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

Details

Stereochemistry ACHIRAL
Molecular Formula C20H22ClN3O
Molecular Weight 355.8619
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMODIAQUINE

SMILES

CCN(CC)Cc1cc(ccc1O)Nc2ccnc3cc(ccc23)Cl

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 355.8619
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
2364
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
72
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Heme degradation by glutathione
Inhibitor
7709
Target ID: Heme polymerization
Inhibitor
7709
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8003
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
1603
substrate
944
substrate
1116

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1344
CYP2C8
645

CYP1A1
323

CYP1A2
971

CYP1B1
88

CYP2A6
482

CYP2B6
616

CYP2C18
143

CYP2C19
911

CYP2E1
604

CYP2J2
52

CYP3A5
372

CYP3A7
109

P-gp
1399
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1519
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
645
 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
323
 minor
CYP1A2
971
 minor
CYP1B1
88
 minor
CYP2C18
143
 minor
CYP2D6
1116
 minor
CYP2J2
52
 minor
CYP3A4
1603
 minor
CYP3A5
372
 minor
CYP2B6
616
 no
CYP2C19
911
 no
CYP2E1
604
 no
CYP3A7
109
 no
P-gp
1399
 no
CYP2A6
482
 unlikely
unlikely
Comment: Since artesunate is mainly metabolized by CYP2A6, drug–drug interaction between artesunate and AQ is unlikely to occur
CYP2C9
944
 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
[Developments in anti-malaria agents: chemical data, structure-activity relationships].
2001 Apr
Ferrocene-chloroquine analogues as antimalarial agents: in vitro activity of ferrochloroquine against 103 Gabonese isolates of Plasmodium falciparum.
2001 Aug
Amodiaquine, sulfadoxine/pyrimethamine, and combination therapy for treatment of uncomplicated falciparum malaria in Kampala, Uganda: a randomised trial.
2001 Aug 4
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.
2001 Jan
Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance.
2001 Jan-Feb
Improved assay method for the determination of pyronaridine in plasma and whole blood by high-performance liquid chromatography for application to clinical pharmacokinetic studies.
2001 Mar 5
[National Network study to perpetuate the surveillance of Plasmodium falciparum sensitivity to antimalarials in Madagascar].
2002
[Center of multidrug-resistant malaria in a forest zone of Cameroon revisited after 14 years].
2002
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.
2002
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.
2002 Apr
Molecular epidemiology of malaria in cameroon. IX. Characteristics of recrudescent and persistent Plasmodium falciparum infections after chloroquine or amodiaquine treatment in children.
2002 Feb
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
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
Glutathione is involved in the antimalarial action of chloroquine and its modulation affects drug sensitivity of human and murine species of Plasmodium.
2003
Antibody responses to Plasmodium falciparum merozoite surface protein-1 and efficacy of amodiaquine in Gabonese children with P. falciparum malaria.
2003 Apr 1
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
Epidemiological models for the spread of anti-malarial resistance.
2003 Feb 19
Safety, efficacy and determinants of effectiveness of antimalarial drugs during pregnancy: implications for prevention programmes in Plasmodium falciparum-endemic sub-Saharan Africa.
2003 Jun
[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
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
Prevention of increasing rates of treatment failure by combining sulfadoxine-pyrimethamine with artesunate or amodiaquine for the sequential treatment of malaria.
2003 Oct 15
Polymorphism in the Plasmodium falciparum chloroquine-resistance transporter protein links verapamil enhancement of chloroquine sensitivity with the clinical efficacy of amodiaquine.
2003 Sep 19
[Pyrido [3,2-b]indol-4-yl-amines--synthesis and investigation of activity against malaria].
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
Human liver aldehyde oxidase: inhibition by 239 drugs.
2004 Jan
Efficacy of pyrimethamine-sulfadoxine in young children with uncomplicated falciparum malaria in rural Burkina Faso.
2004 May 11
Patents

Patents

20010044416
22
20020012680
28

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 Jun 25 20:56:40 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:40 UTC 2021
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 [USP]
Common Name English
AMODIAQUINE [WHO-IP]
Common Name English
AMODIAQUINE [USP MONOGRAPH]
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
4-((7-CHLORO-4-QUINOLYL)AMINO)-.ALPHA.-(DIETHYLAMINO)-O-CRESOL
Common Name English
SUNOQUINE
Common Name English
AMODIAQUINE [WHO-DD]
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 Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
LIVERTOX 47
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NCI_THESAURUS C271
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WHO-ATC P01BA06
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (ART/AMO)
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
WHO-ATC P01BF03
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
Code System Code Type Description
MESH
D000655
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PRIMARY
ECHA (EC/EINECS)
201-669-3
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PRIMARY
EVMPD
SUB05470MIG
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
AMODIAQUINE
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
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 Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY
DRUG BANK
DB00613
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PRIMARY
ChEMBL
CHEMBL682
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PRIMARY
FDA UNII
220236ED28
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PRIMARY
NCI_THESAURUS
C65231
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY
EPA CompTox
86-42-0
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PRIMARY
DRUG CENTRAL
186
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PRIMARY
RXCUI
720
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY RxNorm
INN
1116
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY
HSDB
7457
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY
MERCK INDEX
M1839
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
AMODIAQUINE
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY
CAS
86-42-0
Created by admin on Fri Jun 25 20:56:40 UTC 2021 , Edited by admin on Fri Jun 25 20:56:40 UTC 2021
PRIMARY
Related Record Type Details
ALDEHYDE OXIDASE
METABOLIC ENZYME -> INHIBITOR
IC50
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
Structure of AMODIAQUINE HYDROCHLORIDE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of AMODIAQUINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BENZALDEHYDE, 5-((7-CHLORO-4-QUINOLINYL)AMINO)-2-HYDROXY-, O-METHYLOXIME
METABOLITE -> PARENT
Related Record Type Details
Structure of AMODIAQUINE
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