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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| Targets |
Group I mGluR receptors ( IC50 = 3 μM )
PHCCC targets metabotropic glutamate receptors (mGluRs). It acts as a group I metabotropic glutamate receptor antagonist with an IC50 of ~3 μM. It is also a positive allosteric modulator of mGluR4. Additionally, it acts as a potent antagonist for mGluR2 and mGluR8. It potentiates L-AP4-mediated inhibition of synaptic transmission. |
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| ln Vitro |
PHCCC increased L-(+)-2-amino-4-phosphonobutyric acid's (L-AP4) ability to block transmission at the striatopallidal synapse[2].
In vitro, PHCCC potentiates L-AP4-mediated inhibition of synaptic transmission. It acts as a positive allosteric modulator of mGluR4 with an EC50 of 4.1 μM. It also acts as a group I metabotropic glutamate receptor antagonist with an IC50 of ~3 μM. The compound's ability to modulate multiple mGluR subtypes makes it a valuable tool for studying glutamate signaling. |
| ln Vivo |
PHCCC (75 nmol/2.5 μl; intracerebroventricular) exhibits antiparkinsonian properties in a model of dopamine depletion akinesia[2].
In vivo, PHCCC exhibits proconvulsant action in three models of epileptic seizures in immature rats. It reduces proliferation and promotes differentiation of cerebellar granule cell neuroprecursors. It has dose-dependent anticonflict effects without affecting the threshold current or water intake in rats. It also has anti-Parkinsonian effects. |
| Enzyme Assay |
The activity of PHCCC can be assessed using cell-based functional assays. Cells expressing mGluR4 are treated with varying concentrations of the compound in the presence of a submaximal concentration of glutamate or L-AP4. The potentiation of receptor signaling is measured using downstream signaling assays such as [35S]GTPγS binding or calcium mobilization. The EC50 for potentiation and IC50 for antagonism are determined from dose-response curves.
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| Cell Assay |
To evaluate the cellular effects of PHCCC, neuronal cells are treated with the compound, and the modulation of glutamate-induced signaling is measured. The effects on neuronal proliferation and differentiation can be assessed in cerebellar granule cell cultures. The compound's effects on synaptic transmission can be studied using electrophysiology.
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| Animal Protocol |
In vivo studies with PHCCC typically involve administration to rodents via intraperitoneal or oral routes. In models of epilepsy, the compound's proconvulsant effects are assessed. In models of anxiety or Parkinson's disease, its anticonflict or anti-Parkinsonian effects are evaluated.
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| ADME/Pharmacokinetics |
PHCCC has a molecular formula of C17H14N2O3. Its CAS number is 179068-02-1. The compound is a group I metabotropic glutamate receptor antagonist and a positive allosteric modulator of mGluR4. It is soluble in DMSO and other organic solvents. The purity is typically ≥98%.
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| Toxicity/Toxicokinetics |
Specific toxicology data for PHCCC are not detailed in the available literature. However, its proconvulsant action indicates that it can have significant central nervous system effects. As with all research compounds, standard safety precautions should be taken during handling.
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| References | |
| Additional Infomation |
7-Hydroxyimino-N-phenyl-1,7a-dihydrocyclopropane[b][1]benzopyran-1a-carboxamide is a 1-benzopyran.
PHCCC is a research tool used to study metabotropic glutamate receptor signaling. It is a group I mGluR antagonist and a positive allosteric modulator of mGluR4. It has been used to study epilepsy, anxiety, and Parkinson's disease. It is not a clinically approved drug. |
| Molecular Formula |
C17H14N2O3
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|---|---|
| Molecular Weight |
294.3047
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| Exact Mass |
294.1
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| Elemental Analysis |
C, 69.38; H, 4.79; N, 9.52; O, 16.31
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| CAS # |
179068-02-1
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| Related CAS # |
179068-02-1
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| PubChem CID |
5866327
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
579.1±50.0 °C at 760 mmHg
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| Flash Point |
304.0±30.1 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.700
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| LogP |
1.88
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
22
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| Complexity |
486
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1C2=C([H])C([H])=C([H])C([H])=C2/C(/C2([H])C([H])([H])C12C(N([H])C1C([H])=C([H])C([H])=C([H])C=1[H])=O)=N/O[H]
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| InChi Key |
FPXPIEZPAXSELW-CYVLTUHYSA-N
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| InChi Code |
InChI=1S/C17H14N2O3/c20-16(18-11-6-2-1-3-7-11)17-10-13(17)15(19-21)12-8-4-5-9-14(12)22-17/h1-9,13,21H,10H2,(H,18,20)/b19-15-
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| Chemical Name |
(7E)-7-hydroxyimino-N-phenyl-1,7a-dihydrocyclopropa[b]chromene-1a-carboxamide
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| Synonyms |
PHCCC
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~12.5 mg/mL (~42.5 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (4.25 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (4.25 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 12.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1.25 mg/mL (4.25 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3979 mL | 16.9895 mL | 33.9789 mL | |
| 5 mM | 0.6796 mL | 3.3979 mL | 6.7958 mL | |
| 10 mM | 0.3398 mL | 1.6989 mL | 3.3979 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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