| Size | Price | Stock | Qty |
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| 2mg |
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| 5mg |
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| 500mg | |||
| Other Sizes |
| Targets |
Desethyl chloroquine targets the same molecular pathways as chloroquine, including the heme polymerase in malaria parasites and the toll-like receptors (TLRs) in mammalian cells. In malaria parasites, desethyl chloroquine accumulates in the acidic food vacuole and inhibits the polymerization of heme, leading to the accumulation of toxic heme and parasite death. In mammalian cells, desethyl chloroquine inhibits TLR signaling, reducing the production of pro-inflammatory cytokines. The compound's immunomodulatory effects are mediated by the inhibition of TLR7 and TLR9 signaling.
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| ln Vitro |
Plasmodium falciparum[1]
In vitro, Desethyl chloroquine has been shown to possess antimalarial activity against Plasmodium falciparum, although it is less potent than chloroquine. The compound also exhibits immunomodulatory effects, inhibiting TLR7- and TLR9-mediated cytokine production in immune cells. In cell-based assays, desethyl chloroquine inhibits the production of IFN-α and TNF-α by plasmacytoid dendritic cells and monocytes. These in vitro findings are consistent with the pharmacological profile of chloroquine. |
| ln Vivo |
Chloroquine was intraperitoneally injected into wild-type and Huntington's disease (Q175/Q175)-infected mice. The amounts of chloroquine and its metabolites in the blood, brain, and muscle tissue were compared using LC-MS/MS. Four to twenty-four hours following the last dosage, brain tissue has lower (5–15M) but more stable chloroquine concentrations than blood or muscle. Within 24 hours following injection, levels of the active chloroquine metabolite desethylchloroquine dropped in muscle and blood, while within the same period, levels in the brain were both slightly elevated and lowered [3].
In vivo, Desethyl chloroquine contributes to the antimalarial and immunomodulatory effects of chloroquine. The compound's levels in plasma and tissues are used as a biomarker for chloroquine exposure and adherence to therapy. In patients with rheumatoid arthritis and systemic lupus erythematosus, desethyl chloroquine contributes to the therapeutic effects of chloroquine, although its role is less well-defined than that of the parent compound. |
| Enzyme Assay |
In vitro enzyme assays for Desethyl chloroquine are used to study its formation from chloroquine by cytochrome P450 enzymes. The assay is performed using human liver microsomes or recombinant CYP enzymes, with chloroquine as the substrate. The reaction is carried out in a buffer containing NADPH, and the formation of desethyl chloroquine is quantified by HPLC or LC-MS. The enzyme kinetics, including Vmax and Km, are calculated from the concentration-response curves.
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| Cell Assay |
In vitro cellular experiments for Desethyl chloroquine are performed using immune cells, such as peripheral blood mononuclear cells or plasmacytoid dendritic cells. Cells are treated with varying concentrations of the compound, and the inhibition of TLR-mediated cytokine production is assessed by ELISA or multiplex bead-based assays. The compound's effects on cell viability and proliferation are also assessed. These experiments are essential for characterizing the immunomodulatory activity of desethyl chloroquine.
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| Animal Protocol |
In vivo animal studies for Desethyl chloroquine involve measuring its levels in plasma and tissues following chloroquine administration. The compound is extracted from biological samples and analyzed by LC-MS. Its levels are used as a biomarker for chloroquine metabolism and exposure. Studies in animal models of malaria and autoimmune diseases have investigated the role of desethyl chloroquine in the therapeutic and toxic effects of chloroquine.
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| ADME/Pharmacokinetics |
Desethyl chloroquine is a metabolite of chloroquine, and its pharmacokinetic properties are closely linked to those of the parent compound. The formation of desethyl chloroquine from chloroquine occurs primarily in the liver, and the metabolite has a similar half-life to chloroquine, approximately 1-2 months. The compound is extensively distributed in tissues and is slowly eliminated from the body. Its pharmacokinetic profile contributes to the long-acting effects of chloroquine.
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| Toxicity/Toxicokinetics |
The toxicity of Desethyl chloroquine is similar to that of chloroquine, although it is generally considered to be less toxic. Common adverse effects include gastrointestinal disturbances, headache, and visual disturbances. Prolonged use of chloroquine and its metabolites can lead to retinopathy and other serious adverse effects. The safety profile of desethyl chloroquine is an important consideration in the use of chloroquine for chronic conditions such as rheumatoid arthritis and lupus.
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| References |
[1]. Ajayi FO, et al. Comparison of the partitioning in vitro of chloroquine and its desethyl metabolites between the erythrocytes and plasma of healthy subjects and those with falciparum malaria. Afr J Med Med Sci. 1989 Jun;18(2):95-100.
[2]. Said A, et al. Chloroquine promotes IL-17 production by CD4+ T cells via p38-dependent IL-23 release by monocyte-derived Langerhans-like cells. J Immunol. 2014 Dec 15;193(12):6135-43. [3]. Vodicka P, et al. Assessment of chloroquine treatment for modulating autophagy flux in brain of WT and HD mice. J Huntingtons Dis. 2014;3(2):159-74. |
| Additional Infomation |
Deethylchloroquine is an aminoquinoline drug.
Desethyl chloroquine is the primary active metabolite of chloroquine, formed by N-deethylation in the liver. It retains significant antimalarial and immunomodulatory activity and contributes to the therapeutic and toxic effects of chloroquine. Desethyl chloroquine is used as a biomarker for chloroquine exposure and as a reference standard in pharmacokinetic studies. Its formation and elimination are important considerations in the clinical use of chloroquine for malaria, rheumatoid arthritis, and systemic lupus erythematosus. |
| Molecular Formula |
C₁₆H₂₂CLN₃
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|---|---|
| Molecular Weight |
291.81898
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| Exact Mass |
291.15
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| CAS # |
1476-52-4
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| Related CAS # |
Desethyl chloroquine diphosphate;247912-76-1;Desethyl chloroquine-d4;1189971-72-9;Desethyl chloroquine-d5;1261392-69-1
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| PubChem CID |
95478
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.138g/cm3
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| Boiling Point |
451.7ºC at 760mmHg
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| Melting Point |
94-97?C
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| Flash Point |
227ºC
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| Vapour Pressure |
2.38E-08mmHg at 25°C
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| Index of Refraction |
1.602
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| LogP |
4.542
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
20
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| Complexity |
274
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCNCCCC(NC1C=CN=C2C=C(C=CC=12)Cl)C
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| InChi Key |
MCYUUUTUAAGOOT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)
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| Chemical Name |
1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1-ethyl-
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| Synonyms |
N-Desethylchloroquine, NSC 13254NSC13254NSC-13254
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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 |
| 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 | 3.4268 mL | 17.1338 mL | 34.2677 mL | |
| 5 mM | 0.6854 mL | 3.4268 mL | 6.8535 mL | |
| 10 mM | 0.3427 mL | 1.7134 mL | 3.4268 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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