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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 KeyOVCDSSHSILBFBN-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
Pharmacology
IndicationFor treatment of acute malarial attacks in non-immune subjects.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Fe(II)-protoporphyrin IXSmall moleculeyes
adduct
Plasmodium falciparumnot applicabledetails
Histamine N-methyltransferaseProteinunknown
inhibitor
HumanP50135 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Amodiaquine can be increased when it is combined with Abiraterone.Approved
AcebutololThe metabolism of Acebutolol can be decreased when combined with Amodiaquine.Approved
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with Amodiaquine.Approved, Vet Approved
AceprometazineThe serum concentration of Aceprometazine can be increased when it is combined with Amodiaquine.Approved
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Amodiaquine.Approved
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with Amodiaquine.Approved, Vet Approved
AlprenololThe metabolism of Alprenolol can be decreased when combined with Amodiaquine.Approved, Withdrawn
AmitriptylineThe serum concentration of Amodiaquine can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Amodiaquine can be increased when it is combined with Amlodipine.Approved
AnvirzelThe serum concentration of Anvirzel can be increased when it is combined with Amodiaquine.Investigational
Aop200704The metabolism of Aop200704 can be decreased when combined with Amodiaquine.Investigational
ArotinololThe metabolism of Arotinolol can be decreased when combined with Amodiaquine.Approved
ArsenamideThe serum concentration of Arsenamide can be decreased when it is combined with Amodiaquine.Vet Approved
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Amodiaquine.Approved
AtenololThe metabolism of Atenolol can be decreased when combined with Amodiaquine.Approved
AtorvastatinThe serum concentration of Amodiaquine can be increased when it is combined with Atorvastatin.Approved
BefunololThe metabolism of Befunolol can be decreased when combined with Amodiaquine.Experimental
BenzimidazoleThe serum concentration of Benzimidazole can be decreased when it is combined with Amodiaquine.Experimental
BetaxololThe metabolism of Betaxolol can be decreased when combined with Amodiaquine.Approved
BevantololThe metabolism of Bevantolol can be decreased when combined with Amodiaquine.Approved
BezafibrateThe serum concentration of Amodiaquine can be increased when it is combined with Bezafibrate.Approved
BisoprololThe metabolism of Bisoprolol can be decreased when combined with Amodiaquine.Approved
BithionolThe serum concentration of Bithionol can be decreased when it is combined with Amodiaquine.Withdrawn
BL-1020The serum concentration of BL-1020 can be increased when it is combined with Amodiaquine.Investigational
BopindololThe metabolism of Bopindolol can be decreased when combined with Amodiaquine.Approved
BucindololThe metabolism of Bucindolol can be decreased when combined with Amodiaquine.Investigational
BufuralolThe metabolism of Bufuralol can be decreased when combined with Amodiaquine.Experimental, Investigational
BunamidineThe serum concentration of Bunamidine can be decreased when it is combined with Amodiaquine.Vet Approved
BupranololThe metabolism of Bupranolol can be decreased when combined with Amodiaquine.Approved
CambendazoleThe serum concentration of Cambendazole can be decreased when it is combined with Amodiaquine.Vet Approved
CandesartanThe serum concentration of Amodiaquine can be increased when it is combined with Candesartan.Approved
CarbamazepineThe metabolism of Amodiaquine can be increased when combined with Carbamazepine.Approved, Investigational
CarteololThe metabolism of Carteolol can be decreased when combined with Amodiaquine.Approved
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Amodiaquine.Approved, Investigational
CelecoxibThe metabolism of Amodiaquine can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololThe metabolism of Celiprolol can be decreased when combined with Amodiaquine.Approved, Investigational
CerivastatinThe serum concentration of Amodiaquine can be increased when it is combined with Cerivastatin.Withdrawn
ChloramphenicolThe serum concentration of Amodiaquine can be increased when it is combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe serum concentration of Chloroquine can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
ChloroxylenolThe serum concentration of Chloroxylenol can be decreased when it is combined with Amodiaquine.Approved
