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Trimethadione

Trimethadione structure

CAS No:
127-48-0
Formula:
C6H9NO3
Chemical Name:
Trimethadione
Synonyms:
2,4-Oxazolidinedione,3,5,5-trimethyl-;3,5,5-Trimethyl-2,4-oxazolidinedione;Epidione;Petidion;Petidon;Pitmal;Tridione;Tridone;Trimedal;Trimetadione;Trimethadione;3,3,5-Trimethyl-2,4-diketooxazolidine;Trimetin;Troxidone;Minoaleviatin;Trimethin;Tridion;Absentol;Ptimal;Edion;Trimethadion;Petilep;Epixal;Trioxanona;NSC 15799;NSC 169503;3,5,5-Trimethyl-1,3-oxazolidine-2,4-dione
Categories:
Active Pharmaceutical Ingredients > Nervous System Drugs

Description

White, granular, crystalline substance; camphor-like odor. Soluble in water; freely soluble in alcohol, chloroform, and ether; pH 6.0 (5% solution).

Solid

Trimethadione is an oxazolidinone. It has a role as a geroprotector and an anticonvulsant.|An anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378)|Trimethadione is an Anti-epileptic Agent. The physiologic effect of trimethadione is by means of Decreased Central Nervous System Disorganized Electrical Activity.|Trimethadione is a dione-type anticonvulsant with antiepileptic activity. Trimethadione reduces T-type calcium currents in thalamic neurons, thereby stabilizing neuronal membranes, raising the threshold for repetitive activities in the thalamus and inhibiting corticothalamic transmission. This decreases the abnormal thalamocortical rhythmicity, which is thought to underlie the paroxysmal three-cycle-per-second spike-and-wave pattern seen with absence (petit mal) seizures.

Trimethadione Basic Attributes

Molecular Weight：

143.14

Exact Mass：

143.14

BRN：

121627

EC Number：

204-845-8

UNII：

R7GV3H6FQ4

NSC Number：

759152|169503|15799

DSSTox ID：

DTXSID9021396

NCI Thesaurus Code：

C47772

ATC Code：

N - Nervous system

HScode：

2934999090

Characteristics

PSA：

46.6

XLogP3：

0.3

Appearance：

Solid

Density：

1.3075 (rough estimate)

Melting Point：

46 °C

Boiling Point：

78-80 °C @ Press: 5 Torr

Flash Point：

78-80°C/5mm

Refractive Index：

1.4290 (estimate)

Water Solubility：

soluble in water 50 g/L.

Vapor Pressure：

2.98mmHg at 25°C

Safety Information

Packing level：

Ⅲ

Transport codes：

2811

wgk germany：

hazard class code：

61-20/21/22

safety instructions：

53-22-36/37/39-45

RTECS Number：

RQ2100000

Marks：

Precautionary statement(s)：

P201-P280-P308 + P313

Hazard Statements：

H312-H332-H360

GHS Classification：

|Danger|H312 (88.64%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P201, P202, P261, P271, P280, P281, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P363, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Symptoms of overdose include clumsiness or unsteadiness, coma, dizziness (severe), drowsiness (severe), nausea (severe), and problems with vision.

Protein Binding：

90%

Drug Information

Drug Indication：

Used in the control of absence (petit mal) seizures that are refractory to treatment with other medications.

Pharmacology：

Paramethadione and trimethadione are anticonvulsants indicated in the control of absence (petit mal) seizures that are refractory to treatment with other medications. Dione anticonvulsants are used in the treatment of epilepsy. They act on the central nervous system (CNS) to reduce the number of seizures.

MeSH：

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

Metabolism/Metabolites：

Trimethadione has known human metabolites that include Dimethadione.

Mechanism of Action：

Dione anticonvulsants reduce T-type calcium currents in thalamic neurons, including thalamic relay neurons. It does so via the inhibition of voltage dependent T-type calcium channels. This raises the threshold for repetitive activity in the thalamus, and inhibits corticothalamic transmission. Thus, the abnormal thalamocortical rhythmicity, which is thought to underlie the 3-Hz spike-and-wave discharge seen on electroencephalogram(EEG) with absence seizures, is dampened.

MeSH Entry Terms：

Tridione

Trimethadione Use and Manufacturing

Uses

antifungal

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:143.14
XLogP3:0.3
Hydrogen Bond Acceptor Count:3
Exact Mass:143.058243149
Monoisotopic Mass:143.058243149
Topological Polar Surface Area:46.6
Heavy Atom Count:10
Complexity:197
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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127-48-0 3,5,5-trimethyl-1,3-oxazolidine-2,4-dione

CAS No.: 127-48-0

Grade: Industrial Grade

Content: 95%

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