MedKoo Cat#: 526891 | Name: AV-101

Description:

WARNING: This product is for research use only, not for human or veterinary use.

AV-101, also known as 4-Chlorokynurenine, is a NMDA glycine B receptor antagonist potentially for treatment of major depressive disorder. AV-101 is an orally active small molecule prodrug candidate that in vivo produces a glycine binding site NMDA receptor antagonist. AV-101 is in clinical development by VistaGen Therapeutics. Inc. as a potential new generation, fast-acting antidepressant, and for other central nervous system (CNS) indications.

Chemical Structure

AV-101
AV-101
CAS#153152-32-0 (S-isomer)

Theoretical Analysis

MedKoo Cat#: 526891

Name: AV-101

CAS#: 153152-32-0 (S-isomer)

Chemical Formula: C10H11ClN2O3

Exact Mass: 242.0458

Molecular Weight: 242.66

Elemental Analysis: C, 49.50; H, 4.57; Cl, 14.61; N, 11.54; O, 19.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
2369777-80-8 (S-isomer HCl) 153152-32-0 (S-isomer) 75802-84-5 (racemate)
Synonym
AV-101; AV 101; AV101; 4-Cl-KYN; L-4-Cl-KYN; 4ClKYN; L-4ClKYN; 4-Chlorokynurenine;
IUPAC/Chemical Name
(2S)-2-Amino-4-(2-amino-4-chlorophenyl)-4-oxobutanoic acid
InChi Key
HQLHZNDJQSRKDT-QMMMGPOBSA-N
InChi Code
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
SMILES Code
O=C(O)[C@@H](N)CC(C1=CC=C(Cl)C=C1N)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 242.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zanos P, Piantadosi SC, Wu HQ, Pribut HJ, Dell MJ, Can A, Snodgrass HR, Zarate CA Jr, Schwarcz R, Gould TD. The Prodrug 4-Chlorokynurenine Causes Ketamine-Like Antidepressant Effects, but Not Side Effects, by NMDA/GlycineB-Site Inhibition. J Pharmacol Exp Ther. 2015 Oct;355(1):76-85. doi: 10.1124/jpet.115.225664. Epub 2015 Aug 11. PubMed PMID: 26265321; PubMed Central PMCID: PMC4576668. 2: Tan L, Yu JT, Tan L. The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations. J Neurol Sci. 2012 Dec 15;323(1-2):1-8. doi: 10.1016/j.jns.2012.08.005. Epub 2012 Aug 29. Review. PubMed PMID: 22939820. 3: Linderholm KR, Andersson A, Olsson S, Olsson E, Snodgrass R, Engberg G, Erhardt S. Activation of rat ventral tegmental area dopamine neurons by endogenous kynurenic acid: a pharmacological analysis. Neuropharmacology. 2007 Dec;53(8):918-24. Epub 2007 Sep 20. PubMed PMID: 17959203. 4: Wu HQ, Rassoulpour A, Goodman JH, Scharfman HE, Bertram EH, Schwarcz R. Kynurenate and 7-chlorokynurenate formation in chronically epileptic rats. Epilepsia. 2005 Jul;46(7):1010-6. PubMed PMID: 16026552. 5: Kiss C, Ceresoli-Borroni G, Guidetti P, Zielke CL, Zielke HR, Schwarcz R. Kynurenate production by cultured human astrocytes. J Neural Transm (Vienna). 2003 Jan;110(1):1-14. PubMed PMID: 12541009. 6: Wu HQ, Lee SC, Scharfman HE, Schwarcz R. L-4-chlorokynurenine attenuates kainate-induced seizures and lesions in the rat. Exp Neurol. 2002 Sep;177(1):222-32. PubMed PMID: 12429224. 7: Lee SC, Schwarcz R. Excitotoxic injury stimulates pro-drug-induced 7-chlorokynurenate formation in the rat striatum in vivo. Neurosci Lett. 2001 May 25;304(3):185-8. PubMed PMID: 11343833. 8: Guidetti P, Wu HQ, Schwarcz R. In situ produced 7-chlorokynurenate provides protection against quinolinate- and malonate-induced neurotoxicity in the rat striatum. Exp Neurol. 2000 May;163(1):123-30. PubMed PMID: 10785450. 9: Wu HQ, Lee SC, Schwarcz R. Systemic administration of 4-chlorokynurenine prevents quinolinate neurotoxicity in the rat hippocampus. Eur J Pharmacol. 2000 Mar 3;390(3):267-74. PubMed PMID: 10708733. 10: Wu HQ, Salituro FG, Schwarcz R. Enzyme-catalyzed production of the neuroprotective NMDA receptor antagonist 7-chlorokynurenic acid in the rat brain in vivo. Eur J Pharmacol. 1997 Jan 14;319(1):13-20. PubMed PMID: 9030892. 11: Hokari M, Wu HQ, Schwarcz R, Smith QR. Facilitated brain uptake of 4-chlorokynurenine and conversion to 7-chlorokynurenic acid. Neuroreport. 1996 Dec 20;8(1):15-8. PubMed PMID: 9051744. 12: Naritsin DB, Saito K, Markey SP, Chen CY, Heyes MP. Metabolism of L-tryptophan to kynurenate and quinolinate in the central nervous system: effects of 6-chlorotryptophan and 4-chloro-3-hydroxyanthranilate. J Neurochem. 1995 Nov;65(5):2217-26. PubMed PMID: 7595510. 13: Salituro FG, Tomlinson RC, Baron BM, Palfreyman MG, McDonald IA, Schmidt W, Wu HQ, Guidetti P, Schwarcz R. Enzyme-activated antagonists of the strychnine-insensitive glycine/NMDA receptor. J Med Chem. 1994 Feb 4;37(3):334-6. PubMed PMID: 8308859. 14: Kawashima K, Itoh H, Yoneda N, Hagio K, Moriya T, Chibata I. An intensely sweet analogue of kynurenine: 3-(4-chloroanthraniloyl)-DL-alanine. J Agric Food Chem. 1980 Nov-Dec;28(6):1338-40. PubMed PMID: 7451766.