Page last updated: 2024-09-23

febrifugine

Description

febrifugine: antimalarials; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID63224
CHEMBL ID479432
CHEBI ID4994
SCHEMBL ID142773
MeSH IDM0041312

Synonyms (14)

Synonym
beta-dichroine
nsc 315535
ferbifrugin
dichroin
24159-07-7
febrifugine
3-[3-[(2s,3r)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one
chebi:4994 ,
CHEMBL479432
b-dichroine
SCHEMBL142773
3-[3-[(2s,3r)-3-hydroxy-2-piperidyl]-2-oxo-propyl]quinazolin-4-one
NCGC00485333-01
Q5413935

Research Excerpts

Overview

ExcerptReference
"Febrifugine is an alkaloid isolated from Dichroa febrifuga Lour as the active component against Plasmodium falciparum. "( Meng, L; Wei, L; Zhang, Q; Zhu, S, 2006)
"Febrifugine is an alkaloid isolated from Dichroa febrifuga Lour as the active component against Plasmodium falciparum. "( Gudise, C; Smith, E; Wei, L; Zeng, Y; Zhang, Q; Zhu, S, 2009)
"Febrifugine is an alkaloid isolated from Dichroa febrifuga Lour as the active component against Plasmodium falciparum, but exhibits toxic side effects. "( Chandrashekar, G; Chatterji, D; Meng, L; Robinson, K; Zhu, S, 2012)
"Isofebrifugine (IFE) is an alkaloid with many biological properties."( Tang, C; Wu, J; Xu, J, 2020)
"Febrifugine is an alkaloid with potent antimalarial activity isolated from Dichroa febrifuga and Hydrangea umbellate, and it exists naturally with its diastereomeric component, isofebrifugine. "( Prabhakar, S; Ramanjaneyulu, GS; Rao, BV; Sudhakar, N, 2008)

Effects

ExcerptReference
"Febrifugine derivatives have been used to treat malaria, cancer, fibrosis and inflammatory disease."( Cortese, JF; Dignam, JD; Edenius, M; Hendrick, M; Keller, TL; Kim, YJ; Lee, HK; Mazitschek, R; Rao, A; Sundrud, MS; Whitman, M; Wirth, DF; Yeo, CY; Yum, J; Zocco, D, 2012)

Drug Classes (1)

ClassDescription
quinazolinesAny organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (64)

