501925-31-1,MFCD00095313
Catalog No.:AA00DA8P

501925-31-1 | PNU-120596

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1mg
99+%
in stock  
$7.00   $5.00
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5mg
99+%
in stock  
$21.00   $15.00
- +
10mg
99+%
in stock  
$33.00   $23.00
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50mg
99+%
in stock  
$109.00   $76.00
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100mg
99+%
in stock  
$186.00   $130.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00DA8P
Chemical Name:
PNU-120596
CAS Number:
501925-31-1
Molecular Formula:
C13H14ClN3O4
Molecular Weight:
311.7210
MDL Number:
MFCD00095313
SMILES:
COc1cc(OC)c(cc1NC(=O)Nc1noc(c1)C)Cl
NSC Number:
216666
Properties
Properties
 
BP:
385°C at 760 mmHg  
Form:
Solid  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
360  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
4  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2.2  

Downstream Synthesis Route
61672-67-1    97-50-7   
1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea 

[1]Patent:US2003/236287,2003,A1.Locationinpatent:Page43

3405-77-4    97-50-7   
1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea 

[1]JournalofOrganicChemistry,2017,vol.82,p.992-999

Literature

Title: Electrophysiological investigation of the effect of structurally different bispyridinium non-oxime compounds on human α7-nicotinic acetylcholine receptor activity-An in vitro structure-activity analysis.

Journal: Toxicology letters 20180901

Title: Counteracting desensitization of human α7-nicotinic acetylcholine receptors with bispyridinium compounds as an approach against organophosphorus poisoning.

Journal: Toxicology letters 20180901

Title: Intrinsically low open probability of α7 nicotinic acetylcholine receptors can be overcome by positive allosteric modulation and serum factors leading to the generation of excitotoxic currents at physiological temperatures.

Journal: Molecular pharmacology 20121001

Title: PNU-120596, a positive allosteric modulator of α7 nicotinic acetylcholine receptors, reverses a sub-chronic phencyclidine-induced cognitive deficit in the attentional set-shifting task in female rats.

Journal: Journal of psychopharmacology (Oxford, England) 20120901

Title: The α7 nicotinic ACh receptor agonist compound B and positive allosteric modulator PNU-120596 both alleviate inflammatory hyperalgesia and cytokine release in the rat.

Journal: British journal of pharmacology 20120901

Title: Potential state-selective hydrogen bond formation can modulate activation and desensitization of the α7 nicotinic acetylcholine receptor.

Journal: The Journal of biological chemistry 20120622

Title: Protective effect of PNU-120596, a selective alpha7 nicotinic acetylcholine receptor-positive allosteric modulator, on myocardial ischemia-reperfusion injury in rats.

Journal: Journal of cardiovascular pharmacology 20120601

Title: α7 nicotinic ACh receptors as a ligand-gated source of Ca(2+) ions: the search for a Ca(2+) optimum.

Journal: Advances in experimental medicine and biology 20120101

Title: Somatic integration of single ion channel responses of α7 nicotinic acetylcholine receptors enhanced by PNU-120596.

Journal: PloS one 20120101

Title: Competitive binding at a nicotinic receptor transmembrane site of two α7-selective positive allosteric modulators with differing effects on agonist-evoked desensitization.

Journal: Neuropharmacology 20111201

Title: Investigation of the molecular mechanism of the α7 nicotinic acetylcholine receptor positive allosteric modulator PNU-120596 provides evidence for two distinct desensitized states.

Journal: Molecular pharmacology 20111201

Title: The chimeric gene CHRFAM7A, a partial duplication of the CHRNA7 gene, is a dominant negative regulator of α7*nAChR function.

Journal: Biochemical pharmacology 20111015

Title: Single-channel and structural foundations of neuronal α7 acetylcholine receptor potentiation.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20110928

Title: Neurotoxicity induced by okadaic acid in the human neuroblastoma SH-SY5Y line can be differentially prevented by α7 and β2* nicotinic stimulation.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20110901

Title: Characterizing ligand-gated ion channel receptors with genetically encoded Ca2++ sensors.

