Compound: ethosuximide
SMILES: O=C1NC(=O)CC1(CC)C
InChIKey: HAPOVYFOVVWLRS-UHFFFAOYSA-N
Synonyms: ethosuximide, 77-67-8, Zarontin, Etosuximida, 2-Ethyl-2-methylsuccinimide, 3-Ethyl-3-methylpyrrolidine-2,5-dione, Ethosuxide, Pyknolepsinum, Emeside, Suxilep, Ethosuccimide, Ethosuccinimide, Atysmal, Suxinutin, Etosuximid, Petinimid, Zarondan, Aethosuximide, Thilopemal, Ethosuximidum, 3-Ethyl-3-methyl-2,5-pyrrolidinedione, 3-Methyl-3-ethylsuccinimide, CI-366, 2-Methyl-2-ethylsuccinimide, PM-671, 2,5-Pyrrolidinedione, 3-ethyl-3-methyl-, 3-Ethyl-3-methylsuccinimide, Etosuccimide, Succinimide, 2-ethyl-2-methyl-, CN-10,395, PM 671, alpha-Ethyl-alpha-methylsuccinimide, alpha-Methyl-alpha-ethylsuccinimide, 3-Methyl-3-ethylpyrrolidine-2,5-dione, gamma-Methyl-gamma-ethyl-succinimide, CN-10395, NSC-64013, H 940, H-490, (+-)-2-Ethyl-2-methylsuccinimide, DTXSID7023019, gamma-ethyl-gamma-methyl-succinimide, 5SEH9X1D1D, CI 366, NSC64013, CHEBI:4887, DTXCID203019, Ethosuccimid, Ethylmethylsuccimide, Faes, Etosuximida, 3-ethyl-5-hydroxy-3-methyl-3,4-dihydro-2H-pyrrol-2-one, RefChem:56507, N03AD01, (2RS)-2-Ethyl-2-methylsuccinimide, 201-048-7, Petnidan, Capitus, Ethymal, Ronton, Pentinimid, Peptinimid, Succimitin, Zaraondan, Mesentol, Pemalin, Simatin, Succimal, Suximal, Thetamid, Zarodan, Zartalin, Asamid, Etomal, Pemal, Suxin, Epileo Petit MAL, Piknolepsin, Zarondan-Saft, Simatin(E), C.I. 366, Cl 366, 3-ethyl-3-methyl-pyrrolidine-2,5-dione, MFCD00072123, 3-Ethyl-3-methylpyrroline-2,5-dione, CHEMBL696, .alpha.-Ethyl-.alpha.-methylsuccinimide, Aethosuccimidum, Etosuximide, (+/-)-2-ethyl-2-methylsuccinimide, s4626, .gamma.-Methyl-.gamma.-ethylsuccinimide, Etosuccimide [DCIT], Aethosuximide [German], N-Ethyl methylsuccinimide, Ethosuximidum [INN-Latin], Etosuximida [INN-Spanish], Pyknole.psi.num, Piknole.psi.n, Zarontin (TN), HSDB 1119, SR-01000075863, EINECS 201-048-7, NSC 64013, UNII-5SEH9X1D1D, BRN 0117054, Ethosuximide RS, Ethosuximide CRS, CAS-77-67-8, NCGC00016320-01, Prestwick_611, Ethosuximide [USAN:USP:INN:BAN:JAN], Spectrum_001385, Ethosuximide (Standard), Prestwick0_000165, Prestwick1_000165, Prestwick2_000165, Prestwick3_000165, Spectrum2_001483, Spectrum3_000944, Spectrum4_001051, Spectrum5_001073, ETHOSUXIMIDE [MI], E0746, (.+/-.)-Ethosuximide, ETHOSUXIMIDE [INN], ETHOSUXIMIDE [JAN], 2, 3-ethyl-3-methyl-, E 7138, ETHOSUXIMIDE [HSDB], ETHOSUXIMIDE [USAN], ETHOSUXIMIDE [VANDF], NCIOpen2_000014, Lopac0_000532, SCHEMBL34212, BSPBio_000029, ETHOSUXIMIDE [MART.], KBioGR_001342, KBioSS_001865, 5-21-09-00595 (Beilstein Handbook Reference), DivK1c_000218, ETHOSUXIMIDE [USP-RS], ETHOSUXIMIDE [WHO-DD], ETHOSUXIMIDE [WHO-IP], SPECTRUM1502196, 2,5-Pyrrolidinedione, 3-ethyl-3-methyl-, (+-)-, SPBio_001465, SPBio_001950, BPBio1_000033, GTPL7182, orb1310343, orb3141260, WLN: T5VMVTJ D2 D1, SCHEMBL20541518, Ethosuximide (JP18/USP/INN), Ethosuximide, analytical standard, HMS500K20, HY-B1378R, KBio1_000218, KBio2_001865, KBio2_004433, KBio2_007001, KBio3_002008, NINDS_000218, ETHOSUXIMIDE [ORANGE BOOK], GLXC-06110, HMS1568B11, HMS1921L14, HMS2092D20, HMS2095B11, HMS3261L05, HMS3712B11, HMS3885D12, HMS5083G04, Pharmakon1600-01502196, ETHOSUXIMIDE [EP MONOGRAPH], HY-B1378, MSK10713, ETHOSUXIMIDE [USP MONOGRAPH], Ethosuximide 1.0 mg/ml in Methanol, Tox21_110370, Tox21_500532, BDBM50240424, CCG-39217, EBC-03155, ETHOSUXIMIDUM [WHO-IP LATIN], NSC758192, 3-ethyl-3-methylazolidine-2,5-dione, AKOS005261742, Tox21_110370_1, CS-7976, DB00593, FE22867, LP00532, NSC-758192, SDCCGSBI-0050515.P004, .alpha.