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Amodiaquine.Approved, Vet Approved
CholecalciferolThe serum concentration of Amodiaquine can be increased when it is combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe serum concentration of Amodiaquine can be increased when it is combined with Cimetidine.Approved
ClopidogrelThe serum concentration of Amodiaquine can be increased when it is combined with Clopidogrel.Approved, Nutraceutical
ClorsulonThe serum concentration of Clorsulon can be decreased when it is combined with Amodiaquine.Vet Approved
ClotrimazoleThe serum concentration of Amodiaquine can be increased when it is combined with Clotrimazole.Approved, Vet Approved
CocaineThe serum concentration of Amodiaquine can be increased when it is combined with Cocaine.Approved, Illicit
ColchicineThe serum concentration of Amodiaquine can be increased when it is combined with Colchicine.Approved
CoumaphosThe serum concentration of Coumaphos can be decreased when it is combined with Amodiaquine.Vet Approved
CyclosporineThe serum concentration of Amodiaquine can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Amodiaquine can be decreased when it is combined with Dabrafenib.Approved
DapsoneThe risk or severity of adverse effects can be increased when Amodiaquine is combined with Dapsone.Approved, Investigational
DeferasiroxThe serum concentration of Amodiaquine can be increased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Amodiaquine can be increased when it is combined with Delavirdine.Approved
DeslanosideThe serum concentration of Deslanoside can be increased when it is combined with Amodiaquine.Approved
DextropropoxypheneThe serum concentration of Amodiaquine can be increased when it is combined with Dextropropoxyphene.Approved, Illicit, Withdrawn
DichlorvosThe serum concentration of Dichlorvos can be decreased when it is combined with Amodiaquine.Vet Approved
DiethylcarbamazineThe serum concentration of Diethylcarbamazine can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
DiethylstilbestrolThe serum concentration of Amodiaquine can be increased when it is combined with Diethylstilbestrol.Approved
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Amodiaquine.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Amodiaquine.Approved
DithiazanineThe serum concentration of Dithiazanine can be decreased when it is combined with Amodiaquine.Vet Approved
DoramectinThe serum concentration of Doramectin can be decreased when it is combined with Amodiaquine.Vet Approved
EfavirenzEfavirenz may increase the hepatotoxic activities of Amodiaquine.Approved, Investigational
EltrombopagThe serum concentration of Amodiaquine can be increased when it is combined with Eltrombopag.Approved
EnzalutamideThe serum concentration of Amodiaquine can be increased when it is combined with Enzalutamide.Approved
EprinomectinThe serum concentration of Eprinomectin can be decreased when it is combined with Amodiaquine.Vet Approved
ErlotinibThe serum concentration of Amodiaquine can be increased when it is combined with Erlotinib.Approved, Investigational
EsmololThe metabolism of Esmolol can be decreased when combined with Amodiaquine.Approved
Ethinyl EstradiolThe serum concentration of Amodiaquine can be increased when it is combined with Ethinyl Estradiol.Approved
EtoposideThe serum concentration of Amodiaquine can be increased when it is combined with Etoposide.Approved
FebantelThe serum concentration of Febantel can be decreased when it is combined with Amodiaquine.Vet Approved
FelodipineThe serum concentration of Amodiaquine can be increased when it is combined with Felodipine.Approved, Investigational
FenbendazoleThe serum concentration of Fenbendazole can be decreased when it is combined with Amodiaquine.Vet Approved
FenofibrateThe serum concentration of Amodiaquine can be increased when it is combined with Fenofibrate.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Amodiaquine.Approved
FlubendazoleThe serum concentration of Flubendazole can be decreased when it is combined with Amodiaquine.Approved, Withdrawn
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Amodiaquine.Approved
FluvastatinThe serum concentration of Amodiaquine can be increased when it is combined with Fluvastatin.Approved
FosphenytoinThe metabolism of Amodiaquine can be increased when combined with Fosphenytoin.Approved
GemfibrozilThe serum concentration of Amodiaquine can be increased when it is combined with Gemfibrozil.Approved
HexylresorcinolThe serum concentration of Hexylresorcinol can be decreased when it is combined with Amodiaquine.Approved