Journal: PloS one 20110101

Title: Differential immediate and sustained memory enhancing effects of alpha7 nicotinic receptor agonists and allosteric modulators in rats.

Journal: PloS one 20110101

Title: Tethered agonist analogs as site-specific probes for domains of the human α7 nicotinic acetylcholine receptor that differentially regulate activation and desensitization.

Journal: Molecular pharmacology 20101201

Title: In vitro pharmacological characterization of a novel selective alpha7 neuronal nicotinic acetylcholine receptor agonist ABT-107.

Journal: The Journal of pharmacology and experimental therapeutics 20100901

Title: Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia.

Journal: Dialogues in clinical neuroscience 20100901

Title: Identification of novel alpha7 nAChR positive allosteric modulators with the use of pharmacophore in silico screening methods.

Journal: Bioorganic & medicinal chemistry letters 20100801

Title: The effects of 3,4-methylenedioxymethamphetamine (MDMA) on nicotinic receptors: intracellular calcium increase, calpain/caspase 3 activation, and functional upregulation.

Journal: Toxicology and applied pharmacology 20100501

Title: Biochemical and functional properties of distinct nicotinic acetylcholine receptors in the superior cervical ganglion of mice with targeted deletions of nAChR subunit genes.

Journal: The European journal of neuroscience 20100301

Title: Physiological concentrations of choline activate native alpha7-containing nicotinic acetylcholine receptors in the presence of PNU-120596 [1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)-urea].

Journal: The Journal of pharmacology and experimental therapeutics 20100201

Title: Glutamate-dopamine crosstalk in the rat prefrontal cortex is modulated by Alpha7 nicotinic receptors and potentiated by PNU-120596.

Journal: Journal of molecular neuroscience : MN 20100101

Title: Activation of functional α7-containing nAChRs in hippocampal CA1 pyramidal neurons by physiological levels of choline in the presence of PNU-120596.

Journal: PloS one 20100101

Title: Positive allosteric modulation of alpha7 neuronal nicotinic acetylcholine receptors: lack of cytotoxicity in PC12 cells and rat primary cortical neurons.

Journal: British journal of pharmacology 20091201

Title: Comparative pharmacology and computational modelling yield insights into allosteric modulation of human alpha7 nicotinic acetylcholine receptors.

Journal: Biochemical pharmacology 20091001

Title: Functional alpha 7-containing nicotinic receptors of NG2-expressing cells in the hippocampus.

Journal: Glia 20090801

Title: An allosteric modulator of alpha7 nicotinic receptors, N-(5-Chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholine.

Journal: Molecular pharmacology 20090801

Title: Evaluation of alpha7 nicotinic acetylcholine receptor agonists and positive allosteric modulators using the parallel oocyte electrophysiology test station.

Journal: Assay and drug development technologies 20090801

Title: In vitro pharmacological characterization of a novel allosteric modulator of alpha 7 neuronal acetylcholine receptor, 4-(5-(4-chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)benzenesulfonamide (A-867744), exhibiting unique pharmacological profile.

Journal: The Journal of pharmacology and experimental therapeutics 20090701

Title: Positive modulation of alpha7 nAChR responses in rat hippocampal interneurons to full agonists and the alpha7-selective partial agonists, 4OH-GTS-21 and S 24795.

Journal: Neuropharmacology 20090301

Title: Characterization of compounds on nicotinic acetylcholine receptor alpha7 channels using higher throughput electrophysiology.

Journal: Journal of neuroscience methods 20090215

Title: Desensitization of nicotinic acetylcholine receptors as a strategy for drug development.

Journal: The Journal of pharmacology and experimental therapeutics 20090201

Title: Local and global calcium signals associated with the opening of neuronal alpha7 nicotinic acetylcholine receptors.

Journal: Cell calcium 20090201

Title: Pharmacology of alpha7 nicotinic acetylcholine receptor mediated extracellular signal-regulated kinase signalling in PC12 cells.

