Identification

Name
Amodiaquine
Accession Number
DB00613  (APRD00796)
Type
Small Molecule
Groups
Approved
Description

A 4-aminoquinoquinoline compound with anti-inflammatory properties.

Structure
Thumb
Synonyms
  • Amodiaquina
  • Amodiaquine
  • Amodiaquinum
External IDs
NSC-13453
Product Ingredients
IngredientUNIICASInChI Key
Amodiaquine dihydrochloride dihydrateK6PW2S574L 6398-98-7YVNAYSHNIILOJS-UHFFFAOYSA-N
Amodiaquine hydrochlorideHOE64181MP 69-44-3ROEBJVHPINPMKL-UHFFFAOYSA-N
International/Other Brands
Basoquin / Camoquin (Parke Davis) / Flavoquine
Categories
UNII
220236ED28
CAS number
86-42-0
Weight
Average: 355.861
Monoisotopic: 355.145140048
Chemical Formula
C20H22ClN3O
InChI Key
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

Pharmacology

Indication

For treatment of acute malarial attacks in non-immune subjects.

Structured Indications
Not Available
Pharmacodynamics

Amodiaquine, 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 action

The 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.

TargetActionsOrganism
AFe(II)-protoporphyrin IX
adduct
Plasmodium falciparum
UHistamine N-methyltransferase
inhibitor
Human
Absorption

Rapidly absorbed following oral administration.

Volume of distribution
Not Available
Protein binding
Not 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.

