4-Chlorokynurenine

4-Chlorokynurenine

Clinical data
Other names	4-Cl-KYN; AV-101; 3-(4-Chloroanthraniloyl)-DL-alanine
Routes of administration	By mouth
Drug class	NMDA receptor antagonist
ATC code	None
Legal status
Legal status	US: Investigational New Drug
Pharmacokinetic data
Bioavailability	39–84% (rodents); ≥ 31% (humans)[citation needed]
Elimination half-life	2–3 hours[citation needed]
Identifiers
IUPAC name (2S)-2-Amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid
CAS Number	153152-32-0
PubChem CID	9859632
ChemSpider	151423
UNII	77XLH9L40B
CompTox Dashboard (EPA)	DTXSID30997196
Chemical and physical data
Formula	C10H11ClN2O3
Molar mass	242.66 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(C[C@H](N)C(=O)O)c1ccc(Cl)cc1N
InChI InChI=1S/C10H11ClN2O3/c11-5-1-2-6(7(12)3-5)9(14)4-8(13)10(15)16/h1-3,8H,4,12-13H2,(H,15,16)/t8-/m0/s1 Key:HQLHZNDJQSRKDT-QMMMGPOBSA-N

L-4-Chlorokynurenine (4-Cl-KYN; developmental code name AV-101) is an orally active small molecule prodrug of 7-chlorokynurenic acid, a NMDA receptor antagonist. It was investigated as a potential rapid-acting antidepressant.

AV-101 was discovered at Marion Merrell Dow and its biological activity was explored at University of Maryland. It underwent initial development at Artemis Neuroscience which was acquired by VistaGen in 2003. A phase II clinical trial failed to show any effect over placebo in alleviating treatment-resistant depression.^[1]