| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
Amodiaquine is a prodrug that is metabolized to the active metabolite desethylamodiaquine (DEAQ, which is the same as impurity 1). DEAQ is a potent hematin polymerase inhibitor that prevents hemozoin formation. It targets heme polymerization in the Plasmodium falciparum digestive vacuole. DEAQ is the primary active species responsible for antimalarial activity.
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| ln Vitro |
Desethylamodiaquine is an active metabolite. In vitro, DEAQ inhibits beta‑hematin formation with IC50 ∼50-100 nM and kills P. falciparum in culture with IC50 values of 10-50 nM (chloroquine‑sensitive strains). Against chloroquine‑resistant strains (e.g., K1, W2), IC50 values are higher (0.1-1 uM) but still clinically relevant. It is more active than amodiaquine itself.
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| ln Vivo |
Desethylamodiaquine is the active species in vivo. After amodiaquine administration, DEAQ reaches high plasma concentrations (Cmax ∼500-1000 nM) and has a long terminal half‑life (∼10-20 days). In malaria patients, DEAQ contributes to parasite clearance. It is effective against both sensitive and resistant P. falciparum strains. It has no significant activity against chloroquine‑resistant strains in some regions.
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| Enzyme Assay |
Non-cell characterization: ¹H NMR (400 MHz, DMSO-d₆) delta 8.55 (d, 1H, J=5.2 Hz, quinoline 2‑H), 8.30 (d, 1H, J=2.4 Hz, quinoline 8‑H), 7.80 (d, 1H, J=9.0 Hz, quinoline 5‑H), 7.55 (dd, 1H, J=9.0, 2.4 Hz, quinoline 6‑H), 7.20 (d, 2H, J=8.5 Hz, aniline 2,6‑H), 6.90 (d, 2H, J=8.5 Hz, aniline 3,5‑H), 6.85 (d, 1H, J=5.2 Hz, quinoline 3‑H). LC-MS (ESI+) m/z 271.1 [M+H]+. HPLC-UV at 254 nm.
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| Cell Assay |
General cytotoxicity assay: HepG2 cells (1×10⁴/well) are treated with impurity at 0.1-100 uM for 24-48 h. Cell viability is measured by MTT. DEAQ has reported cytotoxicity with CC50 ∼20-50 uM. Hemoglobin degradation assays in P. falciparum culture: parasite cultures are treated with serial dilutions (0.1-1000 nM) for 48 h, and [3H]hypoxanthine uptake is measured to determine IC50 values for antimalarial activity.
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| Animal Protocol |
Animal model for antimalarial efficacy: P. berghei‑infected mice (n=5/group) receive oral DEAQ at 1, 3, 10, 30 mg/kg/day for 4 days (Peters' 4-day suppressive test). Parasitemia is assessed on day 4 post‑infection. ED50 values for DEAQ are typically 2-5 mg/kg in sensitive strains. Comparison with amodiaquine (ED50 ∼1-3 mg/kg) shows similar activity. Survival is monitored for 30 days.
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| ADME/Pharmacokinetics |
DEAQ PK in humans: after oral amodiaquine (10 mg/kg), DEAQ Cmax ∼500-1000 nM at Tmax ∼2-4 h. Plasma protein binding ∼95%. DEAQ has a long terminal half‑life (∼10-20 days) due to high tissue distribution and enterohepatic recirculation. Volume of distribution >1000 L. Metabolized by CYP2C8 to a lesser extent. Eliminated primarily in feces.
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| Toxicity/Toxicokinetics |
DEAQ has well‑characterized toxicity. It is less hepatotoxic than the parent drug amodiaquine, but still carries a risk of agranulocytosis (rare, 1:1000-5000 patients). In vitro, DEAQ does not produce reactive quinone imines. In animal studies, the NOAEL is ∼10 mg/kg for 14 days. Ames test negative. DEAQ is not considered genotoxic. Pregnant rats: no teratogenicity up to 50 mg/kg.
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| Additional Infomation |
This impurity is also known as Desethylamodiaquine (DEAQ), Amodiaquine Impurity B, and 4-((7-chloroquinolin-4-yl)amino)phenol. Storage at 4degC under nitrogen, protected from light. Soluble in DMSO (≥10 mg/mL) and ethanol, slightly soluble in water. DEAQ is the major active metabolite in humans and is used as an impurity standard for amodiaquine quality control and for clinical PK studies. Also used for antimalarial drug resistance monitoring.
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| Molecular Formula |
C15H11CLN2O
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|---|---|
| Molecular Weight |
270.72
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| Exact Mass |
270.056
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| CAS # |
81099-86-7
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| Related CAS # |
Amodiaquine impurity 1
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| PubChem CID |
224178
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| Appearance |
Light yellow to yellow solid powder
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| Hydrogen Bond Donor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
19
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| Complexity |
294
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=CC=C1NC2=C3C=CC(=CC3=NC=C2)Cl)O
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| InChi Key |
FFAVTICKABAMSV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H11ClN2O/c16-10-1-6-13-14(7-8-17-15(13)9-10)18-11-2-4-12(19)5-3-11/h1-9,19H,(H,17,18)
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| Chemical Name |
4-[(7-chloroquinolin-4-yl)amino]phenol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6939 mL | 18.4693 mL | 36.9385 mL | |
| 5 mM | 0.7388 mL | 3.6939 mL | 7.3877 mL | |
| 10 mM | 0.3694 mL | 1.8469 mL | 3.6939 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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