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Amodiaquine.Vet Approved
IdelalisibThe serum concentration of Amodiaquine can be increased when it is combined with Idelalisib.Approved
IndenololThe metabolism of Indenolol can be decreased when combined with Amodiaquine.Withdrawn
IrbesartanThe serum concentration of Amodiaquine can be increased when it is combined with Irbesartan.Approved, Investigational
IsoniazidThe serum concentration of Amodiaquine can be increased when it is combined with Isoniazid.Approved
IvermectinThe serum concentration of Ivermectin can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
KetoconazoleThe serum concentration of Amodiaquine can be increased when it is combined with Ketoconazole.Approved, Investigational
KetoprofenThe serum concentration of Amodiaquine can be increased when it is combined with Ketoprofen.Approved, Vet Approved
LabetalolThe metabolism of Labetalol can be decreased when combined with Amodiaquine.Approved
LansoprazoleThe serum concentration of Amodiaquine can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe metabolism of Amodiaquine can be decreased when combined with Lapatinib.Approved, Investigational
LevamisoleThe serum concentration of Levamisole can be decreased when it is combined with Amodiaquine.Vet Approved, Withdrawn
LevobunololThe metabolism of Levobunolol can be decreased when combined with Amodiaquine.Approved
LevothyroxineThe serum concentration of Amodiaquine can be increased when it is combined with Levothyroxine.Approved
LicofeloneThe serum concentration of Amodiaquine can be increased when it is combined with Licofelone.Investigational
LiotrixThe serum concentration of Amodiaquine can be increased when it is combined with Liotrix.Approved
LopinavirThe metabolism of Amodiaquine can be decreased when combined with Lopinavir.Approved
LoratadineThe serum concentration of Amodiaquine can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Amodiaquine can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Amodiaquine can be increased when it is combined with Lovastatin.Approved, Investigational
LucanthoneThe serum concentration of Lucanthone can be decreased when it is combined with Amodiaquine.Approved, Investigational
LumacaftorThe serum concentration of Amodiaquine can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe risk or severity of adverse effects can be increased when Amodiaquine is combined with Lumefantrine.Approved
MebendazoleThe serum concentration of Mebendazole can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
Medroxyprogesterone acetateThe serum concentration of Amodiaquine can be increased when it is combined with Medroxyprogesterone acetate.Approved, Investigational
Mefenamic acidThe serum concentration of Amodiaquine can be increased when it is combined with Mefenamic acid.Approved
MefloquineThe risk or severity of adverse effects can be increased when Amodiaquine is combined with Mefloquine.Approved
MeloxicamThe serum concentration of Amodiaquine can be increased when it is combined with Meloxicam.Approved, Vet Approved
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with Amodiaquine.Approved
MethotrimeprazineThe serum concentration of Methotrimeprazine can be increased when it is combined with Amodiaquine.Approved
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with Amodiaquine.Investigational
MetipranololThe metabolism of Metipranolol can be decreased when combined with Amodiaquine.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Amodiaquine.Approved, Investigational
MetronidazoleThe serum concentration of Amodiaquine can be increased when it is combined with Metronidazole.Approved
MifepristoneThe serum concentration of Amodiaquine can be increased when it is combined with Mifepristone.Approved, Investigational
Milbemycin oximeThe serum concentration of Milbemycin oxime can be decreased when it is combined with Amodiaquine.Vet Approved
MometasoneThe serum concentration of Amodiaquine can be increased when it is combined with Mometasone.Approved, Vet Approved
MontelukastThe serum concentration of Amodiaquine can be increased when it is combined with Montelukast.Approved
MorantelThe serum concentration of Morantel can be decreased when it is combined with Amodiaquine.Vet Approved
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Amodiaquine.Approved, Withdrawn
MoxidectinThe serum concentration of Moxidectin can be decreased when it is combined with Amodiaquine.Vet Approved
NadololThe metabolism of Nadolol can be decreased when combined with Amodiaquine.Approved
NicardipineThe serum concentration of Amodiaquine can be increased when it is combined with Nicardipine.Approved