Route of elimination
Not Available
Half life

5.2 ± 1.7 (range 0.4 to 5.5) minutes

Clearance
Not Available
Toxicity

LD50 (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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
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
AcetyldigoxinThe serum concentration of Acetyldigoxin can be increased when it is combined with Amodiaquine.Experimental
AlbendazoleThe serum concentration of Albendazole can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
Albendazole oxideThe serum concentration of Albendazole oxide can be decreased when it is combined with Amodiaquine.Experimental
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
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
ArtemotilThe serum concentration of Artemotil can be decreased when it is combined with Amodiaquine.Experimental
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
BelinostatThe serum concentration of Amodiaquine can be increased when it is combined with Belinostat.Approved, Investigational
BenzimidazoleThe serum concentration of Benzimidazole can be decreased when it is combined with Amodiaquine.Experimental
BepheniumThe serum concentration of Bephenium 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
CarbendazimThe serum concentration of Carbendazim can be decreased when it is combined with Amodiaquine.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 serum concentration of Amodiaquine can be increased when it is 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
ChlorproethazineThe serum concentration of Chlorproethazine can be increased when it is combined with Amodiaquine.Experimental
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
CiclobendazoleThe serum concentration of Ciclobendazole can be decreased when it is combined with Amodiaquine.Experimental
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
CloranololThe metabolism of Cloranolol can be decreased when combined with Amodiaquine.Experimental
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
CrisaboroleThe serum concentration of Amodiaquine can be increased when it is combined with Crisaborole.Approved
CyclosporineThe serum concentration of Amodiaquine can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinThe serum concentration of Cymarin can be increased when it is combined with Amodiaquine.Experimental
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
DesaspidinThe serum concentration of Desaspidin can be decreased when it is combined with Amodiaquine.Experimental
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
DichloropheneThe serum concentration of Dichlorophene can be decreased when it is combined with Amodiaquine.Vet Approved
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
EmetineThe serum concentration of Emetine can be decreased when it is combined with Amodiaquine.Experimental
EnasidenibThe serum concentration of Amodiaquine can be increased when it is combined with Enasidenib.Approved
EnzalutamideThe serum concentration of Amodiaquine can be increased when it is combined with Enzalutamide.Approved
EpanololThe metabolism of Epanolol can be decreased when combined with Amodiaquine.Experimental
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
GitoformateThe serum concentration of Gitoformate can be increased when it is combined with Amodiaquine.Experimental
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
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
Lanatoside CThe serum concentration of Lanatoside C can be increased when it is combined with Amodiaquine.Experimental
LandiololThe metabolism of Landiolol can be decreased when combined with Amodiaquine.Investigational
LansoprazoleThe serum concentration of Amodiaquine can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Amodiaquine can be increased when it is 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 serum concentration of Amodiaquine can be increased when it is 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
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
MepindololThe metabolism of Mepindolol can be decreased when combined with Amodiaquine.Experimental
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
MetildigoxinThe serum concentration of Metildigoxin can be increased when it is combined with Amodiaquine.Experimental
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
MidostaurinThe serum concentration of Amodiaquine can be increased when it is combined with Midostaurin.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
NiridazoleThe serum concentration of Niridazole can be decreased when it is combined with Amodiaquine.Experimental
OleandrinThe serum concentration of Oleandrin can be increased when it is combined with Amodiaquine.Experimental
OltiprazThe serum concentration of Oltipraz can be decreased when it is combined with Amodiaquine.Investigational
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
OxantelThe serum concentration of Oxantel can be decreased when it is combined with Amodiaquine.Experimental
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
PeruvosideThe serum concentration of Peruvoside can be increased when it is combined with Amodiaquine.Experimental
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
Propoxyphene napsylateThe serum concentration of Amodiaquine can be increased when it is combined with Propoxyphene napsylate.Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Amodiaquine.Approved, Investigational
ProscillaridinThe serum concentration of Proscillaridin can be increased when it is combined with Amodiaquine.Experimental
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 serum concentration of Amodiaquine can be increased when it is 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
StibophenThe serum concentration of Stibophen can be decreased when it is combined with Amodiaquine.Experimental
StiripentolThe serum concentration of Amodiaquine can be increased when it is 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
TalinololThe metabolism of Talinolol can be decreased when combined with Amodiaquine.Investigational
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 serum concentration of Amodiaquine can be increased when it is combined with Teriflunomide.Approved
TertatololThe metabolism of Tertatolol can be decreased when combined with Amodiaquine.Experimental
ThiabendazoleThe serum concentration of Thiabendazole can be decreased when it is combined with Amodiaquine.Approved, Vet Approved
ThiazinamThe serum concentration of Thiazinam can be increased when it is combined with Amodiaquine.Experimental
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.Withdrawn
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
TopiroxostatThe serum concentration of Amodiaquine can be increased when it is combined with Topiroxostat.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 Interactions
Not 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
Human Metabolome Database
HMDB14751
KEGG Drug
D02922
KEGG Compound
C07626
PubChem Compound
2165
PubChem Substance
46506940
ChemSpider
2080
BindingDB
50041457
ChEBI
2674
ChEMBL
CHEMBL682
Therapeutic Targets Database
DAP000699
PharmGKB
PA448404
HET
CQA
Wikipedia
Amodiaquine
ATC Codes
P01BF03 — Artesunate and amodiaquineP01BA06 — Amodiaquine
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceMalaria caused by Plasmodium falciparum1
1CompletedTreatmentPlasmodium Infections1
1, 2CompletedTreatmentPlasmodium Infections1
1, 2RecruitingTreatmentDrug Combination / Healthy Volunteers / Pharmacokinetics1
2CompletedPreventionPlasmodium Infections1
2CompletedTreatmentPlasmodium Infections3
2CompletedTreatmentPlasmodium Infections / Severe Malaria1
2, 3CompletedPreventionPlasmodium Infections3
2, 3CompletedTreatmentPlasmodium Infections1
3CompletedPreventionIntermittent Preventive Treatment / Plasmodium Infections1
3CompletedPreventionMalaria caused by Plasmodium falciparum1
3CompletedPreventionPlasmodium Infections2
3CompletedTreatmentMalaria caused by Plasmodium falciparum / Malaria caused by plasmodium vivax / Plasmodium Infections1
3CompletedTreatmentPlasmodium Infections6
3CompletedTreatmentPlasmodium Infections / Pregnancy1
3Not Yet RecruitingPreventionPlasmodium Infections / Respiratory Tract Infections (RTI)1
3Unknown StatusTreatmentUncomplicated Malaria1
4CompletedTreatmentMalaria caused by Plasmodium falciparum2
4CompletedTreatmentPlasmodium Infections2
4CompletedTreatmentUncomplicated Malaria1
4SuspendedNot AvailablePlasmodium Infections1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
Not AvailableCompletedBasic ScienceAnemias1
Not AvailableCompletedTreatmentMalaria caused by Plasmodium falciparum1
Not AvailableCompletedTreatmentPlasmodium Infections1

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)206-208Burckhalter, 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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0570-3940000000-2d4500c74767ebc68cf0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1390000000-e476bc93f0f2236bccdc

Taxonomy

Description
This compound belongs to the class of chemical entities known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organoheterocyclic compounds
Sub Class
Quinolines and derivatives
Direct Parent
4-aminoquinolines
Alternative Parents
Chloroquinolines / p-Aminophenols / Phenylmethylamines / Aniline and substituted anilines / Benzylamines / 1-hydroxy-2-unsubstituted benzenoids / Aminopyridines and derivatives / Aralkylamines / Aryl chlorides / Heteroaromatic compounds
show 7 more
Substituents
Chloroquinoline / Haloquinoline / 4-aminoquinoline / Aminophenol / P-aminophenol / Phenylmethylamine / Benzylamine / Aniline or substituted anilines / Aminopyridine / Phenol
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
quinolines, phenols (CHEBI:2674 ) / a small molecule (CPD-10889 )

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
Uniprot Name
Histamine N-methyltransferase
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
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 un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
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 ]
Details
4. Cytochrome P450 2D6
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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 ]
Details
5. Cytochrome P450 2C9
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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 ]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:41