Journal: British journal of pharmacology 20090201

Title: Intracellular mechanisms underlying the nicotinic enhancement of LTP in the rat dentate gyrus.

Journal: The European journal of neuroscience 20090101

Title: Alpha-conotoxin Arenatus IB[V11L,V16D] [corrected] is a potent and selective antagonist at rat and human native alpha7 nicotinic acetylcholine receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20081101

Title: Positive allosteric modulation of the alpha7 nicotinic acetylcholine receptor: ligand interactions with distinct binding sites and evidence for a prominent role of the M2-M3 segment.

Journal: Molecular pharmacology 20081101

Title: Functional properties of alpha7 nicotinic acetylcholine receptors co-expressed with RIC-3 in a stable recombinant CHO-K1 cell line.

Journal: Assay and drug development technologies 20080401

Title: Allosteric modulators of the alpha7 nicotinic acetylcholine receptor.

Journal: Journal of medicinal chemistry 20080227

Title: Distinct profiles of alpha7 nAChR positive allosteric modulation revealed by structurally diverse chemotypes.

Journal: Molecular pharmacology 20070901

Title: A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20050427

Title: Hurst RS, et al. A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization. J Neurosci, 2005, 25(17), 4396-4405.

Title: Barron SC, et al. An allosteric modulator of alpha7 nicotinic receptors, N-(5-Chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholine. Mol Pharmacol, 2009 76(2), 253-263.

Title: Munro G, et al. The α7 nicotinic ACh receptor agonist compound B and positive allosteric modulator PNU-120596 both alleviate inflammatory hyperalgesia and cytokine release in the rat. Br J Pharmacol, 2012, doi: 10.1111/j.1476-5381.2012.02003.x

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Tags:501925-31-1 Molecular Formula|501925-31-1 MDL|501925-31-1 SMILES|501925-31-1 PNU-120596
Catalog No.: AA00DA8P
501925-31-1,MFCD00095313
501925-31-1 | PNU-120596
Pack Size: 1mg
Purity: 99+%
in stock
$7.00 $5.00
Pack Size: 5mg
Purity: 99+%
in stock
$21.00 $15.00
Pack Size: 10mg
Purity: 99+%
in stock
$33.00 $23.00
Pack Size: 50mg
Purity: 99+%
in stock
$109.00 $76.00
Pack Size: 100mg
Purity: 99+%
in stock
$186.00 $130.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA00DA8P
Chemical Name: PNU-120596
CAS Number: 501925-31-1
Molecular Formula: C13H14ClN3O4
Molecular Weight: 311.7210
MDL Number: MFCD00095313
SMILES: COc1cc(OC)c(cc1NC(=O)Nc1noc(c1)C)Cl
NSC Number: 216666
Properties
BP: 385°C at 760 mmHg  
Form: Solid  
Storage: Keep in dry area;Room Temperature;  
Complexity: 360  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 21  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 4  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2.2  
Downstream Synthesis Route
61672-67-1    97-50-7   
1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea 

[1]Patent:US2003/236287,2003,A1.Locationinpatent:Page43

3405-77-4    97-50-7   
1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea 

[1]JournalofOrganicChemistry,2017,vol.82,p.992-999

Literature fold

Title: Electrophysiological investigation of the effect of structurally different bispyridinium non-oxime compounds on human α7-nicotinic acetylcholine receptor activity-An in vitro structure-activity analysis.

Journal: Toxicology letters20180901

Title: Counteracting desensitization of human α7-nicotinic acetylcholine receptors with bispyridinium compounds as an approach against organophosphorus poisoning.

Journal: Toxicology letters20180901

Title: Intrinsically low open probability of α7 nicotinic acetylcholine receptors can be overcome by positive allosteric modulation and serum factors leading to the generation of excitotoxic currents at physiological temperatures.

Journal: Molecular pharmacology20121001

Title: PNU-120596, a positive allosteric modulator of α7 nicotinic acetylcholine receptors, reverses a sub-chronic phencyclidine-induced cognitive deficit in the attentional set-shifting task in female rats.

