PARAMETHADIONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H11NO3
Molecular Weight	157.1671
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(C)OC(=O)N(C)C1=O

InChI

InChIKey=VQASKUSHBVDKGU-UHFFFAOYSA-N

InChI=1S/C7H11NO3/c1-4-7(2)5(9)8(3)6(10)11-7/h4H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C7H11NO3
Molecular Weight	157.1671
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19298435
Curator's Comment: Other drugs of oxazolidinedione class act by blocking T-type calcium channel (see , but there is no information about interaction between paramethadione

Paramethadione is an anticonvulsant in the oxazolidinedione class developed by the Abbott Laboratories, approved by the Food and Drug Administration in 1949 for the treatment of absence seizures, also called partial seizures. Paramethadione acts to reduce T-type calcium currents in thalamic neurons which has been proposed to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram (EEG) during absence seizures.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated T-type calcium channel 17 Target ID: CHEMBL2362995 Sources: https://www.drugs.com/mmx/paramethadioneanticonvulsants-dione.html	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Absence seizures 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14394344	Primary		Approved 8429	PARADIONE Approved Use Paramethadione, an oxazolidinc derivative (300 mg p.o. t.i.d.), is indicated as an alternate drug in the treatment of refractory absence seizures. Paramethadione raises the threshold for cortical seizures but does not modify the seizure pattern. It decreases projection of focal activity and reduces both repetitive spinal cord transmission and spike-and-wave patterns of absence (petit mal) seizures. Launch Date 1949

C_max

Value	Dose	Co-administered	Analyte	Population
8.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1185541	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		5-ETHYL-5-METHYL-1,3-OXAZOLIDINE-2,4-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1185541	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		PARAMETHADIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
13 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1185541	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		5-ETHYL-5-METHYL-1,3-OXAZOLIDINE-2,4-DIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1185541	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		PARAMETHADIONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
300 mg single, oral Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/1185541/	healthy, 30 - 41 years n = 3 Health Status: healthy Age Group: 30 - 41 years Sex: M Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/1185541/	Sources: https://pubmed.ncbi.nlm.nih.gov/1185541/
300 mg 3 times / day steady, oral Dose: 300 mg, 3 times / day Route: oral Route: steady Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4193708/	healthy, adult Health Status: healthy Condition: pregnancies Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/4193708/	Other AEs: Teratogenicity... Other AEs: Teratogenicity Sources: https://pubmed.ncbi.nlm.nih.gov/4193708/

AEs

AE	Significance	Dose	Population
Teratogenicity		300 mg 3 times / day steady, oral Dose: 300 mg, 3 times / day Route: oral Route: steady Dose: 300 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4193708/	healthy, adult Health Status: healthy Condition: pregnancies Age Group: adult Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/4193708/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C8 693 CYP2E1 667

Drug as victim

Target	Modality	Activity
CYP2C9 1037	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00617	major
CYP2C8 693	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00617	yes
CYP2E1 667	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00617	yes
CYP3A4 1737	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00617	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY508010	https://www.001chemical.com/chem/115-67-3
AHH Chemical co.,ltd	MR-1013790	http://www.ahhchemical.com/product/MR-1013790.html
Ambinter	Amb10843640	http://www.ambinter.com/reference/10843640
BLD Pharm	BD146751	http://www.bldpharm.com/products/115-67-3.html
ChemMol	49400434	http://www.chemmol.com/chemmol/49400434.html
Clearsynth	CS-T-38691	https://www.clearsynth.com/en/CST38691.html
Molcore	MC508010	https://www.molcore.com/product/115-67-3
OChem	30682	http://www.ocheminc.com/index.php?act=psearch&pid=115P673
eNovation Chemicals	D675465	https://www.enovationchem.com/ProductDetails.asp?ProductID=D675465
iChemical	EBD26815	http://www.ichemical.com/chemicals/cas-115-67-3

PubMed

Title	Date	PubMed
Nephrotic syndrome caused by probenecid.	1967 Jan 2	6071127
Possible teratogenicity of trimethadione and paramethadione.	1970 Aug 1	4193708
Paramethadione and metabolite serum levels in humans after a single oral paramethadione dose.	1975 Oct	1185541
The fetal trimethadione syndrome: report of an additional family and further delineation of this syndrome.	1977 Dec	412416
Adverse drug effects in hospitalized elderly: data from the healthcare cost and utilization project.	2010	22291486

Patents

Sample Use Guides

In Vivo Use Guide

For treatment of epilepsy in children, Paramethadione should be administered orally, 300-600 mg 2-3 times a day.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:08:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:08:17 GMT 2023`
Record UNII	Z615FRW64N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PARAMETHADIONE

Official Name

English

3,5-DIMETHYL-5-ETHYLOXAZOLIDINE-2,4-DIONE

Systematic Name

English

PARAMETHADIONE [HSDB]

Common Name

English

5-ETHYL-3,5-DIMETHYLOXAZOLIDINE-2,4-DIONE

Systematic Name

English

PARAMETHADIONE [ORANGE BOOK]

Common Name

English

ISOETHADIONE

Common Name

English

PARAMETHADIONE [MI]

Common Name

English

PARAMETHADIONE [VANDF]

Common Name

English

5-Ethyl-3,5-dimethyl-2,4-oxazolidinedione

Systematic Name

English

Paramethadione [WHO-DD]

Common Name

English

paramethadione [INN]

Common Name

English

2,4-OXAZOLIDINEDIONE, 5-ETHYL-3,5-DIMETHYL-

Systematic Name

English

PARADIONE

Brand Name

English

PARAMETHADIONE [MART.]

Common Name

English

NSC-760129

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C264