Details of the Drug

General Information of Drug (ID: DMTGDN8)

Drug Name

Levetiracetam

Synonyms

102767-28-2; Keppra; (S)-2-(2-Oxopyrrolidin-1-yl)butanamide; Keppra XR; Levetiracetamum; ucb L059; (2S)-2-(2-oxopyrrolidin-1-yl)butanamide; UCB-L 059; UCB-L059; Spritam; (S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; (-)-(S)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide; SIB-S1; UNII-44YRR34555; 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (alphaS)-; UCB-22059; Levetiracetamum [INN-Latin]; Levetiractam; CHEBI:6437; ucb L060; Levetiracetam In Sodium Chloride; 44YRR34555; Levroxa; 1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-,; Keppra; Leviteracetam; Torleva; Levetiracetam [INN]; Ucb L060; Etiracetam levo-isomer; Keppra (TN); L-059; Etiracetam, S-isomer; Keppra, Keppra XR),Levetiracetam; Levetriacetam

Indication

Disease Entry	ICD 11	Status	REF
Epilepsy	8A60-8A68	Approved	[1], [2]
Fibromyalgia	MG30.01	Approved	[3]

Therapeutic Class

Anticonvulsants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

170.21

Topological Polar Surface Area (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2-3 h [4]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [5]
Bioavailability: The bioavailability of drug is 60% [4]
Clearance: The renal clearance of drug is 0.6 mL/min/kg [6]
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 [7]
Half-life: The concentration or amount of drug in body reduced by one-half in 6 - 8 hours [7]
Metabolism: The drug is metabolized via the hepatic [8]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 251.785 micromolar/kg/day [9]
Unbound Fraction: The unbound fraction of drug in plasma is 0.9% [10]
Vd: The volume of distribution (Vd) of drug is 0.5-0.7 L/kg [11]
Water Solubility: The ability of drug to dissolve in water is measured as 1040 mg/mL [5]

Chemical Identifiers

Formula: C8H14N2O2
IUPAC Name: (2S)-2-(2-oxopyrrolidin-1-yl)butanamide
Canonical SMILES: CC[C@@H](C(=O)N)N1CCCC1=O
InChI: 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

Cross-matching ID

PubChem CID: 5284583
ChEBI ID: CHEBI:6437
CAS Number: 102767-28-2
DrugBank ID: DB01202
TTD ID: D0E1XL
VARIDT ID: DR00180
ACDINA ID: D00358

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 3A receptor (HTR3A)	TTPC4TU	5HT3A_HUMAN	Antagonist	[3]
Synaptic vesicle glycoprotein 2A (SV2A)	TTT3P91	SV2A_HUMAN	Modulator	[12]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Levetiracetam

