of Bufuralol can be decreased when combined with Primaquine.
BunamidineThe serum concentration of Bunamidine can be decreased when it is combined with Primaquine.
BupranololThe metabolism of Bupranolol can be decreased when combined with Primaquine.
BuserelinBuserelin may increase the QTc-prolonging activities of Primaquine.
CaffeineThe metabolism of Primaquine can be decreased when combined with Caffeine.
CambendazoleThe serum concentration of Cambendazole can be decreased when it is combined with Primaquine.
CarbamazepineThe metabolism of Primaquine can be increased when combined with Carbamazepine.
CarteololThe metabolism of Carteolol can be decreased when combined with Primaquine.
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Primaquine.
CeliprololThe metabolism of Celiprolol can be decreased when combined with Primaquine.
CeritinibThe serum concentration of Primaquine can be increased when it is combined with Ceritinib.
CeritinibPrimaquine may increase the QTc-prolonging activities of Ceritinib.
ChloroquineThe serum concentration of Chloroquine can be decreased when it is combined with Primaquine.
ChloroquineChloroquine may increase the QTc-prolonging activities of Primaquine.
ChloroxylenolThe serum concentration of Chloroxylenol can be decreased when it is combined with Primaquine.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Primaquine.
ChlorpromazineChlorpromazine may increase the QTc-prolonging activities of Primaquine.
CiprofloxacinCiprofloxacin may increase the QTc-prolonging activities of Primaquine.
CisapridePrimaquine may increase the QTc-prolonging activities of Cisapride.
CitalopramPrimaquine may increase the QTc-prolonging activities of Citalopram.
CitalopramThe metabolism of Primaquine can be decreased when combined with Citalopram.
ClarithromycinPrimaquine may increase the QTc-prolonging activities of Clarithromycin.
ClemastineThe metabolism of Primaquine can be decreased when combined with Clemastine.
ClomipramineClomipramine may increase the QTc-prolonging activities of Primaquine.
ClorsulonThe serum concentration of Clorsulon can be decreased when it is combined with Primaquine.
ClotrimazoleThe metabolism of Primaquine can be decreased when combined with Clotrimazole.
ClozapineClozapine may increase the QTc-prolonging activities of Primaquine.
CobicistatThe metabolism of Primaquine can be decreased when combined with Cobicistat.
ConivaptanThe serum concentration of Primaquine can be increased when it is combined with Conivaptan.
CoumaphosThe serum concentration of Coumaphos can be decreased when it is combined with Primaquine.
CrizotinibPrimaquine may increase the QTc-prolonging activities of Crizotinib.
CrizotinibThe metabolism of Primaquine can be decreased when combined with Crizotinib.
CyclosporineThe metabolism of Primaquine can be decreased when combined with Cyclosporine.
Cyproterone acetateThe serum concentration of Primaquine can be decreased when it is combined with Cyproterone acetate.
DabrafenibDabrafenib may increase the QTc-prolonging activities of Primaquine.
DapsoneThe risk or severity of adverse effects can be increased when Primaquine is combined with Dapsone.
DarunavirThe metabolism of Primaquine can be decreased when combined with Darunavir.
DasatinibThe serum concentration of Primaquine can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Primaquine can be decreased when it is combined with Deferasirox.
DegarelixDegarelix may increase the QTc-prolonging activities of Primaquine.
DelavirdineThe metabolism of Primaquine can be decreased when combined with Delavirdine.
DesfluraneDesflurane may increase the QTc-prolonging activities of Primaquine.
DesipramineDesipramine may increase the QTc-prolonging activities of Primaquine.
DeslanosideThe serum concentration of Deslanoside can be increased when it is combined with Primaquine.
DexamethasoneThe serum concentration of Primaquine can be decreased when it is combined with Dexamethasone.
DichlorvosThe serum concentration of Dichlorvos can be decreased when it is combined with Primaquine.
DiethylcarbamazineThe serum concentration of Diethylcarbamazine can be decreased when it is combined with Primaquine.
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Primaquine.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Primaquine.
DihydroergotamineThe metabolism of Primaquine can be decreased when combined with Dihydroergotamine.
DiltiazemThe metabolism of Primaquine can be decreased when combined with Diltiazem.
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Primaquine.
