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Fusaric acid

pharmaceutical raw materials
Fusaric acid structure

Fusaric acid 

structure
  • CAS No:

    536-69-6

  • Formula:

    C10H13NO2

  • Chemical Name:

    Fusaric acid

  • Synonyms:

    2-Pyridinecarboxylic acid,5-butyl-;Fusaric acid;Picolinic acid,5-butyl-;5-Butyl-2-pyridinecarboxylic acid;5-Butylpicolinic acid;5-n-Butylpyridine-2-carboxylic acid;5-Butyl-2-picolinic acid;NSC 135043;NSC 19870

Description

off-white to faint yellowish crystalline powder


Fusaric acid is a member of pyridines and an aromatic carboxylic acid.|A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis.

Fusaric acid Basic Attributes

179.21600

179.22

208-643-0

JWJ963070N

19870

DTXSID5023085

COLORLESS CRYSTALS

2933399090

Characteristics

50.19000

2.12240

off-white to faint yellowish crystalline powder

1.113g/cm3

96-98 °C

329.2ºC at 760mmHg

152.9ºC

-20ºC

LD50 orally in mice: 230 mg/kg (Ishii)

Safety Information

III

6.1(b)

2811

3

R25

S24/25

US5625000

Xn

P264, P270, P301+P312, P330, P501

H302

A REVIEW WITH 28 REFERENCES OF THE ROLE OF FUSARIC ACID AS A PLANT TOXIN.[KALYANASUNDARAM R; MODE OF ACTION OF FUSARIC ACID; PLANT DIS PROBL PROC INT SYMP 1ST: 142 (1970)]

|Warning|H302 (99.23%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 130 companies from 2 notifications to the ECHA C&L Inventory.

Toxicity

WHEN FUSARIC ACID (100 MG/KG, IP) WAS ADMIN TO MALE MICE 6 HR AFTER ALCOHOL WITHDRAWAL, BRAIN NORADRENALINE, DOPAMINE, & SEROTONIN CONCN WERE 112.8, 186.4, & 652.8 NG/G 4 HR LATER. FUSARIC ACID ADMIN DECREASED BRAIN NORADRENALINE LEVEL ACCOMPANIED BY AN ENHANCED ALCOHOL WITHDRAWAL SYNDROME.

THE TOXIN ISOLATED FROM THE CULTURE MEDIA OF FUSARIUM OXYSPORUM F VASINFECTUM WAS IDENTIFIED AS FUSARIC ACID.

Drug Information

Dopamine Agents; Enzyme Inhibitors; Nucleic Acid Synthesis Inhibitors|EXPTL USE: FUSARIC ACID (100 MG/KG, IP) GIVEN 1.5 HR PRIOR TO WATER-IMMERSION STRESS ALMOST COMPLETELY PREVENTED GASTRIC ULCER FORMATION IN RATS. FUSARIC ACID PROBABLY PREVENTS GASTRIC ULCERATION BY DECREASING NORADRENALINE RELEASE IN THE CNS.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)|Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)

THE METABOLISM OF (14)C-LABELED FUSARIC ACID WAS STUDIED IN MALE & PREGNANT RATS AFTER ORAL ADMIN OF 20 MG/KG. THE MAJOR PART OF RADIOACTIVITY RETAINED IN THE BODY OF MALE RATS WAS IN THE KIDNEY, LIVER, & PLASMA 30 MIN AFTER ADMIN, & DECLINED RAPIDLY THEREAFTER. MOST (92.9%) OF THE DOSE APPEARED IN URINE BY 24 HR AFTER ADMIN & 93.1% BY 48 HR. A CONSIDERABLE AMOUNT OF RADIOACTIVITY APPEARED IN BILE WITHIN 1 HR AFTER ADMIN. AN EASY TRANSFER OF RADIOACTIVITY INTO THE FETUS WAS SHOWN BY RADIOAUTOGRAPHY OF PREGNANT RATS. THE ACTIVITY WAS NOT DETECTED IN THE FETUS IN 24 HR.

ZINC, COBALT, & MOLYBDENUM ENHANCE THE BIOSYNTHESIS OF FUSARIC ACID BY FUSARIUM OXYSPORUM. NICOTINIC ACID WAS SLIGHTLY STIMULATORY, & TRYPTOPHAN, CYSTEINE, & THE COMBINATION OF INDOLEACETATE & SERINE MARKEDLY STIMULATED THE SYNTHESIS.|INDOLEACETIC ACID ALONE INHIBITED FUSARIC ACID FORMATION BY FUSARIUM OXYSPORUM, BUT INDOLEACETATE WITH SERINE HAD A STIMULATORY EFFECT. THE COMBINATION OF INDOLEACETATE & SERINE WITH TRYPTOPHAN INHIBITED THE BIOSYNTHESIS. HOMOSERINE SHOWED STIMULATORY ACTIVITY INDEPENDENT OF THE OTHER COMPOUNDS TESTED SINCE IT WAS NOT AFFECTED BY THEIR PRESENCE.|THE BIOSYNTHETIC PATHWAY FOR FUSARIC ACID WAS INVESTIGATED USING 1-(13)C-LABELED & 2-(13)C-LABELED ASPARTATE. CARBON ATOMS 2, 3, 4, & 7 WERE DERIVED FROM ACETATE VIA ASPARTATE OR A RELATED C4 DICARBOXYLIC ACID, WHEREAS CARBONS 5, 6, 8, 9, 10, & 11 WERE DERIVED MORE DIRECTLY FROM ACETATE. ASPARTIC ACID APPARENTLY IS METABOLIZED TO FUSARIC ACID VIA OXALOACETATE, & L-ASPARTATE SERVES AS A DONOR OF NITROGEN, IN AN AMINOTRANSFERASE REACTION, TO A SEPARATE OXALACETATE POOL OF PRIMARILY ENDOGENOUS ORIGIN.|IN RATS, THE MAJOR METABOLITE OF 5-(N-BUTYL)PICOLINAMIDE IS FUSARIC ACID, WHICH IS A DOPAMINE-BETA-HYDROXYLASE INHIBITOR. HENCE, ADMIN OF THE DRUG LOWERS THE CONCN OF ENDOGENOUS L-NORADRENALINE IN THE BRAIN, HEART, & SPLEEN.

