7-Chlorokynurenic acid

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7-Chlorokynurenic acid
File:7-Chlorokynurenate.png
Systematic (IUPAC) name
7-chloro-4-oxo-1H-quinoline-2-carboxylic acid
Identifiers
CAS Number 18000-24-3
ATC code None
PubChem CID: 1884
ChemSpider 1813
Synonyms 7-chlorokynurenate; 7-CTKA
Chemical data
Formula C10H6ClNO3
Molecular mass 223.61254 g/mol
  • C1=CC2=C(C=C1Cl)NC(=CC2=O)C(=O)O
  • InChI=1S/C10H6ClNO3/c11-5-1-2-6-7(3-5)12-8(10(14)15)4-9(6)13/h1-4H,(H,12,13)(H,14,15)
  • Key:UAWVRVFHMOSAPU-UHFFFAOYSA-N

7-Chlorokynurenic acid (7-CKA) is a drug that acts as a potent and selective noncompetitive antagonist of the glycine site of the NMDA receptor.[1] It produces ketamine-like rapid antidepressant effects in animal models of depression.[2] However, 7-CKA is unable to cross the blood-brain-barrier, and for this reason, is unsuitable for clinical use.[3] As a result, a centrally-penetrant prodrug of 7-CKA, 4-chlorokynurenine (AV-101), has been developed for use in humans, and is being studied in clinical trials as a potential treatment for major depressive disorder.[3][4] In addition to antagonizing the NMDA receptor, 7-CKA also acts as a potent inhibitor of the reuptake of glutamate into synaptic vesicles (or as a vesicular glutamate reuptake inhibitor), an action that it mediates via competitive blockade of vesicular glutamate transporters (Ki = 0.59 mM).[5]

See also

References

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