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Levomilnacipran	DMV26S8	Moderate	Antagonize the effect of Levetiracetam when combined with Levomilnacipran.	Chronic pain [MG30]	[33]
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Coadministration of a Drug Treating the Disease Different from Levetiracetam (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Vilazodone	DM4LECQ	Moderate	Antagonize the effect of Levetiracetam when combined with Vilazodone.	Depression [6A70-6A7Z]	[33]
Vortioxetine	DM6F1PU	Moderate	Antagonize the effect of Levetiracetam when combined with Vortioxetine.	Depression [6A70-6A7Z]	[33]
Milnacipran	DMBFE74	Moderate	Antagonize the effect of Levetiracetam when combined with Milnacipran.	Depression [6A70-6A7Z]	[33]
Desvenlafaxine	DMHD4PE	Moderate	Antagonize the effect of Levetiracetam when combined with Desvenlafaxine.	Depression [6A70-6A7Z]	[33]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Levetiracetam and Esketamine.	Depression [6A70-6A7Z]	[34]
Hydroxychloroquine	DMSIVND	Moderate	Antagonize the effect of Levetiracetam when combined with Hydroxychloroquine.	Malaria [1F40-1F45]	[34]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Levetiracetam and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[35]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Levetiracetam and Lasmiditan.	Migraine [8A80]	[36]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Levetiracetam and Flibanserin.	Mood disorder [6A60-6E23]	[37]
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⏷ Show the Full List of 9 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 27	E00381	83511	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Hydrazine yellow	E00409	164825	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Oleic acid	E00421	445639	Emulsifying agent; Penetration agent; Solubilizing agent
Propylparaben sodium	E00567	23679044	Antimicrobial preservative
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium methylparaben	E00543	23663626	Antimicrobial preservative
Stearic acid	E00079	5281	Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sucralose	E00370	71485	Flavoring agent
Sunset yellow FCF	E00255	17730	Colorant
Ammonia	E00007	222	Alkalizing agent
Ammonium glycyrrhizate pentahydrate	E00600	91826216	Emulsifying agent; Flavoring agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Butylhydroxyanisole	E00308	24667	Antimicrobial preservative; Antioxidant
Calcium hydrogenphosphate	E00294	24441	Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Cetostearyl alcohol	E00353	62238	Emollient; Emulsifying agent; Viscosity-controlling agent
Citric acid monohydrate	E00271	22230	Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Crospovidone	E00626	Not Available	Disintegrant
Dibutyl sebacate	E00160	7986	Plasticizing agent
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Glyceryl dibehenate	E00537	22477175	Binding agent; Coating agent; Flavoring agent; Modified-release agent; Viscosity-controlling agent; lubricant
Hypromellose	E00634	Not Available	Coating agent
Kaolin	E00586	56841936	Adsorbent; Diluent; Suspending agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Medium-chain triglyceride	E00640	Not Available	Emollient; Lubricant; Surfactant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 4000	E00654	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 20	E00664	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium citrate dihydrate	E00369	71474	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
Triethyl citrate	E00128	6506	Plasticizing agent; Solvent
Vinylpyrrolidone	E00668	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water	E00035	962	Solvent
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⏷ Show the Full List of 55 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Levetiracetam 750 mg tablet	750 mg	Oral Tablet	Oral
Levetiracetam 1000 mg tablet	1000 mg	24 HR Extended Release Oral Tablet	Oral
Levetiracetam 1500 mg tablet	1500 mg	24 HR Extended Release Oral Tablet	Oral
Levetiracetam 1000 mg tablet	1000 mg	Tablet for Oral Suspension	Oral
Levetiracetam 250 mg tablet	250 mg	Tablet for Oral Suspension	Oral
Levetiracetam 500 mg tablet	500 mg	Tablet for Oral Suspension	Oral
Levetiracetam 750 mg tablet	750 mg	Tablet for Oral Suspension	Oral
Levetiracetam 250 mg tablet	250 mg	Oral Tablet	Oral
Levetiracetam 500 mg tablet	500 mg	24 HR Extended Release Oral Tablet	Oral
Levetiracetam 750 mg tablet	750 mg	24 HR Extended Release Oral Tablet	Oral
Levetiracetam 500 mg tablet	500 mg	Oral Tablet	Oral
Levetiracetam 1000 mg tablet	1000 mg	Oral Tablet	Oral
Levetiracetam 500 mg tablet	500 mg	24 HR Extended Release Tablet	Oral
Levetiracetam 750 mg tablet	750 mg	24 HR Extended Release Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6826).
2	Use of second-generation antiepileptic drugs in the pediatric population. Paediatr Drugs. 2008;10(4):217-54.
3	Emerging therapies for fibromyalgia. Expert Opin Emerg Drugs. 2008 Mar;13(1):53-62.
4	Bockbrader HN, Wesche D, Miller R, Chapel S, Janiczek N, Burger P: A comparison of the pharmacokinetics and pharmacodynamics of pregabalin and gabapentin. Clin Pharmacokinet. 2010 Oct;49(10):661-9. doi: 10.2165/11536200-000000000-00000.
5	BDDCS applied to over 900 drugs
6	FDA Approved Drugs: Levetiracetam Tablets
7	MedSafe NZ: Levetiracetam
8	Portnoy JM, Dinakar C: Review of cetirizine hydrochloride for the treatment of allergic disorders. Expert Opin Pharmacother. 2004 Jan;5(1):125-35. doi: 10.1517/14656566.5.1.125 .
9	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
10	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
11	DPD Approved Drugs: Levetiracetam
12	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
13	Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46.
14	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
15	MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
16	Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
17	Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
18	Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
19	Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
20	Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.
21	Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, do... Lancet Oncol. 2009 Feb;10(2):115-24.
22	Efficacy of 5-HT3 antagonists and 5-HT4 agonists in irritable bowel syndrome: systematic review and meta-analysis. Am J Gastroenterol. 2009 Jul;104(7):1831-43; quiz 1844.
23	Management of postoperative nausea and vomiting: focus on palonosetron. Ther Clin Risk Manag. 2009 Feb;5(1):21-34.
24	2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
25	Local anesthetics have different mechanisms and sites of action at recombinant 5-HT3 receptors. Reg Anesth Pain Med. 2007 Nov-Dec;32(6):462-70.
26	Cilansetron: a new serotonergic agent for the irritable bowel syndrome with diarrhoea.Expert Opin Investig Drugs.2005 Feb;14(2):185-93.
27	Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships. J Med Chem. 1992 Jan 24;35(2):310-9.
28	mu-Opioid/5-HT4 dual pharmacologically active agents-efforts towards an effective opioid analgesic with less GI and respiratory side effects (Part I). Bioorg Med Chem Lett. 2009 Oct 1;19(19):5679-83.
29	Effect of serotonin (5-HT)3-receptor antagonists YM060, YM114 (KAE-393), ondansetron and granisetron on 5-HT4 receptors and gastric emptying in rodents. Jpn J Pharmacol. 1995 Nov;69(3):205-14.
30	Pharmacological management of epilepsy: recent advances and future prospects. Drugs. 2008;68(14):1925-39.
31	Pharmacological Profile of the Novel Antiepileptic Drug Candidate Padsevonil: Characterization in Rodent Seizure and Epilepsy Models. J Pharmacol Exp Ther. 2020 Jan;372(1):11-20.
32	Emerging drugs for epilepsy. Expert Opin Emerg Drugs. 2007 Sep;12(3):407-22.
33	Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
34	Cerner Multum, Inc. "Australian Product Information.".
35	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
36	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
37	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.