Structure of Empirical Formula
CAS No.: 492-27-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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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 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Target |
|
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 << |
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 |
Tags: Kynurenic acid | Quinurenic acid | iGluR | Endogenous Metabolite | Apoptosis | CXCR | GPR35 | Ionotropic glutamate receptors | CXC chemokine receptors | C-X-C motif chemokine receptors | G Protein-Coupled Receptor 35 | NMDA antagonist | glutamate receptor | α7 nicotinic acetylcholine receptor | GPR35 agonist | CXCR8 | tryptophan metabolite | 492-27-3
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