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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (2) Show 4 proteins XML

enzymes (2)transporters (2) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:28 UTC

HMDB ID

HMDB0015333

Secondary Accession Numbers

HMDB15333

Metabolite Identification

Common Name

Levetiracetam

Description

Levetiracetam is an anticonvulsant medication used to treat epilepsy. Levetiracetam may selectively prevent hypersynchronization of epileptiform burst firing and propagation of seizure activity. Levetiracetam binds to the synaptic vesicle protein SV2A, which is thought to be involved in the regulation of vesicle exocytosis. Although the molecular significance of levetiracetam binding to synaptic vesicle protein SV2A is not understood, levetiracetam and related analogs showed a rank order of affinity for SV2A which correlated with the potency of their antiseizure activity in audiogenic seizure-prone mice.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1202                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       8.458   1.408   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -0.561   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748   0.979   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.414  -2.871   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.501   1.884   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.978   3.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.518   3.349   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.993   1.884   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -1.331   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.331   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -2.871   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   11                                                            
CONECT    3    5    6    9                                                  
CONECT    4   11                                                            
CONECT    5    3    7                                                       
CONECT    6    3   10   11                                                  
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    3    8                                                  
CONECT   10    6   12                                                       
CONECT   11    2    4    6                                                  
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Keppra	Kegg
e Keppra	Kegg
Levitiracetam	HMDB
Etiracetam, R-isomer	HMDB
alpha-Ethyl-2-oxo-1-pyrrolidineacetamide	HMDB
Etiracetam, S-isomer	HMDB
Ucb L060	HMDB
Ucb-L060	HMDB
UCB brand OF levetiracetam	HMDB
Etiracetam	HMDB
Ucb L059	HMDB
Ucb-L059	HMDB
Etiracetam, R isomer	HMDB
UcbL060	HMDB
alpha Ethyl 2 oxo 1 pyrrolidineacetamide	HMDB
Etiracetam, S isomer	HMDB
R-Isomer etiracetam	HMDB
S-Isomer etiracetam	HMDB

