U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C14H18O3
Molecular Weight 234.2915
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIRIPENTOL

SMILES

CC(C)(C)C(/C(/[H])=C(\[H])/c1ccc2c(c1)OCO2)O

InChI

InChIKey=IBLNKMRFIPWSOY-FNORWQNLSA-N
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+

HIDE SMILES / InChI

Molecular Formula C14H18O3
Molecular Weight 234.2915
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description
Curator's Comment:: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000664/WC500036518.pdf

Stiripentol is an anticonvulsant drug used in the treatment of epilepsy. It recently proved to increase the GABAergic transmission in vitro in an experimental model of immature rat. Clinical studies were based on the fact that STP also acts as an inhibitor of CYP3A4, CYP1A2, and CYP2C19 in vivo in epileptic patients. Side effects are largely due to the increase in plasma concentrations of other anticonvulsants and can be reduced by lowering the dose of those drugs. Nausea and vomiting are particularly noted when used in combination with sodium valproate. It appears to increase the potency of phenobarbital, primidone, phenytoin, carbamazepine, clobazam and diazepam.

CNS Activity

Curator's Comment:: Known to be CNS penetrant in rats. Human data not available.

Originator

Curator's Comment:: The product was first identified by BIOCODEX, in 1978 with early clinical development starting in 1980s.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Diacomit

Approved Use

It is indicated for treating severe myoclonic epilepsy in infancy (SMEI, also know as Dravet's syndrome).

Launch Date

1007424000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.5 mg/L
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
2.1 mg/L
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
14 mg/L
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
31 mg × h/L
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
8.3 mg × h/L
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
88 mg × h/L
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.7 h
1000 mg single, oral
dose: 1000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
2 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
10 h
2000 mg single, oral
dose: 2000 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
STIRIPENTOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (15%)
Vomiting (9%)
Salivary hypersecretion (6%)
Fatigue (9%)
Pyrexia (6%)
Bronchitis (6%)
Nasopharyngitis (6%)
Weight decreased (27%)
Weight increased (6%)
Decreased appetite (46%)
Somnolence (67%)
Ataxia (27%)
Hypotonia (18%)
Tremor (15%)
Dysarthria (12%)
Agitation (27%)
Insomnia (12%)
Aggression (9%)
Sources:
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Disc. AE: Status epilepticus, Drowsiness...
AEs leading to
discontinuation/dose reduction:
Status epilepticus (< 1%)
Drowsiness (< 1%)
Balance impaired NOS (< 1%)
Sialorrhea (< 1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dysarthria 12%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Insomnia 12%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Nausea 15%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Tremor 15%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Hypotonia 18%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Agitation 27%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Ataxia 27%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Weight decreased 27%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Decreased appetite 46%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Bronchitis 6%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Nasopharyngitis 6%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Pyrexia 6%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Salivary hypersecretion 6%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Weight increased 6%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Somnolence 67%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Aggression 9%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Fatigue 9%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Vomiting 9%
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Balance impaired NOS < 1%
Disc. AE
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Drowsiness < 1%
Disc. AE
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Sialorrhea < 1%
Disc. AE
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
Status epilepticus < 1%
Disc. AE
50 mg/kg 1 times / day steady, oral
Recommended
Dose: 50 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 50 mg/kg, 1 times / day
Sources:
unhealthy, mean age 9.2 years
Health Status: unhealthy
Age Group: mean age 9.2 years
Sex: M+F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 130 uM]
no
not significant
not significant
not significant
not significant
not significant
yes [IC50 13 uM]
yes [IC50 14 uM]
yes [IC50 2.34 uM]
yes [IC50 6.6 uM]
yes [IC50 6.8 uM]
yes [IC50 9.2 uM]
yes [IC50 92.1 uM]
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes (co-administration study)
Comment: Co-administration of clobazam (CYP3A4 substrate) with stiripentol increased concentrations of clobazam by approximately 2-fold and norclobazam (clobazam active metabolite, CYP2C19 substrate) by 5-fold
Page: 14
yes
yes (co-administration study)
Comment: Co-administration of clobazam (CYP3A4 substrate) with stiripentol increased concentrations of clobazam by approximately 2-fold and norclobazam (clobazam active metabolite, CYP2C19 substrate) by 5-fold
Page: 14
PubMed

