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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C20H22ClN3O.2ClH
Molecular Weight 428.783
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMODIAQUINE HYDROCHLORIDE ANHYDROUS

SMILES

Cl.Cl.CCN(CC)CC1=CC(NC2=CC=NC3=C2C=CC(Cl)=C3)=CC=C1O

InChI

InChIKey=ROEBJVHPINPMKL-UHFFFAOYSA-N
InChI=1S/C20H22ClN3O.2ClH/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);2*1H

HIDE SMILES / InChI
Molecular Formula C20H22ClN3O
Molecular Weight 355.861
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00613 | https://www.drugs.com/international/amodiaquine.html | https://www.ncbi.nlm.nih.gov/pubmed/9825729 | https://www.ncbi.nlm.nih.gov/pubmed/22949374 | https://www.ncbi.nlm.nih.gov/pubmed/18855526

Amodiaquine is a medication used to treat malaria, including Plasmodium falciparum malaria when uncomplicated. 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. The side effects of amodiaquine are generally minor to moderate and are similar to those of chloroquine. Rarely liver problems or low blood cell levels may occur. When taken in excess headaches, trouble seeing, seizures, and cardiac arrest may occur. After oral administration amodiaquine hydrochloride is rapidly absorbed,and undergoes rapid and extensive metabolism to desethylamodiaquine which concentrates in red blood cells. It is likely that desethylamodiaquine, not amodiaquine, is responsible for most of the observed antimalarial activity, and that the toxic effects of amodiaquine after oral administration may in part be due to desethylamodiaquine.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Although in use for more than 40 year, there exists little information regarding the disposition of amodiaquine in man. Chloroquine, a 4-aminoquinoline derivative which resembles amodiaquine structurally, is widely distributed into the body tissues, especially in liver, spleen, kidney, lungs, brain, and spinal cord.

Originator

Approval Year

1950
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Heme degradation by glutathione
3
Target ID: Heme degradation by glutathione
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Coarsucam

Approved Use

Therapeutic Indication. ARTESUNATE AMODIAQUINE WINTHROP is indicated for the treatment of uncomplicated cases of malaria due to Plasmodium falciparum strains which are susceptible to amodiaquine as well as to artesunate.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
415 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
322 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
21 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
77 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.9 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20368402/
270 mg 1 times / day steady-state, oral
dose: 270 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: ARTESUNATE
ARTESUNATE
 AMODIAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
10.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.7 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8983859/
10 mg/kg single, oral
dose: 10 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMODIAQUINE blood
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
73.4 mg 1 times / day multiple, oral
Studied dose
Dose: 73.4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 73.4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
unhealthy, 17 to 76 years
Health Status: unhealthy
Age Group: 17 to 76 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
Other AEs: Agranulocytosis...
Other AEs:
Agranulocytosis
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Other AEs: Leucopenia, Neutropenia...
Other AEs:
Leucopenia (grade 1, 14%)
Neutropenia (grade 1, 14%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Other AEs: Neutropenia...
Other AEs:
Neutropenia (grade 2, 12%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Other AEs: Transaminitis...
Other AEs:
Transaminitis (grade 3, 12%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Disc. AE: Hypersensitivity reaction...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity reaction (6.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (35%)
Vomiting (35%)
Lassitude (grade 2, 60%)
Diarrhoea (15%)
Constipation (10%)
Granulocytopenia (15%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
600 mg 1 times / day multiple, oral
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
unhealthy, median age 20 years
Health Status: unhealthy
Age Group: median age 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Other AEs: Weakness generalised, Dizziness...
Other AEs:
Weakness generalised (84%)
Dizziness (58%)
Vomiting (46%)
Itching (32%)
Nausea (26%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
71.6 mg 1 times / day multiple, oral
Studied dose
Dose: 71.6 mg, 1 times / day
Route: oral
Route: multiple
Dose: 71.6 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
unhealthy, median age 35 years
Health Status: unhealthy
Age Group: median age 35 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
Other AEs: Hepatotoxicity...
Other AEs:
Hepatotoxicity
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
AEs

