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Identification
NameAmodiaquine
Accession NumberDB00613  (APRD00796)
TypeSmall Molecule
GroupsApproved
DescriptionA 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]
Structure
Thumb
Synonyms
Amodiaquina
Amodiaquine
Amodiaquinum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BasoquinNot Available
CamoquinParke Davis
FlavoquineNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Amodiaquine Hydrochloride
Thumb
  • InChI Key: ROEBJVHPINPMKL-UHFFFAOYSA-N
  • Monoisotopic Mass: 427.098495526
  • Average Mass: 428.783
DBSALT000647
Categories
UNII220236ED28
CAS number86-42-0
WeightAverage: 355.861
Monoisotopic: 355.145140048
Chemical FormulaC20H22ClN3O
InChI KeyInChIKey=OVCDSSHSILBFBN-UHFFFAOYSA-N
InChI
InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
IUPAC Name
4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
SMILES
CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct ParentAminoquinolines and derivatives
Alternative Parents
Substituents
  • Chloroquinoline
  • Aminoquinoline
  • Substituted aniline
  • Phenylmethylamine
  • Benzylamine
  • Aminophenol
  • Aralkylamine
  • Phenol
  • Aniline
  • Aminopyridine
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Secondary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment of acute malarial attacks in non-immune subjects.
PharmacodynamicsAmodiaquine, a 4-aminoquinoline similar to chloroquine in structure and activity, has been used as both an antimalarial and an anti-inflammatory agent for more than 40 years. Amodiaquine is at least as effective as chloroquine, and is effective against some chloroquine-resistant strains, although resistance to amodiaquine has been reported. The mode of action of amodiaquine has not yet been determined. 4-Aminoquinolines depress cardiac muscle, impair cardiac conductivity, and produce vasodilatation with resultant hypotension. They depress respiration and cause diplopia, dizziness and nausea.
Mechanism of actionThe mechanism of plasmodicidal action of amodiaquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. The drug binds the free heme preventing the parasite from converting it to a form less toxic. This drug-heme complex is toxic and disrupts membrane function.
Related Articles
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic biotransformation to desethylamodiaquine (the principal biologically active metabolite) is the predominant route of amodiaquine clearance with such a considerable first pass effect that very little orally administered amodiaquine escapes untransformed into the systemic circulation.

SubstrateEnzymesProduct
Amodiaquine
desethylamodiaquineDetails
Route of eliminationNot Available
Half life5.2 ± 1.7 (range 0.4 to 5.5) minutes
ClearanceNot Available
ToxicityLD50 (mouse, intraperitoneal) 225 mg/kg, LD50 (mouse, oral) 550 mg/kg. Symptoms of overdose include headache, drowsiness, visual disturbances, vomiting, hypokalaemia, cardiovascular collapse and cardiac and respiratory arrest. Hypotension, if not treated, may progress rapidly to shock. Electrocardiograms (ECG) may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, broadening of the QRS complex, and progressive bradycardia leading to ventricular fibrillation and/or arrest.
Affected organisms
  • Plasmodium
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9818
Blood Brain Barrier+0.7306
Caco-2 permeable+0.5966
P-glycoprotein substrateSubstrate0.7168
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterNon-inhibitor0.5943
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.5136
CYP450 1A2 substrateInhibitor0.8347
CYP450 2C9 inhibitorNon-inhibitor0.5836
CYP450 2D6 inhibitorInhibitor0.7582
CYP450 2C19 inhibitorInhibitor0.5416
CYP450 3A4 inhibitorNon-inhibitor0.7203
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9202
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8452
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4801 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7619
hERG inhibition (predictor II)Inhibitor0.7306
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Parke davis div warner lambert co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point206-208Burckhalter, J.H., Jones, E.M., Rawlins, A.L., Tendick, F.H, and 2,474,821; July 5,1949; assigned to Parke, Davis & Co.
logP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0088 mg/mLALOGPS
logP4.83ALOGPS
logP3.76ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.29 m3·mol-1ChemAxon
Polarizability38.89 Å3ChemAxon
Number of Rings3ChemAxon
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 Reference

Burckhalter, J.H., Jones, E.M., Rawlins, A.L., Tendick, F.H, and 2,474,821; July 5,1949; assigned to Parke, Davis & Co.

