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Chemical Structure| 492-27-3 Chemical Structure| 492-27-3

Structure of Empirical Formula
CAS No.: 492-27-3

Chemical Structure| 492-27-3

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Kynurenic Acid is a broad spectrum glutamatergic antagonist which can antagonize NMDA, kainate and AMPA receptors.

Synonyms: Quinurenic acid; Kynurenic acid; Kynuronic acid

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Product Details of Empirical Formula

CAS No. :492-27-3
Formula : C10H7NO3
M.W : 189.17
SMILES Code : O=C(C1=NC2=CC=CC=C2C(O)=C1)O
Synonyms :
Quinurenic acid; Kynurenic acid; Kynuronic acid
MDL No. :MFCD00149476
InChI Key :HCZHHEIFKROPDY-UHFFFAOYSA-N
Pubchem ID :3845

Safety of Empirical Formula

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

Target
  • NMDA receptor

In Vitro:

Cell Line
Concentration Treated Time Description References
pancreatic acinar cells 250 µM 8 h Evaluate the protective effects of KYNA and SZR-72 on LO-induced cellular toxicity, results showed KYNA and SZR-72 significantly reduced LO-induced toxicity PMC8567016
murine neonatal cardiomyocytes 20 μM 20 min KynA decreased mitochondrial ROS production and preserved mitochondrial membrane potential in a GPR35-dependent manner PMC9639781
human-derived induced pluripotent stem cells-cardiomyocytes (hIPS-CMs) 20 μM 1 h Simulated ischemia-reperfusion injury, KynA pretreatment protected cell survival in a GPR35-dependent manner PMC9639781
human umbilical cord-derived MSCs (hUC-MSCs) 50 μM 24 h KYNA enhances TSG-6 expression by activating AhR signaling pathway PMC6030103
Primary rat cardiomyocytes 128 µM 4 h KYNA dose-dependently attenuated SI/R-induced cell death, reduced apoptotic markers PMC11416393
H9c2 cells 64 µM 6 h KYNA dose-dependently attenuated SI/R-induced cell death, reduced oxidative stress and LDH release PMC11416393
U-937 monocytic cells 500 µM 24 h KYNA and KYNA analogs attenuated TNF-α production induced by heat inactivated Staphylococcus aureus and increased TSG-6 mRNA expression PMC6611419

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Sprague-Dawley rats Acute necrotizing pancreatitis Intraperitoneal injection 300 mg/kg Single dose, lasted for 24 hours Evaluate the effects of KYNA and SZR-72 on the severity of acute pancreatitis, results showed 300 mg/kg dose significantly alleviated pancreatitis symptoms PMC8567016
C57BL/6J mice LPS-induced sepsis model Intraperitoneal injection 50 mg/kg Administered 24 hours and 2 hours before LPS injection KA significantly reduced serum IL-1β and IL-18 levels in wild-type mice but had no effect in Nlrp3?/? mice PMC9606686
Mice Cardiac ischemia/reperfusion (I/R) injury model Intraperitoneal injection 5 mg/kg Single dose 2 hours or 24 hours prior to ischemia KynA significantly reduced myocardial infarct size and protected cardiac function by activating GPR35 PMC9639781
Sprague-Dawley rats Heatstroke model Intravenous injection 30–100 mg/kg Single dose, 4 hours before heat exposure KYNA preconditioning significantly prolonged survival time in heatstroke rats, attenuated hypotension, hypothalamic neuronal degeneration and apoptosis, reduced apoptosis in spleen, kidney, liver, and lung, upregulated serum IL-10 levels, and downregulated TNF-α and ICAM-1 levels. PMC4009940
Polish Longwool sheep Sheep brain third ventricle cannulation model Intracerebroventricular infusion 20 µg; 100 µg 4 infusions, 30 min each, at 30 min intervals To investigate the effect of KYNA on BDNF and TrkB expression in specific brain regions of sheep. Results showed that KYNA significantly increased BDNF protein concentration and mRNA expression in the hippocampal CA3 field, amygdala, and prefrontal cortex, with effects varying by dose and brain region. PMC11639857
Sprague-Dawley rats Intraabdominal sepsis model Intraperitoneal injection 160 µM/kg Twice at 16h and 22h after induction To evaluate the protective effects of KYNA and its synthetic derivatives on sepsis-associated neutrophil activation and brain mitochondrial dysfunction. Results showed that KYNA and its derivatives significantly reduced sepsis-induced increases in BBB permeability and brain injury marker S100B levels, and improved brain mitochondrial function. PMC8406694