AEs

AESignificanceDosePopulation
Agranulocytosis
73.4 mg 1 times / day multiple, oral
Studied dose
Dose: 73.4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 73.4 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
unhealthy, 17 to 76 years
Health Status: unhealthy
Age Group: 17 to 76 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
Leucopenia grade 1, 14%
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Neutropenia grade 1, 14%
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Neutropenia grade 2, 12%
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Transaminitis grade 3, 12%
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Hypersensitivity reaction 6.7%
Disc. AE
10 mg/kg 1 times / day single, oral
Studied dose
Dose: 10 mg/kg, 1 times / day
Route: oral
Route: single
Dose: 10 mg/kg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Constipation 10%
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Diarrhoea 15%
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Granulocytopenia 15%
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Nausea 35%
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Vomiting 35%
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Lassitude grade 2, 60%
45 mg/kg multiple, oral
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Nausea 26%
600 mg 1 times / day multiple, oral
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
unhealthy, median age 20 years
Health Status: unhealthy
Age Group: median age 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Itching 32%
600 mg 1 times / day multiple, oral
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
unhealthy, median age 20 years
Health Status: unhealthy
Age Group: median age 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Vomiting 46%
600 mg 1 times / day multiple, oral
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
unhealthy, median age 20 years
Health Status: unhealthy
Age Group: median age 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Dizziness 58%
600 mg 1 times / day multiple, oral
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
unhealthy, median age 20 years
Health Status: unhealthy
Age Group: median age 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Weakness generalised 84%
600 mg 1 times / day multiple, oral
Studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
unhealthy, median age 20 years
Health Status: unhealthy
Age Group: median age 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Hepatotoxicity
71.6 mg 1 times / day multiple, oral
Studied dose
Dose: 71.6 mg, 1 times / day
Route: oral
Route: multiple
Dose: 71.6 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
unhealthy, median age 35 years
Health Status: unhealthy
Age Group: median age 35 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946
substrate
1193
substrate
1388

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1741
CYP2C8
810

CYP1A1
389

CYP1A2
1197

CYP1B1
104

CYP2A6
626

CYP2B6
776

CYP2C18
149

CYP2C19
1119

CYP2E1
729

CYP2J2
71

CYP3A5
446

CYP3A7
109

P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1932
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
810
 major
yes (co-administration study)
Comment: When administered with efavirenz, 125%, 78%, 80%, and 42.15% increase in the Tmax, Cmax AUCT and T1/2 of amodiaquine respectively
CYP1A1
389
 minor
CYP1A2
1197
 minor
CYP1B1
104
 minor
CYP2C18
149
 minor
CYP2D6
1388
 minor
CYP2J2
71
 minor
CYP3A4
1946
 minor
CYP3A5
446
 minor
CYP2B6
776
 no
CYP2C19
1119
 no
CYP2E1
729
 no
CYP3A7
109
 no
P-gp
2052
 no
CYP2A6
626
 unlikely
unlikely
Comment: Since artesunate is mainly metabolized by CYP2A6, drug–drug interaction between artesunate and AQ is unlikely to occur
CYP2C9
1193
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:2674
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2674
ChemicalBook
CB8344720
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8344720
eMolecules
27516205
https://www.emolecules.com/cgi-bin/more?vid=27516205
eMolecules
30334305
https://www.emolecules.com/cgi-bin/more?vid=30334305
eMolecules
901375
https://www.emolecules.com/cgi-bin/more?vid=901375
MolPort
MolPort-000-728-509
https://www.molport.com/shop/molecule-link/MolPort-000-728-509
MolPort
MolPort-001-924-563
https://www.molport.com/shop/molecule-link/MolPort-001-924-563
ZINC
ZINC000000608172
http://zinc15.docking.org/substances/ZINC000000608172
PubMed

