stiripentol ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2480 49763-96-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • estiripentol
  • stiripentol
  • diacomit
In animal models, stiripentol antagonizes seizures induced by electric shock, pentetrazole and bicuculline. In rodent models, stiripentol appears to increase brain levels of gamma-aminobutyric acid (GABA) - the major inhibitory neurotransmitter in mammalian brain. This could occur by inhibition of synaptosomal uptake of GABA and/or inhibition of GABA transaminase. Stiripentol has also been shown to enhance GABAA receptor-mediated transmission in the immature rat hippocampus and increase the mean open-duration (but not the frequency) of GABAA receptor chloride channels by a barbiturate-like mechanism. Stiripentol potentiates the efficacy of other anticonvulsants, such as carbamazepine, sodium valproate, phenytoin, phenobarbital and many benzodiazepines, as the result of pharmacokinetic interactions. The second effect of stiripentol is mainly based on metabolic inhibition of several isoenzymes, in particular CYP450 3A4 and 2C19, involved in the hepatic metabolism of other anti-epileptic medicines.
  • Molecular weight: 234.30
  • Formula: C14H18O3
  • CLOGP: 3.21
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 38.69
  • ALOGS: -2.76
  • ROTB: 3

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 213.40 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Jan. 4, 2007 EMA BIOCODEX
Aug. 20, 2018 FDA BIOCODEX SA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Status epilepticus 130.00 63.73 26 231 13380 50591487

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Somnolence 80.58 75.41 37 491 203608 64294596

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N03AX17 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Other antiepileptics
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Myoclonic seizure indication 37356005
Severe myoclonic epilepsy in infancy indication 230437002




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
250MG DIACOMIT BIOCODEX SA N206709 Aug. 20, 2018 RX CAPSULE ORAL Aug. 20, 2023 NEW CHEMICAL ENTITY
500MG DIACOMIT BIOCODEX SA N206709 Aug. 20, 2018 RX CAPSULE ORAL Aug. 20, 2023 NEW CHEMICAL ENTITY
250MG/PACKET DIACOMIT BIOCODEX SA N207223 Aug. 20, 2018 RX FOR SUSPENSION ORAL Aug. 20, 2023 NEW CHEMICAL ENTITY
500MG/PACKET DIACOMIT BIOCODEX SA N207223 Aug. 20, 2018 RX FOR SUSPENSION ORAL Aug. 20, 2023 NEW CHEMICAL ENTITY
250MG DIACOMIT BIOCODEX SA N206709 Aug. 20, 2018 RX CAPSULE ORAL Aug. 20, 2025 INDICATED FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH DRAVET SYNDROME (DS) IN PATIENTS 2 YEARS OF AGE AND OLDER TAKING CLOBAZAM
500MG DIACOMIT BIOCODEX SA N206709 Aug. 20, 2018 RX CAPSULE ORAL Aug. 20, 2025 INDICATED FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH DRAVET SYNDROME (DS) IN PATIENTS 2 YEARS OF AGE AND OLDER TAKING CLOBAZAM
250MG/PACKET DIACOMIT BIOCODEX SA N207223 Aug. 20, 2018 RX FOR SUSPENSION ORAL Aug. 20, 2025 INDICATED FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH DRAVET SYNDROME (DS) IN PATIENTS 2 YEARS OF AGE AND OLDER TAKING CLOBAZAM
500MG/PACKET DIACOMIT BIOCODEX SA N207223 Aug. 20, 2018 RX FOR SUSPENSION ORAL Aug. 20, 2025 INDICATED FOR THE TREATMENT OF SEIZURES ASSOCIATED WITH DRAVET SYNDROME (DS) IN PATIENTS 2 YEARS OF AGE AND OLDER TAKING CLOBAZAM

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 3A4 Enzyme WOMBAT-PK
Sodium- and chloride-dependent GABA transporter 1 Transporter IC50 4.30 WOMBAT-PK
Cytochrome P450 1A2 Enzyme WOMBAT-PK
Cytochrome P450 2C19 Enzyme WOMBAT-PK

External reference:

IDSource
D05928 KEGG_DRUG
4038316 VANDF
C0075262 UMLSCUI
CHEBI:94435 CHEBI
CHEMBL1983350 ChEMBL_ID
DB09118 DRUGBANK_ID
5311454 PUBCHEM_CID
3760 INN_ID
C021092 MESH_SUPPLEMENTAL_RECORD_UI
5469 IUPHAR_LIGAND_ID
R02XOT8V8I UNII
2054968 RXNORM
132894 MMSL
23339 MMSL
d06643 MMSL
012569 NDDF
427946009 SNOMEDCT_US
428221002 SNOMEDCT_US
137767-55-6 SECONDARY_CAS_RN

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Diacomit HUMAN PRESCRIPTION DRUG LABEL 1 68418-7939 CAPSULE 250 mg ORAL NDA 29 sections
Diacomit HUMAN PRESCRIPTION DRUG LABEL 1 68418-7940 CAPSULE 500 mg ORAL NDA 29 sections
Diacomit HUMAN PRESCRIPTION DRUG LABEL 1 68418-7941 POWDER, FOR SUSPENSION 250 mg ORAL NDA 29 sections
Diacomit HUMAN PRESCRIPTION DRUG LABEL 1 68418-7942 POWDER, FOR SUSPENSION 500 mg ORAL NDA 29 sections