Compound: Levetiracetam
SMILES: O=C1N([C@H](C(=O)N)CC)CCC1
InChIKey: HPHUVLMMVZITSG-LURJTMIESA-N
Synonyms: Levetiracetam, 102767-28-2, Keppra, (2S)-2-(2-oxopyrrolidin-1-yl)butanamide, Keppra XR, Spritam, UCB-L 059, ucb L059, matever, Levetiracetame, Levetiracetamum, UCB-L059, Elepsia, (S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide, Levetiracetam sun, E Keppra, Elepsia XR, Levetiracetam teva, Levetiracetam accord, Levetiracetam actavis, Levetiracetam hospira, 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (alphaS)-, (-)-(S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide, UCB-22059, UCB 22059, NSC-760119, Levetiracetam In Sodium Chloride, AGB-101, N03AX14, 44YRR34555, LEVETIRACETAM RATIOPHARM, CHEBI:6437, DTXSID9023207, LEVETIRACETAM ACTAVIS GROUP, 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (S)-, Desitrend, Roweepra, Levetiracetam ER, Etiracetam, R, Etiracetam, S, Levetiracetam oral, Etiracetam, S-, R-isomer Etiracetam, S-isomer Etiracetam, LEVERTIRACETAM, Levetiracetam Injection, RefChem:5943, ucb-L060, UcbL060, Levetiracetam Levetiracetam, Levetiracetam Extended-release, DTXCID503207, ELEPSIA XR 1000 MG, ELEPSIA XR 1500 MG, UCB6474, alpha ethyl 2 oxo 1 Pyrrolidineacetamide, 1-Pyrrolidineacetamide, Alpha-ethyl-2-oxo-,(S)-, 600-348-9, (S)-2-(2-Oxopyrrolidin-1-yl)butanamide, SIB-S1, MFCD03265610, Levetiracetam [INN], Levetiracetamum [INN-Latin], Levroxa, (S)-(-)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide, Leviteracetam, Levipil, Torleva, (S)-Levetiracetam, SMR000466303, Keppra (TN), Levesam 500, Etiracetam levo-isomer, SR-01000759400, s1356, UNII-44YRR34555, HSDB 7528, Levetiracetam CRS, 1-Pyrrolidineacetamide, a-ethyl-2-oxo-; a-Ethyl-2-oxo-1-pyrrolidineacetamide; Etiracetam; UCB 6474; (2RS)-2-(2-Oxopyrrolidin-1-yl)butanamide, Levetiracetam [USAN:USP:INN:BAN], E keppra (TN), (S)-2-(2-Oxo-1-pyrrolidinyl)butyramide, L-059, LEVETIRACETAM [MI], LEVETIRACETAM [JAN], CHEMBL1286, LEVETIRACETAM [HSDB], LEVETIRACETAM [USAN], LEVETIRACETAM [VANDF], MLS000759403, MLS001424069, MLS006010215, BIDD:GT0242, LEVETIRACETAM [MART.], SCHEMBL118843, LEVETIRACETAM [USP-RS], LEVETIRACETAM [WHO-DD], GTPL6826, Levetiracetam (JAN/USP/INN), orb1310850, orb3141186, SCHEMBL6650425, LEVETIRACETAM [EMA EPAR], HPHUVLMMVZITSG-LURJTMIESA-N, Levetiracetam - Bio-X trade mark, Levetiracetam, >=98% (HPLC), Levetiracetam, analytical standard, GLXC-03020, HMS2051D07, HMS2089L20, HMS2235I18, HMS3262H11, HMS3713P16, HMS3884O11, Levetiracetam, 1mg/ml in Methanol, Pharmakon1600-01502265, LEVETIRACETAM [EP IMPURITY], LEVETIRACETAM [ORANGE BOOK], ALBB-027275, HY-B0106, MSK10598, LEVETIRACETAM [EP MONOGRAPH], LEVETIRACETAM [USP IMPURITY], Tox21_500835, BDBM50422542, EBC-06279, LEVETIRACETAM [USP MONOGRAPH], NSC760119, STL388027, Levetiracetam 1.0 mg/ml in Methanol, AKOS015841981, AC-1479, CCG-100928, CS-1854, DB01202, FL24879, KS-1176, LP00835, NC00178, NSC 760119, SDCCGSBI-0633760.P001, NCGC00186028-01, NCGC00186028-13, NCGC00261520-01, (S)-2-(2-oxopyrrolidin-1-yl)butyramide, BL164623, (s)-2-(2-oxopyrrolidin-1-yl) butyramide, (a-S)-a-Ethyl-2-oxo-1-pyrrolidineacetamide, L0234, SW197558-3, C07841, D00709, EN300-244575, AB00639945-06, AB00639945_07, AB00639945_08, F079444, (S)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE, 1-Pyrrolidineacetamide, |A-ethyl-2-oxo-, (|AS)-, SR-01000759400-4, SR-01000759400-5, BRD-K49404994-001-09-1, BRD-K49404994-001-10-9, BRD-K49404994-001-11-7, Z1255435426, (-)-(S)-.ALPHA.-ETHYL-2-OXO-1-PYRROLIDINEACETAMIDE, 1-Pyrrolidineacetamide, .alpha.-ethyl-2-oxo-, (.alpha.S)-, Levetiracetam Working Standard (Secondary Reference Standard), Levetiracetam, European Pharmacopoeia (EP) Reference Standard, Levetiracetam, United States Pharmacopeia (USP) Reference Standard, (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide (2S)-2-(2-Oxo-pyrrolidin-1-yl)butanamide, Levitiracetam, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C8H14N2O2
molecular_weight: 170.21 g/mol
exact_mass: 170.105527694 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 12
topological_polar_surface_area: 63.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ethyl acetate
color: Crystals from ethyl acetate
odor: Faint
melting_point: 115-119C
solubility: 104g/100mL
vapor_pressure: 3.5X10-6 mm Hg at 25 °C
Descriptions:
pubchem: Levetiracetam is a pyrrolidinone and carboxamide that is N-methylpyrrolidin-2-one in which one of the methyl hydrogens is replaced by an aminocarbonyl group, while another is replaced by an ethyl group (the S enantiomer). An anticonvulsant, it is used for the treatment of epilepsy in both human and veterinary medicine. It has a role as an anticonvulsant, a xenobiotic and an environmental contaminant.
chebi: A pyrrolidinone and carboxamide that is <em>N</em>-methylpyrrolidin-2-one in which one of the methyl hydrogens is replaced by an aminocarbonyl group, while another is replaced by an ethyl group (the <i>S</i> enantiomer). An anticonvulsant, it is used for the treatment of epilepsy in both human and veterinary medicine.
chembl: LEVETIRACETAM is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Levetiracetam, sold under the brand name Keppra among others, is an antiepileptic drug (medication) used to treat epilepsy. It is used for partial-onset, myoclonic, or tonic–clonic seizures, and is taken either by mouth as an immediate or extended release formulation or by injection into a vein.
Common side effects of levetiracetam include sleepiness, dizziness, feeling tired, and aggression. Severe side effects may include psychosis, suicide, and allergic reactions such as Stevens–Johnson syndrome or anaphylaxis.  Levetiracetam is the S-enantiomer of etiracetam. It acts as a synaptic vesicle glycoprotein 2A (SV2A) ligand.
Levetiracetam was approved for medical use in the United States in 1999 and is available as a generic medication. In 2023, it was the 101st most commonly prescribed medication in the United States, with more than 6 million prescriptions. It is on the World Health Organization's List of Essential Medicines.