Drug Details

General Information of the Drug (ID: DR3991)
Name
Levetiracetam
Synonyms
Levetiracetam; 102767-28-2; Keppra; (S)-2-(2-Oxopyrrolidin-1-yl)butanamide; Keppra XR; ucb L059; UCB-L 059; (2S)-2-(2-oxopyrrolidin-1-yl)butanamide; UCB-L059; Levetiracetamum; Spritam; (S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; SIB-S1; (-)-(S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; UNII-44YRR34555; 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (alphaS)-; MFCD03265610; UCB-22059; Levetiracetamum [INN-Latin]; CHEBI:6437; Levetiracetam In Sodium Chloride; UCB 22059; 44YRR34555; Levroxa; (S)-(-)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide; (S)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE; matever; Leviteracetam; Levipil; Torleva; Elepsia XR; (S)-Levetiracetam; SMR000466303; Keppra (TN); Levesam 500; Etiracetam levo-isomer; SR-01000759400; Levetiracetame; E Keppra; HSDB 7528; N03AX14; Levetiracetam [USAN:USP:INN:BAN]; E keppra (TN); Levetiracetam solution; (S)-2-(2-Oxo-1-pyrrolidinyl)butyramide; L-059; 2(S)-(2-OXOPYRROLIDIN-1-YL)BUTYRAMIDE; CHEMBL1286; 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (S)-; MLS000759403; MLS001424069; MLS006010215; BIDD:GT0242; SCHEMBL118843; GTPL6826; Levetiracetam (JAN/USP/INN); DTXSID9023207; AGB-101; Levetiracetam, >=98% (HPLC); Levetiracetam, analytical standard; HMS2051D07; HMS2089L20; HMS2235I18; HMS3262H11; HMS3713P16; HMS3884O11; Pharmakon1600-01502265; ACT02712; ALBB-027275; BCP11856; HY-B0106; ZINC1547851; Tox21_500835; ANW-41693; BDBM50422542; NSC760119; s1356; STL388027; Levetiracetam 1.0 mg/ml in Methanol; AKOS015841981; AB13957; AC-1479; CCG-100928; CS-1854; DB01202; KS-1176; LP00835; LS41261; MCULE-5120797917; NC00178; NSC 760119; NSC-760119; SDCCGSBI-0633760.P001; (2S)-(2-Oxopyrrolidin-1-yl)butyramide; NCGC00186028-01; NCGC00186028-13; NCGC00261520-01; (S)-2-(2-oxopyrrolidin-1-yl)butyramide; (s)-2-(2-oxopyrrolidin-1-yl) butyramide; (2S)-2-(2-oxo-1-pyrrolidinyl)butanamide; AB0012613; AM20070676; L0234; SW197558-3; C07841; D00709; M-2814; AB00639945-06; AB00639945_07; AB00639945_08; 767L282; A800616; (2S)-2-(2-oxidanylidenepyrrolidin-1-yl)butanamide; Q-201292; SR-01000759400-4; SR-01000759400-5; (ALPHAS)-ALPHA-ETHYL-2-OXO-1-PYRROLIDINEACETAMIDE; UNII-230447L0GL component HPHUVLMMVZITSG-LURJTMIESA-N; Levetiracetam, European Pharmacopoeia (EP) Reference Standard; (??S)???-??-???Ethyl-???2-???oxo-1-???pyrrolidineacetamide; Levetiracetam, United States Pharmacopeia (USP) Reference Standard; (-)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide (2S)-2-(2-Oxo-pyrrolidin-1-yl)butanamide; Levetiracetam solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material; Levitiracetam, Pharmaceutical Secondary Standard; Certified Reference Material
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Molecular Type
Small molecule
Disease Pain [ICD-11: MG30-MG3Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2-3 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Bioavailability
The bioavailability of drug is 60%
Clearance
The renal clearance of drug is 0.6 mL/min/kg
Elimination
Approximately 66% of the administered dose of levetiracetam is excreted in the urine as unchanged drug, while only 0.3% of the total dose is excreted via the feces
Half-life
The concentration or amount of drug in body reduced by one-half in 6 - 8 hours
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 251.785 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.9%
Vd
The volume of distribution (Vd) of drug is 0.5-0.7 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 1040 mg/mL
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Formula
C8H14N2O2
PubChem CID
5284583
Canonical SMILES
CCC(C(=O)N)N1CCCC1=O
InChI
1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1
InChIKey
HPHUVLMMVZITSG-LURJTMIESA-N
CAS Number
CAS 102767-28-2
ChEBI ID
CHEBI:6437
TTD Drug ID
D0E1XL
DrugBank ID
DB01202
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Xanthotoxin      Cullen corylifolium     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Adult male Albino Swiss mice weighing 22-26 g were used in this study.
                    Experimental
                    Result(s)		 XANT in combination with levetiracetam exerts beneficial anticonvulsant pharmacodynamic interactions in the 6 Hz mouse psychomotor seizure model.
Target and Pathway
Target(s) Serotonin receptor 3A (HTR3A)  Molecule Info  [1]
Synaptic vesicle glycoprotein 2A (SV2A)  Molecule Info  [3]
KEGG Pathway ECM-receptor interaction Click to Show/Hide
2 Serotonergic synapse
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
Panther Pathway 5HT3 type receptor mediated signaling pathway Click to Show/Hide
Reactome Ligand-gated ion channel transport Click to Show/Hide
WikiPathways SIDS Susceptibility Pathways Click to Show/Hide
2 Iron uptake and transport
References
Reference 1 Emerging therapies for fibromyalgia. Expert Opin Emerg Drugs. 2008 Mar;13(1):53-62.
Reference 2 Xanthotoxin enhances the anticonvulsant potency of levetiracetam and valproate in the 6-Hz corneal stimulation model in mice. Fundam Clin Pharmacol. 2021 Jul 2.
Reference 3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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