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

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
2554
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
102
Targets

Targets

Primary TargetPharmacologyConditionPotency
Heme degradation by glutathione
3
Target ID: Heme degradation by glutathione
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
1737
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1461
CYP2C8
693

CYP1A1
349

CYP1A2
1054

CYP1B1
92

CYP2A6
543

CYP2B6
664

CYP2C18
138

CYP2C19
991

CYP2E1
667

CYP2J2
56

CYP3A5
395

CYP3A7
110

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1650
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2C8
693
 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
349
 minor
CYP1A2
1054
 minor
CYP1B1
92
 minor
CYP2C18
138
 minor
CYP2D6
1217
 minor
CYP2J2
56
 minor
CYP3A4
1737
 minor
CYP3A5
395
 minor
CYP2B6
664
 no
CYP2C19
991
 no
CYP2E1
667
 no
CYP3A7
110
 no
P-gp
1537
 no
CYP2A6
543
 unlikely
unlikely
Comment: Since artesunate is mainly metabolized by CYP2A6, drug–drug interaction between artesunate and AQ is unlikely to occur
CYP2C9
1037
 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
[Evaluation of efficacy and tolerance of amodiaquine versus chloroquine in the treatment of uncomplicated malaria outbreak in children of Gabon].
2001 Aug
Synthesis and in vitro and in vivo antimalarial activity of new 4-anilinoquinolines.
2001 Aug 16
[Resistance of Plasmodium falciparum to 3 antimalarials in Turbo (Antioquia, Colombia), 1998].
2001 Jan
Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance.
2001 Jan-Feb
Antimalarial drugs exacerbate rat liver microsomal lipid peroxidation in the presence of oxidants.
2001 Jun
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
[Treatment of malaria in children: 1. Uncomplicated malaria].
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
[In vivo sensitivity of Plasmodium falciparum to amino-4-quinolines and sulfadoxine pyrimethamine in Agou (Ivory Coast)].
2002 Apr
Amodiaquine-artesunate versus amodiaquine for uncomplicated Plasmodium falciparum malaria in African children: a randomised, multicentre trial.
2002 Apr 20
Inhibition of P. falciparum by steroids isolated from Solanum nudum.
2002 Feb
Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate.
2002 Feb
[Management of child fever in the battle against malaria in Brazzaville].
2002 Mar
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
Evaluation of the quality of amodiaquine and sulphadoxine/pyrimethamine tablets sold by private wholesale pharmacies in Dar Es Salaam Tanzania.
2003 Apr
Questions about the antimalarial amodiaquine.
2003 Apr 5
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
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
The efficacy of antimalarial monotherapies, sulphadoxine-pyrimethamine and amodiaquine in East Africa: implications for sub-regional policy.
2003 Oct
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
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
Antimalarial efficacy of sulfadoxine-pyrimethamine, amodiaquine and a combination of chloroquine plus sulfadoxine-pyrimethamine in Bundi Bugyo, western Uganda.
2004 Apr
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
32

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.
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]-α-(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 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
LIVERTOX NBK548404
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
NCI_THESAURUS C271
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
WHO-ATC P01BA06
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (ART/AMO)
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
WHO-ATC P01BF03
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
Code System Code Type Description
MESH
D000655
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PRIMARY
ECHA (EC/EINECS)
201-669-3
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PRIMARY
CHEBI
2674
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PRIMARY
EVMPD
SUB05470MIG
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
NSC
13453
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
AMODIAQUINE
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
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 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
DRUG BANK
DB00613
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
ChEMBL
CHEMBL682
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PRIMARY
FDA UNII
220236ED28
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
NCI_THESAURUS
C65231
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022597
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
SMS_ID
100000089876
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
DRUG CENTRAL
186
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
RXCUI
720
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY RxNorm
INN
1116
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
HSDB
7457
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
MERCK INDEX
m1839
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
AMODIAQUINE
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
CAS
86-42-0
Created by admin on Fri Dec 15 14:59:18 GMT 2023 , Edited by admin on Fri Dec 15 14:59:18 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of AMODIAQUINE
METABOLITE ACTIVE (PARENT)
Structure of DESETHYLAMODIAQUINE
SALT/SOLVATE (PARENT)
Structure of AMODIAQUINE HYDROCHLORIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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