Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1=CC=C(N=C1)C(O)=O
InChI
InChIKey=DGMPVYSXXIOGJY-UHFFFAOYSA-N
InChI=1S/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13)
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Fusaric acid (J-butylpicolinic acid) is a fungal toxin with low to moderate toxicity synthesized by some Fusurium species which cause infections in cereal grains and other agricultural commodities. It may potentiate the effects of other Fusurium toxins. Fusaric acid is a potent inhibitor of DNA synthesis. Fusaric acid has potent anti-proliferative activity in vitro on various normal and cancer cell lines and suggest that it exhibits some cytotoxic specificity for growing and confluent colorectal adenocarcinoma and mammary adenocarcinoma cell lines. Fusaric acid is known as a potent dopamine-beta-hydroxylase inhibitor of high specificity. Fusaric acid calcium salt elicited the hypotensive response primarily through the reduction of total peripheral vascular resistance index.
CNS Activity
Curator's Comment: The effect of fusaric acid 150-450 mg daily on tardive dyskinesia and mental state was studied in 15 chronic psychogeriatric patients. The patient's previous drug treatment was maintained unchanged during the experiment. Fusaric acid significantly relieved oro-facial dyskinesia, tremor, and rigidity, and it improved the mental state of the patients (BPRS).
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3102 |
0.1 µM [IC50] | ||
Target ID: CHEMBL614446 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Secondary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antimycobacterial activity of fusaric acid from a mangrove endophyte and its metal complexes. | 2011-07 |
|
| A differential drug screen for compounds that select against antibiotic resistance. | 2010-12-08 |
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| Cu(II): a "signaling molecule" of the mangrove endophyte Fusarium oxysporum ZZF51? | 2010-12 |
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| Increased anion channel activity is an unavoidable event in ozone-induced programmed cell death. | 2010-10-13 |
|
| Feed contaminated with Fusarium toxins alter lymphocyte proliferation and apoptosis in primiparous sows during the perinatal period. | 2010-10 |
|
| FliO regulation of FliP in the formation of the Salmonella enterica flagellum. | 2010-09-30 |
|
| Quantitative determination of gibberellins by high performance liquid chromatography from various gibberellins producing Fusarium strains. | 2010-08 |
|
| The role of coupled positive feedback in the expression of the SPI1 type three secretion system in Salmonella. | 2010-07-29 |
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| Caripyrin, a new inhibitor of infection-related morphogenesis in the rice blast fungus Magnaporthe oryzae. | 2010-06 |
|
| Identification, mycotoxin risk and pathogenicity of Fusarium species associated with fig endosepsis in Apulia, Italy. | 2010-05 |
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| Identification and profiling of volatile metabolites of the biocontrol fungus Trichoderma atroviride by HS-SPME-GC-MS. | 2010-05 |
|
| Toxin induction and protein extraction from Fusarium spp. cultures for proteomic studies. | 2010-02-16 |
|
| Fusaric acid as a novel proton-affinitive derivatizing reagent for highly sensitive quantification of hydroxysteroids by LC-ESI-MS/MS. | 2010-02 |
|
| [Study of specificity of fungistatic effect of trichothecene mycotoxins]. | 2009-11-27 |
|
| The nuclear protein Sge1 of Fusarium oxysporum is required for parasitic growth. | 2009-10 |
|
| Complete genome sequence of the sugarcane nitrogen-fixing endophyte Gluconacetobacter diazotrophicus Pal5. | 2009-09-23 |
|
| Effect of bacitracin on tetracycline resistance in Escherichia coli and Salmonella. | 2009-09-18 |
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| Involvement of RNA-binding protein Hfq in the osmotic-response regulation of invE gene expression in Shigella sonnei. | 2009-05-28 |
|
| The HU regulon is composed of genes responding to anaerobiosis, acid stress, high osmolarity and SOS induction. | 2009 |
|
| Influence of mineral amendment on disease suppressive activity of Pseudomonas fluorescens to Fusarium wilt of chickpea. | 2009 |
|
| GAC1, a gene encoding a putative GTPase-activating protein, regulates bikaverin biosynthesis in Fusarium verticillioides. | 2008-10-31 |
|
| Complete genome sequence of the N2-fixing broad host range endophyte Klebsiella pneumoniae 342 and virulence predictions verified in mice. | 2008-07-25 |
|
| In vitro selection for Fusarium wilt resistance in Gladiolus. | 2008-05 |
|
| Genetic or pharmacological blockade of noradrenaline synthesis enhances the neurochemical, behavioral, and neurotoxic effects of methamphetamine. | 2008-04 |
|
| Bikaverin and fusaric acid from Fusarium oxysporum show antioomycete activity against Phytophthora infestans. | 2008-03 |
|
| Mycotoxins and the pet food industry: toxicological evidence and risk assessment. | 2007-10-20 |
|