General References
  1. Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. [PubMed:7618347 ]
  2. Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. [PubMed:1567466 ]
External Links
ATC CodesP01BA06P01BF03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Amodiaquine can be increased when it is combined with Abiraterone.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Amodiaquine.
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with Amodiaquine.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Amodiaquine.
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Amodiaquine.
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with Amodiaquine.
AlprenololThe metabolism of Alprenolol can be decreased when combined with Amodiaquine.
AmitriptylineThe serum concentration of Amodiaquine can be increased when it is combined with Amitriptyline.
AmlodipineThe serum concentration of Amodiaquine can be increased when it is combined with Amlodipine.
ArotinololThe metabolism of Arotinolol can be decreased when combined with Amodiaquine.
ArsenamideThe serum concentration of Arsenamide can be decreased when it is combined with Amodiaquine.
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Amodiaquine.
ArtemetherThe serum concentration of Artemether can be decreased when it is combined with Amodiaquine.
AtenololThe metabolism of Atenolol can be decreased when combined with Amodiaquine.
AtorvastatinThe serum concentration of Amodiaquine can be increased when it is combined with Atorvastatin.
BefunololThe metabolism of Befunolol can be decreased when combined with Amodiaquine.
BenzimidazoleThe serum concentration of Benzimidazole can be decreased when it is combined with Amodiaquine.
BetaxololThe metabolism of Betaxolol can be decreased when combined with Amodiaquine.
BevantololThe metabolism of Bevantolol can be decreased when combined with Amodiaquine.
BezafibrateThe serum concentration of Amodiaquine can be increased when it is combined with Bezafibrate.
BisoprololThe metabolism of Bisoprolol can be decreased when combined with Amodiaquine.
BithionolThe serum concentration of Bithionol can be decreased when it is combined with Amodiaquine.
BopindololThe metabolism of Bopindolol can be decreased when combined with Amodiaquine.
BufuralolThe metabolism of Bufuralol can be decreased when combined with Amodiaquine.
BunamidineThe serum concentration of Bunamidine can be decreased when it is combined with Amodiaquine.
BupranololThe metabolism of Bupranolol can be decreased when combined with Amodiaquine.
CambendazoleThe serum concentration of Cambendazole can be decreased when it is combined with Amodiaquine.
CandesartanThe serum concentration of Amodiaquine can be increased when it is combined with Candesartan.
CarbamazepineThe metabolism of Amodiaquine can be increased when combined with Carbamazepine.
CarteololThe metabolism of Carteolol can be decreased when combined with Amodiaquine.
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Amodiaquine.
CelecoxibThe metabolism of Amodiaquine can be decreased when combined with Celecoxib.
CeliprololThe metabolism of Celiprolol can be decreased when combined with Amodiaquine.
CerivastatinThe serum concentration of Amodiaquine can be increased when it is combined with Cerivastatin.
ChloramphenicolThe serum concentration of Amodiaquine can be increased when it is combined with Chloramphenicol.
ChloroquineThe serum concentration of Chloroquine can be decreased when it is combined with Amodiaquine.
ChloroxylenolThe serum concentration of Chloroxylenol can be decreased when it is combined with Amodiaquine.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Amodiaquine.
CholecalciferolThe serum concentration of Amodiaquine can be increased when it is combined with Cholecalciferol.
CimetidineThe serum concentration of Amodiaquine can be increased when it is combined with Cimetidine.
ClopidogrelThe serum concentration of Amodiaquine can be increased when it is combined with Clopidogrel.
ClorsulonThe serum concentration of Clorsulon can be decreased when it is combined with Amodiaquine.
ClotrimazoleThe serum concentration of Amodiaquine can be increased when it is combined with Clotrimazole.
CocaineThe serum concentration of Amodiaquine can be increased when it is combined with Cocaine.
ColchicineThe serum concentration of Amodiaquine can be increased when it is combined with Colchicine.
CoumaphosThe serum concentration of Coumaphos can be decreased when it is combined with Amodiaquine.
CyclosporineThe serum concentration of Amodiaquine can be increased when it is combined with Cyclosporine.
DabrafenibThe serum concentration of Amodiaquine can be decreased when it is combined with Dabrafenib.
