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Chemistry

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Also known as: 5-butylpicolinic acid, 536-69-6, 5-butylpyridine-2-carboxylic acid, Fusarinic acid, 2-pyridinecarboxylic acid, 5-butyl-, 5-butyl-2-pyridinecarboxylic acid
Molecular Formula
C10H13NO2
Molecular Weight
179.22  g/mol
InChI Key
DGMPVYSXXIOGJY-UHFFFAOYSA-N
FDA UNII
JWJ963070N

Fusaric 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.
1 2D Structure

Fusaric Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-butylpyridine-2-carboxylic acid
2.1.2 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)
2.1.3 InChI Key
DGMPVYSXXIOGJY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCC1=CN=C(C=C1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
JWJ963070N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5 Butyl 2 Pyridinedicarboxylic Acid

2. 5-butyl-2-pyridinedicarboxylic Acid

3. Acid, 5-butyl-2-pyridinedicarboxylic

4. Acid, Fusaric

5. Calcium Fusarate

6. Fusarate, Calcium

2.3.2 Depositor-Supplied Synonyms

1. 5-butylpicolinic Acid

2. 536-69-6

3. 5-butylpyridine-2-carboxylic Acid

4. Fusarinic Acid

5. 2-pyridinecarboxylic Acid, 5-butyl-

6. 5-butyl-2-pyridinecarboxylic Acid

7. Picolinic Acid, 5-butyl-

8. 5-n-butylpyridine-2-carboxylic Acid

9. 5-butyl-pyridine-2-carboxylic Acid

10. Chembl24510

11. Chebi:5199

12. Jwj963070n

13. Nsc19870

14. Tnp00268

15. Nsc-19870

16. Ncgc00015441-04

17. Cas-536-69-6

18. 5-butylpyridine-3-carboxylic Acid

19. Hsdb 3487

20. Einecs 208-643-0

21. Mfcd00006298

22. Nsc 19870

23. Brn 0125804

24. Unii-jwj963070n

25. Prestwick_233

26. 5-n-butylpicolinic Acid

27. Prestwick0_000442

28. Prestwick1_000442

29. Prestwick2_000442

30. Prestwick3_000442

31. 5-n-butyl Picolinic Acid

32. Lopac-f-6513

33. Dsstox_cid_3085

34. Fusaric Acid [mi]

35. Fusaric Acid [jan]

36. Dsstox_rid_76868

37. Fusaric Acid [hsdb]

38. Dsstox_gsid_23085

39. Lopac0_000526

40. Oprea1_115508

41. Wln: T6nj Bvq E4

42. 5-n-butyl-2-picolinic Acid

43. Bspbio_000484

44. 5-22-02-00384 (beilstein Handbook Reference)

45. Mls002153813

46. Fusaric Acid [mart.]

47. Schembl178006

48. Spbio_002423

49. Bpbio1_000534

50. Dtxsid5023085

51. Hms1569i06

52. Hms2096i06

53. Hms2230m05

54. Hms3261j13

55. Hms3369p03

56. Zinc1531682

57. Tox21_110149

58. Tox21_500526

59. Bdbm50000439

60. Stl564384

61. Akos015891748

62. Ccg-204616

63. Fusaric Acid, From Gibberella Fujikuroi

64. Lp00526

65. Sdccgsbi-0050509.p002

66. Ncgc00015441-01

67. Ncgc00015441-02

68. Ncgc00015441-03

69. Ncgc00015441-05

70. Ncgc00015441-06

71. Ncgc00015441-07

72. Ncgc00015441-08

73. Ncgc00015441-10

74. Ncgc00015441-15

75. Ncgc00093919-01

76. Ncgc00093919-02

77. Ncgc00093919-03

78. Ncgc00261211-01

79. As-57621

80. Smr001233184

81. Db-052375

82. Hy-128483

83. Cs-0099145

84. Eu-0100526

85. F0227

86. Ft-0626585

87. A19903

88. F 6513

89. F-9000

90. T72585

91. 5-butyl-pyridine-2-carboxylic Acid (fusaric Acid)

