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Also known as: 153152-32-0, L-4-chlorokynurenine, Av-101, L-4-cl-kyn, 77xlh9l40b, 4-chloro kynurenine

Molecular Formula

C₁₀H₁₁ClN₂O₃

Molecular Weight

242.66 g/mol

InChI Key

HQLHZNDJQSRKDT-QMMMGPOBSA-N

FDA UNII

77XLH9L40B

L-4-chlorokynurenine is an orally bioavailable, blood brain barrier (BBB) penetrating, chlorinated analog of the endogenous neuromodulator kynurenic acid and prodrug of 7-chlorokynurenic acid (7-Cl-KYNA), a N-methyl-D-aspartate receptor (NMDA-R) antagonist at the glycine-coagonist (GlyB) site, with potential anti-hyperalgesic, neuroprotective and anti-epileptic activities. Unlike 7-Cl-KYNA, L-4-chlorokynurenine, upon oral administration, crosses the BBB and is enzymatically converted, through transamination, within activated astrocytes located at sites of injury in the central nervous system (CNS) to its active metabolite, 7-Cl-KYNA, which allows for high levels of this active metabolite at these specific sites. In turn, 7-Cl-KYNA selectively binds to and blocks the GlyB site within the NMDA receptors. This inhibits both NMDA-R overstimulation by the excitatory neurotransmitter glutamate and NMDA-R-mediated excitotoxicity, which prevents neuronal damage and induces analgesia. In addition, another metabolite, 4-chloro-3-hydroxyanthranilic acid, inhibits the synthesis of quinolinic acid, an endogenous NMDA receptor agonist, thereby further preventing excitotoxic damage. Compared to conventional NMDA-R antagonists, NMDA-R GlyB-specific antagonists appear to have fewer side effects.

1 2D Structure

4-Chlorokynurenine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid

2.1.2 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

2.1.3 InChI Key

HQLHZNDJQSRKDT-QMMMGPOBSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1Cl)N)C(=O)CC(C(=O)O)N

2.1.5 Isomeric SMILES

C1=CC(=C(C=C1Cl)N)C(=O)C[C@@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

77XLH9L40B

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 153152-32-0

2. L-4-chlorokynurenine

3. Av-101

4. L-4-cl-kyn

5. 77xlh9l40b

6. 4-chloro Kynurenine

7. J578.071c

8. (s)-2-amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic Acid

9. 4-cl-kyn

10. (s)-4-chlorokynurenine

11. 4-chloro-l-kynurenine

12. Starbld0018860

13. Unii-77xlh9l40b

14. Schembl727370

15. 3-(4-chloroanthraniloyl)alanine

16. Zinc6092007

17. Db12878

18. Benzenebutanoic Acid, Alpha,2-diamino-4-chloro-gamma-oxo-, (s)

19. Benzenebutanoic Acid, .alpha.,2-diamino-4-chloro-.gamma.-oxo-, (s)

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₁ClN₂O₃
Molecular Weight	242.66 g/mol
XLogP3	-1.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	242.0458199 g/mol
Monoisotopic Mass	242.0458199 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	285
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1