Details of the Drug

General Information of Drug (ID: DMR5ZUP)

Drug Name

Paramethadione

Synonyms

Isoethadione; Paradione; Parametadiona; Parametadione; Paramethadionum; Parametadione [DCIT]; A 348; Paradione (TN); Parametadiona [INN-Spanish]; Paramethadione (INN); Paramethadione [BAN:INN]; Paramethadione [INN:BAN]; Paramethadionum [INN-Latin]; 3,5-Dimethyl-5-ethyloxazolidine-2,4-dione; 5-Ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione; 5-Ethyl-3,5-dimethyl-2,4-oxazolidinedione

Indication

Disease Entry	ICD 11	Status	REF
Absence epilepsy	N.A.	Approved	[1]
Epilepsy	8A60-8A68	Approved	[1]
Fetal trimethadione syndrome	LD2F.0Y	Approved	[2]
Seizure disorder	8A6Z	Approved	[2]
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Therapeutic Class

Anticonvulsants

Affected Organisms

Humans and other mammals

ATC Code

N03AC01: Paramethadione

N03AC: Oxazolidine derivatives

N03A: ANTIEPILEPTICS

N03: ANTIEPILEPTICS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

157.17

Logarithm of the Partition Coefficient (xlogp)

0.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is rapidly absorbed via the digestive tract []
Half-life: The concentration or amount of drug in body reduced by one-half in 12 - 24 hours [3]
Metabolism: The drug is metabolized via the hepatic []

Chemical Identifiers

Formula: C7H11NO3
IUPAC Name: 5-ethyl-3,5-dimethyl-1,3-oxazolidine-2,4-dione
Canonical SMILES: CCC1(C(=O)N(C(=O)O1)C)C
InChI: InChI=1S/C7H11NO3/c1-4-7(2)5(9)8(3)6(10)11-7/h4H2,1-3H3
InChIKey: VQASKUSHBVDKGU-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 8280
ChEBI ID: CHEBI:7921
CAS Number: 115-67-3
UNII: Z615FRW64N
DrugBank ID: DB00617
TTD ID: D09JBP
INTEDE ID: DR1239

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated calcium channel alpha Cav3.1 (CACNA1G)	TT729IR	CAC1G_HUMAN	Blocker	[4]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[5]
Cytochrome P450 2E1 (CYP2E1)	DEVDYN7	CP2E1_HUMAN	Substrate	[6]
Cytochrome P450 2C9 (CYP2C9)_{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Absence epilepsy

ICD Disease Classification

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Voltage-gated calcium channel alpha Cav3.1 (CACNA1G)	DTT	CACNA1G	3.88E-01	-0.06	-0.18
Voltage-gated calcium channel alpha Cav3.1 (CACNA1G)	DTT	CACNA1G	9.84E-01	-0.01	-0.03
Cytochrome P450 2E1 (CYP2E1)	DME	CYP2E1	4.20E-02	-1.71E-01	-3.15E-01
Cytochrome P450 2E1 (CYP2E1)	DME	CYP2E1	3.07E-01	-2.23E-02	-1.46E-01
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	8.99E-01	-6.93E-03	-1.36E-02
Cytochrome P450 2C9 (CYP2C9)	DME	CYP2C9	9.21E-01	7.31E-03	6.10E-02
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	4.66E-01	4.25E-02	1.20E-01
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	4.75E-01	5.15E-02	3.64E-01

