Febrifugine

• CAT Number: M017405
• CAS Number: 24159-07-7
• Molecular Formula: C16H19N3O3
• Molecular Weight: 301.34
• Purity: ≥95%
• Synonyms: Febrifugine;β-dichroine;Febrifugine，Isofebrifugine;3-[3-[(2R,3S)-3-Hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone;BETA-Febrifugine;3-(3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one
• Target: Parasite
• Storage: -20°C
• IUPAC Name: 3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one
• 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
• InChIKey: FWVHWDSCPKXMDB-UHFFFAOYSA-N
• SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O

Febrifugine（Cat No.:M017405）is a natural alkaloid extracted from the roots of Dichroa febrifuga, a plant traditionally used in Chinese medicine to treat malaria. It exhibits potent antimalarial activity by inhibiting the parasite’s dihydrofolate reductase, disrupting DNA synthesis and cell replication. Febrifugine has also demonstrated anti-inflammatory and immunomodulatory properties, making it a focus of research for autoimmune and inflammatory diseases. Despite its efficacy, febrifugine’s toxicity and side effects have limited its clinical use, prompting the development of synthetic analogs like halofuginone for safer therapeutic applications.

Reference

1: Zhang JY, Liu ZH, Liu XQ, Feng WH, Yang LX, Wang ZM, Li C. [Simultaneous determination of febrifugine and isofebrifugine in Dichroa febrifuga root by HPLC method]. Zhongguo Zhong Yao Za Zhi. 2017 May;42(9):1711-1716. doi: 10.19540/j.cnki.cjcmm.20170224.017. Chinese. PubMed PMID: 29082694.
2: Pandey RK, Kumbhar BV, Srivastava S, Malik R, Sundar S, Kunwar A, Prajapati VK. Febrifugine analogues as Leishmania donovani trypanothione reductase inhibitors: binding energy analysis assisted by molecular docking, ADMET and molecular dynamics simulation. J Biomol Struct Dyn. 2017 Jan;35(1):141-158. doi: 10.1080/07391102.2015.1135298. Epub 2016 Apr 4. PubMed PMID: 27043972.
3: Pandey RK, Narula A, Naskar M, Srivastava S, Verma P, Malik R, Shah P, Prajapati VK. Exploring dual inhibitory role of febrifugine analogues against Plasmodium utilizing structure-based virtual screening and molecular dynamic simulation. J Biomol Struct Dyn. 2017 Mar;35(4):791-804. doi: 10.1080/07391102.2016.1161560. Epub 2016 Apr 18. PubMed PMID: 26984239.
4: Herman JD, Pepper LR, Cortese JF, Estiu G, Galinsky K, Zuzarte-Luis V, Derbyshire ER, Ribacke U, Lukens AK, Santos SA, Patel V, Clish CB, Sullivan WJ Jr, Zhou H, Bopp SE, Schimmel P, Lindquist S, Clardy J, Mota MM, Keller TL, Whitman M, Wiest O, Wirth DF, Mazitschek R. The cytoplasmic prolyl-tRNA synthetase of the malaria parasite is a dual-stage target of febrifugine and its analogs. Sci Transl Med. 2015 May 20;7(288):288ra77. doi: 10.1126/scitranslmed.aaa3575. PubMed PMID: 25995223; PubMed Central PMCID: PMC4675670.
5: Mai HD, Thanh GV, Tran VH, Vu VN, Vu VL, Le CV, Nguyen TL, Phi TD, Truong BN, Chau VM, Pham VC. Synthesis and biological evaluation of febrifugine analogues. Nat Prod Commun. 2014 Dec;9(12):1717-20. PubMed PMID: 25632466.
6: McLaughlin NP, Evans P, Pines M. The chemistry and biology of febrifugine and halofuginone. Bioorg Med Chem. 2014 Apr 1;22(7):1993-2004. doi: 10.1016/j.bmc.2014.02.040. Epub 2014 Mar 1. Review. PubMed PMID: 24650700.
7: Kikuchi H, Horoiwa S, Kasahara R, Hariguchi N, Matsumoto M, Oshima Y. Synthesis of febrifugine derivatives and development of an effective and safe tetrahydroquinazoline-type antimalarial. Eur J Med Chem. 2014 Apr 9;76:10-9. doi: 10.1016/j.ejmech.2014.01.036. Epub 2014 Jan 25. PubMed PMID: 24565569.