Isosafrole
Isosafrole, a stiripentol analog, is a potent LDH inhibitor. Stiripentol is a new-generation antiepileptic drug, and its chemical structure is unrelated to other antiepileptic drugs. Seizures and epileptiform activity are reduced by inhibition of the metabolic pathway via lactate dehydrogenase (LDH), which is a component of the astrocyte-neuron lactate shuttle.
Isosafrole is a substructure of stiripentol that lacks the hydroxyl group and tertiary-butyl group of stiripentol. Isosafrole strongly inhibited the pyruvate-to-lactate conversion by both LDH1 and LDH5, suggesting that it inhibits lactate production itself. Isosafrole (200 to 300 mg/kg ip) strongly suppressed spontaneous high-voltage spikes and paroxysmal discharges in the kainate model in vivo. Isosafrole suppresses seizures in vivo. Going by the lactate reduction by ketogenic diets, LDH inhibitors for the pyruvate-to-lactate conversion, such as isosafrole, would be more effective for antiepileptic actions.
References:
[1]. Sada N, Lee S2, Katsu T et al. Epilepsy treatment. Targeting LDH enzymes with a stiripentol analog to treat epilepsy. Science. 2015 Mar 20;347(6228):1362-7.
| Physical Appearance | A yellow oil |
| Storage | Store at -20°C |
| M.Wt | 162.19 |
| Cas No. | 120-58-1 |
| Formula | C10H10O2 |
| Solubility | insoluble in H2O; ≥76.4 mg/mL in EtOH; ≥8.8 mg/mL in DMSO |
| Chemical Name | (E)-6-(prop-1-en-1-yl)benzo[d][1,3]dioxole |
| SDF | Download SDF |
| Canonical SMILES | C/C=C/C1=CC=C2C(OCO2)=C1 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Vitro experiment [1]: | |
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Target |
Human LDHs (LDH1 and LDH5) |
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Preparation method |
The solubility of this compound in DMSO is >8.8mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
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Reacting condition |
500 μM |
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Applications |
Isosafrole strongly inhibited the pyruvate-to-lactate conversion by both LDH1 and LDH5, suggesting that it inhibited lactate production itself. |
| Animal experiment [1]: | |
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Animal models |
Kainate mice model |
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Dosage form |
100 to 300 mg/kg; intraperitoneal injection |
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Application |
In the hippocampus of mice 2 weeks after the kainate injection, Isosafrole (200 to 300 mg/kg) strongly suppressed spontaneous high-voltage spikes and paroxysmal discharges. Isosafrole was an LDH inhibitor that suppressed seizures in vivo. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Sada N, Lee S2, Katsu T et al. Epilepsy treatment. Targeting LDH enzymes with a stiripentol analog to treat epilepsy. Science. 2015 Mar 20;347(6228):1362-7. |
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Quality Control & MSDS
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Chemical structure
