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)
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 |
|---|---|---|
| Biology of schizophrenia: Mental effects of dopamine-beta-hydroxylase inhibition in normal men. | 1977 Jan 1 |
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| Catechol and indole metabolism in rostral ventrolateral medulla change synchronously with changing blood pressure. | 1989 May |
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| A concise synthesis of fusaric acid and (S)-(+)-fusarinolic acid. | 2001 Jan 26 |
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| Synthesis and characterization of immobilized dopamine beta-hydroxylase in membrane-bound and solubilized formats. | 2001 Mar 28 |
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| Effect of fusaric acid and phytoanticipins on growth of rhizobacteria and Fusarium oxysporum. | 2002 Nov |
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| Antioxidant nutrients and mycotoxins. | 2002 Nov 15 |
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| Effects of feeding a blend of grains naturally contaminated with Fusarium mycotoxins on feed intake, serum chemistry, and hematology of horses, and the efficacy of a polymeric glucomannan mycotoxin adsorbent. | 2003 Sep |
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| Influence of fusaric acid on phenazine-1-carboxamide synthesis and gene expression of Pseudomonas chlororaphis strain PCL1391. | 2005 Aug |
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| Yeast polysaccharide affects fusaric acid content in maize root rot. | 2005 Dec |
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| Distribution of gibberellin biosynthetic genes and gibberellin production in the Gibberella fujikuroi species complex. | 2005 Jun |
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| Plasma phenoloxidase of the larval tobacco budworm, Heliothis virescens, is virucidal. | 2006 |
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| Morphological mutants of Gibberella fujikuroi for enhanced production of gibberellic acid. | 2006 |
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| Analysis of Canadian and Irish forage, oats and commercially available equine concentrate feed for pathogenic fungi and mycotoxins. | 2007 Apr 1 |
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| Biodiversity of Fusarium species in Mexico associated with ear rot in maize, and their identification using a phylogenetic approach. | 2007 Jan |
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| In vitro selection for Fusarium wilt resistance in Gladiolus. | 2008 May |
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| GAC1, a gene encoding a putative GTPase-activating protein, regulates bikaverin biosynthesis in Fusarium verticillioides. | 2008 Sep-Oct |
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| The nuclear protein Sge1 of Fusarium oxysporum is required for parasitic growth. | 2009 Oct |
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| Effect of bacitracin on tetracycline resistance in Escherichia coli and Salmonella. | 2009 Sep 18 |
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| Complete genome sequence of the sugarcane nitrogen-fixing endophyte Gluconacetobacter diazotrophicus Pal5. | 2009 Sep 23 |
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| Quantitative determination of gibberellins by high performance liquid chromatography from various gibberellins producing Fusarium strains. | 2010 Aug |
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| Cu(II): a "signaling molecule" of the mangrove endophyte Fusarium oxysporum ZZF51? | 2010 Dec |
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| A differential drug screen for compounds that select against antibiotic resistance. | 2010 Dec 8 |
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| Fusaric acid as a novel proton-affinitive derivatizing reagent for highly sensitive quantification of hydroxysteroids by LC-ESI-MS/MS. | 2010 Feb |
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| Identification, mycotoxin risk and pathogenicity of Fusarium species associated with fig endosepsis in Apulia, Italy. | 2010 May |
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| Antimycobacterial activity of fusaric acid from a mangrove endophyte and its metal complexes. | 2011 Jul |
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.
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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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3487
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SUBSTANCE RECORD