DapsoneThe risk or severity of adverse effects can be increased when Amodiaquine is combined with Dapsone.
DeferasiroxThe serum concentration of Amodiaquine can be increased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Amodiaquine can be increased when it is combined with Delavirdine.
DeslanosideThe serum concentration of Deslanoside can be increased when it is combined with Amodiaquine.
DextropropoxypheneThe serum concentration of Amodiaquine can be increased when it is combined with Dextropropoxyphene.
DichlorvosThe serum concentration of Dichlorvos can be decreased when it is combined with Amodiaquine.
DiethylcarbamazineThe serum concentration of Diethylcarbamazine can be decreased when it is combined with Amodiaquine.
DiethylstilbestrolThe serum concentration of Amodiaquine can be increased when it is combined with Diethylstilbestrol.
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Amodiaquine.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Amodiaquine.
DithiazanineThe serum concentration of Dithiazanine can be decreased when it is combined with Amodiaquine.
DoramectinThe serum concentration of Doramectin can be decreased when it is combined with Amodiaquine.
EfavirenzEfavirenz may increase the hepatotoxic activities of Amodiaquine.
EltrombopagThe serum concentration of Amodiaquine can be increased when it is combined with Eltrombopag.
EnzalutamideThe serum concentration of Amodiaquine can be increased when it is combined with Enzalutamide.
EprinomectinThe serum concentration of Eprinomectin can be decreased when it is combined with Amodiaquine.
ErlotinibThe serum concentration of Amodiaquine can be increased when it is combined with Erlotinib.
EsmololThe metabolism of Esmolol can be decreased when combined with Amodiaquine.
Ethinyl EstradiolThe serum concentration of Amodiaquine can be increased when it is combined with Ethinyl Estradiol.
EtoposideThe serum concentration of Amodiaquine can be increased when it is combined with Etoposide.
FebantelThe serum concentration of Febantel can be decreased when it is combined with Amodiaquine.
FelodipineThe serum concentration of Amodiaquine can be increased when it is combined with Felodipine.
FenbendazoleThe serum concentration of Fenbendazole can be decreased when it is combined with Amodiaquine.
FenofibrateThe serum concentration of Amodiaquine can be increased when it is combined with Fenofibrate.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Amodiaquine.
FlubendazoleThe serum concentration of Flubendazole can be decreased when it is combined with Amodiaquine.
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Amodiaquine.
FluvastatinThe serum concentration of Amodiaquine can be increased when it is combined with Fluvastatin.
FosphenytoinThe metabolism of Amodiaquine can be increased when combined with Fosphenytoin.
GemfibrozilThe serum concentration of Amodiaquine can be increased when it is combined with Gemfibrozil.
HexylresorcinolThe serum concentration of Hexylresorcinol can be decreased when it is combined with Amodiaquine.
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Amodiaquine.
IdelalisibThe serum concentration of Amodiaquine can be increased when it is combined with Idelalisib.
IndenololThe metabolism of Indenolol can be decreased when combined with Amodiaquine.
IrbesartanThe serum concentration of Amodiaquine can be increased when it is combined with Irbesartan.
IsoniazidThe serum concentration of Amodiaquine can be increased when it is combined with Isoniazid.
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Amodiaquine.
KetoconazoleThe serum concentration of Amodiaquine can be increased when it is combined with Ketoconazole.
KetoprofenThe serum concentration of Amodiaquine can be increased when it is combined with Ketoprofen.
LabetalolThe metabolism of Labetalol can be decreased when combined with Amodiaquine.
LansoprazoleThe serum concentration of Amodiaquine can be increased when it is combined with Lansoprazole.
LapatinibThe metabolism of Amodiaquine can be decreased when combined with Lapatinib.
LevamisoleThe serum concentration of Levamisole can be decreased when it is combined with Amodiaquine.
LevobunololThe metabolism of Levobunolol can be decreased when combined with Amodiaquine.
LevothyroxineThe serum concentration of Amodiaquine can be increased when it is combined with Levothyroxine.
LicofeloneThe serum concentration of Amodiaquine can be increased when it is combined with Licofelone.
LiotrixThe serum concentration of Amodiaquine can be increased when it is combined with Liotrix.
LopinavirThe metabolism of Amodiaquine can be decreased when combined with Lopinavir.
