Details of the Drug

General Information of Drug (ID: DMMSDOY)

Drug Name

Stiripentol

Synonyms

Diacomit; ME-2080; Stiripentol (oral); Stiripentol (oral), Laboratoires Biocodex

Indication

Disease Entry	ICD 11	Status	REF
Dravet syndrome	8A61.11	Approved	[1]
Epilepsy	8A60-8A68	Approved	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

234.29

Logarithm of the Partition Coefficient (xlogp)

3.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 0.5-1 h [3]
Bioavailability: The bioavailability of drug is 3%-4% [3]
Elimination: About 73% of total administered dose is found in urine as metabolites, while further 13-24% of the total dose is recovered in faeces as unchanged substance [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 4.5 - 13 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 213.4036 micromolar/kg/day [5]
Vd: The volume of distribution (Vd) of drug is 1.03 L/kg [6]

Chemical Identifiers

Formula: C14H18O3
IUPAC Name: (E)-1-(1,3-benzodioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
Canonical SMILES: CC(C)(C)C(/C=C/C1=CC2=C(C=C1)OCO2)O
InChI: 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+
InChIKey: IBLNKMRFIPWSOY-FNORWQNLSA-N

Cross-matching ID

PubChem CID: 5311454
ChEBI ID: CHEBI:94435
CAS Number: 49763-96-4
DrugBank ID: DB09118
TTD ID: D02XSA
INTEDE ID: DR1507
ACDINA ID: D01440