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Levomilnacipran	DMV26S8	Moderate	Antagonize the effect of Paramethadione when combined with Levomilnacipran.	Chronic pain [MG30]	[7]
Olopatadine	DMKMWQG	Moderate	Additive CNS depression effects by the combination of Paramethadione and Olopatadine.	Conjunctiva disorder [9A60]	[8]
Ethanol	DMDRQZU	Moderate	Additive CNS depression effects by the combination of Paramethadione and Ethanol.	Cystitis [GC00]	[8]
Sertraline	DM0FB1J	Moderate	Antagonize the effect of Paramethadione when combined with Sertraline.	Depression [6A70-6A7Z]	[7]
Vilazodone	DM4LECQ	Moderate	Antagonize the effect of Paramethadione when combined with Vilazodone.	Depression [6A70-6A7Z]	[7]
Paroxetine	DM5PVQE	Moderate	Antagonize the effect of Paramethadione when combined with Paroxetine.	Depression [6A70-6A7Z]	[7]
Vortioxetine	DM6F1PU	Moderate	Antagonize the effect of Paramethadione when combined with Vortioxetine.	Depression [6A70-6A7Z]	[7]
Milnacipran	DMBFE74	Moderate	Antagonize the effect of Paramethadione when combined with Milnacipran.	Depression [6A70-6A7Z]	[7]
Escitalopram	DMFK9HG	Moderate	Antagonize the effect of Paramethadione when combined with Escitalopram.	Depression [6A70-6A7Z]	[7]
Desvenlafaxine	DMHD4PE	Moderate	Antagonize the effect of Paramethadione when combined with Desvenlafaxine.	Depression [6A70-6A7Z]	[7]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Paramethadione and Esketamine.	Depression [6A70-6A7Z]	[9]
Hydroxychloroquine	DMSIVND	Moderate	Antagonize the effect of Paramethadione when combined with Hydroxychloroquine.	Malaria [1F40-1F45]	[9]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Paramethadione and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[10]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Paramethadione and Lasmiditan.	Migraine [8A80]	[11]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Paramethadione and Flibanserin.	Mood disorder [6A60-6E23]	[12]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Paramethadione and Thalidomide.	Multiple myeloma [2A83]	[8]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Paramethadione and Ocrelizumab.	Multiple sclerosis [8A40]	[13]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive immunosuppressive effects by the combination of Paramethadione and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[14]
Apraclonidine	DMO4PVE	Moderate	Additive CNS depression effects by the combination of Paramethadione and Apraclonidine.	Optic nerve disorder [9C40]	[15]
Dextropropoxyphene	DM23HCX	Major	Additive CNS depression effects by the combination of Paramethadione and Dextropropoxyphene.	Pain [MG30-MG3Z]	[16]
Buprenorphine	DMPRI8G	Major	Additive CNS depression effects by the combination of Paramethadione and Buprenorphine.	Pain [MG30-MG3Z]	[17]
Tizanidine	DMR2IQ4	Moderate	Additive CNS depression effects by the combination of Paramethadione and Tizanidine.	Tonus and reflex abnormality [MB47]	[18]
Ganciclovir	DM1MBYQ	Moderate	Additive myelosuppressive effects by the combination of Paramethadione and Ganciclovir.	Virus infection [1A24-1D9Z]	[9]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Paramethadione and Valganciclovir.	Virus infection [1A24-1D9Z]	[9]
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References

1	Paramethadione FDA Label
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: 7261).
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Prophylactic and therapeutic functions of T-type calcium blockers against noise-induced hearing loss. Hear Res. 2007 Apr;226(1-2):52-60.
5	Involvement of cytochrome P450 2C9, 2E1 and 3A4 in trimethadione N-demethylation in human microsomes. J Clin Pharm Ther. 2003 Dec;28(6):493-6.
6	Cytochrome P450 2E1: its clinical and toxicological role. J Clin Pharm Ther. 2000 Jun;25(3):165-75.
7	Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
8	Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
9	Cerner Multum, Inc. "Australian Product Information.".
10	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
11	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
12	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
13	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
14	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
15	Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.
16	Hansen BS, Dam M, Brandt J, et al "Influence of dextropropoxyphene on steady state serum levels and protein binding of three anti-epileptic drugs in man." Acta Neurol Scand 61 (1980): 357-67. [PMID: 6998251]
17	Sekar M, Mimpriss TJ "Buprenorphine, benzodiazepines and prolonged respiratory depression." Anaesthesia 42 (1987): 567-8. [PMID: 3592200]
18	Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.