-Methyl-.alpha.-ethylsuccinimide, IDI1_000218, NCGC00015418-02, NCGC00015418-03, NCGC00015418-04, NCGC00015418-05, NCGC00015418-06, NCGC00015418-08, NCGC00015418-09, NCGC00015418-15, NCGC00093923-01, NCGC00093923-02, NCGC00093923-03, NCGC00093923-04, NCGC00261217-01, 3-Ethyl-3-methyl-2, 5-pyrrolidinedione, AS-16859, DA-63296, SBI-0050515.P003, 2, 5-Pyrrolidinedione, 3-ethyl-3-methyl-, AB00052288, EU-0100532, NS00010826, ST51037248, (RS)-3-Ethyl-3-methylpyrrolidine-2,5-dione, C07505, D00539, D70258, EN300-123801, AB00052288_04, zarontin3-Ethyl-3-methyl-pyrrolidine-2,5-dione, Q421567, SR-01000075863-1, SR-01000075863-3, SR-01000075863-5, 3-Ethyl-3-methyl-pyrrolidine-2,5-dione(Ethosuximide), BRD-A99633051-001-04-7, BRD-A99633051-001-05-4, BRD-A99633051-001-07-0, BRD-A99633051-001-08-8, 3-Ethyl-3-methyl-pyrrolidine-2,5-dione (ethosuximide), Z384975088, 4-ethyl-5-hydroxy-4-methyl-3,4-dihydro-2H-pyrrol-2-one, 2,5-PYRROLIDINEDIONE, 3-ETHYL-3-METHYL-, (+/-)-, Ethosuximide, European Pharmacopoeia (EP) Reference Standard, Ethosuximide, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C7H11NO2
molecular_weight: 141.17 g/mol
exact_mass: 141.078978594 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 10
topological_polar_surface_area: 46.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from acetone and ether
color: Crystals from acetone and ether
odor: CHARACTERISTIC ODOR
Descriptions:
pubchem: Ethosuximide is a dicarboximide that is pyrrolidine-2,5-dione in which the hydrogens at position 3 are substituted by one methyl and one ethyl group. An antiepileptic, it is used in the treatment of absence seizures and may be used for myoclonic seizures, but is ineffective against tonic-clonic seizures. It has a role as a geroprotector, a T-type calcium channel blocker and an anticonvulsant. It is a dicarboximide and a pyrrolidinone.
chebi: A  dicarboximide that is pyrrolidine-2,5-dione in which the hydrogens at position 3 are substituted by one methyl and one ethyl group. An antiepileptic, it is used in the treatment of absence seizures and may be used for myoclonic seizures, but is ineffective against tonic-clonic seizures.
chembl: ETHOSUXIMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Ethosuximide, sold under the brand name Zarontin among others, is a medication used to treat absence seizures. It may be used by itself or with other antiseizure medications such as valproic acid. Ethosuximide is taken by mouth.
Ethosuximide is usually well tolerated. Common side effects include loss of appetite, abdominal pain, diarrhea, and feeling tired. Serious side effects include suicidal thoughts, low blood cell levels, and lupus erythematosus. It is unclear if it has adverse effects on the fetus during pregnancy. Ethosuximide is in the succinimide family of medications. Its mechanism of action is thought to be due to antagonism of the postsynaptic T-type voltage-gated calcium channel.
Ethosuximide was approved for medical use in the United States in 1960. It is on the World Health Organization's List of Essential Medicines. Ethosuximide is available as a generic medication. As of 2019, its availability was limited in many countries, with concerns about price fixing in the United States.