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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| Effects of selective adrenoceptor agonists and antagonists on aggressive behavior elicited by apomorphine, DL-dopa and fusaric acid in REM-sleep-deprived rats. | 1991 Jul |
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| A concise synthesis of fusaric acid and (S)-(+)-fusarinolic acid. | 2001 Jan 26 |
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| Apoptosis induced by picolinic acid-related compounds in HL-60 cells. | 2001 Oct |
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| 5-n-Butylpyridine-2-carboxylate-copper(II) and -iron(III) complexes. | 2002 Oct |
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| HPLC analysis of fusaric acid, 9,10-dehydrofusaric acid and their methyl esters, toxic metabolites from weed pathogenic Fusarium species. | 2002 Sep-Oct |
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| Role of reactive oxygen species and antioxidants in plant disease resistance. | 2003 Apr |
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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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| Pleiotropic effect of the insertion of the Agrobacterium rhizogenes rolD gene in tomato ( Lycopersicon esculentum Mill.). | 2003 Sep |
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| Picolinic acids as inhibitors of dopamine beta-monooxygenase: QSAR and putative binding site. | 2004 Dec |
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| Mycotic keratitis: profile of Fusarium species and their mycotoxins. | 2004 Feb |
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| Neuromodulation of the locomotor network by dopamine in the isolated spinal cord of newborn rat. | 2004 Mar |
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| Influence of environmental conditions on the production of phenazine-1-carboxamide by Pseudomonas chlororaphis PCL1391. | 2004 May |
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| Bacterial genome adaptation to niches: divergence of the potential virulence genes in three Burkholderia species of different survival strategies. | 2005 Dec 7 |
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| Distribution of gibberellin biosynthetic genes and gibberellin production in the Gibberella fujikuroi species complex. | 2005 Jun |
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| Mycotoxin producing Fusarium species associated with plant disease on potato, wheat, corn and animal diseases in northwest Iran. | 2006 |
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| Morphological mutants of Gibberella fujikuroi for enhanced production of gibberellic acid. | 2006 |
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| Early physiological responses of Arabidopsis thaliana cells to fusaric acid: toxic and signalling effects. | 2006 |
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| Fusaric acid induces apoptosis in saffron root-tip cells: roles of caspase-like activity, cytochrome c, and H2O2. | 2006 Dec |
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| Enhanced growth inhibition of squamous cell carcinoma of the head and neck by combination therapy of fusaric acid and paclitaxel or carboplatin. | 2006 Nov 8 |
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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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| Genetic or pharmacological blockade of noradrenaline synthesis enhances the neurochemical, behavioral, and neurotoxic effects of methamphetamine. | 2008 Apr |
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| Complete genome sequence of the N2-fixing broad host range endophyte Klebsiella pneumoniae 342 and virulence predictions verified in mice. | 2008 Jul 25 |
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| [Study of specificity of fungistatic effect of trichothecene mycotoxins]. | 2009 Mar-Apr |
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| Involvement of RNA-binding protein Hfq in the osmotic-response regulation of invE gene expression in Shigella sonnei. | 2009 May 28 |
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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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| Toxin induction and protein extraction from Fusarium spp. cultures for proteomic studies. | 2010 Feb 16 |
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| Caripyrin, a new inhibitor of infection-related morphogenesis in the rice blast fungus Magnaporthe oryzae. | 2010 Jun |
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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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| Identification and profiling of volatile metabolites of the biocontrol fungus Trichoderma atroviride by HS-SPME-GC-MS. | 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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m5613
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FUSARIC ACID
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3442
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208-643-0
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3487
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SUBSTANCE RECORD