FUSARIC ACID SUPPRESSED RAPID EYE MOVEMENT (REM) SLEEP IN CATS BUT HAD NO SIGNIFICANT EFFECT ON SLOW WAVE SLEEP. REM SLEEP USUALLY REBOUNDED AFTER A PERIOD OF DRUG-INDUCED SUPPRESSION, INDICATING THAT, ALTHOUGH FUSARIC ACID SUPPRESSED THE PERIPHERAL MANIFESTATIONS OF REM, THE BIOLOGICAL NEED FOR REM WAS NOT ALTERED.|FUSARIC ACID INHIBITED NORADRENALINE & DOPAMINE UPTAKE IN SYNAPTOSOMES FROM RAT HYPOTHALAMUS & CORPUS STRIATUM. THE BASAL OVERFLOW OF NORADRENALINE & DOPAMINE FROM BRAIN STEM & CORPUS STRIATUM SLICES WAS STIMULATED BY FUSARIC ACID. THE DATA SHOW THAT FUSARIC ACID, A DOPAMINE-BETA-HYDROXYLASE INHIBITOR, ALSO EXERTS MARKED EFFECTS IN THE CNS BY INTERFERING WITH OTHER SYNAPTOSOMAL FUNCTIONS.|FUSARIC ACID (100 MG/KG, IP) INCREASED THE LEVELS OF TRYPTOPHAN, SEROTONIN, & 5-HYDROXYINDOLEACETIC ACID IN RAT BRAIN & THE LEVEL OF FREE TRYPTOPHAN IN THE BLOOD INDICATING THAT IN ADDITION TO ITS CNS EFFECT, FUSARIC ACID EXERTS A PERIPHERAL ACTION ON SEROTONIN METABOLISM BY INHIBITING TRYPTOPHAN BINDING TO SERUM ALBUMIN.|FUSARIC ACID (75 MG/KG, IP), AN INHIBITOR OF DOPAMINE BETA-HYDROXYLASE, EFFECTIVE IN THE RELIEF OF TREMORS, RIGIDITY, & SPEECH DIFFICULTIES ASSOCIATED WITH PARKINSONS DISEASE, INCREASED THE BRAIN SEROTONIN LEVELS & DECREASED THE BRAIN NORADRENALINE LEVELS OF RATS.|FUSARIC ACID (FA) INCREASED MONOSYNAPTIC REFLEX NEURAL ACTIVITY IN A DOSE-DEPENDENT MANNER IN CATS. FA DID NOT INCREASE THE BLOOD PRESSURE BUT INHIBITED THE SYNTHESIS OF NOREPINEPHRINE FROM DOPAMINE.

5 Butyl 2 pyridinedicarboxylic Acid

Fusaric acid Use and Manufacturing

Methods of Manufacturing

HARDEGGER, NIKLES, HELV CHIM ACTA 39, 505 (1956)...|LARGE QUANTITIES OF FUSARIC ACID WERE PRODUCED BY FUSARIUM SPECIES GROWN ON A MODIFIED RICHARDS MEDIUM CONTAINING 2 MOLAR, BUT NOT 0.05 MOLAR GLUCOSE.|ANTIBIOTIC (WILTING AGENT) FIRST ISOLATED FROM THE FUNGUS FUSARIUM HETEROSPORIUM, NEES: YABUTA ET AL, J AGR CHEM SOC JAPAN 10, 1059 (1934). ISOLATION FROM OTHER FUSARIUM SPECIES & FROM GIBBERELLA FUJIKUROI & SYNTHESIS: PLATTNER ET AL, HELV CHIM ACTA 37, 1379 (1954).

Uses

A medical research tool.

2-Pyridinecarboxylic acid, 5-butyl-: INACTIVE|ADDITION OF EXCESSIVE AMOUNTS OF ZINC (30 MG/L) TO THE MEDIUM OF VIRULENT STRAIN OF FUSARIUM OXYSPORUM VASINFECTUM DECREASED THE CONTENT OF FUSARIC ACID BY 40% IN COMPARISON TO THAT IN THE SAME STRAIN GROWN ON MEDIUM WITH A NORMAL AMOUNT OF ZINC (0.2 MG/L). EXCESSIVE ZINC APPARENTLY ALTERS THE METABOLIC PATHWAY ASSOCIATED WITH FUSARIC ACID FORMATION & LEADS TO ACTIVATION OF THE DEHYDROGENASE SYSTEM. THE MAIN EFFECT OF EXCESSIVE ZINC APPEARS NOT TO BE LOSS OF VIABILITY BY PATHOGENIC FORMS, BUT LOSS OF VIRULENCE.

DETERMINATION OF FUSARIC ACID IN BIOLOGICAL FLUIDS BY GAS-LIQUID CHROMATOGRAPHY. THE METHOD HAS A LOWER LIMIT OF SENSITIVITY OF 0.1 MCG/ML.

Computed Properties

Molecular Weight:179.22
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:179.094628657
Monoisotopic Mass:179.094628657
Topological Polar Surface Area:50.2
Heavy Atom Count:13
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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