Stiripentol

Modify Date: 2024-01-04 20:11:29

Stiripentol Structure
Stiripentol structure
 Common Name Stiripentol
CAS Number 49763-96-4 Molecular Weight 234.291
Density 1.1±0.1 g/cm3 Boiling Point 365.4±11.0 °C at 760 mmHg
Molecular Formula C14H18O3 Melting Point 73-74ºC
MSDS Chinese USA Flash Point 174.8±19.3 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Stiripentol


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.

 Names

Name Stiripentol
Synonym More Synonyms

 Stiripentol Biological Activity

Description 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
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

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SB3393000
CHEMICAL NAME :
1-Penten-3-ol, 4,4-dimethyl-1-(3,4-methylenedioxyphenyl)-
CAS REGISTRY NUMBER :
49763-96-4
BEILSTEIN REFERENCE NO. :
1313047
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C14-H18-O3
MOLECULAR WEIGHT :
234.32
WISWESSER LINE NOTATION :
T56 BO DO CHJ G1U1YQX1&1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 34,199,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1471 mg/kg
TOXIC EFFECTS :
Behavioral - anticonvulsant
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 34,199,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 34,199,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 13,41,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
72 mg/kg
TOXIC EFFECTS :
Behavioral - anticonvulsant
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 34,199,1984 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6400 mg/kg
SEX/DURATION :
female 2 week(s) pre-mating - 18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
REPTED Reproductive Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1987- Volume(issue)/page/year: 7,439,1993

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
RIDADR NONH for all modes of transport

 Articles37

More Articles
The efficacy of bromides, stiripentol and levetiracetam in two patients with malignant migrating partial seizures in infancy.

Epileptic Disord. 13(1) , 22-6, (2011)

The syndrome of malignant migrating partial seizures in infancy is a devastating, age-specific, epileptic encephalopathy, which still presents an aetiological, pathophysiological and therapeutic probl...

Stiripentol in refractory status epilepticus.

Epilepsia 54 Suppl 6 , 103-5, (2013)

Benzodiazepines (BZDs), which enhance γ-aminobutyric acid (GABAA ) receptor-mediated inhibition, are the first-line therapy for treatment of status epilepticus (SE). However, pharmacoresistance to BZD...

[Clinical and genetic diagnosis of Dravet syndrome: report of 20 cases].

Ideggyogy. Sz. 61(11-12) , 402-8, (2008)

Severe myoclonic epilepsy in infancy (SMEI; Dravet's syndrome) is a malignant epilepsy syndrome characterized by prolonged febrile hemiconvulsions or generalized seizures starting in the first year of...

 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]
1-Penten-3-ol, 1-(1,3-benzodioxol-5-yl)-4,4-dimethyl-, (1E)-
(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
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