| Identification | Back Directory | [Name]
Febrifugine | [CAS]
24159-07-7 | [Synonyms]
febrifugin
Febrifugine
β-dichroine
Radix Dichroae
BETA-Febrifugine
Febrifugine USP/EP/BP
Febrifugine，Isofebrifugine
Febrifugine (6-Desoxyswietenine)
3-(3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one
3-[3-[(2R,3S)-3-Hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone
4(3H)-Quinazolinone, 3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]- | [Molecular Formula]
C16H19N3O3 | [MOL File]
24159-07-7.mol | [Molecular Weight]
301.344 |
| Chemical Properties | Back Directory | [Melting point ]
139-140°; mp 154-156° | [alpha ]
D25 +6° (c = 0.5 in chloroform); D25 +28° (c = 0.5 in ethanol) | [Boiling point ]
508.2±60.0 °C(Predicted) | [density ]
1.39 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMF: 1.5 mg/ml; DMSO: 3.0 mg/ml; Ethanol: 0.1 mg/ml; PBS (pH 7.2): 2.5 mg/ml | [form ]
A crystalline solid | [pka]
14.61±0.40(Predicted) | [color ]
White to off-white | [InChI]
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 | [InChIKey]
FWVHWDSCPKXMDB-CABCVRRESA-N | [SMILES]
N1C2=C(C=CC=C2)C(=O)N(CC(=O)C[C@@H]2[C@@H](O)CCCN2)C=1 | [CAS DataBase Reference]
24159-07-7 |
| Hazard Information | Back Directory | [Description]
Febrifugine is a quinazolinone alkaloid originally isolated from D. febrifuga that has antimalarial activity.1,2 It reduces parasitemia and decreases mortality in mice infected with the P. berghei strain NK65 when administered at a dose of 1 mg/kg per day beginning prior to or on the day of infection.3 | [Chemical Properties]
It is soluble in organic solvents such as methanol, ethanol, and DMSO, and is derived from Changshan. | [Uses]
Febrifugine is a quinazoline alkaloid with significant antimalarial and anticancerous efficacy. Febrifugine is an NRF2 inhibitor, that works with halofuginone for the treatment of chemo- and radio-resistant forms of cancer. Febrifugine analogs also functions as antimalarial, anticancer agents and in the prevention of chicken coccidiosis. | [IC 50]
Plasmodium | [storage]
Store at -20°C | [References]
[1] J. B. KOEPFLI John A B Jr J F Mead. AN ALKALOID WITH HIGH ANTIMALARIAL ACTIVITY FROM DICHROA FEBRIFUGA1[J]. Journal of the American Chemical Society, 1947, 69 7: 1837. DOI: 10.1021/ja01199a513
[2] NOEL P. MCLAUGHLIN Mark P Paul Evans. The chemistry and biology of febrifugine and halofuginone[J]. Bioorganic & Medicinal Chemistry, 2014, 22 7: Pages 1993-2004. DOI: 10.1016/j.bmc.2014.02.040
[3] KIYOSHI MURATA . Potentiation by febrifugine of host defense in mice against plasmodium berghei NK65[J]. Biochemical pharmacology, 1999, 58 10: Pages 1593-1601. DOI: 10.1016/s0006-2952(99)00244-0 |
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