Febrifugine Chemical Properties

Melting point:

139-140°; mp 154-156°

alpha 

D25 +6° (c = 0.5 in chloroform); D25 +28° (c = 0.5 in ethanol)

Density 

1.39

storage temp. 

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

Boiling point:

508.2±60.0 °C(Predicted)

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

Safety Information

Toxicity

LD50 orally in white mice: 2.5-3.0 mg/kg (Koepfli, 1949)

Febrifugine Usage And Synthesis

Description

Febrifugine is a quinazolinone alkaloid originally isolated from D. febrifuga that has antimalarial activity. 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.

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

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

Febrifugine(24159-07-7)Related Product Information

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