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

Details

Stereochemistry RACEMIC
Molecular Formula C14H18O3
Molecular Weight 234.2909
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of STIRIPENTOL

SMILES

CC(C)(C)C(O)C=CC1=CC=C2OCOC2=C1

InChI

InChIKey=IBLNKMRFIPWSOY-UHFFFAOYSA-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

HIDE SMILES / InChI

Molecular Formula C14H18O3
Molecular Weight 234.2909
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description

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

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Diacomit
PubMed

PubMed

TitleDatePubMed
Infant monkey hyperexcitability after prenatal exposure to antiepileptic compounds.
1996 Oct
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
stiripentol was found to reduce synaptosomal GABA uptake (IC50 5x10-5) and to slightly increase (+22%) brain concentrations of GABA after “in vivo” administration (300 mg/kg i.p.).
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:45:16 UTC 2019
Edited
by admin
on Mon Oct 21 20:45:16 UTC 2019
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
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
EU-Orphan Drug EU/3/01/071
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
FDA ORPHAN DRUG 266108
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
WHO-VATC QN03AX17
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
NCI_THESAURUS C264
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
EMA ASSESSMENT REPORTS DIACOMIT (AUTHORIZED: MYOCLONIC EPILEPSY, JUVENILE)
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
WHO-ATC N03AX17
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
Code System Code Type Description
MERCK INDEX
M10218
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY Merck Index
CAS
137767-55-6
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
CAS
131206-47-8
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
SUPERCEDED
INN
3760
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
EPA CompTox
49763-96-4
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
MESH
C021092
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
CAS
49763-96-4
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
NON-SPECIFIC STEREOCHEMISTRY
WIKIPEDIA
STIRIPENTOL
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
IUPHAR
5469
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
ChEMBL
CHEMBL1983350
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
EVMPD
SUB10654MIG
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
DRUG BANK
DB09118
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
ECHA (EC/EINECS)
256-480-9
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
NCI_THESAURUS
C152433
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
PRIMARY
PUBCHEM
39524
Created by admin on Mon Oct 21 20:45:16 UTC 2019 , Edited by admin on Mon Oct 21 20:45:16 UTC 2019
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
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
Tmax PHARMACOKINETIC FED CONDITIONS

ORAL

Biological Half-life PHARMACOKINETIC