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

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

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
[Developments in anti-malaria agents: chemical data, structure-activity relationships].
2001 Apr
Amodiaquine, sulfadoxine/pyrimethamine, and combination therapy for treatment of uncomplicated falciparum malaria in Kampala, Uganda: a randomised trial.
2001 Aug 4
Cardiac effects of amodiaquine and sulfadoxine-pyrimethamine in malaria-infected African patients.
2001 Dec
Evaluation under field conditions of the colourimetric DELI-microtest for the assessment of Plasmodium falciparum drug resistance.
2001 Jan-Feb
Plasmodium falciparum in Kenya: high prevalence of drug-resistance-associated polymorphisms in hospital admissions with severe malaria in an epidemic area.
2001 Oct
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.
2002
[Which medication should be used to treat uncomplicated malaria when chloroquine becomes ineffective in Western Côte d'Ivoire?].
2002
A randomized comparison of chloroquine, amodiaquine and their combination with pyrimethamine-sulfadoxine in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children.
2002 Apr
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.
2002 Apr
In vitro sensitivity of Plasmodium falciparum to amodiaquine compared with other major antimalarials in Madagascar.
2002 Dec
Clinical status and implications of antimalarial drug resistance.
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
Differential effects of 4-aminoquinoline-containing antimalarial drugs on hemoglobin digestion in Plasmodium falciparum-infected erythrocytes.
2002 Feb 1
The safety and efficacy of sulfadoxine-pyrimethamine, amodiaquine, and their combination in the treatment of uncomplicated Plasmodium falciparum malaria.
2002 Jul
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter.
2002 Jun
Molecular characterisation of drug-resistant Plasmodium falciparum from Thailand.
2002 Oct 14
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
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
Polymorphism in two merozoite surface proteins of Plasmodium falciparum isolates from Gabon.
2003 May 9
The efficacy of antimalarial monotherapies, sulphadoxine-pyrimethamine and amodiaquine in East Africa: implications for sub-regional policy.
2003 Oct
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
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 HYDROCHLORIDE ANHYDROUS
Common Name English
AMODIAQUINE DIHYDROCHLORIDE, ANHYDROUS
Common Name English
PHENOL, 4-((7-CHLORO-4-QUINOLINYL)AMINO)-2-((DIETHYLAMINO)METHYL)-, DIHYDROCHLORIDE
Common Name English
O-CRESOL, 4-((7-CHLORO-4-QUINOLYL)AMINO)-.ALPHA.-(DIETHYLAMINO)-, DIHYDROCHLORIDE ANHYDROUS
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
PUBCHEM
6246
Created by admin on Fri Dec 15 15:52:03 GMT 2023 , Edited by admin on Fri Dec 15 15:52:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-706-0
Created by admin on Fri Dec 15 15:52:03 GMT 2023 , Edited by admin on Fri Dec 15 15:52:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID20219036
Created by admin on Fri Dec 15 15:52:03 GMT 2023 , Edited by admin on Fri Dec 15 15:52:03 GMT 2023
PRIMARY
FDA UNII
HOE64181MP
Created by admin on Fri Dec 15 15:52:03 GMT 2023 , Edited by admin on Fri Dec 15 15:52:03 GMT 2023
PRIMARY
CAS
69-44-3
Created by admin on Fri Dec 15 15:52:03 GMT 2023 , Edited by admin on Fri Dec 15 15:52:03 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of AMODIAQUINE
NIH
NCATS
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