LoratadineThe serum concentration of Amodiaquine can be increased when it is combined with Loratadine.
LosartanThe serum concentration of Amodiaquine can be increased when it is combined with Losartan.
LovastatinThe serum concentration of Amodiaquine can be increased when it is combined with Lovastatin.
LucanthoneThe serum concentration of Lucanthone can be decreased when it is combined with Amodiaquine.
LumacaftorThe serum concentration of Amodiaquine can be increased when it is combined with Lumacaftor.
LumefantrineThe risk or severity of adverse effects can be increased when Amodiaquine is combined with Lumefantrine.
MebendazoleThe serum concentration of Mebendazole can be decreased when it is combined with Amodiaquine.
Medroxyprogesterone acetateThe serum concentration of Amodiaquine can be increased when it is combined with Medroxyprogesterone acetate.
Mefenamic acidThe serum concentration of Amodiaquine can be increased when it is combined with Mefenamic acid.
MefloquineThe risk or severity of adverse effects can be increased when Amodiaquine is combined with Mefloquine.
MeloxicamThe serum concentration of Amodiaquine can be increased when it is combined with Meloxicam.
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with Amodiaquine.
MethotrimeprazineThe serum concentration of Methotrimeprazine can be increased when it is combined with Amodiaquine.
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with Amodiaquine.
MetipranololThe metabolism of Metipranolol can be decreased when combined with Amodiaquine.
MetoprololThe metabolism of Metoprolol can be decreased when combined with Amodiaquine.
MetronidazoleThe serum concentration of Amodiaquine can be increased when it is combined with Metronidazole.
MifepristoneThe serum concentration of Amodiaquine can be increased when it is combined with Mifepristone.
Milbemycin oximeThe serum concentration of Milbemycin oxime can be decreased when it is combined with Amodiaquine.
MometasoneThe serum concentration of Amodiaquine can be increased when it is combined with Mometasone.
MontelukastThe serum concentration of Amodiaquine can be increased when it is combined with Montelukast.
MorantelThe serum concentration of Morantel can be decreased when it is combined with Amodiaquine.
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Amodiaquine.
MoxidectinThe serum concentration of Moxidectin can be decreased when it is combined with Amodiaquine.
NadololThe metabolism of Nadolol can be decreased when combined with Amodiaquine.
NicardipineThe serum concentration of Amodiaquine can be increased when it is combined with Nicardipine.
NiclosamideThe serum concentration of Niclosamide can be decreased when it is combined with Amodiaquine.
NifedipineThe serum concentration of Amodiaquine can be increased when it is combined with Nifedipine.
NilotinibThe serum concentration of Amodiaquine can be increased when it is combined with Nilotinib.
NilutamideThe serum concentration of Amodiaquine can be increased when it is combined with Nilutamide.
NilvadipineThe serum concentration of Amodiaquine can be increased when it is combined with Nilvadipine.
OuabainThe serum concentration of Ouabain can be increased when it is combined with Amodiaquine.
OxamniquineThe serum concentration of Oxamniquine can be decreased when it is combined with Amodiaquine.
OxfendazoleThe serum concentration of Oxfendazole can be decreased when it is combined with Amodiaquine.
OxibendazoleThe serum concentration of Oxibendazole can be decreased when it is combined with Amodiaquine.
OxprenololThe metabolism of Oxprenolol can be decreased when combined with Amodiaquine.
OxybutyninThe serum concentration of Amodiaquine can be increased when it is combined with Oxybutynin.
ParoxetineThe serum concentration of Amodiaquine can be increased when it is combined with Paroxetine.
PenbutololThe metabolism of Penbutolol can be decreased when combined with Amodiaquine.
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Amodiaquine.
PhenelzineThe serum concentration of Amodiaquine can be increased when it is combined with Phenelzine.
PhenobarbitalThe metabolism of Amodiaquine can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Amodiaquine can be increased when combined with Phenytoin.
PindololThe metabolism of Pindolol can be decreased when combined with Amodiaquine.
PioglitazoneThe serum concentration of Amodiaquine can be increased when it is combined with Pioglitazone.
PiperazineThe serum concentration of Piperazine can be decreased when it is combined with Amodiaquine.