Assay IDTitleYearJournalArticle
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID636377Acute toxicity in po dosed Sprague-Dawley rat assessed as maximum tolerated dose2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID268573Toxicity in po dosed ICR mouse2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID636375Antimalarial activity against blood stage of Plasmodium berghei NK65 infected in po dosed rat assessed as minimum curative dose2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID427288Antimalarial activity against Plasmodium berghei infected ICR mice (Mus musculus) daily intraperitoneal dose for 4 days by Thompson test2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents.
AID401077Activation of LPS-induced NO production in BCG-treated ICR mouse macrophages at 1 mg/kg/day, po administered for 3 days before BCG immunization measured after 72 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID268571Selectivity for L929 cells over Plasmodium falciparum FCR3 as EC50 ratio2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID72016In vitro cytotoxicity against mouse mammary FM3A cells2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Potent antimalarial febrifugine analogues against the plasmodium malaria parasite.
AID268569Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 by pLDH reporter assay2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID636368Antimalarial activity against chloroquine-resistant Plasmodium falciparum TM6 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID159609In vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum K11999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite.
AID263349Antimalarial activity against chloroquine-resistant Plasmodium falciparum W22006Bioorganic & medicinal chemistry letters, Apr-01, Volume: 16, Issue:7
Synthesis and evaluation of febrifugine analogues as potential antimalarial agents.
AID427289Toxicity in Plasmodium berghei infected ICR mice (Mus musculus) dosed intraperitoneally once daily for 4 days by Thompson test2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents.
AID401080Cytotoxicity against ICR mouse macrophages assessed as cell viability at 1 mg/kg/day after 72 hrs by MTT assay1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID232455Selectivity ratio between cytotoxicity to antimalarial activity was determined2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite.
AID152132In vitro antimalarial activity against Plasmodium falciparum FCR32003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite.
AID636366Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID636370Antimalarial activity against Plasmodium falciparum TM4 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID401078Activation of NO production in BCG-treated ICR mouse macrophages at 1 mg/kg/day, po administered for 3 days before BCG immunization measured after 72 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID234639Selectivity is the ratio of antimalarial activity and cytotoxicity1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite.
AID268572Antimalarial activity against Plasmodium berghei NK65 infected ICR mice (Mus musculus) peroral dose2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1125531Antimalarial activity against Plasmodium berghei infected in mouse2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
The chemistry and biology of febrifugine and halofuginone.
AID130240Compound was tested for antimalarial activity against mice (Mus musculus) malaria parasite Plasmodium berghei in vivo and the samples were administarted intraperitoneally.1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite.
AID636365Antimalarial activity against Plasmodium falciparum PH3 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID401081Activation of LPS-induced NO production in BCG-treated ICR mouse macrophages at 5 mg/kg/day, po administered for 3 days before BCG immunization measured after 24 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID268570Cytotoxicity against mouse L929 cells by MTT assay2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID151827In vivo effective dose for antimalarial activity by intraperitoneal dose2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite.
AID357024Cytotoxicity against human NUGC cells2001Journal of natural products, Jul, Volume: 64, Issue:7
Hydrachine A, a novel alkaloid from the roots of Hydrangea chinensis.
AID71872Cytotoxicity against FM3A mouse mammary cells2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite.
AID401071Activation of LPS-induced NO production in BCG-treated ICR mouse macrophages at 50 to 1000 mg/kg/day, po administered for 3 days before BCG immunization measured after 24 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID427290Therapeutic index, ratio of MTD for Plasmodium berghei infected ICR mice (Mus musculus) to MCD for Plasmodium berghei2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents.
AID636378Therapeutic index, ratio of MTD for Sprague-Dawley rat to MCD for blood stage of Plasmodium berghei NK652012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID1125529Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCR-3 assessed as growth inhibition2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
The chemistry and biology of febrifugine and halofuginone.
AID401072Antiinflammatory activity against po dosed ICR mouse assessed as number of peritoneal exudate cells1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID636369Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID72011Compound was tested for cytotoxicity against FM3A mouse mammary cells. 1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite.
AID160044In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCR31999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite.
AID268574Therapeutic index; LD50 for ICR mice (Mus musculus)/ED50 against Plasmodium berghei NK652006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID401073Increase in LPS-induced NO production in ICR mouse at 1 mg/kg/day, po 0 to 2 days administered before BCG immunization measured after 24 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID158649In vivo antimalarial activity against Plasmodium berghei infected mice (Mus musculus)2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Potent antimalarial febrifugine analogues against the plasmodium malaria parasite.
AID636373Antimalarial activity against blood stage of Plasmodium berghei NK65 infected in po dosed rat assessed as inhibition of parasite growth2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID263350Cytotoxicity against rat hepatocytes2006Bioorganic & medicinal chemistry letters, Apr-01, Volume: 16, Issue:7
Synthesis and evaluation of febrifugine analogues as potential antimalarial agents.
AID401082Toxicity in ICR mouse assessed as occurrence of diarrhea at 5 mg/kg/day, po1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID235325Selectivity ratio of cytotoxicity against FM3A cells to antimalarial activity against Plasmodium falciparum FCR3 2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Potent antimalarial febrifugine analogues against the plasmodium malaria parasite.
AID427287Antiplasmodial activity after 48 hrs against chloroquine-resistant Plasmodium falciparum W2 in human erythrocytes by [3H]hypoxanthine uptake2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological evaluation of febrifugine analogues as potential antimalarial agents.
AID636371Antimalarial activity against chloroquine-resistant Plasmodium falciparum VS/1 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID401074Increase in LPS-induced NO production in ICR mouse at 1 mg/kg/day, po 0 to 2 days administered after BCG immunization measured after 24 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID128177Compound was tested for antimalarial activity against mice (Mus musculus) malaria parasite Plasmodium berghei in vivo and the samples were administarted intraperitoneally.1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
New type of febrifugine analogues, bearing a quinolizidine moiety, show potent antimalarial activity against Plasmodium malaria parasite.
AID1125530Antimalarial activity against Plasmodium falciparum assessed as growth inhibition2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
The chemistry and biology of febrifugine and halofuginone.
AID68949In vitro antimalarial activity against the Plasmodium falciparum FCR32002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Potent antimalarial febrifugine analogues against the plasmodium malaria parasite.
AID357023Cytotoxicity against human HONE1 cells2001Journal of natural products, Jul, Volume: 64, Issue:7
Hydrachine A, a novel alkaloid from the roots of Hydrangea chinensis.
AID268568Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCR3 by pLDH reporter assay2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Exploration of a new type of antimalarial compounds based on febrifugine.
AID401079Cytotoxicity against LPS-stimulated ICR mouse macrophages assessed as cell viability at 1 mg/kg/day after 72 hrs of LPS challenge by MTT assay1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID636367Antimalarial activity against Plasmodium falciparum Dd2 infected in human A positive erythrocytes assessed as inhibition of [G-3H]-hypoxanthine uptake after 24 hrs by liquid scintillation counting2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Febrifugine analogue compounds: synthesis and antimalarial evaluation.
AID158676In vivo antimalarial activity against Plasmodium berghei infected mice (Mus musculus)2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Potent antimalarial febrifugine analogues against the plasmodium malaria parasite.
AID263348Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D62006Bioorganic & medicinal chemistry letters, Apr-01, Volume: 16, Issue:7
Synthesis and evaluation of febrifugine analogues as potential antimalarial agents.
AID401070Activation of LPS-induced NO production in BCG-treated ICR mouse macrophages at 1 mg/kg/day, po administered for 3 days before BCG immunization measured after 24 hrs of LPS challenge by Griess reagent method1998Journal of natural products, Jun-26, Volume: 61, Issue:6
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
AID151829In vivo effective dose for antimalarial activity by intraperitoneal dose2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Metabolites of febrifugine and its synthetic analogue by mouse liver S9 and their antimalarial activity against Plasmodium malaria parasite.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (56)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (7.14)18.7374
1990's3 (5.36)18.2507
2000's24 (42.86)29.6817
2010's18 (32.14)24.3611
2020's7 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (3.39%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other57 (96.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Synthesis of febrifugine derivatives and development of an effective and safe tetrahydroquinazoline-type antimalarial.
European journal of medicinal chemistry, Apr-09, Volume: 76
2014
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, Volume: 96, Issue: 5
2019
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (2)

ArticleYear
Combination effects of chloroquine with the febrifugine and isofebrifugine mixture against a blood-induced infection with chloroquine-resistant Plasmodium berghei NK65 in ICR mice.
Phytotherapy research : PTR, Volume: 17, Issue: 10
2003
Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga.
Journal of natural products, Jun-26, Volume: 61, Issue: 6
1998
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]