Chemical Formula

C₈H₁₄N₂O₂

Average Molecular Weight

170.209

Monoisotopic Molecular Weight

170.105527702

IUPAC Name

(2R)-2-(2-oxopyrrolidin-1-yl)butanamide

Traditional Name

levitiracetam

CAS Registry Number

102767-28-2

SMILES

CC[C@@H](N1CCCC1=O)C(N)=O

InChI Identifier

InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m1/s1

InChI Key

HPHUVLMMVZITSG-ZCFIWIBFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Fatty amide
Pyrrolidone
2-pyrrolidone
Fatty acyl
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Primary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0015333)
Membrane (HMDB: HMDB0015333)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015333)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	298 g/L	Not Available
LogP	-0.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	298 g/L	ALOGPS
logP	-0.64	ALOGPS
logP	-0.59	ChemAxon
logS	0.24	ALOGPS
pKa (Strongest Acidic)	16.09	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.08 m³·mol⁻¹	ChemAxon
Polarizability	17.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.827	31661259
DarkChem	[M-H]-	135.825	31661259
DeepCCS	[M+H]+	145.284	30932474
DeepCCS	[M-H]-	142.819	30932474
DeepCCS	[M-2H]-	178.319	30932474
DeepCCS	[M+Na]+	153.823	30932474
AllCCS	[M+H]+	137.8	32859911
AllCCS	[M+H-H2O]+	133.7	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	135.3	32859911
AllCCS	[M+Na-2H]-	136.6	32859911
AllCCS	[M+HCOO]-	138.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levetiracetam	CC[C@@H](N1CCCC1=O)C(N)=O	2188.7	Standard polar	33892256
Levetiracetam	CC[C@@H](N1CCCC1=O)C(N)=O	1700.7	Standard non polar	33892256
Levetiracetam	CC[C@@H](N1CCCC1=O)C(N)=O	1605.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levetiracetam,1TMS,isomer #1	CC[C@H](C(=O)N[Si](C)(C)C)N1CCCC1=O	1644.5	Semi standard non polar	33892256
Levetiracetam,1TMS,isomer #1	CC[C@H](C(=O)N[Si](C)(C)C)N1CCCC1=O	1678.1	Standard non polar	33892256
Levetiracetam,1TMS,isomer #1	CC[C@H](C(=O)N[Si](C)(C)C)N1CCCC1=O	2426.0	Standard polar	33892256
Levetiracetam,2TMS,isomer #1	CC[C@H](C(=O)N([Si](C)(C)C)[Si](C)(C)C)N1CCCC1=O	1731.6	Semi standard non polar	33892256
Levetiracetam,2TMS,isomer #1	CC[C@H](C(=O)N([Si](C)(C)C)[Si](C)(C)C)N1CCCC1=O	1812.3	Standard non polar	33892256
Levetiracetam,2TMS,isomer #1	CC[C@H](C(=O)N([Si](C)(C)C)[Si](C)(C)C)N1CCCC1=O	2239.4	Standard polar	33892256
Levetiracetam,1TBDMS,isomer #1	CC[C@H](C(=O)N[Si](C)(C)C(C)(C)C)N1CCCC1=O	1854.6	Semi standard non polar	33892256
Levetiracetam,1TBDMS,isomer #1	CC[C@H](C(=O)N[Si](C)(C)C(C)(C)C)N1CCCC1=O	1930.3	Standard non polar	33892256
Levetiracetam,1TBDMS,isomer #1	CC[C@H](C(=O)N[Si](C)(C)C(C)(C)C)N1CCCC1=O	2473.3	Standard polar	33892256
Levetiracetam,2TBDMS,isomer #1	CC[C@H](C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1CCCC1=O	2156.5	Semi standard non polar	33892256
Levetiracetam,2TBDMS,isomer #1	CC[C@H](C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1CCCC1=O	2267.4	Standard non polar	33892256
Levetiracetam,2TBDMS,isomer #1	CC[C@H](C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N1CCCC1=O	2334.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Levetiracetam GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9300000000-c7be6e1922b5359940b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levetiracetam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-QTOF , positive-QTOF	splash10-0fb9-0900000000-5d10dc46b3d8459f5136	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-eed0f7c0281298a901e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-904c39fde7b4a564f4f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-043119aa2fce9bf106a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-baaa7247861e2a0c32dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-0udi-0900000000-e4d3bcf5f9604374d974	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-0fb9-0900000000-c54dadca90f9667c5e5e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-43e7dddd01af30559674	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-bcf3b82b0418f01f7c88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-af204f882b93928b3786	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-2900000000-0d85e8e75dfd969db153	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-6900000000-8038b6a6542f48ef1db6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-0fb9-0900000000-b79c1cd502a80d2cc5a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-b2783da92be1f5956300	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-656f696fd6f22abd3b8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-05fe19e5eb84577847c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-1900000000-b7a6c4f29c539bcb255c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-004i-4900000000-159b3785ab54ec35d7ae	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Levetiracetam LC-ESI-ITFT , positive-QTOF	splash10-0udi-0900000000-4576e782d08537cb54d3	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levetiracetam 10V, Positive-QTOF	splash10-00di-0900000000-ec0076a60bef1bfe06dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levetiracetam 20V, Positive-QTOF	splash10-0fb9-2900000000-22b720450ebfea704554	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levetiracetam 40V, Positive-QTOF	splash10-0006-9100000000-17a515534beb406070e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levetiracetam 10V, Negative-QTOF	splash10-014i-0900000000-7470975ba67c5de6162e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levetiracetam 20V, Negative-QTOF	splash10-00pl-5900000000-50443438445390c4345a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levetiracetam 40V, Negative-QTOF	splash10-0006-9000000000-517ee6018ae48754d1b7	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01202	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01202	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

390096

KEGG Compound ID

C07841

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levetiracetam

METLIN ID

Not Available

PubChem Compound

441341

PDB ID

Not Available

ChEBI ID

352567

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Voltage-dependent N-type calcium channel subunit alpha-1B