PiroxicamThe serum concentration of Amodiaquine can be increased when it is combined with Piroxicam.
PonatinibThe serum concentration of Amodiaquine can be increased when it is combined with Ponatinib.
PractololThe metabolism of Practolol can be decreased when combined with Amodiaquine.
PravastatinThe serum concentration of Amodiaquine can be increased when it is combined with Pravastatin.
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Amodiaquine.
PrimidoneThe metabolism of Amodiaquine can be increased when combined with Primidone.
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with Amodiaquine.
PromazineThe serum concentration of Promazine can be increased when it is combined with Amodiaquine.
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Amodiaquine.
PropafenoneThe serum concentration of Amodiaquine can be increased when it is combined with Propafenone.
PropranololThe metabolism of Propranolol can be decreased when combined with Amodiaquine.
PyrantelThe serum concentration of Pyrantel can be decreased when it is combined with Amodiaquine.
PyrimethamineThe serum concentration of Amodiaquine can be increased when it is combined with Pyrimethamine.
PyrviniumThe serum concentration of Pyrvinium can be decreased when it is combined with Amodiaquine.
QuercetinThe serum concentration of Amodiaquine can be increased when it is combined with Quercetin.
QuinacrineThe serum concentration of Quinacrine can be decreased when it is combined with Amodiaquine.
QuinineThe serum concentration of Amodiaquine can be increased when it is combined with Quinine.
RabeprazoleThe metabolism of Amodiaquine can be decreased when combined with Rabeprazole.
RaloxifeneThe serum concentration of Amodiaquine can be increased when it is combined with Raloxifene.
RegorafenibThe serum concentration of Amodiaquine can be increased when it is combined with Regorafenib.
RifampicinThe serum concentration of Amodiaquine can be increased when it is combined with Rifampicin.
RifapentineThe metabolism of Amodiaquine can be increased when combined with Rifapentine.
RitonavirThe serum concentration of Amodiaquine can be increased when it is combined with Ritonavir.
RosiglitazoneThe serum concentration of Amodiaquine can be increased when it is combined with Rosiglitazone.
RutinThe serum concentration of Amodiaquine can be increased when it is combined with Rutin.
SalmeterolThe serum concentration of Amodiaquine can be increased when it is combined with Salmeterol.
SaquinavirThe serum concentration of Amodiaquine can be increased when it is combined with Saquinavir.
SecobarbitalThe metabolism of Amodiaquine can be increased when combined with Secobarbital.
SimvastatinThe serum concentration of Amodiaquine can be increased when it is combined with Simvastatin.
Sodium stibogluconateThe serum concentration of Sodium stibogluconate can be decreased when it is combined with Amodiaquine.
SorafenibThe serum concentration of Amodiaquine can be increased when it is combined with Sorafenib.
SotalolThe metabolism of Sotalol can be decreased when combined with Amodiaquine.
SpironolactoneThe serum concentration of Amodiaquine can be increased when it is combined with Spironolactone.
StiripentolThe metabolism of Amodiaquine can be decreased when combined with Stiripentol.
SulfamethoxazoleThe serum concentration of Amodiaquine can be increased when it is combined with Sulfamethoxazole.
SulfaphenazoleThe serum concentration of Amodiaquine can be increased when it is combined with Sulfaphenazole.
SuraminThe serum concentration of Suramin can be decreased when it is combined with Amodiaquine.
TamoxifenThe serum concentration of Amodiaquine can be increased when it is combined with Tamoxifen.
TegaserodThe serum concentration of Amodiaquine can be increased when it is combined with Tegaserod.
TerfenadineThe serum concentration of Amodiaquine can be increased when it is combined with Terfenadine.
TeriflunomideThe metabolism of Amodiaquine can be decreased when combined with Teriflunomide.
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Amodiaquine.
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with Amodiaquine.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Amodiaquine.
TiclopidineThe serum concentration of Amodiaquine can be increased when it is combined with Ticlopidine.
TimololThe metabolism of Timolol can be decreased when combined with Amodiaquine.
TioconazoleThe serum concentration of Amodiaquine can be increased when it is combined with Tioconazole.
TolbutamideThe serum concentration of Amodiaquine can be increased when it is combined with Tolbutamide.
