Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H22ClN3O |
| Molecular Weight | 355.861 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1
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)
| Molecular Formula | C20H22ClN3O |
| Molecular Weight | 355.861 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Developments in anti-malaria agents: chemical data, structure-activity relationships]. | 2001 Apr |
|
| "One-pot" synthesis and antimalarial activity of formamidine derivatives of 4-anilinoquinoline. | 2001 Aug |
|
| Synthesis and in vitro and in vivo antimalarial activity of new 4-anilinoquinolines. | 2001 Aug 16 |
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| 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 |
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| [Resistance of Plasmodium falciparum to 3 antimalarials in Turbo (Antioquia, Colombia), 1998]. | 2001 Jan |
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| 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 |
|
| Acute asymptomatic hepatitis in a healthy normal volunteer exposed to 2 oral doses of amodiaquine and artesunate. | 2001 Sep-Oct |
|
| [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 |
|
| In vitro sensitivity of Plasmodium falciparum to amodiaquine compared with other major antimalarials in Madagascar. | 2002 Dec |
|
| Sulfadoxine/pyrimethamine alone or with amodiaquine or artesunate for treatment of uncomplicated malaria: a longitudinal randomised trial. | 2002 Dec 21-28 |
|
| Molecular epidemiology of malaria in cameroon. IX. Characteristics of recrudescent and persistent Plasmodium falciparum infections after chloroquine or amodiaquine treatment in children. | 2002 Feb |
|
| Clinical status and implications of antimalarial drug resistance. | 2002 Feb |
|
| Differential effects of 4-aminoquinoline-containing antimalarial drugs on hemoglobin digestion in Plasmodium falciparum-infected erythrocytes. | 2002 Feb 1 |
|
| Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum must be delayed in Africa. | 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 |
|
| [Management of child fever in the battle against malaria in Brazzaville]. | 2002 Mar |
|
| In vitro activities of ferrochloroquine against 55 Senegalese isolates of Plasmodium falciparum in comparison with those of standard antimalarial drugs. | 2002 Mar |
|
| Paracellular tightness and catabolism restrict histamine permeation in the proximal colon of pigs. | 2002 Oct |
|
| Chloroquine resistance in Plasmodium falciparum malaria parasites conferred by pfcrt mutations. | 2002 Oct 4 |
|
| Questions about the antimalarial amodiaquine. | 2003 Apr 5 |
|
| Chloroquine efficacy in the treatment of uncomplicated malaria at three sentinel sites in northern Togo. | 2003 Dec |
|
| 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 |
|
| Efficacy of amodiaquine alone and combined with sulfadoxine-pyrimethamine and of sulfadoxine pyrimethamine combined with artesunate. | 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 |
|
| Chloroquine, sulfadoxine-pyrimethamine and amodiaquine efficacy for the treatment of uncomplicated Plasmodium falciparum malaria in Upper Nile, south Sudan. | 2003 Mar-Apr |
|
| Prevention of increasing rates of treatment failure by combining sulfadoxine-pyrimethamine with artesunate or amodiaquine for the sequential treatment of malaria. | 2003 Oct 15 |
|
| 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 |
|
| Potentiation of the antimalarial action of chloroquine in rodent malaria by drugs known to reduce cellular glutathione levels. | 2003 Sep 1 |
|
| Drug resistant falciparum malaria and the use of artesunate-based combinations: focus on clinical trials sponsored by TDR. | 2003 Sep-Dec |
|
| Antimalarial drug toxicity: a review. | 2004 |
|
| [Pyrido [3,2-b]indol-4-yl-amines--synthesis and investigation of activity against malaria]. | 2004 Apr |
|
| In vitro efficacy of antimalarial drugs against Plasmodium vivax on the western border of Thailand. | 2004 Apr |
|
| Malaria intermittent preventive treatment in infants, chemoprophylaxis, and childhood vaccinations. | 2004 Apr 24 |
|
| Efficacy of sulphadoxine-pyrimethamine alone or combined with amodiaquine or chloroquine for the treatment of uncomplicated falciparum malaria in Ugandan children. | 2004 Feb |
|
| Efficacy of chloroquine, amodiaquine, sulphadoxine-pyrimethamine and combination therapy with artesunate in Mozambican children with non-complicated malaria. | 2004 Feb |
|
| Developing artemisinin based drug combinations for the treatment of drug resistant falciparum malaria: A review. | 2004 Jan-Mar |
|
| Molecular analysis of Plasmodium falciparum from drug treatment failure patients in Papua New Guinea. | 2004 Mar |
|
| Efficacy of pyrimethamine-sulfadoxine in young children with uncomplicated falciparum malaria in rural Burkina Faso. | 2004 May 11 |
|
| A new method for detection of pfmdr1 mutations in Plasmodium falciparum DNA using real-time PCR. | 2004 May 7 |
Patents
Sample Use Guides
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
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
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admin
on
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on
Tue Oct 22 00:48:32 UTC 2019
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| Record UNII |
220236ED28
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.1
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LIVERTOX |
47
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NCI_THESAURUS |
C271
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WHO-ATC |
P01BA06
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.1 (ART/AMO)
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WHO-ATC |
P01BF03
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| Code System | Code | Type | Description | ||
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D000655
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201-669-3
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SUB05470MIG
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AMODIAQUINE
Created by
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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. | ||
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2165
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DB00613
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CHEMBL682
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PRIMARY | |||
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C65231
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86-42-0
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720
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1116
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PRIMARY | |||
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86-42-0
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PRIMARY | |||
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M1839
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PRIMARY | Merck Index | ||
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AMODIAQUINE
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PRIMARY | |||
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86-42-0
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