PubMed

TitleDatePubMed
Infant monkey hyperexcitability after prenatal exposure to antiepileptic compounds.
1996 Oct
Preclinical evaluation of newly approved and potential antiepileptic drugs against cocaine-induced seizures.
1999 Sep
Stiripentol.
2005 Jul
Patents

Sample Use Guides

Initial dose is 50 mg/kg per day. This may be increased up to 100 mg/kg per day, with a maximum of 4 g/day.
Route of Administration: Oral
stiripentol was found to reduce synaptosomal GABA uptake (IC50 5x10-5)
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:30:58 UTC 2021
Edited
by admin
on Fri Jun 25 21:30:58 UTC 2021
Record UNII
R02XOT8V8I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STIRIPENTOL
EMA EPAR   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
BCX-2600
Code English
STIRIPENTOL [MI]
Common Name English
STIRIPENTOL [MART.]
Common Name English
STIRIPENTOL [USAN]
Common Name English
STIRIPENTOL [WHO-DD]
Common Name English
DIACOMIT
Brand Name English
STIRIPENTOL [ORANGE BOOK]
Common Name English
1-(1,3-BENZODIOXOL-5-YL)-4,4-DIMETHYL-1-PENTEN-3-OL
Systematic Name English
BCX 2600
Code English
STIRIPENTOL [EMA EPAR]
Common Name English
STIRIPENTOL [INN]
Common Name English
STIRIPENTOL [JAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 800820
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
EU-Orphan Drug EU/3/01/071
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
FDA ORPHAN DRUG 266108
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
WHO-VATC QN03AX17
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
EMA ASSESSMENT REPORTS DIACOMIT (AUTHORIZED: MYOCLONIC EPILEPSY, JUVENILE)
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
WHO-ATC N03AX17
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2480
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
MERCK INDEX
M10218
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY Merck Index
CAS
137767-55-6
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
FDA UNII
R02XOT8V8I
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
RXCUI
2054968
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
INN
3760
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
EPA CompTox
49763-96-4
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
CAS
131206-47-8
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
SUPERSEDED
MESH
C021092
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
CAS
49763-96-4
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
LACTMED
Stiripentol
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
WIKIPEDIA
STIRIPENTOL
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
IUPHAR
5469
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL1983350
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
EVMPD
SUB10654MIG
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
DRUG BANK
DB09118
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
256-480-9
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
NCI_THESAURUS
C152433
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
PUBCHEM
5311454
Created by admin on Fri Jun 25 21:30:58 UTC 2021 , Edited by admin on Fri Jun 25 21:30:58 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INHIBITOR
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
IC50
METABOLIC ENZYME -> INHIBITOR
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> INHIBITOR
METABOLIC ENZYME -> INHIBITOR
ENANTIOMER -> RACEMATE
BINDER->LIGAND
Stiripentol binds extensively to circulating plasma proteins (about 9
Related Record Type Details
METABOLITE INACTIVE -> PARENT
Recovery of Metabolite X from urine after deglucuronization; urine was accumulated for 12hr after a single oral dose of 600mg (a single subject); Recovered metabolites total: 439.8mg
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
trace amount from one subject
IN-VIVO
FECAL
METABOLITE INACTIVE -> PARENT
Recovery of para-hydroxy metabolite from urine after deglucuronization; urine was accumulated for 12hr after a single oral dose of 600mg (a single subject); Recovered metabolites total: 439.8mg
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
Recovery of Metabolite XII from urine after deglucuronization; urine was accumulated for 12hr after a single oral dose of 600mg (a single subject); Recovered metabolites total: 439.8mg
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
Recovery of Metabolite XI from urine after deglucuronization; urine was accumulated for 12hr after a single oral dose of 600mg (a single subject); Recovered metabolites total: 439.8mg
IN-VIVO
URINE
METABOLITE INACTIVE -> PARENT
IN-VIVO
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
log P CHEMICAL
Tmax PHARMACOKINETIC FED CONDITIONS

ORAL

Biological Half-life PHARMACOKINETIC