TRIMETHADIONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H9NO3
Molecular Weight	143.1406
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN1C(=O)OC(C)(C)C1=O

InChI

InChIKey=IRYJRGCIQBGHIV-UHFFFAOYSA-N

InChI=1S/C6H9NO3/c1-6(2)4(8)7(3)5(9)10-6/h1-3H3

HIDE SMILES / InChI

Molecular Formula	C6H9NO3
Molecular Weight	143.1406
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Trimethadione (brand name is TRIDIONE) is an oxazolidinedione compound that was developed as an antiepileptic agent for control of petit mal seizures that are refractory to treatment with other drugs. Tridione does not modify the maximal seizure pattern in patients undergoing electroconvulsive therapy and has a sedative effect that may increase to the point of ataxia when excessive doses are used. Trimethadione acts as a voltage-activated T-type Ca2+ channel blocker. Trimethadione is rapidly absorbed from the gastrointestinal tract. It is demethylated by liver microsomes to the active metabolite, dimethadione. Approximately 3% of a daily dose of tridione is recovered in the urine as the unchanged drug. The majority of trimethadione is excreted slowly by the kidney in the form of dimethadione.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated T-type calcium channel 19	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Petit mal seizures 1	Primary		Approved 8,583	TRIDIONE

C_max

Value	Dose	Co-administered	Analyte	Population
6 μg/mL	4 mg/kg single, oral		TRIMETHADIONE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
148 μg × h/mL	4 mg/kg single, oral		TRIMETHADIONE serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
14.2 h	4 mg/kg single, oral		TRIMETHADIONE serum	Homo sapiens

Doses

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Dose	Population	Adverse events
150 mg 4 times / day multiple, oral	unhealthy, 16 years	Disc. AE: Hepatitis...
0.3 g 3 times / day multiple, oral	unhealthy, 23 years	Disc. AE: Aplastic anemia...
0.3 g 3 times / day multiple, oral	unhealthy, 23 years	Disc. AE: Agranulocytosis, Thrombocytopenia...
24 g 1 times / day multiple, oral Studied dose	unhealthy

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AEs

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AE	Significance	Dose	Population
Hepatitis	1 patient Disc. AE	150 mg 4 times / day multiple, oral	unhealthy, 16 years
Aplastic anemia	grade 5, 1 patient Disc. AE	0.3 g 3 times / day multiple, oral	unhealthy, 23 years
Agranulocytosis	grade 5, 1 patient Disc. AE	0.3 g 3 times / day multiple, oral	unhealthy, 23 years
Thrombocytopenia	grade 5, 1 patient Disc. AE	0.3 g 3 times / day multiple, oral	unhealthy, 23 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193		inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
T-type Ca2+ channels 3 Ca2+ channels 59	CYP 303 CYP1A2 1,197 CYP2E1 729

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
Ca2+ channels 62	inhibitor 4,027	yes
T-type Ca2+ channels 3	inhibitor 4,027	yes

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Drug as victim

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Target	Modality	Activity
CYP1A2 1,197	substrate 4,014	inconclusive
CYP 303	substrate 4,014	likely
CYP2C9 1,193	substrate 4,014	yes
CYP2E1 729	substrate 4,014	yes
CYP3A4 1,946	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY515757	https://www.001chemical.com/chem/127-48-0
3B Scientific (Wuhan) Corp	3B3-053075	http://www.3bsc.com/index/pro_info.php?id=91540
AA Blocks	AA000WG2	https://www.aablocks.com/goods/Goods/detail?id=AA000WG2
Aaron Chemicals	AR000X7U	http://www.aaronchem.com/127-48-0
abcr GmbH	AB133755	http://www.abcr.com/shop/en/AB133755

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PubMed

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Title	Date	PubMed
Di-n-propylacetic acid--profile of anticonvulsant activity in mice.	1976 Feb	779804
Fetal anticonvulsant syndrome in rats: dose- and period-response relationships of prenatal diphenylhydantoin, trimethadione and phenobarbital exposure on the structural and functional development of the offspring.	1983 Nov	6195326
A model of chronic spontaneous petit mal-like seizures in the rat: comparison with pentylenetetrazol-induced seizures.	1984 Jun	6426943
Anticonvulsive and convulsive effects of lidocaine: comparison with those of phenytoin, and implications for mechanism of action concepts.	1988 Sep	2905779
Effects of antiepileptic drugs on absence-like and tonic seizures in the spontaneously epileptic rat, a double mutant rat.	1988 Sep-Oct	3137016

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Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dosage: 0.9-2.4 grams daily in 3 or 4 equally divided doses (i.e., 300−600 mg 3 or 4 times daily). Initially, give 0.9 gram daily; increase this dose by 300 mg at weekly intervals until therapeutic results are seen or until toxic symptoms appear. Children's Dosage: Usually 0.3-0.9 gram daily in 3 or 4 equally divided doses.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	R7GV3H6FQ4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRIMETHADIONE

Official Name

English

TRIDIONE

Preferred Name

English

EPIDIONE

Common Name

English

TRIMETHADIONE [WHO-IP]

Common Name

English

TRIMETHADIONE [EP MONOGRAPH]

Common Name

English

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Classification Tree

Code System

Code

Decreased Disorganized Electrical Activity

NDF-RT

N0000008486

Oxazolidine derivatives

WHO-ATC

N03AC02

Established Pharmacologic Class

NDF-RT

N0000175753

Oxazolidine derivatives

WHO-VATC

QN03AC02

Agent Affecting Nervous System

NCI_THESAURUS

C264

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Code System

Code

Type

Description

DRUG CENTRAL

2751

PRIMARY

IUPHAR

7316

PRIMARY

SMS_ID

100000076924

PRIMARY

MESH

D014293

PRIMARY

PUBCHEM

5576

PRIMARY

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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Amount:

9 % (average)

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Related Record

Type

Details


					ALU9NPM703

DIMETHADIONE

METABOLITE ACTIVE -> PARENT

Comments:

Metabolite to parent drug ratio in non-uraemic human plasma.

Interaction Type:

METABOLITE TO PARENT DRUG RATIO

Qualification:

PLASMA; URINE

Amount:

RELATIONSHIP_AMOUNT 24 METABOLITE/PARENT RATIO (average)


					ALU9NPM703

DIMETHADIONE

METABOLITE ACTIVE -> PARENT

Comments:

Dimethadione has anticonvulsant activity and has been used clinically in the treatment of petit mal epilepsy.

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Related Record

Type

Details


					R7GV3H6FQ4

TRIMETHADIONE

ACTIVE MOIETY

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SMILES

InChI

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator