Drug/Small Molecule:
amodiaquine

PharmGKB contains no dosing guidelines for this drug/small molecule. To report known genotype-based dosing guidelines, or if you are interested in developing guidelines, click here.

PharmGKB has no annotated drug labels with pharmacogenomic information for this drug/small molecule. If you know of a drug label with PGx, send us a message.

PharmGKB contains no Clinical Variants that meet the highest level of criteria.

To see more Clinical Variants with lower levels of criteria, click the button at the bottom of the page.

Disclaimer: The PharmGKB's clinical annotations reflect expert consensus based on clinical evidence and peer-reviewed literature available at the time they are written and are intended only to assist clinicians in decision-making and to identify questions for further research. New evidence may have emerged since the time an annotation was submitted to the PharmGKB. The annotations are limited in scope and are not applicable to interventions or diseases that are not specifically identified.

The annotations do not account for individual variations among patients, and cannot be considered inclusive of all proper methods of care or exclusive of other treatments. It remains the responsibility of the health-care provider to determine the best course of treatment for a patient. Adherence to any guideline is voluntary, with the ultimate determination regarding its application to be made solely by the clinician and the patient. PharmGKB assumes no responsibility for any injury or damage to persons or property arising out of or related to any use of the PharmGKB clinical annotations, or for any errors or omissions.

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This is a non-comprehensive list of genetic tests with pharmacogenetics relevance, typically submitted by the manufacturer and manually curated by PharmGKB. The information listed is provided for educational purposes only and does not constitute an endorsement of any listed test or manufacturer.

A more complete listing of genetic tests is found at the Genetic Testing Registry (GTR).

PGx Test Variants Assayed Gene?

The table below contains information about pharmacogenomic variants on PharmGKB. Please follow the link in the "Variant" column for more information about a particular variant. Each link in the "Variant" column leads to the corresponding PharmGKB Variant Page. The Variant Page contains summary data, including PharmGKB manually curated information about variant-drug pairs based on individual PubMed publications. The PMIDs for these PubMed publications can be found on the Variant Page.

The tags in the first column of the table indicate what type of information can be found on the corresponding Variant Page.

Links in the "Gene" column lead to PharmGKB Gene Pages.

Gene ? Variant?
(138)
Alternate Names / Tag SNPs ? Drugs ? Alleles ?
(+ chr strand)
Function ? Amino Acid?
Translation
VIP No VIP available VA CYP2C8 *2 N/A N/A N/A
VIP No VIP available VA CYP2C8 *3 N/A N/A N/A
No VIP available CA VA
rs1050828 153764217C>T, 16571G>A, 202G>A, 292G>A, 4682155C>T, Asahi, G6PD:202G>A, Val68Met, Val98Met
C > T
Not Available
Val68Met
rs10509681 1196A>G, 35506A>G, 47603213T>C, 890A>G, 96798749T>C, 986A>G, A1196G, CYP2C8*3, CYP2C8: K399R, Lys297Arg, Lys329Arg, Lys399Arg
T > C
Missense
Lys329Arg
rs11572080 110G>A, 206G>A, 416G>A, 47631494C>T, 7225G>A, 96827030C>T, Arg139Lys, Arg37Lys, Arg69Lys, CYP2C8*3, CYP2C8: R139K, G416A, R139K, rs11572080 G>A
C > T
Missense
Arg69Lys
rs11572103 16149A>T, 47622570T>A, 499A>T, 595A>T, 805A>T, 96818106T>A, A805T, CYP2C8*2, CYP2C8: I269F, Ile167Phe, Ile199Phe, Ile269Phe
T > A
Missense
Ile199Phe
Alleles, Functions, and Amino Acid Translations are all sourced from dbSNP 138
2D structure from PubChem
provided by PubChem

Overview

Generic Names
  • Amodiaquin
  • Amodiaquine USP24
  • Amodiaquine, ring-closed
  • amodiaquine hydrochloride
Trade Names
  • Basoquin
  • CAM-AQ1
  • CAM-AQI
  • Camochin
  • Camoquin
  • Camoquin HCL
  • Camoquinal
  • Camoquine
  • Flavoquin
  • Flavoquine
  • Miaquin
Brand Mixture Names
  • Camoprima Infatabs (amodiaquine + primaquine)

PharmGKB Accession Id:
PA448404

Description

A 4-aminoquinoquinoline compound with anti-inflammatory properties.

Source: Drug Bank

Indication

For treatment of acute malarial attacks in non-immune subjects.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

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.

Source: Drug Bank

Pharmacology

Amodiaquine, a 4-aminoquinoline similar to chloroquine in structure and activity, has been used as both an antimalarial and an anti-inflammatory agent for more than 40 years. Amodiaquine is at least as effective as chloroquine, and is effective against some chloroquine-resistant strains, although resistance to amodiaquine has been reported. The mode of action of amodiaquine has not yet been determined. 4-Aminoquinolines depress cardiac muscle, impair cardiac conductivity, and produce vasodilatation with resultant hypotension. They depress respiration and cause diplopia, dizziness and nausea.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic biotransformation to desethylamodiaquine (the principal biologically active metabolite) is the predominant route of amodiaquine clearance with such a considerable first pass effect that very little orally administered amodiaquine escapes untransformed into the systemic circulation.

Source: Drug Bank

Absorption

Rapidly absorbed following oral administration.

Source: Drug Bank

Half-Life

5.2 +/- 1.7 (range 0.4 to 5.5) minutes

Source: Drug Bank

Toxicity

LD 50 (mouse, intraperitoneal) 225 mg/kg, LD 50 (mouse, oral) 550 mg/kg. Symptoms of overdose include headache, drowsiness, visual disturbances, vomiting, hypokalaemia, cardiovascular collapse and cardiac and respiratory arrest. Hypotension, if not treated, may progress rapidly to shock. Electrocardiograms (ECG) may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, broadening of the QRS complex, and progressive bradycardia leading to ventricular fibrillation and/or arrest.

Source: Drug Bank

Chemical Properties

Chemical Formula

C20H22ClN3O

Source: Drug Bank

Isomeric SMILES

CCN(CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O

Source: Drug Bank

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

Source: Drug Bank

Canonical SMILES

CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1

Source: Drug Bank

Average Molecular Weight

355.861

Source: Drug Bank

Monoisotopic Molecular Weight

355.145140048

Source: Drug Bank

PharmGKB Curated Pathways

Pathways created internally by PharmGKB based primarily on literature evidence.

External Pathways

Links to non-PharmGKB pathways.

PharmGKB contains no links to external pathways for this drug. To report a pathway, click here.

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

EvidenceGene
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available PW
CYP1A1
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available PW
CYP1B1
CYP2C8
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
G6PD

Drug Targets

Gene Description
HBA1 (source: Drug Bank)
HNMT (source: Drug Bank)
No related drugs are available.

Curated Information ?

EvidenceDisease
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
Malaria
No Dosing Guideline available No Drug Label available CA No Variant Annotation available No VIP available No VIP available
Malaria, Falciparum

Publications related to amodiaquine: 20

No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available VIP No VIP available
PharmGKB summary: very important pharmacogene information for cytochrome P450, family 2, subfamily C, polypeptide 8. Pharmacogenetics and genomics. 2013. Aquilante Christina L, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Malaria pharmacogenomics: return to the future. Pharmacogenomics. 2013. Gil Jp. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available VIP No VIP available
CYP2C8 status of patients with malaria influences selection of Plasmodium falciparum pfmdr1 alleles after amodiaquine-artesunate treatment. The Journal of infectious diseases. 2013. Cavaco Isa, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
PharmGKB summary: very important pharmacogene information for G6PD. Pharmacogenetics and genomics. 2012. McDonagh Ellen M, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available VIP No VIP available
Human genetic variation is associated with Plasmodium falciparum drug resistance. The Journal of infectious diseases. 2011. Paganotti Giacomo M, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Pharmacogenetics of antimalarial drugs: effect on metabolism and transport. The Lancet infectious diseases. 2009. Kerb Reinhold, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Human CYP2C8: structure, substrate specificity, inhibitor selectivity, inducers and polymorphisms. Current drug metabolism. 2009. Lai Xin-Sheng, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Amodiaquine-associated adverse effects after inadvertent overdose and after a standard therapeutic dose. Ghana medical journal. 2009. Adjei G O, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Application of pharmacogenomics to malaria: a holistic approach for successful chemotherapy. Pharmacogenomics. 2009. Mehlotra Rajeev K, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available VA No VIP available No VIP available
Effect of concomitant artesunate administration and cytochrome P4502C8 polymorphisms on the pharmacokinetics of amodiaquine in Ghanaian children with uncomplicated malaria. Antimicrobial agents and chemotherapy. 2008. Adjei George O, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
Amodiaquine pharmacogenetics. Pharmacogenomics. 2008. Gil Jose Pedro. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Clinical pharmacology of artemisinin-based combination therapies. Clinical pharmacokinetics. 2008. German Polina I, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
An open label, randomised trial of artesunate+amodiaquine, artesunate+chlorproguanil-dapsone and artemether-lumefantrine for the treatment of uncomplicated malaria. PloS one. 2008. Owusu-Agyei Seth, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
High risk of severe anaemia after chlorproguanil-dapsone+artesunate antimalarial treatment in patients with G6PD (A-) deficiency. PloS one. 2008. Fanello Caterina I, et al. PubMed
Amodiaquine metabolism is impaired by common polymorphisms in CYP2C8: implications for malaria treatment in Africa. Clinical pharmacology and therapeutics. 2007. Parikh S, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
CYP2C8 and antimalaria drug efficacy. Pharmacogenomics. 2007. Gil J P, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Amodiaquine, its desethylated metabolite, or both, inhibit the metabolism of debrisoquine (CYP2D6) and losartan (CYP2C9) in vivo. European journal of clinical pharmacology. 2006. Wennerholm Agneta, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Short communication: high prevalence of the cytochrome P450 2C8*2 mutation in Northern Ghana. Tropical medicine & international health : TM & IH. 2005. Röwer Susanne, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Antimalarial drug toxicity: a review. Drug safety : an international journal of medical toxicology and drug experience. 2004. Taylor W Robert J, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate. The Journal of pharmacology and experimental therapeutics. 2002. Li Xue-Qing, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00613
PDB:
CQA
ChEBI:
2674
KEGG Compound:
C07626
KEGG Drug:
D02922
PubChem Compound:
2165
PubChem Substance:
46506940
9828
ChemSpider:
2080
HET:
CQA
Therapeutic Targets Database:
DAP000699

Clinical Trials

These are trials that mention amodiaquine and are related to either pharmacogenetics or pharmacogenomics.

Common Searches

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Sources for PharmGKB drug information: DrugBank, Open Eye Scientific Software.