| Effects of foodborne Fusarium mycotoxins with and without a polymeric glucomannan mycotoxin adsorbent on food intake and nutrient digestibility, body weight, and physical and clinicopathologic variables of mature dogs. | 2007-10 |
|
| Analysis of Canadian and Irish forage, oats and commercially available equine concentrate feed for pathogenic fungi and mycotoxins. | 2007-04-01 |
|
| Biodiversity of Fusarium species in Mexico associated with ear rot in maize, and their identification using a phylogenetic approach. | 2007-01 |
|
| Fusaric acid induces apoptosis in saffron root-tip cells: roles of caspase-like activity, cytochrome c, and H2O2. | 2006-12 |
|
| Enhanced growth inhibition of squamous cell carcinoma of the head and neck by combination therapy of fusaric acid and paclitaxel or carboplatin. | 2006-11-08 |
|
| The effect of single agent oral fusaric acid (FA) on the growth of subcutaneously xenografted SCC-1 cells in a nude mouse model. | 2006-09 |
|
| A putative role for fusaric acid in biocontrol of the parasitic angiosperm Orobanche ramosa. | 2006-05 |
|
| Plasma phenoloxidase of the larval tobacco budworm, Heliothis virescens, is virucidal. | 2006 |
|
| Mycotoxin producing Fusarium species associated with plant disease on potato, wheat, corn and animal diseases in northwest Iran. | 2006 |
|
| Growth-inhibiting effects of concentrations of fusaric acid on the growth of Bacillus mojavensis and other biocontrol Bacillus species. | 2006 |
|
| Morphological mutants of Gibberella fujikuroi for enhanced production of gibberellic acid. | 2006 |
|
| Early physiological responses of Arabidopsis thaliana cells to fusaric acid: toxic and signalling effects. | 2006 |
|
| Bacterial genome adaptation to niches: divergence of the potential virulence genes in three Burkholderia species of different survival strategies. | 2005-12-07 |
|
| Yeast polysaccharide affects fusaric acid content in maize root rot. | 2005-12 |
|
| Generation and characterization of reduced virulence Fusarium oxysporum f. sp. lycopersici mutants through plasmid-vector insertion. | 2005-08 |
|
| Influence of fusaric acid on phenazine-1-carboxamide synthesis and gene expression of Pseudomonas chlororaphis strain PCL1391. | 2005-08 |
|
| Distribution of gibberellin biosynthetic genes and gibberellin production in the Gibberella fujikuroi species complex. | 2005-06 |
|
| Effects of some naturally occurring iron ion chelators on in vitro superoxide radical formation. | 2005 |
|
| Picolinic acids as inhibitors of dopamine beta-monooxygenase: QSAR and putative binding site. | 2004-12 |
|
| Defense responses of Fusarium oxysporum to 2,4-diacetylphloroglucinol, a broad-spectrum antibiotic produced by Pseudomonas fluorescens. | 2004-11 |
|
| Role of chemotaxis toward fusaric acid in colonization of hyphae of Fusarium oxysporum f. sp. radicis-lycopersici by Pseudomonas fluorescens WCS365. | 2004-11 |
|
| Effects of selective adrenoceptor agonists and antagonists on aggressive behavior elicited by apomorphine, DL-dopa and fusaric acid in REM-sleep-deprived rats. | 1991-07 |
|
| Catechol and indole metabolism in rostral ventrolateral medulla change synchronously with changing blood pressure. | 1989-05 |
|
| Biology of schizophrenia: Mental effects of dopamine-beta-hydroxylase inhibition in normal men. | 1977-01-01 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: The effect of fusaric acid 150-450 mg daily on tardive dyskinesia and mental state was studied in 15 chronic psychogeriatric patients. https://www.ncbi.nlm.nih.gov/pubmed/331875
Intravenous administration of fusaric acid at a dose of 10-30 mg/kg to anesthestized dogs brought about an immediate and dose-dependent decline in blood pressure, increase in heart rate, rise in superior mesenteric arterial blood flow, fall in femoral arterial blood flow and stimulation of respiration.
Route of Administration:
Intravenous
Within 24 h of exposure to 500 uM fusaric acid, most of the human colon adenocarcinoma LoVo cells were blocked at random in the cell cycle and approximately 80% of the cells were dead after 30 h. When cultured human normal WI-38 fibroblasts were exposed to 500 uM fusaric acid (5-butylpicolinic acid), cell proliferation ceases.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:36:29 GMT 2025
by
admin
on
Mon Mar 31 17:36:29 GMT 2025
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| Record UNII |
JWJ963070N
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| Record Status |
Validated (UNII)
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| Record Version |
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19870
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JWJ963070N
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536-69-6
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DTXSID5023085
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m5613
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FUSARIC ACID
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3442
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208-643-0
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D005669
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