DisopyramidePrimaquine may increase the QTc-prolonging activities of Disopyramide.
DithiazanineThe serum concentration of Dithiazanine can be decreased when it is combined with Primaquine.
DofetilidePrimaquine may increase the QTc-prolonging activities of Dofetilide.
DolasetronDolasetron may increase the QTc-prolonging activities of Primaquine.
DomperidonePrimaquine may increase the QTc-prolonging activities of Domperidone.
DoramectinThe serum concentration of Doramectin can be decreased when it is combined with Primaquine.
DoxepinDoxepin may increase the QTc-prolonging activities of Primaquine.
DoxycyclineThe metabolism of Primaquine can be decreased when combined with Doxycycline.
DronedaronePrimaquine may increase the QTc-prolonging activities of Dronedarone.
DronedaroneThe metabolism of Primaquine can be decreased when combined with Dronedarone.
DroperidolDroperidol may increase the QTc-prolonging activities of Primaquine.
EfavirenzThe serum concentration of Primaquine can be decreased when it is combined with Efavirenz.
EliglustatPrimaquine may increase the QTc-prolonging activities of Eliglustat.
EnzalutamideThe serum concentration of Primaquine can be decreased when it is combined with Enzalutamide.
EprinomectinThe serum concentration of Eprinomectin can be decreased when it is combined with Primaquine.
EribulinEribulin may increase the QTc-prolonging activities of Primaquine.
ErythromycinPrimaquine may increase the QTc-prolonging activities of Erythromycin.
ErythromycinThe metabolism of Primaquine can be decreased when combined with Erythromycin.
EscitalopramPrimaquine may increase the QTc-prolonging activities of Escitalopram.
Eslicarbazepine acetateThe serum concentration of Primaquine can be decreased when it is combined with Eslicarbazepine acetate.
EsmololThe metabolism of Esmolol can be decreased when combined with Primaquine.
EtravirineThe serum concentration of Primaquine can be decreased when it is combined with Etravirine.
EzogabineEzogabine may increase the QTc-prolonging activities of Primaquine.
FamotidineFamotidine may increase the QTc-prolonging activities of Primaquine.
FebantelThe serum concentration of Febantel can be decreased when it is combined with Primaquine.
FelbamateFelbamate may increase the QTc-prolonging activities of Primaquine.
FenbendazoleThe serum concentration of Fenbendazole can be decreased when it is combined with Primaquine.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Primaquine.
FingolimodFingolimod may increase the QTc-prolonging activities of Primaquine.
FlecainidePrimaquine may increase the QTc-prolonging activities of Flecainide.
FlubendazoleThe serum concentration of Flubendazole can be decreased when it is combined with Primaquine.
FluconazoleFluconazole may increase the QTc-prolonging activities of Primaquine.
FluoxetinePrimaquine may increase the QTc-prolonging activities of Fluoxetine.
FlupentixolPrimaquine may increase the QTc-prolonging activities of Flupentixol.
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Primaquine.
FluvoxamineThe metabolism of Primaquine can be decreased when combined with Fluvoxamine.
FormoterolFormoterol may increase the QTc-prolonging activities of Primaquine.
FosamprenavirThe metabolism of Primaquine can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Primaquine can be increased when it is combined with Fosaprepitant.
FoscarnetFoscarnet may increase the QTc-prolonging activities of Primaquine.
FosphenytoinThe metabolism of Primaquine can be increased when combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Primaquine can be increased when it is combined with Fusidic Acid.
Gadobenic acidGadobenic acid may increase the QTc-prolonging activities of Primaquine.
GalantamineGalantamine may increase the QTc-prolonging activities of Primaquine.
GemifloxacinPrimaquine may increase the QTc-prolonging activities of Gemifloxacin.
GoserelinGoserelin may increase the QTc-prolonging activities of Primaquine.
GranisetronGranisetron may increase the QTc-prolonging activities of Primaquine.
HaloperidolHaloperidol may increase the QTc-prolonging activities of Primaquine.
HexylresorcinolThe serum concentration of Hexylresorcinol can be decreased when it is combined with Primaquine.
HistrelinHistrelin may increase the QTc-prolonging activities of Primaquine.
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Primaquine.
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Primaquine.
