| Identification | Back Directory | [Name]
STIRIPENTOL | [CAS]
49763-96-4 | [Synonyms]
bcx2600
RCX-2600
Diacomit
STIRIPENTOL
1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-o
1-(1,3-BENZODIOXOL-5YL)-4,4-DIMETHYL-1-PENTEN-3-OL
1-PENTEN-3-OL, 1-(1,3-BENZODIOXOL-5-YL)-4,4-DIMETHYL-
4,4-dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-o
4,4-dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-ol
1-(Benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
(RS)-(E)-4,4-dimethyl-1-[3,4(methylenedioxy)-phenyl]-1-penten-3-ol | [EINECS(EC#)]
256-480-9 | [Molecular Formula]
C14H18O3 | [MDL Number]
MFCD00869310 | [MOL File]
49763-96-4.mol | [Molecular Weight]
234.29 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
73-74°C | [Boiling point ]
365.4±11.0 °C(Predicted) | [density ]
1.139±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: ≥20mg/mL | [form ]
powder | [pka]
14.45±0.20(Predicted) | [color ]
white to beige | [InChI]
InChI=1S/C14H18O3/c1-14(2,3)13(15)7-5-10-4-6-11-12(8-10)17-9-16-11/h4-8,13,15H,9H2,1-3H3 | [InChIKey]
IBLNKMRFIPWSOY-FNORWQNLSA-N | [SMILES]
C(C1=CC=C2OCOC2=C1)=CC(O)C(C)(C)C | [CAS DataBase Reference]
49763-96-4 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
An antiepileptic drug | [Uses]
An epilepsy drug. It has been used as co-therapy for treatment of epilepsy | [Description]
Stiripentol is a third-generation antiepileptic compound.1 It is a positive allosteric modulator of GABAA receptors, potentiating GABA-mediated activation to a greater extent in receptors expressing α3 subunits and to a lower extent in those containing β1 or ε subunits.2 It also inhibits GABA reuptake in vitro and increases the release of GABA in neonatal rat hippocampal slices.1,3 Stiripentol (500 μM) inhibits lactate dehydrogenase (LDH), blocking both lactate-to-pyruvate and pyruvate-to-lactate conversions by human LDH1 and LDH5.4 Formulations containing stiripentol have been used in the adjunctive treatment of seizures associated with Dravet syndrome. | [Definition]
ChEBI: 1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol is a phenylpropanoid. | [Biochem/physiol Actions]
Anti-convulsant drug | [Synthesis]
A method for the preparation of Stiripentol comprising the steps of:
(1) 120g of piperonal was put into a mixed solvent of 0.2L of ethanol and 2.4L of distilled water, 160g of solid NaOH, 2.6g of benzyltributylammonium chloride and 120g of meth | [storage]
Store at -20°C | [References]
[1] ?USZCZKI J J. Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions[J]. Pharmacological Reports, 2009, 61 2: Pages 197-216. DOI: 10.1016/s1734-1140(09)70024-6
[2] FISHER J L. The anti-convulsant stiripentol acts directly on the GABAA receptor as a positive allosteric modulator[J]. Neuropharmacology, 2009, 56 1: Pages 190-197. DOI: 10.1016/j.neuropharm.2008.06.004
[3] PASCALE P. QUILICHINI. Stiripentol, a Putative Antiepileptic Drug, Enhances the Duration of Opening of GABAA-Receptor Channels[J]. Epilepsia, 2006, 47 4: 704-716. DOI: 10.1111/j.1528-1167.2006.00497.x
[4] NAGISA SADA. Targeting LDH enzymes with a stiripentol analog to treat epilepsy[J]. Science, 2015, 347 6228. DOI: 10.1126/science.aaa1299 |
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