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA(A) receptor gamma-3 (GABRG3)	TTEX6LM	GBRG3_HUMAN	Modulator	[7]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[8]
Mephenytoin 4-hydroxylase (CYP2C19)_{Main DME}	DEGTFWK	CP2CJ_HUMAN	Substrate	[9]
Cytochrome P450 1A2 (CYP1A2)_{Main DME}	DEJGDUW	CP1A2_HUMAN	Substrate	[10]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[10]
Cytochrome P450 2C19 (CYP2C19)	OTFMJYYE	CP2CJ_HUMAN	Gene/Protein Processing	[10]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Stiripentol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Major	Increased metabolism of Stiripentol caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[11]
Arn-509	DMT81LZ	Major	Increased metabolism of Stiripentol caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[12]
Oliceridine	DM6MDCF	Major	Decreased metabolism of Stiripentol caused by Oliceridine mediated inhibition of CYP450 enzyme.	Acute pain [MG31]	[13]
Troleandomycin	DMUZNIG	Moderate	Decreased metabolism of Stiripentol caused by Troleandomycin mediated inhibition of CYP450 enzyme.	Bacterial infection [1A00-1C4Z]	[12]
HKI-272	DM6QOVN	Major	Decreased metabolism of Stiripentol caused by HKI-272 mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[14]
LY2835219	DM93VBZ	Moderate	Decreased metabolism of Stiripentol caused by LY2835219 mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[15]
Levonorgestrel	DM1DP7T	Moderate	Decreased metabolism of Stiripentol caused by Levonorgestrel mediated inhibition of CYP450 enzyme.	Contraceptive management [QA21]	[16]
Lumacaftor	DMCLWDJ	Major	Increased metabolism of Stiripentol caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[12]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Stiripentol caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[12]
OPC-34712	DMHG57U	Major	Decreased metabolism of Stiripentol caused by OPC-34712 mediated inhibition of CYP450 enzyme.	Depression [6A70-6A7Z]	[17]
Polatuzumab vedotin	DMF6Y0L	Moderate	Decreased metabolism of Stiripentol caused by Polatuzumab vedotin mediated inhibition of CYP450 enzyme.	Diffuse large B-cell lymphoma [2A81]	[18]
Ripretinib	DM958QB	Moderate	Decreased metabolism of Stiripentol caused by Ripretinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[19]
MK-1439	DM215WE	Minor	Decreased metabolism of Stiripentol caused by MK-1439 mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[20]
Levamlodipine	DM92S6N	Moderate	Decreased metabolism of Stiripentol caused by Levamlodipine mediated inhibition of CYP450 enzyme.	Hypertension [BA00-BA04]	[21]
Lesinurad	DMUR64T	Moderate	Increased metabolism of Stiripentol caused by Lesinurad mediated induction of CYP450 enzyme.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[12]
Eluxadoline	DMYZ0P1	Moderate	Decreased metabolism of Stiripentol caused by Eluxadoline mediated inhibition of CYP450 enzyme.	Irritable bowel syndrome [DD91]	[22]
Pemigatinib	DM819JF	Major	Decreased metabolism of Stiripentol caused by Pemigatinib mediated inhibition of CYP450 enzyme.	Liver cancer [2C12]	[12]
Brigatinib	DM7W94S	Major	Decreased metabolism of Stiripentol caused by Brigatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[19]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Stiripentol caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[12]
Pralsetinib	DMWU0I2	Moderate	Decreased metabolism of Stiripentol caused by Pralsetinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[23]
Capmatinib	DMYCXKL	Moderate	Decreased metabolism of Stiripentol caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[24]
GDC-0199	DMH0QKA	Major	Decreased metabolism of Stiripentol caused by GDC-0199 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[19]
Acalabrutinib	DM7GCVW	Major	Decreased metabolism of Stiripentol caused by Acalabrutinib mediated inhibition of CYP450 enzyme.	Mature B-cell lymphoma [2A85]	[25]
LGX818	DMNQXV8	Major	Decreased metabolism of Stiripentol caused by LGX818 mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[26]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Stiripentol and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[27]
Rimegepant	DMHOAUG	Moderate	Decreased metabolism of Stiripentol caused by Rimegepant mediated inhibition of CYP450 enzyme.	Migraine [8A80]	[28]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Stiripentol and Lasmiditan.	Migraine [8A80]	[29]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Stiripentol caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[12]
Entrectinib	DMMPTLH	Major	Decreased metabolism of Stiripentol caused by Entrectinib mediated inhibition of CYP450 enzyme.	Non-small cell lung cancer [2C25]	[19]
S-297995	DM26IH8	Moderate	Decreased metabolism of Stiripentol caused by S-297995 mediated inhibition of CYP450 enzyme.	Opioid use disorder [6C43]	[12]
Istradefylline	DM20VSK	Moderate	Decreased metabolism of Stiripentol caused by Istradefylline mediated inhibition of CYP450 enzyme.	Parkinsonism [8A00]	[30]
Darolutamide	DMV7YFT	Minor	Decreased metabolism of Stiripentol caused by Darolutamide mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[31]
Upadacitinib	DM32B5U	Moderate	Decreased metabolism of Stiripentol caused by Upadacitinib mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[32]