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT03557684 Depression Early Phase 1 Recruiting July 31, 2020 United States, California ... More >> UCLA Cousins Center for Psychoneuroimmunology Recruiting Los Angeles, California, United States, 90095 Contact: Gracie Pineda    310-825-8425    grpineda@g.ucla.edu    Principal Investigator: Joshua H Cho, MD, PhD Less <<
NCT00573300 - Completed - United States, Massachusetts ... More >> Freedom Trail Clinic Boston, Massachusetts, United States, 02114 Less <<
NCT02234752 Schizophrenia ... More >> Schizoaffective Disorder Less << Phase 2 Terminated(Funding no longer a... More >>vailable and PI no longer working at the institution) Less << - United States, Maryland ... More >> Sheppard Pratt Health System Baltimore, Maryland, United States, 21204 Less <<
NCT03285399 - Completed - Nepal ... More >> Siddhi Memorial Hospital (SMH),Bhelukhel, Bhimsensthan Bhaktapur, Nepal, P.O.Box 40 Less <<
NCT02234752 - Terminated(Funding no longer a... More >>vailable and PI no longer working at the institution) Less << - -
NCT03513822 Neuralgia Chr... More >>onic Pain Inflammation Less << Phase 3 Recruiting November 2018 France ... More >> Raymond Poincaré Hospital Recruiting Garches, Hauts De Seine, France, 92380 Contact: Cyril QUEMENEUR, Resident    0033681193981    c.quemeneur@gmx.com    Contact: Valeria Martinez, MD, PhD    0033601819222    valeria.martinez@aphp.fr Less <<
NCT03539835 Cancer Not Applicable Recruiting September 2019 United States, Georgia ... More >> Winship Cancer Institute Recruiting Atlanta, Georgia, United States, 30322 Contact: Monica Serra, MD    404-727-6123    monica.christine.serra@emory.edu Less <<
NCT02992899 PostTraumatic Stress Disorder Not Applicable Recruiting July 2019 United States, Georgia ... More >> Emory University Recruiting Atlanta, Georgia, United States, 30322 Contact: Stacy Ladd    404-712-2014    sladd2@emory.edu Less <<
NCT03125083 Skin Restricted Lupus ... More >> Psychiatric Disorders Less << Not Applicable Recruiting December 2018 France ... More >> CHU Clermont-Ferrand Recruiting Clermont-Ferrand, France, 63003 Contact: Patrick LACARIN    04 73 75 11 95    placarin@chu-clermontferrand.fr    Principal Investigator: Isabelle JALENQUES Less <<
NCT01975584 Schizophrenia ... More >> Schizoaffective Disorder Less << Not Applicable Completed - United States, Maryland ... More >> Maryland Psychiatric Research Center Catonsville, Maryland, United States, 21228 Less <<
NCT03014518 - Recruiting August 2019 United States, Ohio ... More >> The Cleveland Clinic Recruiting Cleveland, Ohio, United States, 44195 Contact: Tatiana Falcone, M.D.    216-444-7459    falcont1@ccf.org Less <<
NCT01304355 - Unknown January 2012 Ireland ... More >> Cork University Hospial Recruiting Cork, Ireland Contact: Gerard Clarke, PhD    00353214901415    g.clarke@ucc.ie    Principal Investigator: Gerard Clarke, PhD          Principal Investigator: Timothy G Dinan, Professor          Principal Investigator: John F Cryan, PhD          University College Cork Recruiting Cork, Ireland Contact: Gerard Clarke, PhD    00353214901415    g.clarke@ucc.ie    Principal Investigator: Gerard Clarke, PhD          Principal Investigator: Timothy G Dinan, Professor          Principal Investigator: John F Cryan, PhD Less <<
NCT02067975 Schizophrenia Phase 2 Phase 3 Recruiting December 2018 United States, Maryland ... More >> Maryland Psychiatric Research Center Recruiting Catonsville, Maryland, United States, 21228 Principal Investigator: Robert W. Buchanan, M.D. Less <<
NCT02340325 Cicatrix Cica... More >>trix, Hypertrophic Keloid Less << Phase 1 Completed - Canada, British Columbia ... More >> BCPFF Burn & Wound Healing Lab Vancouver, British Columbia, Canada, V5Z1M9 Less <<
NCT03583554 Healthy Phase 1 Phase 2 Recruiting March 31, 2019 United States, Texas ... More >> Michael E. DeBakey VA Medical Center Recruiting Houston, Texas, United States, 77030 Contact: Marijn Lijffijt, PhD    713-798-5642    marijn.lijffijt@bcm.edu    Sub-Investigator: Sanjay J. Mathew, MD          Sub-Investigator: Alan C. Swann, MD Less <<
NCT01558570 - Completed - United States, Maryland ... More >> Maryland Psychiatric Research Center Catonsville, Maryland, United States, 21228 Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

5.29mL

1.06mL

0.53mL

26.43mL

5.29mL

2.64mL

52.86mL

10.57mL

5.29mL

References

 

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