N-Desethyl amodiaquine |
Catalog No.GC36709
One-Click Copy Product Info
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N-Desethyl amodiaquine is an antiparasitic agent, has inhibitory for strains V1/S and 3D7 with IC50 values of 97nM and 25nM, respectively.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 79352-78-6
Sample solution is provided at 25 µL, 10mM.
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N-Desethyl amodiaquine is an antiparasitic agent, has inhibitory for strains V1/S and 3D7 with IC50 values of 97nM and 25nM, respectively[1]. N-Desethyl amodiaquine is the major metabolite of the antimalarial compound aminodiaquine, produced by the action of cytochrome P450 isoform 2C8[2]. N-Desethyl amodiaquine is highly active against Plasmodium falciparum and can synergize with amodiaquine, usually used in the research of malaria[3-4].
In vitro, treatment with N-Desethyl amodiaquine significantly blocked viral replication in both Huh 7 and Vero E6 cell lines infected with Ebola virus, with IC50 values of 2.8μM and 11μM[5]. Treatment of RAW264.7 cells with N-Desethyl amodiaquine (8, 16, 33, or 66μM) for 1h before 6h intoxication with 500ng/mL protective antigen (PA)+ 500ng/mL lethal factor (LF) inhibited proteinase B activity in a dose-dependent manner and reduced toxin-mediated cytotoxicity[6].
In vivo, intravenous injection of N-Desethyl amodiaquine (3, 6mg/kg) inhibits PA-LF induced death in the Sprague−Dawley rat model by inhibiting cytosolic entry of LF[6]. Oral administration of N-Desethyl amodiaquine every 12h for 5 days at 5, 10, and 50mg/kg protects mice challenged with B. Anthracis Spores while decreasing survival times at increased N-Desethyl amodiaquine doses[7].
References:
[1] Sasi, P., Abdulrahaman, A., Mwai, L., Muriithi, S., Straimer, J., Schieck, E., Rippert, A., Bashraheil, M., Salim, A., Peshu, J., Awuondo, K., Lowe, B., Pirmohamed, M., Winstanley, P., Ward, S., Nzila, A., & Borrmann, S. (2009). In vivo and in vitro efficacy of amodiaquine against Plasmodium falciparum in an area of continued use of 4-aminoquinolines in East Africa. The Journal of infectious diseases, 199(11), 1575–1582.
[2] Li, X. Q., Björkman, A., Andersson, T. B., Ridderström, M., & Masimirembwa, C. M. (2002). 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, 300(2), 399–407.
[3] Mariga, S. T., Gil, J. P., Sisowath, C., Wernsdorfer, W. H., & Björkman, A. (2004). Synergism between amodiaquine and its major metabolite, desethylamodiaquine, against Plasmodium falciparum in vitro. Antimicrobial agents and chemotherapy, 48(11), 4089–4096.
[4] Childs, G. E., Boudreau, E. F., Milhous, W. K., Wimonwattratee, T., Pooyindee, N., Pang, L., & Davidson, D. E., Jr (1989). A comparison of the in vitro activities of amodiaquine and desethylamodiaquine against isolates of Plasmodium falciparum. The American journal of tropical medicine and hygiene, 40(1), 7–11.
[5] DeWald, L. E., Johnson, J. C., Gerhardt, D. M., Torzewski, L. M., Postnikova, E., Honko, A. N., Janosko, K., Huzella, L., Dowling, W. E., Eakin, A. E., Osborn, B. L., Gahagen, J., Tang, L., Green, C. E., Mirsalis, J. C., Holbrook, M. R., Jahrling, P. B., Dyall, J., & Hensley, L. E. (2019). In Vivo Activity of Amodiaquine against Ebola Virus Infection. Scientific reports, 9(1), 20199.
[6] Zilbermintz, L., Leonardi, W., Jeong, S. Y., Sjodt, M., McComb, R., Ho, C. L., Retterer, C., Gharaibeh, D., Zamani, R., Soloveva, V., Bavari, S., Levitin, A., West, J., Bradley, K. A., Clubb, R. T., Cohen, S. N., Gupta, V., & Martchenko, M. (2015). Identification of agents effective against multiple toxins and viruses by host-oriented cell targeting. Scientific reports, 5, 13476.
[7] Martchenko Shilman, M., Bartolo, G., Alameh, S., Peterson, J. W., Lawrence, W. S., Peel, J. E., Sivasubramani, S. K., Beasley, D. W. C., Cote, C. K., Demons, S. T., Halasahoris, S. A., Miller, L. L., Klimko, C. P., Shoe, J. L., Fetterer, D. P., McComb, R., Ho, C. C., Bradley, K. A., Hartmann, S., Cheng, L. W., … West, J. (2021). In Vivo Activity of Repurposed Amodiaquine as a Host-Targeting Therapy for the Treatment of Anthrax. ACS infectious diseases, 7(8), 2176–2191.
| Cell experiment [1]: | |
Cell lines | RAW264.7 cells |
Preparation Method | RAW264.7 cells untreated with drugs were lysed, and equal amount of cathepsin B containing protein lysate was added to the substrate solution with and without AQ, CQ, N-Desethyl amodiaquine, or DECQ at concentrations of 4, 8, 16, 33, or 66μM. Cellular cathepsin B activity with and without drugs was tested by pre-treating cells with drugs for 1 hour, followed by lysing cells and testing cathepsin B activity with a fluorescently labeled substrate. The activity of 0.5ng/μl of purified human cathepsin B was mixed with and without drugs without pre-incubation and detected with a fluorescently labeled substrate. Fluorescence intensity indicating cathepsin B activity was measured at an excitation wavelength of 370nm and emission wave length of 450nm. |
Reaction Conditions | 8, 16, 33, or 66μM; 1h |
Applications | N-Desethyl amodiaquine inhibited proteinase B activity in a dose-dependent manner. |
| Animal experiment [1]: | |
Animal models | Sprague-Dawley rats |
Preparation Method | Five Male Sprague-Dawley rats (226 to 250g; Charles River) per group were used. Animals were injected intravenously with a lethal dose of anthrax toxin (LD100) and were intravenously co-injected with N-Desethyl amodiaquine at 1.5, 3.0, or 6.0mg/kg. Rats were monitored for signs of clinical illness or death for 14 days after the challenge. |
Dosage form | 1.5, 3.0, or 6.0mg/kg ; i.v. |
Applications | N-Desethyl amodiaquine(3,6mg/kg) inhibits LF-PA-induced death by Inhibiting cytosolic entry of LF. |
References: | |
| Cas No. | 79352-78-6 | SDF | |
| Canonical SMILES | OC1=CC=C(NC2=CC=NC3=CC(Cl)=CC=C23)C=C1CNCC | ||
| Formula | C18H18ClN3O | M.Wt | 327.81 |
| Solubility | DMSO: 125 mg/mL (381.32 mM) | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.0505 mL | 15.2527 mL | 30.5055 mL |
| 5 mM | 610.1 μL | 3.0505 mL | 6.1011 mL |
| 10 mM | 305.1 μL | 1.5253 mL | 3.0505 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 13 reference(s) in Google Scholar.)