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MedKoo Cat#: 584686 | Name: Febrifugine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Febrifugine is a quinazolinone alkaloid originally isolated from D. febrifuga that has antimalarial activity. Febrifugine exhibits strong antimalarial activity against Plasmodium falciparum, the most insidious malaria causative agent. The adverse effects of febrifugine include diarrhoea, vomiting and liver toxicity. Febrifugine is an antimalarial, the active component of the Chinese herb Chang Shan. Recent studies indicate that its mechanism of action is as an inhibitor of prolyl-transfer RNA synthetase (ProRS).

Chemical Structure

Febrifugine
Febrifugine
CAS#24159-07-7 (free base)

Theoretical Analysis

MedKoo Cat#: 584686

Name: Febrifugine

CAS#: 24159-07-7 (free base)

Chemical Formula: C16H19N3O3

Exact Mass: 301.1426

Molecular Weight: 301.35

Elemental Analysis: C, 63.77; H, 6.36; N, 13.94; O, 15.93

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
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Related CAS #
24159-07-7 (free base) 32434-42-7 (2HCl)
Synonym
Ferbifrugin; beta-Dichroine; (+)-Febrifugine; trans-(+)-Febrifugine; NSC 315535; NSC315535; NSC-315535
IUPAC/Chemical Name
3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone
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
SMILES Code
O=C1N(CC(C[C@H]2NCCC[C@@H]2O)=O)C=NC3=C1C=CC=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 301.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Smullen S, McLaughlin NP, Evans P. Chemical synthesis of febrifugine and analogues. Bioorg Med Chem. 2018 May 15;26(9):2199-2220. doi: 10.1016/j.bmc.2018.04.027. Epub 2018 Apr 12. PMID: 29681487. 2: 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. PMID: 24650700. 3: Mitsui Y, Miura M, Kato K. In vitro effects of febrifugine on Schistosoma mansoni adult worms. Trop Med Health. 2020 Jun 4;48:42. doi: 10.1186/s41182-020-00230-x. PMID: 32518498; PMCID: PMC7271449. 4: Pandey RK, Ojha R, Devender M, Sebastian P, Namdeo M, Kumbhar BV, Sundar S, Maurya R, Prajapati VK. Febrifugine dihydrochloride as a new oral chemotherapeutic agent against visceral leishmaniasis infection. Exp Parasitol. 2022 May-Jun;236-237:108250. doi: 10.1016/j.exppara.2022.108250. Epub 2022 Apr 4. PMID: 35390313. 5: Zhu S, Chandrashekar G, Meng L, Robinson K, Chatterji D. Febrifugine analogue compounds: synthesis and antimalarial evaluation. Bioorg Med Chem. 2012 Jan 15;20(2):927-32. doi: 10.1016/j.bmc.2011.11.053. Epub 2011 Dec 2. PMID: 22182577; PMCID: PMC3259200. 6: Zhang JY, Liu XQ, Yang LX, Feng WH, Wang ZM, Li C. [Investigation on stability and degradation kinetics of febrifugine]. Zhongguo Zhong Yao Za Zhi. 2017 Aug;42(16):3178-3184. Chinese. doi: 10.19540/j.cnki.cjcmm.2017.0126. PMID: 29171238. 7: Murata K, Takano F, Fushiya S, Oshima Y. Potentiation by febrifugine of host defense in mice against Plasmodium berghei NK65. Biochem Pharmacol. 1999 Nov 15;58(10):1593-601. doi: 10.1016/s0006-2952(99)00244-0. PMID: 10535750. 8: Maiden TMM, Mbelesi N, Procopiou PA, Swanson S, Harrity JPA. A convergent strategy towards febrifugine and related compounds. Org Biomol Chem. 2018 Jun 6;16(22):4159-4169. doi: 10.1039/c8ob00935j. PMID: 29786725. 9: Autreto PA, Lavarda FC. Febrifugine derivative antimalarial activity: quantum mechanical predictors. Rev Inst Med Trop Sao Paulo. 2008 Jan-Feb;50(1):21-4. doi: 10.1590/s0036-46652008000100005. PMID: 18327483. 10: Jiang S, Zeng Q, Gettayacamin M, Tungtaeng A, Wannaying S, Lim A, Hansukjariya P, Okunji CO, Zhu S, Fang D. Antimalarial activities and therapeutic properties of febrifugine analogs. Antimicrob Agents Chemother. 2005 Mar;49(3):1169-76. doi: 10.1128/AAC.49.3.1169-1176.2005. PMID: 15728920; PMCID: PMC549280. 11: Zhang JY, Fan XR, Liu XQ, Yu XW, Yang LX, Guo ZT, Feng WH, Wang ZM, Li C. [Quantitative determination of febrifugine by proton nuclear magnetic resonance spectroscopy with internal standard method]. Zhongguo Zhong Yao Za Zhi. 2018 Jan;43(1):134-138. Chinese. doi: 10.19540/j.cnki.cjcmm.20171027.005. PMID: 29552823. 12: Wang F, Zhang G, Zang C, Pan H, Ma L, Li C, Hou H, Su P, Gao Y, Sun J, Ye Z. Preparation and In Vitro/Vivo Evaluation of Nano-Liposomal Form of Febrifugine Hydrochloride. J Nanosci Nanotechnol. 2020 Apr 1;20(4):2558-2566. doi: 10.1166/jnn.2020.17186. PMID: 31492276. 13: Cheng CC. Structural similarity between febrifugine and chloroquine. J Theor Biol. 1976 Jul 7;59(2):497-501. doi: 10.1016/0022-5193(76)90186-7. PMID: 957703. 14: Li PP, Zhang L, Wang JP. Research Note: Study on the residue depletion of febrifugine and isofebrifugine in broiler chicken. Poult Sci. 2021 Oct;100(10):101390. doi: 10.1016/j.psj.2021.101390. Epub 2021 Jul 22. PMID: 34391965; PMCID: PMC8374448. 15: Zhu S, Meng L, Zhang Q, Wei L. Synthesis and evaluation of febrifugine analogues as potential antimalarial agents. Bioorg Med Chem Lett. 2006 Apr 1;16(7):1854-8. doi: 10.1016/j.bmcl.2006.01.009. Epub 2006 Jan 24. PMID: 16434194; PMCID: PMC2072810. 16: 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. Chinese. doi: 10.19540/j.cnki.cjcmm.20170224.017. PMID: 29082694. 17: Takeuchi Y, Oshige M, Azuma K, Abe H, Harayama T. Concise synthesis of dl- febrifugine. Chem Pharm Bull (Tokyo). 2005 Jul;53(7):868-9. doi: 10.1248/cpb.53.868. PMID: 15997158. 18: Kikuchi H, Tasaka H, Hirai S, Takaya Y, Iwabuchi Y, Ooi H, Hatakeyama S, Kim HS, Wataya Y, Oshima Y. Potent antimalarial febrifugine analogues against the plasmodium malaria parasite. J Med Chem. 2002 Jun 6;45(12):2563-70. doi: 10.1021/jm010448q. PMID: 12036365. 19: Zhu S, Zhang Q, Gudise C, Wei L, Smith E, Zeng Y. Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents. Bioorg Med Chem. 2009 Jul 1;17(13):4496-502. doi: 10.1016/j.bmc.2009.05.011. Epub 2009 May 9. PMID: 19467876; PMCID: PMC2746662. 20: 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. PMID: 27043972.