NiclosamideThe serum concentration of Niclosamide can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
NifedipineThe serum concentration of Amodiaquine can be increased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Amodiaquine can be increased when it is combined with Nilotinib.Approved, Investigational
NilutamideThe serum concentration of Amodiaquine can be increased when it is combined with Nilutamide.Approved
NilvadipineThe serum concentration of Amodiaquine can be increased when it is combined with Nilvadipine.Approved
OuabainThe serum concentration of Ouabain can be increased when it is combined with Amodiaquine.Approved
OxamniquineThe serum concentration of Oxamniquine can be decreased when it is combined with Amodiaquine.Approved
OxfendazoleThe serum concentration of Oxfendazole can be decreased when it is combined with Amodiaquine.Vet Approved
OxibendazoleThe serum concentration of Oxibendazole can be decreased when it is combined with Amodiaquine.Investigational, Vet Approved
OxprenololThe metabolism of Oxprenolol can be decreased when combined with Amodiaquine.Approved
OxybutyninThe serum concentration of Amodiaquine can be increased when it is combined with Oxybutynin.Approved, Investigational
ParoxetineThe serum concentration of Amodiaquine can be increased when it is combined with Paroxetine.Approved, Investigational
PenbutololThe metabolism of Penbutolol can be decreased when combined with Amodiaquine.Approved, Investigational
PerazineThe serum concentration of Perazine can be increased when it is combined with Amodiaquine.Investigational
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Amodiaquine.Approved
PhenelzineThe serum concentration of Amodiaquine can be increased when it is combined with Phenelzine.Approved
PhenobarbitalThe metabolism of Amodiaquine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Amodiaquine can be increased when combined with Phenytoin.Approved, Vet Approved
PindololThe metabolism of Pindolol can be decreased when combined with Amodiaquine.Approved
PioglitazoneThe serum concentration of Amodiaquine can be increased when it is combined with Pioglitazone.Approved, Investigational
PiperazineThe serum concentration of Piperazine can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
PiroxicamThe serum concentration of Amodiaquine can be increased when it is combined with Piroxicam.Approved, Investigational
PonatinibThe serum concentration of Amodiaquine can be increased when it is combined with Ponatinib.Approved
PractololThe metabolism of Practolol can be decreased when combined with Amodiaquine.Approved
PravastatinThe serum concentration of Amodiaquine can be increased when it is combined with Pravastatin.Approved
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
PrimidoneThe metabolism of Amodiaquine can be increased when combined with Primidone.Approved, Vet Approved
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with Amodiaquine.Approved, Vet Approved
PromazineThe serum concentration of Promazine can be increased when it is combined with Amodiaquine.Approved, Vet Approved
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Amodiaquine.Approved
PropafenoneThe serum concentration of Amodiaquine can be increased when it is combined with Propafenone.Approved
PropiopromazineThe serum concentration of Propiopromazine can be increased when it is combined with Amodiaquine.Vet Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Amodiaquine.Approved, Investigational
PyrantelThe serum concentration of Pyrantel can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
PyrimethamineThe serum concentration of Amodiaquine can be increased when it is combined with Pyrimethamine.Approved, Vet Approved
PyrviniumThe serum concentration of Pyrvinium can be decreased when it is combined with Amodiaquine.Approved
QuercetinThe serum concentration of Amodiaquine can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Quinacrine can be decreased when it is combined with Amodiaquine.Approved
QuinineThe serum concentration of Amodiaquine can be increased when it is combined with Quinine.Approved
RabeprazoleThe metabolism of Amodiaquine can be decreased when combined with Rabeprazole.Approved, Investigational
RaloxifeneThe serum concentration of Amodiaquine can be increased when it is combined with Raloxifene.Approved, Investigational
RegorafenibThe serum concentration of Amodiaquine can be increased when it is combined with Regorafenib.Approved
RifampicinThe serum concentration of Amodiaquine can be increased when it is combined with Rifampicin.Approved
RifapentineThe metabolism of Amodiaquine can be increased when combined with Rifapentine.Approved
