Xanthurenic acid

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Xanthurenic acid[1]
Xanthurenic acid.png
IUPAC name
8-Hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
Other names
Xanthuric acid
8-Hydroxykynurenic acid
4,8-Dihydroxyquinaldic acid
59-00-7 N
ChemSpider 5497 N
EC Number 200-410-1
Jmol interactive 3D Image
KEGG C02470 N
PubChem 5699
Molar mass 205.17 g/mol
Appearance Yellow crystals
Melting point 286 °C (547 °F; 559 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Xanthurenic acid, or xanthurenate, is a chemical shown to induce gametogenesis of Plasmodium falciparum, the parasite that causes malaria.[2][3] It is found in the gut of the Anopheles mosquito.

Xanthurenic acid is a metabolic intermediate that accumulates and is excreted by pyridoxine (vitamin B6) deficient animals after the ingestion of tryptophan.[1][4]

Xanthurenic acid is suspected to be an endogenous agonist for Group II metabotropic glutamate receptors in humans.[5] It is also known to be a potent inhibitor of the reuptake of glutamate into synaptic vesicles (or a vesicular glutamate reuptake inhibitor), an action that it mediates via competitive blockade of vesicular glutamate transporters (Ki = 0.19 mM).[6]

See also[edit]


  1. ^ a b Merck Index, 11th Edition, 9977.
  2. ^ Billker, O; Lindo, V; Panico, M; Etienne, AE; Paxton, T; Dell, A; Rogers, M; Sinden, RE; Morris, HR (March 19, 1998). "Identification of xanthurenic acid as the putative inducer of malaria development in the mosquito". Nature 392 (6673): 289–292. doi:10.1038/32667. PMID 9521324. 
  3. ^ Garcia, GE; Wirtz, RA; Barr, JR; Woolfitt, A; Rosenberg, R (May 15, 1998). "Xanthurenic acid induces gametogenesis in Plasmodium, the malaria parasite.". The Journal of biological chemistry 273 (20): 12003–5. doi:10.1074/jbc.273.20.12003. PMID 9575140. 
  4. ^ Xanthurenic acid at Sigma-Aldrich
  5. ^ Copeland, C. S.; Neale, S. A.; Salt, T. E. (2013). "Actions of Xanthurenic Acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus". Neuropharmacology 66: 133–142. doi:10.1016/j.neuropharm.2012.03.009. PMID 22491023. 
  6. ^ Bartlett RD, Esslinger CS, Thompson CM, Bridges RJ (1998). "Substituted quinolines as inhibitors of L-glutamate transport into synaptic vesicles". Neuropharmacology 37 (7): 839–46. PMID 9776380.