PubMed

TitleDatePubMed
[National Network study to perpetuate the surveillance of Plasmodium falciparum sensitivity to antimalarials in Madagascar].
2002
[Treatment of malaria in children: 1. Uncomplicated malaria].
2002
In vitro sensitivity of Plasmodium falciparum to amodiaquine compared with other major antimalarials in Madagascar.
2002 Dec
Sulfadoxine/pyrimethamine alone or with amodiaquine or artesunate for treatment of uncomplicated malaria: a longitudinal randomised trial.
2002 Dec 21-28
Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum must be delayed in Africa.
2002 Jul
The safety and efficacy of sulfadoxine-pyrimethamine, amodiaquine, and their combination in the treatment of uncomplicated Plasmodium falciparum malaria.
2002 Jul
Molecular epidemiology of malaria in Cameroon. X. Evaluation of PFMDR1 mutations as genetic markers for resistance to amino alcohols and artemisinin derivatives.
2002 Jun
Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells.
2002 Nov
Efficacy of amodiaquine for uncomplicated Plasmodium falciparum malaria in Harper, Liberia.
2002 Nov-Dec
Paracellular tightness and catabolism restrict histamine permeation in the proximal colon of pigs.
2002 Oct
Molecular characterisation of drug-resistant Plasmodium falciparum from Thailand.
2002 Oct 14
Chloroquine resistance in Plasmodium falciparum malaria parasites conferred by pfcrt mutations.
2002 Oct 4
The effects of chloroquine, amodiaquine and chloroquine plus chlorpheniramine on the disposition kinetics of the hepatomegaly associated with acute, uncomplicated, Plasmodium falciparum malaria in children.
2002 Sep
Monitoring the drug-sensitivity of Plasmodium falciparum in coastal towns in Madagascar by use of in vitro chemosensitivity and mutation detection tests.
2002 Sep
Amodiaquine for treating malaria.
2003
Evaluation of the quality of amodiaquine and sulphadoxine/pyrimethamine tablets sold by private wholesale pharmacies in Dar Es Salaam Tanzania.
2003 Apr
Antibody responses to Plasmodium falciparum merozoite surface protein-1 and efficacy of amodiaquine in Gabonese children with P. falciparum malaria.
2003 Apr 1
Questions about the antimalarial amodiaquine.
2003 Apr 5
Atovaquone and proguanil versus amodiaquine for the treatment of Plasmodium falciparum malaria in African infants and young children.
2003 Dec 1
Distinguishing recrudescence from reinfection in a longitudinal antimalarial drug efficacy study: comparison of results based on genotyping of msp-1, msp-2, and glurp.
2003 Feb
Comparative efficacy of aminoquinoline-antifolate combinations for the treatment of uncomplicated falciparum malaria in Kampala, Uganda.
2003 Feb
Epidemiological models for the spread of anti-malarial resistance.
2003 Feb 19
High-performance liquid chromatographic method for determination of amodiaquine, chloroquine and their monodesethyl metabolites in biological samples.
2003 Jan 15
Efficacy of amodiaquine alone and combined with sulfadoxine-pyrimethamine and of sulfadoxine pyrimethamine combined with artesunate.
2003 Jun
Safety, efficacy and determinants of effectiveness of antimalarial drugs during pregnancy: implications for prevention programmes in Plasmodium falciparum-endemic sub-Saharan Africa.
2003 Jun
A randomized comparison of chloroquine and chloroquine plus ketotifen in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children.
2003 Mar
[Efficacy of amodiaquine and sulfadoxine/pyrimethamine in the treatment of malaria not complicated by Plasmodium falciparum in Nariño, Colombia, 1999-2002].
2003 Mar
Conductometric and indirect AAS determination of antimalarials.
2003 Mar 26
Chloroquine, sulfadoxine-pyrimethamine and amodiaquine efficacy for the treatment of uncomplicated Plasmodium falciparum malaria in Upper Nile, south Sudan.
2003 Mar-Apr
Effect of intermittent treatment with amodiaquine on anaemia and malarial fevers in infants in Tanzania: a randomised placebo-controlled trial.
2003 May 31
Vendor-to-vendor education to improve malaria treatment by private drug outlets in Bungoma District, Kenya.
2003 May 7
Polymorphism in two merozoite surface proteins of Plasmodium falciparum isolates from Gabon.
2003 May 9
Isoquine and related amodiaquine analogues: a new generation of improved 4-aminoquinoline antimalarials.
2003 Nov 6
Amodiaquine treatment of uncomplicated malaria in children, in an area of chloroquine-resistant Plasmodium falciparum in north-central Nigeria.
2003 Oct
The efficacy of antimalarial monotherapies, sulphadoxine-pyrimethamine and amodiaquine in East Africa: implications for sub-regional policy.
2003 Oct
Prevention of increasing rates of treatment failure by combining sulfadoxine-pyrimethamine with artesunate or amodiaquine for the sequential treatment of malaria.
2003 Oct 15
Rapid clearance of Plasmodium falciparum hyperparasitaemia after oral amodiaquine treatment in patients with uncomplicated malaria.
2003 Sep
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.
2003 Sep
Polymorphism in the Plasmodium falciparum chloroquine-resistance transporter protein links verapamil enhancement of chloroquine sensitivity with the clinical efficacy of amodiaquine.
2003 Sep 19
Drug resistant falciparum malaria and the use of artesunate-based combinations: focus on clinical trials sponsored by TDR.
2003 Sep-Dec
[Pyrido [3,2-b]indol-4-yl-amines--synthesis and investigation of activity against malaria].
2004 Apr
In vitro efficacy of antimalarial drugs against Plasmodium vivax on the western border of Thailand.
2004 Apr
Antimalarial efficacy of sulfadoxine-pyrimethamine, amodiaquine and a combination of chloroquine plus sulfadoxine-pyrimethamine in Bundi Bugyo, western Uganda.
2004 Apr
Malaria intermittent preventive treatment in infants, chemoprophylaxis, and childhood vaccinations.
2004 Apr 24
Efficacy of sulphadoxine-pyrimethamine alone or combined with amodiaquine or chloroquine for the treatment of uncomplicated falciparum malaria in Ugandan children.
2004 Feb
Efficacy of chloroquine, amodiaquine, sulphadoxine-pyrimethamine and combination therapy with artesunate in Mozambican children with non-complicated malaria.
2004 Feb
Effects of solvent composition and ionic strength on the interaction of quinoline antimalarials with ferriprotoporphyrin IX.
2004 Jan
Selective and sensitive liquid chromatographic assay of amodiaquine and desethylamodiaquine in whole blood spotted on filter paper.
2004 Jan 5
Efficacy of pyrimethamine-sulfadoxine in young children with uncomplicated falciparum malaria in rural Burkina Faso.
2004 May 11
A new method for detection of pfmdr1 mutations in Plasmodium falciparum DNA using real-time PCR.
2004 May 7
Patents

