Ethosuximide

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Ethosuximide
other names	( RS ) -3-ethyl-3-methylpyrrolidine-2,5-dione; (±) -3-Ethyl-3-methylpyrrolidine-2,5-dione; rac -3-ethyl-3-methylpyrrolidine-2,5-dione;
Molecular formula	C 7 H 11 NO 2
External identifiers / databases
EC number	201-048-7
ECHA InfoCard	100,000,954
PubChem	3291
DrugBank	DB00593
Wikidata	Q421567
Drug information
ATC code	N03 AD01
Drug class	Anti-epileptic
properties
Molar mass	141.17 g · mol -1
solubility	soluble in ethanol (100 mg / ml)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	1820 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ethosuximide is an antispasmodic medicine used to treat epilepsy . Its chemical structure is similar to that of phenytoin , which is also used for anti-epileptic therapy .

Mechanism of action and area of application

Ethosuximide reduces voltage-dependent calcium currents by inhibiting the T-type calcium channels in the intralaminar nucleus of the thalamus .

It is mainly used for the treatment of generalized absences, especially of childhood (childhood absence epilepsy ). This form of epilepsy shows typical seizure patterns in the form of 3 Hz spike- wave complexes on the electroencephalogram . Ethosuximide is a first choice and has a super additive effect to valproic acid when combined with it. Ethosuximide is also indicated for myoclonus in adolescents ( impulsive petit mal ) when other drugs were not effective or were not tolerated.

The elimination takes place largely via the liver, the half-life ( half-life ) is around 48 to 60 hours, in children around 30 hours. Concomitant use of valproic acid can increase the half-life of ethosuximide by competitive inhibition of metabolism, whereas concomitant use of carbamazepine induces a higher plasma clearance .

Side effects

Depending on the dose, nausea, vomiting, hiccups, tiredness, headache, depression, movement disorders and psychoses can occur. Irrespective of the dose, various skin rashes including Stevens-Johnson syndrome and changes in the blood count have been described.

chemistry

Ethosuximide is a chiral drug with a stereocenter . The racemate , the 1: 1 mixture of the ( S ) and the ( R ) isomers, is used therapeutically .

Enantiomers of ethosuximide
CAS no. 39122-20-8	CAS no. 39122-19-5

Trade names

Monopreparations

Petinimid (A, CH), Petnidan (D), Suxilep (D), Suxinutin (A)

Individual evidence

↑ ^a ^b ^c Datasheet Ethosuximide from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
↑ Data sheet ETHOSUXIMIDE CRS (PDF) at EDQM , accessed on July 21, 2008.
↑ Ethosuximide seems to be the best choice , DAZ 23/2010.
↑ Ernst Mutschler , Gerd Geisslinger, Heyo K. Kroemer , Sabine Menzel, Peter Ruth: Mutschler drug effects. Pharmacology - Clinical Pharmacology - Toxicology. 10th edition. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2012, ISBN 3-80-472898-7 . P. 290.
↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 182.

[Sigma-1] Datasheet Ethosuximide from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).

[Ph._Eur.-2] Data sheet ETHOSUXIMIDE CRS (PDF) at EDQM , accessed on July 21, 2008.

[3] Ethosuximide seems to be the best choice , DAZ 23/2010.

[4] Ernst Mutschler , Gerd Geisslinger, Heyo K. Kroemer , Sabine Menzel, Peter Ruth: Mutschler drug effects. Pharmacology - Clinical Pharmacology - Toxicology. 10th edition. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2012, ISBN 3-80-472898-7 . P. 290.

[Rote_Liste-5] Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 182.