LDE225	DMM9F25	Major	Decreased metabolism of Stiripentol caused by LDE225 mediated inhibition of CYP450 enzyme.	Skin cancer [2C30-2C37]	[33]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Stiripentol caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[12]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Stiripentol caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[19]
LEE011	DMMX75K	Moderate	Decreased metabolism of Stiripentol caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[12]
Pitolisant	DM8RFNJ	Moderate	Decreased metabolism of Stiripentol caused by Pitolisant mediated inhibition of CYP450 enzyme.	Somnolence [MG42]	[12]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Stiripentol caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[34]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Stiripentol caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[12]
Fluticasone	DMGCSVF	Moderate	Decreased metabolism of Stiripentol caused by Fluticasone mediated inhibition of CYP450 enzyme.	Vasomotor/allergic rhinitis [CA08]	[19]
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⏷ Show the Full List of 41 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Aspartame	E00402	134601	Flavoring agent
Erythrosine sodium anhydrous	E00324	27872	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Vanillin	E00049	1183	Flavoring agent
Carmellose sodium	E00625	Not Available	Disintegrant
Dextrin	E00359	62698	Binding agent; Diluent; Microencapsulating agent; Stiffening agent; Suspending agent; Viscosity-controlling agent
Dextrose anhydrous	E00394	107526	Binding agent; Diluent; Flavoring agent; Tonicity agent
Gelatin	E00630	Not Available	Other agent
Hypromellose	E00634	Not Available	Coating agent
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Sorbitan tristearate	E00516	17800859	Dispersing agent; Emulsifying agent; Solubilizing agent; Surfactant; Suspending agent; Vaccine adjuvant
Hydroxyethyl cellulose	E00700	Not Available	Coating agent; Suspending agent; Binding agent; Viscosity-controlling agent
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⏷ Show the Full List of 14 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Stiripentol 250 mg powder	250 mg	Powder	Oral
Stiripentol 500 mg powder	500 mg	Powder	Oral
Stiripentol 250 mg capsule	250 mg	Capsule	Oral
Stiripentol 500 mg capsule	500 mg	Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	The effects of stiripentol on GABA(A) receptors.Epilepsia. 2011 Apr;52 Suppl 2:76-8.
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5469).
3	Serrano-Rodriguez JM, Gomez-Diez M, Esgueva M, Castejon-Riber C, Mena-Bravo A, Priego-Capote F, Ayala N, Caballero JMS, Munoz A: Pharmacokinetic/pharmacodynamic modeling of benazepril and benazeprilat after administration of intravenous and oral doses of benazepril in healthy horses. Res Vet Sci. 2017 Oct;114:117-122. doi: 10.1016/j.rvsc.2017.03.016. Epub 2017 Mar 28.
4	European Medicines Agency (EMA): DIACOMIT Summary of Product Characteristics
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Trojnar MK, Wojtal K, Trojnar MP, Czuczwar SJ: Stiripentol. A novel antiepileptic drug. Pharmacol Rep. 2005 Mar-Apr;57(2):154-60.
7	Stiripentol, a putative antiepileptic drug, enhances the duration of opening of GABA-A receptor channels. Epilepsia. 2006 Apr;47(4):704-16.
8	Product characteristics of Diacomit.
9	FDA Label of Diacomit. The 2020 official website of the U.S. Food and Drug Administration.
10	Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
11	Product Information. Tibsovo (ivosidenib). Agios Pharmaceuticals, Cambridge, MA.
12	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
13	Product Information. Olinvyk (oliceridine). Trevena Inc, Chesterbrook, PA.
14	Abbas R, Hug BA, Leister C, Burns J, Sonnichsen D "Pharmacokinetics of oral neratinib during co-administration of ketoconazole in healthy subjects." Br J Clin Pharmacol 71 (2011): 522-7. [PMID: 21395644]
15	Product Information. Verzenio (abemaciclib). Lilly, Eli and Company, Indianapolis, IN.
16	EMEA. European Medicines Agency "EPARs. European Union Public Assessment Reports.".
17	Product Information. Rexulti (brexpiprazole). Otsuka American Pharmaceuticals Inc, Rockville, MD.
18	Product Information. Polivy (polatuzumab vedotin). Genentech, South San Francisco, CA.
19	Cerner Multum, Inc. "Australian Product Information.".
20	Product Information. Pifeltro (doravirine). Merck & Company Inc, Whitehouse Station, NJ.
21	Canadian Pharmacists Association.
22	Product Information. Viberzi (eluxadoline). Actavis Pharma, Inc., Parsippany, NJ.
23	Product Information. Gavreto (pralsetinib). Blueprint Medicines Corporation, Cambridge, MA.
24	Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
25	Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
26	Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
27	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
28	Product Information. Nurtec ODT (rimegepant). Biohaven Pharmaceuticals, New Haven, CT.
29	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
30	Product Information. Nourianz (istradefylline). Kyowa Kirin, Inc, Bedminster, NJ.
31	Product Information. Nubeqa (darolutamide). Bayer HealthCare Pharmaceuticals Inc., Whippany, NJ.
32	Product Information. Rinvoq (upadacitinib). AbbVie US LLC, North Chicago, IL.
33	Product Information. Odomzo (sonidegib). Novartis Pharmaceuticals, East Hanover, NJ.
34	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.