Journal: Journal of psychopharmacology (Oxford, England)20120901

Title: The α7 nicotinic ACh receptor agonist compound B and positive allosteric modulator PNU-120596 both alleviate inflammatory hyperalgesia and cytokine release in the rat.

Journal: British journal of pharmacology20120901

Title: Potential state-selective hydrogen bond formation can modulate activation and desensitization of the α7 nicotinic acetylcholine receptor.

Journal: The Journal of biological chemistry20120622

Title: Protective effect of PNU-120596, a selective alpha7 nicotinic acetylcholine receptor-positive allosteric modulator, on myocardial ischemia-reperfusion injury in rats.

Journal: Journal of cardiovascular pharmacology20120601

Title: α7 nicotinic ACh receptors as a ligand-gated source of Ca(2+) ions: the search for a Ca(2+) optimum.

Journal: Advances in experimental medicine and biology20120101

Title: Somatic integration of single ion channel responses of α7 nicotinic acetylcholine receptors enhanced by PNU-120596.

Journal: PloS one20120101

Title: Competitive binding at a nicotinic receptor transmembrane site of two α7-selective positive allosteric modulators with differing effects on agonist-evoked desensitization.

Journal: Neuropharmacology20111201

Title: Investigation of the molecular mechanism of the α7 nicotinic acetylcholine receptor positive allosteric modulator PNU-120596 provides evidence for two distinct desensitized states.

Journal: Molecular pharmacology20111201

Title: The chimeric gene CHRFAM7A, a partial duplication of the CHRNA7 gene, is a dominant negative regulator of α7*nAChR function.

Journal: Biochemical pharmacology20111015

Title: Single-channel and structural foundations of neuronal α7 acetylcholine receptor potentiation.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20110928

Title: Neurotoxicity induced by okadaic acid in the human neuroblastoma SH-SY5Y line can be differentially prevented by α7 and β2* nicotinic stimulation.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20110901

Title: Characterizing ligand-gated ion channel receptors with genetically encoded Ca2++ sensors.

Journal: PloS one20110101

Title: Differential immediate and sustained memory enhancing effects of alpha7 nicotinic receptor agonists and allosteric modulators in rats.

Journal: PloS one20110101

Title: Tethered agonist analogs as site-specific probes for domains of the human α7 nicotinic acetylcholine receptor that differentially regulate activation and desensitization.

Journal: Molecular pharmacology20101201

Title: In vitro pharmacological characterization of a novel selective alpha7 neuronal nicotinic acetylcholine receptor agonist ABT-107.

Journal: The Journal of pharmacology and experimental therapeutics20100901

Title: Beyond the dopamine receptor: novel therapeutic targets for treating schizophrenia.

Journal: Dialogues in clinical neuroscience20100901

Title: Identification of novel alpha7 nAChR positive allosteric modulators with the use of pharmacophore in silico screening methods.

Journal: Bioorganic & medicinal chemistry letters20100801

Title: The effects of 3,4-methylenedioxymethamphetamine (MDMA) on nicotinic receptors: intracellular calcium increase, calpain/caspase 3 activation, and functional upregulation.

Journal: Toxicology and applied pharmacology20100501

Title: Biochemical and functional properties of distinct nicotinic acetylcholine receptors in the superior cervical ganglion of mice with targeted deletions of nAChR subunit genes.

Journal: The European journal of neuroscience20100301

Title: Physiological concentrations of choline activate native alpha7-containing nicotinic acetylcholine receptors in the presence of PNU-120596 [1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)-urea].

Journal: The Journal of pharmacology and experimental therapeutics20100201

Title: Glutamate-dopamine crosstalk in the rat prefrontal cortex is modulated by Alpha7 nicotinic receptors and potentiated by PNU-120596.

Journal: Journal of molecular neuroscience : MN20100101

Title: Activation of functional α7-containing nAChRs in hippocampal CA1 pyramidal neurons by physiological levels of choline in the presence of PNU-120596.

