U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H22ClN3O
Molecular Weight 355.861
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMODIAQUINE

SMILES

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

InChI

InChIKey=OVCDSSHSILBFBN-UHFFFAOYSA-N
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)

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

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
2432
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
92
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Heme degradation by glutathione
Inhibitor
8146
Target ID: Heme polymerization
Inhibitor
8146
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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
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
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
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
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
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
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
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
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
Doses

Doses

DosePopulationAdverse events​
73.4 mg 1 times / day multiple, oral (mean)
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
n = 7
Health Status: unhealthy
Condition: malaria
Age Group: 17 to 76 years
Sex: M+F
Population Size: 7
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
n = 15
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 15
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/
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
n = 7
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 7
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
Co-administed with::
artesunate(4 mg/kg; single dose)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
n = 8
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 8
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
n = 8
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 8
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/
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
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
n = 220
Health Status: unhealthy
Condition: malaria
Age Group: median age 20 years
Sex: F
Population Size: 220
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 (mean)
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
n = 2
Health Status: unhealthy
Condition: malaria
Age Group: median age 35 years
Sex: M+F
Population Size: 2
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 (mean)
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
n = 7
Health Status: unhealthy
Condition: malaria
Age Group: 17 to 76 years
Sex: M+F
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
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
n = 15
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 15
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
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
n = 7
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 7
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
n = 7
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 7
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
Co-administed with::
artesunate(4 mg/kg; single dose)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
healthy, 18 to 45 years
n = 8
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 8
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
n = 8
Health Status: healthy
Age Group: 18 to 45 years
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/18415093/
Constipation 10%
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Diarrhoea 15%
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Granulocytopenia 15%
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Nausea 35%
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Vomiting 35%
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
Lassitude grade 2, 60%
45 mg/kg multiple, oral (mean)
Studied dose
Dose: 45 mg/kg
Route: oral
Route: multiple
Dose: 45 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/6761007/
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: onchocerciasis
Age Group: adult
Sex: M
Population Size: 20
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
n = 220
Health Status: unhealthy
Condition: malaria
Age Group: median age 20 years
Sex: F
Population Size: 220
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
n = 220
Health Status: unhealthy
Condition: malaria
Age Group: median age 20 years
Sex: F
Population Size: 220
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
n = 220
Health Status: unhealthy
Condition: malaria
Age Group: median age 20 years
Sex: F
Population Size: 220
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
n = 220
Health Status: unhealthy
Condition: malaria
Age Group: median age 20 years
Sex: F
Population Size: 220
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
n = 220
Health Status: unhealthy
Condition: malaria
Age Group: median age 20 years
Sex: F
Population Size: 220
Sources:
https://pubmed.ncbi.nlm.nih.gov/17046467/
Hepatotoxicity
71.6 mg 1 times / day multiple, oral (mean)
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
n = 2
Health Status: unhealthy
Condition: malaria
Age Group: median age 35 years
Sex: M+F
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/3082410/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1670
substrate
985
substrate
1168

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1401
CYP2C8
670

CYP1A1
344

CYP1A2
1013

CYP1B1
90

CYP2A6
510

CYP2B6
648

CYP2C18
138

CYP2C19
955

CYP2E1
633

CYP2J2
54

CYP3A5
383

CYP3A7
110

P-gp
1491
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1588
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
670
 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
344
 minor
CYP1A2
1013
 minor
CYP1B1
90
 minor
CYP2C18
138
 minor
CYP2D6
1168
 minor
CYP2J2
54
 minor
CYP3A4
1670
 minor
CYP3A5
383
 minor
CYP2B6
648
 no
CYP2C19
955
 no
CYP2E1
633
 no
CYP3A7
110
 no
P-gp
1491
 no
CYP2A6
510
 unlikely
unlikely
Comment: Since artesunate is mainly metabolized by CYP2A6, drug–drug interaction between artesunate and AQ is unlikely to occur
CYP2C9
985
 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
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
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
PubMed