IbandronateIbandronate may increase the QTc-prolonging activities of Primaquine.
IbutilidePrimaquine may increase the QTc-prolonging activities of Ibutilide.
IdelalisibThe serum concentration of Primaquine can be increased when it is combined with Idelalisib.
IloperidonePrimaquine may increase the QTc-prolonging activities of Iloperidone.
ImatinibThe metabolism of Primaquine can be decreased when combined with Imatinib.
ImipramineImipramine may increase the QTc-prolonging activities of Primaquine.
IndacaterolIndacaterol may increase the QTc-prolonging activities of Primaquine.
IndapamideIndapamide may increase the QTc-prolonging activities of Primaquine.
IndenololThe metabolism of Indenolol can be decreased when combined with Primaquine.
IndinavirThe metabolism of Primaquine can be decreased when combined with Indinavir.
IsavuconazoniumThe metabolism of Primaquine can be decreased when combined with Isavuconazonium.
IsofluraneIsoflurane may increase the QTc-prolonging activities of Primaquine.
IsradipineIsradipine may increase the QTc-prolonging activities of Primaquine.
ItraconazoleItraconazole may increase the QTc-prolonging activities of Primaquine.
IvabradineIvabradine may increase the QTc-prolonging activities of Primaquine.
IvacaftorThe serum concentration of Primaquine can be increased when it is combined with Ivacaftor.
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Primaquine.
KetoconazoleKetoconazole may increase the QTc-prolonging activities of Primaquine.
LabetalolThe metabolism of Labetalol can be decreased when combined with Primaquine.
LapatinibLapatinib may increase the QTc-prolonging activities of Primaquine.
LenvatinibPrimaquine may increase the QTc-prolonging activities of Lenvatinib.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Primaquine.
LevamisoleThe serum concentration of Levamisole can be decreased when it is combined with Primaquine.
LevobunololThe metabolism of Levobunolol can be decreased when combined with Primaquine.
LevofloxacinPrimaquine may increase the QTc-prolonging activities of Levofloxacin.
LidocaineThe metabolism of Primaquine can be decreased when combined with Lidocaine.
LithiumLithium may increase the QTc-prolonging activities of Primaquine.
LopinavirPrimaquine may increase the QTc-prolonging activities of Lopinavir.
LopinavirThe metabolism of Primaquine can be decreased when combined with Lopinavir.
LovastatinThe metabolism of Primaquine can be decreased when combined with Lovastatin.
LucanthoneThe serum concentration of Lucanthone can be decreased when it is combined with Primaquine.
LuliconazoleThe serum concentration of Primaquine can be increased when it is combined with Luliconazole.
LumefantrineThe risk or severity of adverse effects can be increased when Primaquine is combined with Lumefantrine.
MaprotilineMaprotiline may increase the QTc-prolonging activities of Primaquine.
MebendazoleThe serum concentration of Mebendazole can be decreased when it is combined with Primaquine.
MefloquineThe risk or severity of adverse effects can be increased when Primaquine is combined with Mefloquine.
MefloquineMefloquine may increase the QTc-prolonging activities of Primaquine.
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with Primaquine.
MethadoneMethadone may increase the QTc-prolonging activities of Primaquine.
MethotrimeprazineThe serum concentration of Methotrimeprazine can be increased when it is combined with Primaquine.
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Primaquine.
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with Primaquine.
MetipranololThe metabolism of Metipranolol can be decreased when combined with Primaquine.
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Primaquine.
MetoprololThe metabolism of Metoprolol can be decreased when combined with Primaquine.
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Primaquine.
MexiletineThe metabolism of Primaquine can be decreased when combined with Mexiletine.
MifepristoneMifepristone may increase the QTc-prolonging activities of Primaquine.
Milbemycin oximeThe serum concentration of Milbemycin oxime can be decreased when it is combined with Primaquine.
MirabegronMirabegron may increase the QTc-prolonging activities of Primaquine.
MirtazapineMirtazapine may increase the QTc-prolonging activities of Primaquine.
MitotaneThe serum concentration of Primaquine can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Primaquine can be decreased when it is combined with Modafinil.
MoexiprilMoexipril may increase the QTc-prolonging activities of Primaquine.
MorantelThe serum concentration of Morantel can be decreased when it is combined with Primaquine.