Patents

20010044416
23
20020012680
29

Sample Use Guides

In Vivo Use Guide
For the treatment of acute malarial attacks in non-immune subjects: 600 mg of the base, followed by 200 mg after 6 hours, then 400 mg daily on each of the subsequent two days. Doses may be taken with meals to lessen gastric upset.
Route of Administration: Oral
In Vitro Use Guide
The FCR3 strain of Plasmodium falciparum was synchronized and cultivated to the trophozoite stage. Synchronized cultures were seeded at the ring stage and allowed to grow for another 20 hr until most parasites reached the trophozoite stage; parasitemia and cell number were determined, and cultures were cultured 6 drug for 1,2,3 and 4 h. One milliliter of culture was washed twice in wash medium (culture medium without plasma, 37°) to remove the drug, and cells were seeded in 24-well culture plates in full culture medium supplemented with 5 mCi/mL of [3H]hypoxanthine. After 4 hr of further cultivation, triplicate samples were transferred into 96-well plates, and parasiteassociated radioactivity was determined using the Filtermate/Matrix 96 Direct Beta counter. Inhibition of parasite growth was calculated compared to untreated controls.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:11:25 GMT 2025
Edited
by admin
on Mon Mar 31 18:11:25 GMT 2025
Record UNII
HOE64181MP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMODIAQUINE HYDROCHLORIDE ANHYDROUS
Common Name English
O-CRESOL, 4-((7-CHLORO-4-QUINOLYL)AMINO)-.ALPHA.-(DIETHYLAMINO)-, DIHYDROCHLORIDE ANHYDROUS
Preferred Name English
AMODIAQUINE DIHYDROCHLORIDE, ANHYDROUS
Common Name English
PHENOL, 4-((7-CHLORO-4-QUINOLINYL)AMINO)-2-((DIETHYLAMINO)METHYL)-, DIHYDROCHLORIDE
Common Name English
4-((7-CHLORO-4-QUINOLYL)AMINO)-.ALPHA.-(DIETHYLAMINO)-O-CRESOL DIHYDROCHLORIDE
Common Name English
AMODIAQUINE DIHYDROCHLORIDE ANHYDROUS
Common Name English
Code System Code Type Description
SMS_ID
100000085160
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
PUBCHEM
6246
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-706-0
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID20219036
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
FDA UNII
HOE64181MP
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
CAS
69-44-3
Created by admin on Mon Mar 31 18:11:25 GMT 2025 , Edited by admin on Mon Mar 31 18:11:25 GMT 2025
PRIMARY
Related Record Type Details
Structure of AMODIAQUINE HYDROCHLORIDE
SOLVATE->ANHYDROUS
Structure of AMODIAQUINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of AMODIAQUINE
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