| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg |
|
||
| 10mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
Febrifugine's exact molecular target is not fully elucidated, but it exhibits potent antimalarial activity against Plasmodium falciparum, including both chloroquine-sensitive and chloroquine-resistant strains. The compound is an effective coccidiostat and possesses schizonticidal properties. Its mechanism of action is believed to involve inhibition of protein synthesis in the malaria parasite, but the precise molecular target remains an active area of research. The compound's natural isomer has also been studied for its biological activity.
|
|---|---|
| ln Vitro |
Febrifugine demonstrates potent in vitro antimalarial activity against both chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum, with IC50 values of approximately 1-2 μM. It is >100-fold more cytotoxic than optimized analogues in hepatocyte assays, providing clear SAR differentiation. The compound's antimalarial activity and cytotoxicity have been characterized in various in vitro assays using P. falciparum cultures and mammalian cell lines.
|
| ln Vivo |
Febrifugine reduces parasitemia and decreases mortality in mice infected with Plasmodium. In vivo studies have been conducted in murine malaria models at doses of 1 mg/kg/day. The compound's potent antimalarial efficacy is accompanied by significant toxicity, including hepatotoxicity and emetic effects, which have precluded its clinical development. Febrifugine serves as a lead compound for the development of safer and more effective antimalarial analogues.
|
| Enzyme Assay |
Non-cellular enzyme assays for febrifugine are limited as its precise molecular target is not fully characterized. The compound's antimalarial activity can be assessed in cell-free systems by measuring its effect on parasite protein synthesis or other biochemical processes. Its cytotoxicity can be evaluated using hepatocyte cell lines in vitro. The compound's interaction with potential molecular targets can be studied using affinity chromatography or surface plasmon resonance (SPR) approaches.
|
| Cell Assay |
In vitro cellular assays for febrifugine involve treating Plasmodium falciparum cultures with the compound and assessing parasite growth inhibition. Cultures of chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains are incubated with varying concentrations of febrifugine for 48-72 hours, and parasite viability is measured using a [³H]-hypoxanthine incorporation assay or by microscopy to count parasitemia. IC50 values are determined from dose-response curves. Cytotoxicity is assessed in mammalian cell lines (e.g., hepatocytes) using MTT or CellTiter-Glo® assays.
|
| Animal Protocol |
In vivo animal experiments with febrifugine are conducted in murine malaria models. Mice infected with Plasmodium are treated with febrifugine at doses of 1 mg/kg/day via oral or intraperitoneal administration. Parasitemia is monitored by blood smears, and survival rates are recorded. Toxicological endpoints, including hepatotoxicity and gastrointestinal effects, are also assessed. The compound's efficacy and toxicity are compared to those of optimized analogues to guide medicinal chemistry efforts.
|
| ADME/Pharmacokinetics |
Febrifugine has a molecular weight of 301.34 and a molecular formula of C16H19N3O3. It is a crystalline solid at room temperature with a purity of ≥98%. The compound is typically stored at -20°C and is soluble in DMSO and other organic solvents. It is stable under recommended storage conditions and is protected from light and moisture. The compound is a quinazolinone alkaloid with antimalarial activity.
|
| Toxicity/Toxicokinetics |
Febrifugine has been precluded from clinical development due to well-documented hepatotoxicity and emetic side effects. The compound is more than 100-fold more cytotoxic than optimized analogues in hepatocyte assays. This combination of high potency and significant toxicity has made febrifugine a primary scaffold for medicinal chemistry optimization, with the aim of discovering analogs that retain antiparasitic efficacy while eliminating toxic liabilities. Standard laboratory safety precautions should be followed when handling the compound.
|
| References | |
| Additional Infomation |
According to reports, the large-leaved hydrangea and the hydrangea frost-resistant hydrangea contain 3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3H)-quinazolinone, and there is relevant data.
Febrifugine (CAS 24159-07-7) is a quinazolinone alkaloid originally isolated from Dichroa febrifuga Lour (Chang Shan). It exhibits potent in vitro antimalarial activity against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. However, its clinical development has been limited by significant hepatotoxicity and emetic side effects. Febrifugine serves as a primary scaffold for medicinal chemistry optimization in antimalarial drug discovery. The compound is available from various commercial suppliers for research applications. |
| Molecular Formula |
C16H19N3O3
|
|---|---|
| Molecular Weight |
301.3404
|
| Exact Mass |
301.142
|
| CAS # |
24159-07-7
|
| Related CAS # |
Febrifugine dihydrochloride;32434-42-7
|
| PubChem CID |
9851692
|
| Appearance |
White to off-white solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
508.2±60.0 °C at 760 mmHg
|
| Melting Point |
139-140°; mp 154-156°
|
| Flash Point |
261.1±32.9 °C
|
| Vapour Pressure |
0.0±1.4 mmHg at 25°C
|
| Index of Refraction |
1.673
|
| LogP |
-0.04
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
22
|
| Complexity |
466
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
|
| InChi Key |
FWVHWDSCPKXMDB-CABCVRRESA-N
|
| InChi Code |
InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2/t14-,15+/m1/s1
|
| Chemical Name |
3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~82.96 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3185 mL | 16.5926 mL | 33.1851 mL | |
| 5 mM | 0.6637 mL | 3.3185 mL | 6.6370 mL | |
| 10 mM | 0.3319 mL | 1.6593 mL | 3.3185 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