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Primaquine.
MoxidectinThe serum concentration of Moxidectin can be decreased when it is combined with Primaquine.
MoxifloxacinMoxifloxacin may increase the QTc-prolonging activities of Primaquine.
NadololThe metabolism of Nadolol can be decreased when combined with Primaquine.
NafcillinThe serum concentration of Primaquine can be decreased when it is combined with Nafcillin.
NefazodoneThe metabolism of Primaquine can be decreased when combined with Nefazodone.
NelfinavirNelfinavir may increase the QTc-prolonging activities of Primaquine.
NetupitantThe serum concentration of Primaquine can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Primaquine can be decreased when combined with Nevirapine.
NicardipineNicardipine may increase the QTc-prolonging activities of Primaquine.
NiclosamideThe serum concentration of Niclosamide can be decreased when it is combined with Primaquine.
NilotinibPrimaquine may increase the QTc-prolonging activities of Nilotinib.
NilotinibThe metabolism of Primaquine can be decreased when combined with Nilotinib.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Primaquine.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Primaquine.
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Primaquine.
NortriptylineNortriptyline may increase the QTc-prolonging activities of Primaquine.
OctreotideOctreotide may increase the QTc-prolonging activities of Primaquine.
OfloxacinPrimaquine may increase the QTc-prolonging activities of Ofloxacin.
OlanzapineOlanzapine may increase the QTc-prolonging activities of Primaquine.
OlaparibThe metabolism of Primaquine can be decreased when combined with Olaparib.
OlodaterolOlodaterol may increase the QTc-prolonging activities of Primaquine.
OndansetronOndansetron may increase the QTc-prolonging activities of Primaquine.
OsimertinibThe serum concentration of Primaquine can be increased when it is combined with Osimertinib.
OuabainThe serum concentration of Ouabain can be increased when it is combined with Primaquine.
OxamniquineThe serum concentration of Oxamniquine can be decreased when it is combined with Primaquine.
OxfendazoleThe serum concentration of Oxfendazole can be decreased when it is combined with Primaquine.
OxibendazoleThe serum concentration of Oxibendazole can be decreased when it is combined with Primaquine.
OxprenololThe metabolism of Oxprenolol can be decreased when combined with Primaquine.
OxytocinOxytocin may increase the QTc-prolonging activities of Primaquine.
PalbociclibThe serum concentration of Primaquine can be increased when it is combined with Palbociclib.
PaliperidonePrimaquine may increase the QTc-prolonging activities of Paliperidone.
PanobinostatPrimaquine may increase the QTc-prolonging activities of Panobinostat.
ParoxetineParoxetine may increase the QTc-prolonging activities of Primaquine.
PasireotidePasireotide may increase the QTc-prolonging activities of Primaquine.
PazopanibPrimaquine may increase the QTc-prolonging activities of Pazopanib.
Peginterferon alfa-2bThe serum concentration of Primaquine can be increased when it is combined with Peginterferon alfa-2b.
PenbutololThe metabolism of Penbutolol can be decreased when combined with Primaquine.
PentamidinePentamidine may increase the QTc-prolonging activities of Primaquine.
PentobarbitalThe metabolism of Primaquine can be increased when combined with Pentobarbital.
PerflutrenPerflutren may increase the QTc-prolonging activities of Primaquine.
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Primaquine.
PhenobarbitalThe metabolism of Primaquine can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Primaquine can be increased when combined with Phenytoin.
PimozidePrimaquine may increase the QTc-prolonging activities of Pimozide.
PindololThe metabolism of Pindolol can be decreased when combined with Primaquine.
PiperazineThe serum concentration of Piperazine can be decreased when it is combined with Primaquine.
PosaconazolePosaconazole may increase the QTc-prolonging activities of Primaquine.
PractololThe metabolism of Practolol can be decreased when combined with Primaquine.
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Primaquine.
PrilocaineThe risk or severity of adverse effects can be increased when Primaquine is combined with Prilocaine.
PrimidoneThe metabolism of Primaquine can be increased when combined with Primidone.
ProcainamidePrimaquine may increase the QTc-prolonging activities of Procainamide.
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with Primaquine.
PromazineThe serum concentration of Promazine can be increased when it is combined with Primaquine.
