Trimethadione
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318950

CAS#: 127-48-0

Description: Trimethadione is an oxazolidinedione anticonvulsant. It is most commonly used to treat epileptic conditions that are resistant to other treatments. Trimethadione (TMO) has the properties required of probe drugs for the evaluation of hepatic drug-oxidizing capacity in humans in vivo. TMO is demethylated to dimethadione (DMO), its only metabolite, in the liver after oral administration.


Chemical Structure

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Trimethadione
CAS# 127-48-0

Theoretical Analysis

MedKoo Cat#: 318950
Name: Trimethadione
CAS#: 127-48-0
Chemical Formula: C6H9NO3
Exact Mass: 143.05824
Molecular Weight: 143.142
Elemental Analysis: C, 50.35; H, 6.34; N, 9.79; O, 33.53

Price and Availability

Size Price Availability Quantity
5.0g USD 450.0 2 Weeks
10.0g USD 650.0 2 Weeks
20.0g USD 950.0 2 Weeks
50.0g USD 1750.0 2 Weeks
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Synonym: Tridione; Trimethadione; Trimetin; Troxidone.

IUPAC/Chemical Name: 3,5,5-trimethyl-1,3-oxazolidine-2,4-dione

InChi Key: IRYJRGCIQBGHIV-UHFFFAOYSA-N

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

SMILES Code: O=C(N1C)OC(C)(C)C1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 143.142 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Pastore V, Wasowski C, Higgs J, Mangialavori IC, Bruno-Blanch LE, Marder M. A synthetic bioisoster of trimethadione and phenytoin elicits anticonvulsant effect, protects the brain oxidative damage produced by seizures and exerts antidepressant action in mice. Eur Neuropsychopharmacol. 2014 Aug;24(8):1405-14. doi: 10.1016/j.euroneuro.2014.04.005. Epub 2014 May 2. PubMed PMID: 24846538.

2: Pastore V, Sabatier L, Enrique A, Marder M, Bruno-Blanch LE. Synthesis and anticonvulsant activity of bioisosteres of trimethadione, N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides from α-hydroxyamides. Bioorg Med Chem. 2013 Feb 15;21(4):841-6. doi: 10.1016/j.bmc.2012.12.033. Epub 2013 Jan 3. PubMed PMID: 23321016.

3: Qin W, Hu ZY, Tong JW, Meng J, You XF, Zhang JP. [Toxic effects of trimethadione on zebrafish early development]. Yi Chuan. 2012 Sep;34(9):1165-73. Chinese. PubMed PMID: 23017458.

4: Weston AD, Brown NA, Ozolinš TR. Co-variation in frequency and severity of cardiovascular and skeletal defects in Sprague-Dawley rats after maternal administration of dimethadione, the N-demethylated metabolite of trimethadione. Birth Defects Res B Dev Reprod Toxicol. 2011 Jun;92(3):206-15. doi: 10.1002/bdrb.20302. Epub 2011 Jun 2. PubMed PMID: 21638752.

5: Barton ME, Eberle EL, Shannon HE. The antihyperalgesic effects of the T-type calcium channel blockers ethosuximide, trimethadione, and mibefradil. Eur J Pharmacol. 2005 Oct 3;521(1-3):79-85. Epub 2005 Sep 19. PubMed PMID: 16171802.

6: Fleeman TL, Cappon GD, Hurtt ME. Postnatal closure of membranous ventricular septal defects in Sprague-Dawley rat pups after maternal exposure with trimethadione. Birth Defects Res B Dev Reprod Toxicol. 2004 Jun;71(3):185-90. PubMed PMID: 15282739.

7: Tanaka E, Kurata N, Yasuhara H. 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. PubMed PMID: 14651673.

8: Nakamura H, Tanaka E, Kaneko M, Iwakawa M, Hori T, Ikebukuro K, Amagai T, Ohkawa H. The clinical importance of the trimethadione tolerance test as a method for quantitative assessment of hepatic functional reserve in patients with biliary atresia. J Clin Pharm Ther. 2001 Dec;26(6):417-24. PubMed PMID: 11722678.

9: Nagai T. [Fetal trimethadione syndrome]. Ryoikibetsu Shokogun Shirizu. 2001;(33):704. Review. Japanese. PubMed PMID: 11462643.

10: Nakane Y. [Fetal trimethadione effects]. Ryoikibetsu Shokogun Shirizu. 2000;(30 Pt 5):94-5. Review. Japanese. PubMed PMID: 11057156.

11: Nishimura Y, Kurata N, Iwase M, Li H, Yasuhara H. The effects of organic solvents on trimethadione n-demethylation in rats. Res Commun Mol Pathol Pharmacol. 1999;104(2):229-39. PubMed PMID: 10634315.

12: Tanaka E, Ishikawa A, Horie T. In vivo and in vitro trimethadione oxidation activity of the liver from various animal species including mouse, hamster, rat, rabbit, dog, monkey and human. Hum Exp Toxicol. 1999 Jan;18(1):12-6. PubMed PMID: 10025363.

13: Kurata N, Nishimura Y, Iwase M, Fischer NE, Tang BK, Inaba T, Yasuhara H. Trimethadione metabolism by human liver cytochrome P450: evidence for the involvement of CYP2E1. Xenobiotica. 1998 Nov;28(11):1041-7. PubMed PMID: 9879636.

14: Tanaka E, Taniguchi T, Sawa Y, Ohmori S, Kitada M, Horie T. Trimethadione metabolism and microsomal monooxygenases in untreated and phenobarbital-treated rhesus monkeys. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Aug;120(2):317-20. PubMed PMID: 9827046.

15: Tanaka E, Ishikawa A, Abei M, Kobayashi S. Trimethadione as a probe drug to estimate hepatic oxidizing capacity in humans. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1996 Nov;115(3):211-6. Review. PubMed PMID: 9375358.

16: Nishimura Y, Kurata N, Watanabe M, Uchida E, Yasuhara H. Trimethadione N-demethylation by rat liver CYP2E1 in vitro. Res Commun Mol Pathol Pharmacol. 1996 Jul;93(1):43-56. PubMed PMID: 8865369.

17: Zhang YF, Gibbs JW 3rd, Coulter DA. Anticonvulsant drug effects on spontaneous thalamocortical rhythms in vitro: ethosuximide, trimethadione, and dimethadione. Epilepsy Res. 1996 Feb;23(1):15-36. PubMed PMID: 8925801.

18: Tanaka E, Funae Y. Trimethadione: metabolism and assessment of hepatic drug-oxidizing capacity. Methods Enzymol. 1996;272:163-9. PubMed PMID: 8791774.

19: Tanaka E, Osada A, Ishikawa A, Nakamura T, Momose Y, Mikami T, Fukao K, Horie T. Influence of partial hepatectomy in dogs on trimethadione metabolism and microsomal monooxygenases. Xenobiotica. 1995 Dec;25(12):1301-10. PubMed PMID: 8719906.

20: Abei M, Tanaka E, Tanaka N, Matsuzaki Y, Ikegami T, Ishikawa A, Osuga T. Clinical significance of the trimethadione tolerance test in chronic hepatitis: a useful indicator of hepatic drug metabolizing capacity. J Gastroenterol. 1995 Aug;30(4):478-84. PubMed PMID: 7550858.