Fusaric acid

Fusaric acid
Names

Preferred IUPAC name 5-Butylpyridine-2-carboxylic acid
Other names 5-Butylpicolinic acid Fusarinic acid
Identifiers
CAS Number	536-69-6^Y
3D model (Jmol)	Interactive image
ChemSpider	3324^N
ECHA InfoCard	100.007.859
EC Number	208-643-0
KEGG	C10146^N
MeSH	D005669
PubChem	3442
InChI 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)^N Key: DGMPVYSXXIOGJY-UHFFFAOYSA-N^N InChI=1/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13) Key: DGMPVYSXXIOGJY-UHFFFAOYAD
SMILES CCCCC1=CN=C(C=C1)C(=O)O
Properties
Chemical formula	C₁₀H₁₃NO₂
Molar mass	179.22 g·mol⁻¹
Melting point	97 to 98 °C (207 to 208 °F; 370 to 371 K)
Related compounds
Related compounds	picolinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Fusaric acid is a picolinic acid derivative.

Antibiotic (wilting agent) first isolated from the fungus Fusarium heterosporium.^[1]

It is typically isolated from various Fusarium species, and has been proposed for a various therapeutic applications. However, it is primarily used as a research tool.

Its mechanism of action is not well understood. It likely inhibits Dopamine beta-hydroxylase (the enzyme that converts dopamine to norepinephrine). It may also have other actions, such as the inhibition of cell proliferation and DNA synthesis. Fusaric acid and analogues also reported as quorum sensing inhibitors.^[2]

It is used to make bupicomide.

References

↑ Yabuta et al., J. Agric. Chem. Soc. Jpn. 10, 1059 (1934).
↑ Tung et al., Eur. J. Med. Chem. dx.doi.org/10.1016/j.ejmech.2016.11.044.

Monoamine metabolism modulators

Common
(non-specific)

AAAD

MAO

Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone

Inhibitors: MAO-B selective: Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAH	Inhibitors: 3,4-Dihydroxystyrene

TH	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

DBH	Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	Inhibitors: CGS-19281A SKF-64139 SKF-7698

COMT	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nitecapone Tolcapone

Tryptamines
(serotonin, melatonin)

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

See also: Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake and release modulators • Monoamine neurotoxins

Authority control	GND: 4155722-0

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