PromazinePromazine may increase the QTc-prolonging activities of Primaquine.
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Primaquine.
PromethazinePromethazine may increase the QTc-prolonging activities of Primaquine.
PropafenonePrimaquine may increase the QTc-prolonging activities of Propafenone.
PropofolPropofol may increase the QTc-prolonging activities of Primaquine.
PropranololThe metabolism of Propranolol can be decreased when combined with Primaquine.
ProtriptylineProtriptyline may increase the QTc-prolonging activities of Primaquine.
PyrantelThe serum concentration of Pyrantel can be decreased when it is combined with Primaquine.
PyrviniumThe serum concentration of Pyrvinium can be decreased when it is combined with Primaquine.
QuetiapinePrimaquine may increase the QTc-prolonging activities of Quetiapine.
QuinacrineThe serum concentration of Quinacrine can be decreased when it is combined with Primaquine.
QuinidinePrimaquine may increase the QTc-prolonging activities of Quinidine.
QuininePrimaquine may increase the QTc-prolonging activities of Quinine.
RanolazineRanolazine may increase the QTc-prolonging activities of Primaquine.
RifabutinThe metabolism of Primaquine can be increased when combined with Rifabutin.
RifampicinThe metabolism of Primaquine can be increased when combined with Rifampicin.
RifapentineThe metabolism of Primaquine can be increased when combined with Rifapentine.
RilpivirineRilpivirine may increase the QTc-prolonging activities of Primaquine.
RisperidoneRisperidone may increase the QTc-prolonging activities of Primaquine.
RitonavirRitonavir may increase the QTc-prolonging activities of Primaquine.
RopiniroleThe metabolism of Primaquine can be decreased when combined with Ropinirole.
SalbutamolSalbutamol may increase the QTc-prolonging activities of Primaquine.
SalmeterolSalmeterol may increase the QTc-prolonging activities of Primaquine.
SaquinavirPrimaquine may increase the QTc-prolonging activities of Saquinavir.
SertralineSertraline may increase the QTc-prolonging activities of Primaquine.
SevofluraneSevoflurane may increase the QTc-prolonging activities of Primaquine.
SildenafilThe metabolism of Primaquine can be decreased when combined with Sildenafil.
SiltuximabThe serum concentration of Primaquine can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Primaquine can be increased when it is combined with Simeprevir.
Sodium NitriteThe risk or severity of adverse effects can be increased when Primaquine is combined with Sodium Nitrite.
Sodium stibogluconateThe serum concentration of Sodium stibogluconate can be decreased when it is combined with Primaquine.
SolifenacinSolifenacin may increase the QTc-prolonging activities of Primaquine.
SorafenibSorafenib may increase the QTc-prolonging activities of Primaquine.
SotalolPrimaquine may increase the QTc-prolonging activities of Sotalol.
St. John's WortThe serum concentration of Primaquine can be decreased when it is combined with St. John&#39;s Wort.
StiripentolThe serum concentration of Primaquine can be increased when it is combined with Stiripentol.
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Primaquine.
SulfisoxazolePrimaquine may increase the QTc-prolonging activities of Sulfisoxazole.
SulfisoxazoleThe metabolism of Primaquine can be decreased when combined with Sulfisoxazole.
SunitinibSunitinib may increase the QTc-prolonging activities of Primaquine.
SuraminThe serum concentration of Suramin can be decreased when it is combined with Primaquine.
TamoxifenTamoxifen may increase the QTc-prolonging activities of Primaquine.
TelaprevirThe metabolism of Primaquine can be decreased when combined with Telaprevir.
TelavancinPrimaquine may increase the QTc-prolonging activities of Telavancin.
TelithromycinTelithromycin may increase the QTc-prolonging activities of Primaquine.
TenofovirThe metabolism of Primaquine can be decreased when combined with Tenofovir.
TerbutalineTerbutaline may increase the QTc-prolonging activities of Primaquine.
TeriflunomideThe serum concentration of Primaquine can be decreased when it is combined with Teriflunomide.
TetrabenazinePrimaquine may increase the QTc-prolonging activities of Tetrabenazine.
TheophyllineThe metabolism of Primaquine can be decreased when combined with Theophylline.
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Primaquine.
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with Primaquine.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Primaquine.