PubMed

TitleDatePubMed
In vitro sensitivity of Plasmodium falciparum to amodiaquine compared with other major antimalarials in Madagascar.
2002 Dec
Glutathione is involved in the antimalarial action of chloroquine and its modulation affects drug sensitivity of human and murine species of Plasmodium.
2003
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
Molecular epidemiology of malaria in Cameroon. XV. Experimental studies on serum substitutes and supplements and alternative culture media for in vitro drug sensitivity assays using fresh isolates of Plasmodium falciparum.
2003 Aug
Short report: association between chloroquine and amodiaquine resistance and allelic variation in the Plasmodium falciparum multiple drug resistance 1 gene and the chloroquine resistance transporter gene in isolates from the upper Nile in southern Sudan.
2003 Aug
Chloroquine efficacy in the treatment of uncomplicated malaria at three sentinel sites in northern Togo.
2003 Dec
Atovaquone and proguanil versus amodiaquine for the treatment of Plasmodium falciparum malaria in African infants and young children.
2003 Dec 1
Epidemiological models for the spread of anti-malarial resistance.
2003 Feb 19
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
[Misunderstood neurological side effects of amodiaquine: apropos of 35 cases in children at Central University Hospital of Yopougon at Abidjan, Côte d' Ivoire].
2003 Nov
Antimalarial compounds: from bench to bedside.
2003 Nov
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
Plasmodium falciparum gametocytaemia in Nigerian children: before, during and after treatment with antimalarial drugs.
2003 Sep
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
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.
2003 Sep 1
Potentiation of the antimalarial action of chloroquine in rodent malaria by drugs known to reduce cellular glutathione levels.
2003 Sep 1
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
Antimalarial drug toxicity: a review.
2004
[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
A randomized trial of amodiaquine and artesunate alone and in combination for the treatment of uncomplicated falciparum malaria in children from Burkina Faso.
2004 Apr
Can amodiaquine be used safely during pregnancy?
2004 Apr
Malaria intermittent preventive treatment in infants, chemoprophylaxis, and childhood vaccinations.
2004 Apr 24
Liquid chromatographic determination of amodiaquine in human plasma.
2004 Apr 25
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
Human liver aldehyde oxidase: inhibition by 239 drugs.
2004 Jan
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
Developing artemisinin based drug combinations for the treatment of drug resistant falciparum malaria: A review.
2004 Jan-Mar
Molecular analysis of Plasmodium falciparum from drug treatment failure patients in Papua New Guinea.
2004 Mar
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 Fri Dec 16 15:50:49 UTC 2022
Edited
by admin
on Fri Dec 16 15:50:49 UTC 2022
Record UNII
220236ED28
Record Status Validated (UNII)
Record Version
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Name Type Language
AMODIAQUINE
HSDB   INN   MART.   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
AMODIAQUINE [WHO-IP]
Common Name English
AMODIAQUINE [USP MONOGRAPH]
Common Name English
Amodiaquine [WHO-DD]
Common Name English
AMODIAQUIN [MI]
Common Name English
AMODIAQUINE [HSDB]
Common Name English
PHENOL, 4-((7-CHLORO-4-QUINOLINYL)AMINO)-2-((DIETHYLAMINO)METHYL)-
Systematic Name English
AMODIAQUINE [VANDF]
Common Name English
amodiaquine [INN]
Common Name English
AMODIAQUINUM [WHO-IP LATIN]
Common Name English
NSC-13453
Code English
AMODIAQUINE [USP IMPURITY]
Common Name English
4-[(7-Chloro-4-quinolyl)amino]-?-(diethylamino)-O-cresol
Common Name English
SUNOQUINE
Common Name English
AMODIAQUINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
LIVERTOX NBK548404
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
NCI_THESAURUS C271
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
WHO-ATC P01BA06
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (ART/AMO)
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
WHO-ATC P01BF03
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
Code System Code Type Description
MESH
D000655
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
ECHA (EC/EINECS)
201-669-3
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
CHEBI
2674
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
EVMPD
SUB05470MIG
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
NSC
13453
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
AMODIAQUINE
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY Description: A yellow, crystalline powder; odourless. Solubility: Practically insoluble in water. Category: Antimalarial drug. Storage: Amodiaquine should be kept in a tightly closed container. Definition: Amodiaquine contains not less than 97.0% and not more than 103.0% of C20H22ClN3O, calculated with reference to the anhydrous substance.
PUBCHEM
2165
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
DRUG BANK
DB00613
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
ChEMBL
CHEMBL682
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PRIMARY
FDA UNII
220236ED28
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
NCI_THESAURUS
C65231
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
DAILYMED
220236ED28
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
EPA CompTox
DTXSID2022597
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
DRUG CENTRAL
186
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
RXCUI
720
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY RxNorm
INN
1116
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
HSDB
7457
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
MERCK INDEX
M1839
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY Merck Index
WIKIPEDIA
AMODIAQUINE
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
CAS
86-42-0
Created by admin on Fri Dec 16 15:50:49 UTC 2022 , Edited by admin on Fri Dec 16 15:50:49 UTC 2022
PRIMARY
Related Record Type Details
ALDEHYDE OXIDASE
METABOLIC ENZYME -> INHIBITOR
IC50
Structure of AMODIAQUINE HYDROCHLORIDE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of AMODIAQUINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of BENZALDEHYDE, 5-((7-CHLORO-4-QUINOLINYL)AMINO)-2-HYDROXY-, O-METHYLOXIME
METABOLITE -> PARENT
Structure of 4-((7-CHLORANYLQUINOLIN-4-YL)AMINO)-2-(ETHYLAMINOMETHYL)PHENOL
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of AMODIAQUINE
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