Ethosuximide
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MedKoo CAT#: 317850

CAS#: 77-67-8

Description: Ethosuximide is a succinimide anticonvulsant, used mainly in absence seizures. Ethosuximide suppresses the paroxysmal three cycle per second spike and wave activity associated with lapses of consciousness which is common in absence (petit mal) seizures. The frequency of epileptiform attacks is reduced, apparently by depression of the motor cortex and elevation of the threshold of the central nervous system to convulsive stimuli.

Chemical Structure

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Ethosuximide
CAS# 77-67-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317850
Name: Ethosuximide
CAS#: 77-67-8
Chemical Formula: C7H11NO2
Exact Mass: 141.08
Molecular Weight: 141.168
Elemental Analysis: C, 59.56; H, 7.85; N, 9.92; O, 22.67

Price and Availability

Size Price Availability Quantity
5g USD 250 2 weeks
25g USD 650 2 weeks
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Synonym: Emeside, Ethosuccimid, Ethosuximide, Ethylmethylsuccimide, Ethymal, Zarontin.

IUPAC/Chemical Name: 3-Ethyl-3-methyl-2,5-pyrrolidinedione

InChi Key: HAPOVYFOVVWLRS-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)

SMILES Code: O=C(C(C)(CC)C1)NC1=O

Appearance: White to off-white crystalline 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

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Ethosuximide improves the phenotypes of multiple neurodegenerative disease models and blocks the low voltage activated T-type calcium channel.
In vitro activity: Ethosuximide at clinically relevant concentrations inhibited GIRK channels expressed in Xenopus oocytes. The inhibition was concentration-dependent, but voltage-independent, and time-independent during each voltage pulse. Reference: Neuropharmacology. 2009 Feb;56(2):499-506. https://pubmed.ncbi.nlm.nih.gov/18977371/
In vivo activity: Intraperitoneal pre-treatment (30 min prior) of mice with ethosuximide (10.0–30.0 mg/kg) produced a dose-dependent inhibition of itch responses in male (Fig. 1a) and female (Fig. 1b) mice injected with histamine. Ethosuximide was also able to decrease the time mice spent scratching when co-delivered subcutaneously (100.0–1000.0 μg) with histamine in either male (Fig. 1c) or female (Fig. 1d) mice. Similarly, systemically delivered ethosuximide (10.0–30.0 mg/kg) elicited dose-dependent inhibition of scratching behaviour of male (Fig. 2a) and female (Fig. 2b) subjects that received chloroquine diphosphate. Likewise, ethosuximide produced a significant reduction of itch responses when co-delivered (100.0–1000.0 μg) with chloroquine in male (Fig. 2c) and female (Fig. 2d). Reference: Mol Brain. 2021; 14: 46. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7927410/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 64.0 453.36
Ethanol 28.0 198.35
Water 28.0 198.35

Preparing Stock Solutions

The following data is based on the product molecular weight 141.17 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
Formulation protocol: 1. Kobayashi T, Hirai H, Iino M, Fuse I, Mitsumura K, Washiyama K, Kasai S, Ikeda K. Inhibitory effects of the antiepileptic drug ethosuximide on G protein-activated inwardly rectifying K+ channels. Neuropharmacology. 2009 Feb;56(2):499-506. doi: 10.1016/j.neuropharm.2008.10.003. Epub 2008 Oct 17. PMID: 18977371. 2. Gadotti VM, Zamponi GW. Ethosuximide inhibits acute histamine- and chloroquine-induced scratching behavior in mice. Mol Brain. 2021 Mar 2;14(1):46. doi: 10.1186/s13041-021-00762-1. PMID: 33653383; PMCID: PMC7927410. 3. Kerckhove N, Boudieu L, Ourties G, Bourdier J, Daulhac L, Eschalier A, Mallet C. Ethosuximide improves chronic pain-induced anxiety- and depression-like behaviors. Eur Neuropsychopharmacol. 2019 Dec;29(12):1419-1432. doi: 10.1016/j.euroneuro.2019.10.012. Epub 2019 Nov 22. PMID: 31767519.
In vitro protocol: 1. Kobayashi T, Hirai H, Iino M, Fuse I, Mitsumura K, Washiyama K, Kasai S, Ikeda K. Inhibitory effects of the antiepileptic drug ethosuximide on G protein-activated inwardly rectifying K+ channels. Neuropharmacology. 2009 Feb;56(2):499-506. doi: 10.1016/j.neuropharm.2008.10.003. Epub 2008 Oct 17. PMID: 18977371.
In vivo protocol: 1. Gadotti VM, Zamponi GW. Ethosuximide inhibits acute histamine- and chloroquine-induced scratching behavior in mice. Mol Brain. 2021 Mar 2;14(1):46. doi: 10.1186/s13041-021-00762-1. PMID: 33653383; PMCID: PMC7927410. 2. Kerckhove N, Boudieu L, Ourties G, Bourdier J, Daulhac L, Eschalier A, Mallet C. Ethosuximide improves chronic pain-induced anxiety- and depression-like behaviors. Eur Neuropsychopharmacol. 2019 Dec;29(12):1419-1432. doi: 10.1016/j.euroneuro.2019.10.012. Epub 2019 Nov 22. PMID: 31767519.

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1: Gören MZ, Onat F. Ethosuximide: from bench to bedside. CNS Drug Rev. 2007 Summer;13(2):224-39. Review. PubMed PMID: 17627674.

2: Posner EB, Mohamed K, Marson AG. Ethosuximide, sodium valproate or lamotrigine for absence seizures in children and adolescents. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD003032. Review. PubMed PMID: 16235312.

3: Posner EB, Mohamed K, Marson AG. A systematic review of treatment of typical absence seizures in children and adolescents with ethosuximide, sodium valproate or lamotrigine. Seizure. 2005 Mar;14(2):117-22. Review. PubMed PMID: 15694565.

4: Posner EB, Mohamed K, Marson AG. Ethosuximide, sodium valproate or lamotrigine for absence seizures in children and adolescents. Cochrane Database Syst Rev. 2003;(3):CD003032. Review. Update in: Cochrane Database Syst Rev. 2005;(4):CD003032. PubMed PMID: 12917940.

5: Wallace SJ. Myoclonus and epilepsy in childhood: a review of treatment with valproate, ethosuximide, lamotrigine and zonisamide. Epilepsy Res. 1998 Jan;29(2):147-54. Review. PubMed PMID: 9477147.

6: Battino D, Estienne M, Avanzini G. Clinical pharmacokinetics of antiepileptic drugs in paediatric patients. Part I: Phenobarbital, primidone, valproic acid, ethosuximide and mesuximide. Clin Pharmacokinet. 1995 Oct;29(4):257-86. Review. PubMed PMID: 8549027.

7: Ichiba M, Kitazawa S. [Ethosuximide]. Nihon Rinsho. 1995 Feb;53 Su Pt 1:915-7. Review. Japanese. PubMed PMID: 8753586.

8: Massey GV, Dunn NL, Heckel JL, Myer EC, Russell EC. Aplastic anemia following therapy for absence seizures with ethosuximide. Pediatr Neurol. 1994 Jul;11(1):59-61. Review. PubMed PMID: 7986296.

9: Millership JS, Mifsud J, Collier PS. The metabolism of ethosuximide. Eur J Drug Metab Pharmacokinet. 1993 Oct-Dec;18(4):349-53. Review. PubMed PMID: 8020533.

10: Wallace SJ. Use of ethosuximide and valproate in the treatment of epilepsy. Neurol Clin. 1986 Aug;4(3):601-16. Review. PubMed PMID: 3092003.