RitonavirThe serum concentration of Amodiaquine can be increased when it is combined with Ritonavir.Approved, Investigational
RosiglitazoneThe serum concentration of Amodiaquine can be increased when it is combined with Rosiglitazone.Approved, Investigational
RutinThe serum concentration of Amodiaquine can be increased when it is combined with Rutin.Experimental
SalmeterolThe serum concentration of Amodiaquine can be increased when it is combined with Salmeterol.Approved
SaquinavirThe serum concentration of Amodiaquine can be increased when it is combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Amodiaquine can be increased when combined with Secobarbital.Approved, Vet Approved
SimvastatinThe serum concentration of Amodiaquine can be increased when it is combined with Simvastatin.Approved
Sodium stibogluconateThe serum concentration of Sodium stibogluconate can be decreased when it is combined with Amodiaquine.Approved, Investigational
SorafenibThe serum concentration of Amodiaquine can be increased when it is combined with Sorafenib.Approved, Investigational
SotalolThe metabolism of Sotalol can be decreased when combined with Amodiaquine.Approved
SpironolactoneThe serum concentration of Amodiaquine can be increased when it is combined with Spironolactone.Approved
StiripentolThe metabolism of Amodiaquine can be decreased when combined with Stiripentol.Approved
SulfamethoxazoleThe serum concentration of Amodiaquine can be increased when it is combined with Sulfamethoxazole.Approved
SulfaphenazoleThe serum concentration of Amodiaquine can be increased when it is combined with Sulfaphenazole.Approved
SuraminThe serum concentration of Suramin can be decreased when it is combined with Amodiaquine.Approved
TamoxifenThe serum concentration of Amodiaquine can be increased when it is combined with Tamoxifen.Approved
TegaserodThe serum concentration of Amodiaquine can be increased when it is combined with Tegaserod.Investigational, Withdrawn
TerfenadineThe serum concentration of Amodiaquine can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe metabolism of Amodiaquine can be decreased when combined with Teriflunomide.Approved
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with Amodiaquine.Withdrawn
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Amodiaquine.Approved
TiclopidineThe serum concentration of Amodiaquine can be increased when it is combined with Ticlopidine.Approved
TimololThe metabolism of Timolol can be decreased when combined with Amodiaquine.Approved
TioconazoleThe serum concentration of Amodiaquine can be increased when it is combined with Tioconazole.Approved
TolbutamideThe serum concentration of Amodiaquine can be increased when it is combined with Tolbutamide.Approved
TrametinibThe serum concentration of Amodiaquine can be increased when it is combined with Trametinib.Approved
TriazolamThe serum concentration of Amodiaquine can be increased when it is combined with Triazolam.Approved
TrichlorfonThe serum concentration of Trichlorfon can be decreased when it is combined with Amodiaquine.Vet Approved
TriclabendazoleThe serum concentration of Triclabendazole can be decreased when it is combined with Amodiaquine.Investigational
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with Amodiaquine.Approved
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with Amodiaquine.Approved, Vet Approved
TrimethoprimTrimethoprim may increase the neutropenic activities of Amodiaquine.Approved, Vet Approved
TroglitazoneThe serum concentration of Amodiaquine can be increased when it is combined with Troglitazone.Withdrawn
TroleandomycinThe serum concentration of Amodiaquine can be increased when it is combined with Troleandomycin.Approved
Valproic AcidThe serum concentration of Amodiaquine can be increased when it is combined with Valproic Acid.Approved, Investigational
VismodegibThe serum concentration of Amodiaquine can be increased when it is combined with Vismodegib.Approved
WarfarinThe serum concentration of Amodiaquine can be increased when it is combined with Warfarin.Approved
ZafirlukastThe serum concentration of Amodiaquine can be increased when it is combined with Zafirlukast.Approved, Investigational
ZidovudineZidovudine may increase the neutropenic activities of Amodiaquine.Approved
Food InteractionsNot 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 CodesP01BF03P01BA06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot 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
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

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