92. Q905703

93. Sr-01000075634

94. Sr-01000075634-1

95. Brd-k87049188-001-03-6

96. Fusaric Acid, For Hplc Derivatization, >=99.0% (hplc)

97. 4-(acetylamino)-6-nitro-1,3-benzenedicarboxylicacid

98. Cqv

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 179.22 g/mol
Molecular Formula C10H13NO2
XLogP32.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass179.094628657 g/mol
Monoisotopic Mass179.094628657 g/mol
Topological Polar Surface Area50.2 Ų
Heavy Atom Count13
Formal Charge0
Complexity170
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Dopamine Agents; Enzyme Inhibitors; Nucleic Acid Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


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.

OSUMI Y ET AL; PREVENTIVE EFFECT OF FUSARIC ACID, A DOPAMINE BETA-HYDROXYLASE INHIBITOR, ON THE GASTRIC ULCERATION INDUCED BY WATER-IMMERSION STRESS IN RATS; JAP J PHARMACOL 23(6) 904 (1973)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)


Enzyme Inhibitors

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.)


Dopamine Agents

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.)


5.2 Absorption, Distribution and Excretion

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.

MATSUZAKI M ET AL; ABSORPTION, DISTRIBUTION AND EXCRETION OF 14C-FUSARIC ACID IN THE RAT; JPN J ANTIBIOT 29(5) 456 (1976)


5.3 Metabolism/Metabolites

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.

YASAKOVA EI, BEKKER ZE; EFFECT OF NITROGEN-CONTAINING COMPOUNDS AND TRACE ELEMENTS ON BIOSYNTHESIS OF FUSARIC ACID IN LABORATORY CULTURE; EKOL FIZIOL METODY BORBE FUZARIOZNYM VILTOM KHLOP 2: 190 (1973)


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.

AZIMOVA RM; EFFECT OF AMINO ACIDS PARTICIPATING IN BIOGENESIS OF PYRIDINES ON BIOSYNTHESIS OF FUSARIC ACID; EKOL FIZIOL METODY BORBE FUZARIOZNYM VILTOM KHLOP 2: 200 (1973)


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.

DESATY D ET AL; USE OF CARBON-13 IN BIOSYNTHETIC STUDIES. INCORPORATION OF ISOTOPICALLY LABELED ACETATE AND ASPARTATE INTO FUSARIC ACID; CAN J BIOCHEM 46(10) 1293 (1968)


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.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 92


5.4 Mechanism of Action

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.

SATOH T, TANAKA R; SELECTIVE SUPPRESSION OF RAPID EYE MOVEMENT SLEEP (REM) BY FUSARIC ACID, AN INHIBITOR OF DOPAMINE BETA-OXIDASE; EXPERIENTIA 29(2) 177 (1973)


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.

FISCHER HD ET AL; INTERACTION AT THE SYNAPTIC LEVEL OF FUSARIC ACID WITH NEUROTRANSMITTERS; ACTA BIOL MED GER 39(8-9) 935 (1980)


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.

BONNAY MM ET AL; PERIPHERAL EFFECT OF FUSARIC ACID, A DOPAMINE BETA-HYDROXYLASE INHIBITOR, ON SEROTONIN METABOLISM; BIOCHEM PHARMACOL 23(19) 2770 (1974)


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.

HIDAKA H; FUSARIC (5-BUTYLPICOLINIC) ACID, AN INHIBITOR OF DOPAMINE BETA-HYDROXYLASE, AFFECTS SEROTONIN AND NORADRENALINE; NATURE (LONDON) 231(5297) 54 (1971)


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.

WATANABE Y ET AL; EFFECTS OF FUSARIC (5-BUTYLPICOLINIC) ACID ON THE MONOSYNAPTIC REFLEX NEURAL ACTIVITY OF CAT SPINAL CORD; TOKAI J EXP CLIN MED 6(4) 443 (1981)


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