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1B gives rise to N-type calcium currents. N-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by omega-conotoxin-GVIA (omega-CTx-GVIA) and by omega-agatoxin- IIIA (omega-Aga-IIIA). They are however insensitive to dihydropyridines (DHP), and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing alpha-1B subunit may play a role in directed migration of immature neurons
Gene Name:: CACNA1B
Uniprot ID:: Q00975
Molecular weight:: 262493.8

References

De Smedt T, Raedt R, Vonck K, Boon P: Levetiracetam: the profile of a novel anticonvulsant drug-part I: preclinical data. CNS Drug Rev. 2007 Spring;13(1):43-56. [PubMed:17461889 ]
Lukyanetz EA, Shkryl VM, Kostyuk PG: Selective blockade of N-type calcium channels by levetiracetam. Epilepsia. 2002 Jan;43(1):9-18. [PubMed:11879381 ]

Enzyme Details

2. Synaptic vesicle glycoprotein 2A

General function:: Involved in transmembrane transport
Specific function:: Plays a role in the control of regulated secretion in neural and endocrine cells, enhancing selectively low-frequency neurotransmission. Positively regulates vesicle fusion by maintaining the readily releasable pool of secretory vesicles
Gene Name:: SV2A
Uniprot ID:: Q7L0J3
Molecular weight:: 82694.7

References

Lynch BA, Lambeng N, Nocka K, Kensel-Hammes P, Bajjalieh SM, Matagne A, Fuks B: The synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam. Proc Natl Acad Sci U S A. 2004 Jun 29;101(26):9861-6. Epub 2004 Jun 21. [PubMed:15210974 ]
Stahl SM: Psychopharmacology of anticonvulsants: levetiracetam as a synaptic vesicle protein modulator. J Clin Psychiatry. 2004 Sep;65(9):1162-3. [PubMed:15367040 ]
Lambeng N, Grossmann M, Chatelain P, Fuks B: Solubilization and immunopurification of rat brain synaptic vesicle protein 2A with maintained binding properties. Neurosci Lett. 2006 May 1;398(1-2):107-12. Epub 2006 Jan 24. [PubMed:16434140 ]
Gillard M, Chatelain P, Fuks B: Binding characteristics of levetiracetam to synaptic vesicle protein 2A (SV2A) in human brain and in CHO cells expressing the human recombinant protein. Eur J Pharmacol. 2006 Apr 24;536(1-2):102-8. Epub 2006 Mar 10. [PubMed:16556440 ]
Newton HB, Dalton J, Goldlust S, Pearl D: Retrospective analysis of the efficacy and tolerability of levetiracetam in patients with metastatic brain tumors. J Neurooncol. 2007 Sep;84(3):293-6. Epub 2007 Apr 13. [PubMed:17431542 ]
Johannessen Landmark C: Antiepileptic drugs in non-epilepsy disorders: relations between mechanisms of action and clinical efficacy. CNS Drugs. 2008;22(1):27-47. [PubMed:18072813 ]
De Smedt T, Raedt R, Vonck K, Boon P: Levetiracetam: the profile of a novel anticonvulsant drug-part I: preclinical data. CNS Drug Rev. 2007 Spring;13(1):43-56. [PubMed:17461889 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: 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. Epub 2006 Oct 10. [PubMed:17045309 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: 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. Epub 2006 Oct 10. [PubMed:17045309 ]
Luna-Tortos C, Fedrowitz M, Loscher W: Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75. doi: 10.1016/j.neuropharm.2008.08.032. Epub 2008 Sep 11. [PubMed:18824002 ]

Showing metabocard for Levetiracetam (HMDB0015333)

MOL for HMDB0015333 (Levetiracetam)

3D MOL for HMDB0015333 (Levetiracetam)

3D SDF for HMDB0015333 (Levetiracetam)

3D-SDF for HMDB0015333 (Levetiracetam)

PDB for HMDB0015333 (Levetiracetam)

3D PDB for HMDB0015333 (Levetiracetam)

SMILES for HMDB0015333 (Levetiracetam)

INCHI for HMDB0015333 (Levetiracetam)

Structure for HMDB0015333 (Levetiracetam)

3D Structure for HMDB0015333 (Levetiracetam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

Transporters

References

References