TrametinibThe serum concentration of Amodiaquine can be increased when it is combined with Trametinib.
TriazolamThe serum concentration of Amodiaquine can be increased when it is combined with Triazolam.
TrichlorfonThe serum concentration of Trichlorfon can be decreased when it is combined with Amodiaquine.
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with Amodiaquine.
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with Amodiaquine.
TrimethoprimTrimethoprim may increase the neutropenic activities of Amodiaquine.
TroglitazoneThe serum concentration of Amodiaquine can be increased when it is combined with Troglitazone.
TroleandomycinThe serum concentration of Amodiaquine can be increased when it is combined with Troleandomycin.
Valproic AcidThe serum concentration of Amodiaquine can be increased when it is combined with Valproic Acid.
VismodegibThe serum concentration of Amodiaquine can be increased when it is combined with Vismodegib.
WarfarinThe serum concentration of Amodiaquine can be increased when it is combined with Warfarin.
ZafirlukastThe serum concentration of Amodiaquine can be increased when it is combined with Zafirlukast.
ZidovudineZidovudine may increase the neutropenic activities of Amodiaquine.
Food InteractionsNot Available

Targets

1. Fe(II)-protoporphyrin IX
Kind
Small molecule
Organism
Plasmodium falciparum
Pharmacological action
yes
Actions
adduct
References
  1. de Villiers KA, Marques HM, Egan TJ: The crystal structure of halofantrine-ferriprotoporphyrin IX and the mechanism of action of arylmethanol antimalarials. J Inorg Biochem. 2008 Aug;102(8):1660-7. doi: 10.1016/j.jinorgbio.2008.04.001. Epub 2008 Apr 20. [PubMed:18508124 ]
  2. Weissbuch I, Leiserowitz L: Interplay between malaria, crystalline hemozoin formation, and antimalarial drug action and design. Chem Rev. 2008 Nov;108(11):4899-914. doi: 10.1021/cr078274t. [PubMed:19006402 ]
  3. Sullivan DJ Jr, Gluzman IY, Russell DG, Goldberg DE: On the molecular mechanism of chloroquine's antimalarial action. Proc Natl Acad Sci U S A. 1996 Oct 15;93(21):11865-70. [PubMed:8876229 ]
  4. Schwedhelm KF, Horstmann M, Faber JH, Reichert Y, Bringmann G, Faber C: The novel antimalarial compound dioncophylline C forms a complex with heme in solution. ChemMedChem. 2007 Apr;2(4):541-8. [PubMed:17315144 ]
  5. Egan TJ, Ncokazi KK: Effects of solvent composition and ionic strength on the interaction of quinoline antimalarials with ferriprotoporphyrin IX. J Inorg Biochem. 2004 Jan;98(1):144-52. [PubMed:14659643 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Histamine n-methyltransferase activity
Specific Function:
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:
HNMT
Uniprot ID:
P50135
Molecular Weight:
33294.765 Da
References
  1. Yokoyama A, Mori S, Takahashi HK, Kanke T, Wake H, Nishibori M: Effect of amodiaquine, a histamine N-methyltransferase inhibitor, on, Propionibacterium acnes and lipopolysaccharide-induced hepatitis in mice. Eur J Pharmacol. 2007 Mar 8;558(1-3):179-84. Epub 2006 Nov 22. [PubMed:17222819 ]
  2. Nowak JZ, Zandarowska E: Effect of amodiaquine on histamine level and histamine-methyltransferase activity in the rat brain. Arch Immunol Ther Exp (Warsz). 1980;28(6):927-30. [PubMed:6789797 ]
  3. Barth H, Lorenz W, Troidl H: Effect of amodiaquine on gastric histamine methyltransferase and on histamine-stimulated gastric secretion. Br J Pharmacol. 1975 Nov;55(3):321-7. [PubMed:1203620 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 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 ]
  2. Li XQ, Bjorkman A, Andersson TB, Ridderstrom M, Masimirembwa CM: Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate. J Pharmacol Exp Ther. 2002 Feb;300(2):399-407. [PubMed:11805197 ]
  3. Walsky RL, Obach RS: Validated assays for human cytochrome P450 activities. Drug Metab Dispos. 2004 Jun;32(6):647-60. [PubMed:15155557 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally 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 ]
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
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23