Journal: PloS one20100101

Title: Positive allosteric modulation of alpha7 neuronal nicotinic acetylcholine receptors: lack of cytotoxicity in PC12 cells and rat primary cortical neurons.

Journal: British journal of pharmacology20091201

Title: Comparative pharmacology and computational modelling yield insights into allosteric modulation of human alpha7 nicotinic acetylcholine receptors.

Journal: Biochemical pharmacology20091001

Title: Functional alpha 7-containing nicotinic receptors of NG2-expressing cells in the hippocampus.

Journal: Glia20090801

Title: An allosteric modulator of alpha7 nicotinic receptors, N-(5-Chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholine.

Journal: Molecular pharmacology20090801

Title: Evaluation of alpha7 nicotinic acetylcholine receptor agonists and positive allosteric modulators using the parallel oocyte electrophysiology test station.

Journal: Assay and drug development technologies20090801

Title: In vitro pharmacological characterization of a novel allosteric modulator of alpha 7 neuronal acetylcholine receptor, 4-(5-(4-chlorophenyl)-2-methyl-3-propionyl-1H-pyrrol-1-yl)benzenesulfonamide (A-867744), exhibiting unique pharmacological profile.

Journal: The Journal of pharmacology and experimental therapeutics20090701

Title: Positive modulation of alpha7 nAChR responses in rat hippocampal interneurons to full agonists and the alpha7-selective partial agonists, 4OH-GTS-21 and S 24795.

Journal: Neuropharmacology20090301

Title: Characterization of compounds on nicotinic acetylcholine receptor alpha7 channels using higher throughput electrophysiology.

Journal: Journal of neuroscience methods20090215

Title: Desensitization of nicotinic acetylcholine receptors as a strategy for drug development.

Journal: The Journal of pharmacology and experimental therapeutics20090201

Title: Local and global calcium signals associated with the opening of neuronal alpha7 nicotinic acetylcholine receptors.

Journal: Cell calcium20090201

Title: Pharmacology of alpha7 nicotinic acetylcholine receptor mediated extracellular signal-regulated kinase signalling in PC12 cells.

Journal: British journal of pharmacology20090201

Title: Intracellular mechanisms underlying the nicotinic enhancement of LTP in the rat dentate gyrus.

Journal: The European journal of neuroscience20090101

Title: Alpha-conotoxin Arenatus IB[V11L,V16D] [corrected] is a potent and selective antagonist at rat and human native alpha7 nicotinic acetylcholine receptors.

Journal: The Journal of pharmacology and experimental therapeutics20081101

Title: Positive allosteric modulation of the alpha7 nicotinic acetylcholine receptor: ligand interactions with distinct binding sites and evidence for a prominent role of the M2-M3 segment.

Journal: Molecular pharmacology20081101

Title: Functional properties of alpha7 nicotinic acetylcholine receptors co-expressed with RIC-3 in a stable recombinant CHO-K1 cell line.

Journal: Assay and drug development technologies20080401

Title: Allosteric modulators of the alpha7 nicotinic acetylcholine receptor.

Journal: Journal of medicinal chemistry20080227

Title: Distinct profiles of alpha7 nAChR positive allosteric modulation revealed by structurally diverse chemotypes.

Journal: Molecular pharmacology20070901

Title: A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience20050427

Title: Hurst RS, et al. A novel positive allosteric modulator of the alpha7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization. J Neurosci, 2005, 25(17), 4396-4405.

Title: Barron SC, et al. An allosteric modulator of alpha7 nicotinic receptors, N-(5-Chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholine. Mol Pharmacol, 2009 76(2), 253-263.

Title: Munro G, et al. The α7 nicotinic ACh receptor agonist compound B and positive allosteric modulator PNU-120596 both alleviate inflammatory hyperalgesia and cytokine release in the rat. Br J Pharmacol, 2012, doi: 10.1111/j.1476-5381.2012.02003.x

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