CAS Number49763-96-4
Synonyms1-(1,3-Benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol; 4,4-Dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-ol; 4,4-dimethyl-1-[3,4(methylenedioxy)-phenyl]-1-penten-3-ol,Diacomit; Stiripentol; Stiripentol [USAN:INN]; (1E)-1-(1,3-Benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol; (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol; UNII:R02XOT8V8I
Molecular FormulaC14H18O3
Molecular Weight234.29
Purity≥98 (HPLC)%
Density1.1±0.1 g/cm3
Boiling Point365.4±11.0 °C at 760 mmHg
Melting Point73-74ºC
Appearancepowder
EINECS256-480-9
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 49763-96-4 |
| Catalog No. | 2A-9012512 |
| Chinese Name | 司替戊醇 |
| Synonyms | 1-(1,3-Benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol; 4,4-Dimethyl-1-(3,4-methylenedioxyphenyl)-1-penten-3-ol; 4,4-dimethyl-1-[3,4(methylenedioxy)-phenyl]-1-penten-3-ol,Diacomit; Stiripentol; Stiripentol [USAN:INN]; (1E)-1-(1,3-Benzodioxol-5-yl)-4,4-dimethyl-1-penten-3-ol; (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol; UNII:R02XOT8V8I |
| Molecular Formula | C14H18O3 |
| Molecular Weight | 234.29 |
| Purity | ≥98 (HPLC) |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 365.4±11.0 °C at 760 mmHg |
| Melting Point | 73-74ºC |
| Appearance | powder |
| Storage Condition | <0°C; avoid heating |
| Application | Stiripentol (STP) is an anticonvulsant that can inhibit the N-demethylation of CLB to N-desmethylclobazam (NCLB) mediated by CYP3A4 (non-competitively) and CYP2C19 (competitively), with Ki values of 1 |
| EINECS | 256-480-9 |
| PubChem ID | 329824570 |
| MDL Number | MFCD00869310 |
| SMILES | CC(C)(C)C(O)\C=C\c1ccc2OCOc2c1 |
| 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/b7-5+ |
| InChI Key | IBLNKMRFIPWSOY-FNORWQNLSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| MSDS | msds/12512_1_49763_96_4.pdf |
| Bioactivity | Stiripentol (STP) is an anticonvulsant agent, which can inhibit N-demethylation of CLB to NCLB mediatated by CYP3A4 (noncompetitively) and CYP2C19 (competitively) with Ki of 1.59±0.07 and 0.516±0.065 μM and IC50 of 1.58 and 3.29 μM, respectively. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Research Areas >> Neurological Disease Target IC50: 1.58 μM (CYP3A4), 3.29 μM (CYP2C19)[1] Ki: 1.59±0.07μM (CYP3A4), 0.516±0.065 μM (CYP2C19)[1] In Vitro Stiripentol (STP) is an anticonvulsant agent, which can inhibit N-demethylation of CLB to N-desmethylclobazam (NCLB) mediated by CYP3A4 (noncompetitively) and CYP2C19 (competitively). The inhibition of CLB demethylation by Stiripentol (STP) is best described by a noncompetitive inhibition model with apparent Ki=1.6 μM for the cDNA-expressing CYP3A4 and by a competitive inhibition model with Ki=0.52 μM for the cDNA-expressing CYP2C19. Formation of OH-NCLB from NCLB by cDNA-expressing CYP2C19 is competitively inhibited by Stiripentol (STP) with a Ki=0.14 μM[1]. In Vivo In mice treating with Stiripentol (STP) monotherapy, the difference between BT1 (39.67±1.09°C) and BT2 (41.32±1.05°C) reaches statistical significance (t=3.097, p<0.05). The difference in BT2 between Stiripentol (STP) monotherapy and CLB monotherapy is statistically significant (t=2.615, p<0.05). In mice treating with Stiripentol (STP)+CLB combination therapy, the difference between BT1 (40.18±0.58°C) and BT2 (43.03±0.49°C) reaches statistical significance (t=10.44, p<0.01)[2]. Cell Assay The inhibition constants (apparent Ki) of Stiripentol (STP) for CLB demethylation by CYP3A4 and CYP2C19 are determined using various concentrations of CLB (2, 10, 20, 40, 60, and 100 μM) with increasing concentrations of Stiripentol (STP) (0, 0.5, 1, 2, and 5 μM). Concerning NCLB hydroxylation by CYP2C19, the apparent Ki is similarly determined with different concentrations of NCLB (1.5, 4, 6, 8, 12, and 14 μM) and STP (0, 0.1, 0.5, 1, and 2 μM). IC50 values are determined by coincubation of the substrate at concentration in the range of the therapeutic plasma concentrations (2 μM CLB or 14 μM NCLB) with increasing concentrations of Stiripentol (STP) (0.001, 0.002, 0.005, 0.01, 0.05, 0.1, 0.25, 2, 5, and 10 μM)[1]. Animal Admin Two age groups, p1M (n=18, age 4 weeks) and p5M (n=18, age 5-10 months), of Scn1aRX/+ mice are assigned in this experiment. Both groups are divided randomly into three subgroups (n=6), and each subgroup is administered Stiripentol (STP) (300 mg/kg) alone, CLB (6.62 mg/kg) alone, or a combination of Stiripentol (STP) (p1M; 150 mg/kg, p5M; 300 mg/kg) and CLB (6.62 mg/kg). All drugs are administered by intraperitoneal injection (i.p.) after a 48-h recovery from baseline seizure study. Blood samples are collected at 1 h and 20 min after administration of CLB or STP+CLB for measurement of plasma concentrations of CLB and N-desmethylclobazam, respectively[2]. References [1]. Giraud C, et al. In vitro and in vivo inhibitory effect of stiripentol on clobazam metabolism.Drug Metab Dispos. 2006 Apr;34(4):608-11. Epub 2006 Jan 13. [2]. Cao D, et al. Efficacy of stiripentol in hyperthermia-induced seizures in a mouse model of Dravet syndrome. Epilepsia. 2012 Jul;53(7):1140-5. Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 365.4±11.0 °C at 760 mmHg Melting Point 73-74ºC Molecular Formula C14H18O3 Molecular Weight 234.291 Flash Point 174.8±19.3 °C Exact Mass 234.125595 PSA 38.69000 LogP 3.39 Vapour Pressure 0.0±0.9 mmHg at 25°C Index of Refraction 1.579 InChIKey IBLNKMRFIPWSOY-FNORWQNLSA-N SMILES CC(C)(C)C(O)C=Cc1ccc2c(c1)OCO2 |
| Use of | Properties Articles37 Name Stiripentol Synonym More Synonyms Stiripentol Biological Activity Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Research Areas >> Neurological Disease References [1]. Giraud C, et al. In vitro and in vivo inhibitory effect of stiripentol on clobazam metabolism.Drug Metab Dispos. 2006 Apr;34(4):608-11. Epub 2006 Jan 13. [2]. Cao D, et al. Efficacy of stiripentol in hyperthermia-induced seizures in a mouse model of Dravet syndrome. Epilepsia. 2012 Jul;53(7):1140-5. Chemical & Physical Properties Molecular Formula C14H18O3 Exact Mass 234.125595 PSA 38.69000 Index of Refraction 1.579 InChIKey IBLNKMRFIPWSOY-FNORWQNLSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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