ThiothixeneThiothixene may increase the QTc-prolonging activities of Primaquine.
TiclopidineThe metabolism of Primaquine can be decreased when combined with Ticlopidine.
TimololThe metabolism of Timolol can be decreased when combined with Primaquine.
TizanidineTizanidine may increase the QTc-prolonging activities of Primaquine.
TocilizumabThe serum concentration of Primaquine can be decreased when it is combined with Tocilizumab.
TolterodineTolterodine may increase the QTc-prolonging activities of Primaquine.
ToremifenePrimaquine may increase the QTc-prolonging activities of Toremifene.
TrazodoneTrazodone may increase the QTc-prolonging activities of Primaquine.
TreprostinilTreprostinil may increase the QTc-prolonging activities of Primaquine.
TrichlorfonThe serum concentration of Trichlorfon can be decreased when it is combined with Primaquine.
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with Primaquine.
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with Primaquine.
TrimethoprimTrimethoprim may increase the QTc-prolonging activities of Primaquine.
TrimipramineTrimipramine may increase the QTc-prolonging activities of Primaquine.
TriptorelinTriptorelin may increase the QTc-prolonging activities of Primaquine.
VandetanibPrimaquine may increase the QTc-prolonging activities of Vandetanib.
VardenafilVardenafil may increase the QTc-prolonging activities of Primaquine.
VemurafenibThe serum concentration of Primaquine can be increased when it is combined with Vemurafenib.
VemurafenibPrimaquine may increase the QTc-prolonging activities of Vemurafenib.
VenlafaxineVenlafaxine may increase the QTc-prolonging activities of Primaquine.
VerapamilThe metabolism of Primaquine can be decreased when combined with Verapamil.
VilanterolVilanterol may increase the QTc-prolonging activities of Primaquine.
VoriconazoleVoriconazole may increase the QTc-prolonging activities of Primaquine.
VorinostatVorinostat may increase the QTc-prolonging activities of Primaquine.
ZiprasidonePrimaquine may increase the QTc-prolonging activities of Ziprasidone.
ZiprasidoneThe metabolism of Primaquine can be decreased when combined with Ziprasidone.
ZuclopenthixolPrimaquine may increase the QTc-prolonging activities of Zuclopenthixol.
Food Interactions
  • Take with food to decrease dyspepsia.

Targets

1. Fe(II)-protoporphyrin IX
Kind
Small molecule
Organism
Plasmodium falciparum
Pharmacological action
yes
Actions
antagonist
References
  1. Dorn A, Vippagunta SR, Matile H, Jaquet C, Vennerstrom JL, Ridley RG: An assessment of drug-haematin binding as a mechanism for inhibition of haematin polymerisation by quinoline antimalarials. Biochem Pharmacol. 1998 Mar 15;55(6):727-36. [PubMed:9586944 ]
  2. Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. [PubMed:14967191 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
other/unknown
General Function:
Structural molecule activity
Specific Function:
Blocks interferon-dependent interphase and stimulates DNA synthesis in cells. Involved in the translational regulation of the human papillomavirus type 16 E7 mRNA (HPV16 E7).
Gene Name:
KRT7
Uniprot ID:
P08729
Molecular Weight:
51385.11 Da
References
  1. Heard CM, Monk BV, Modley AJ: Binding of primaquine to epidermal membranes and keratin. Int J Pharm. 2003 May 12;257(1-2):237-44. [PubMed:12711178 ]
  2. Basso LG, Rodrigues RZ, Naal RM, Costa-Filho AJ: Effects of the antimalarial drug primaquine on the dynamic structure of lipid model membranes. Biochim Biophys Acta. 2011 Jan;1808(1):55-64. doi: 10.1016/j.bbamem.2010.08.009. Epub 2010 Aug 14. [PubMed:20713019 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Nadph dehydrogenase (quinone) activity
Specific Function:
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
Molecular Weight:
25918.4 Da
References
  1. Graves PR, Kwiek JJ, Fadden P, Ray R, Hardeman K, Coley AM, Foley M, Haystead TA: Discovery of novel targets of quinoline drugs in the human purine binding proteome. Mol Pharmacol. 2002 Dec;62(6):1364-72. [PubMed:12435804 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
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 unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23