Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2023-02-21 17:18:27 UTC

HMDB ID

HMDB0015212

Secondary Accession Numbers

HMDB15212

Metabolite Identification

Common Name

Vigabatrin

Description

Vigabatrin is only found in individuals that have used or taken this drug. It is an analogue of gamma-aminobutyric acid. It is an irreversible inhibitor of 4-aminobutyrate transaminase, the enzyme responsible for the catabolism of gamma-aminobutyric acid. (From Martindale The Extra Pharmacopoeia, 31st ed)It is believed that vigabatrin increases brain concentrations of gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter in the CNS, by irreversibly inhibiting enzymes that catabolize GABA (gamma-aminobutyric acid transaminase GABA-T) or block the reuptake of GABA into glia and nerve endings. Vigabatrin may also work by suppressing repetitive neuronal firing through inhibition of voltage-sensitive sodium channels.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Amino-5-hexenoic acid	ChEBI
gamma-Vinyl gaba	ChEBI
gamma-Vinyl-gamma-aminobutyric acid	ChEBI
GVG	ChEBI
Vigabatrina	ChEBI
Vigabatrine	ChEBI
Vigabatrinum	ChEBI
Sabril	Kegg
4-Amino-5-hexenoate	Generator
g-Vinyl gaba	Generator
Γ-vinyl gaba	Generator
g-Vinyl-g-aminobutyrate	Generator
g-Vinyl-g-aminobutyric acid	Generator
gamma-Vinyl-gamma-aminobutyrate	Generator
Γ-vinyl-γ-aminobutyrate	Generator
Γ-vinyl-γ-aminobutyric acid	Generator
Acid, gamma-vinyl-gamma-aminobutyric	HMDB
Yamanouchi brand OF vigabatrin	HMDB
gamma Vinyl gaba	HMDB
gamma-Vinyl-gaba	HMDB
Sabrilex	HMDB
Vigabatrin aventis brand	HMDB
Hoechst brand OF vigabatrin	HMDB
Vigabatrin hoechst brand	HMDB
gamma Vinyl gamma aminobutyric acid	HMDB
Aventis brand OF vigabatrin	HMDB
Vigabatrin yamanouchi brand	HMDB

Chemical Formula

C₆H₁₁NO₂

Average Molecular Weight

129.157

Monoisotopic Molecular Weight

129.078978601

IUPAC Name

4-aminohex-5-enoic acid

Traditional Name

vigabatrin

CAS Registry Number

60643-86-9

SMILES

NC(CCC(O)=O)C=C

InChI Identifier

InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

InChI Key

PJDFLNIOAUIZSL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Medium-chain fatty acid
Amino fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-amino acid (CHEBI:63638 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	96.6 g/L	Not Available
LogP	0.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	96.6 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.1	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.29 m³·mol⁻¹	ChemAxon
Polarizability	13.64 Å³	ChemAxon
Number of Rings	0	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]+	128.818	31661259
DarkChem	[M-H]-	123.387	31661259
DeepCCS	[M+H]+	125.889	30932474
DeepCCS	[M-H]-	122.94	30932474
DeepCCS	[M-2H]-	159.838	30932474
DeepCCS	[M+Na]+	134.586	30932474
AllCCS	[M+H]+	132.2	32859911
AllCCS	[M+H-H2O]+	128.0	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.3	32859911
AllCCS	[M-H]-	128.3	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	134.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.5 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8316 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	282.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vigabatrin	NC(CCC(O)=O)C=C	2193.5	Standard polar	33892256
Vigabatrin	NC(CCC(O)=O)C=C	1078.6	Standard non polar	33892256
Vigabatrin	NC(CCC(O)=O)C=C	1186.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vigabatrin,1TMS,isomer #1	C=CC(N)CCC(=O)O[Si](C)(C)C	1226.2	Semi standard non polar	33892256
Vigabatrin,1TMS,isomer #2	C=CC(CCC(=O)O)N[Si](C)(C)C	1365.7	Semi standard non polar	33892256
Vigabatrin,2TMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C	1378.7	Semi standard non polar	33892256
Vigabatrin,2TMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C	1424.2	Standard non polar	33892256
Vigabatrin,2TMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C)N[Si](C)(C)C	1553.5	Standard polar	33892256
Vigabatrin,2TMS,isomer #2	C=CC(CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1557.9	Semi standard non polar	33892256
Vigabatrin,2TMS,isomer #2	C=CC(CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1461.2	Standard non polar	33892256
Vigabatrin,2TMS,isomer #2	C=CC(CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1801.4	Standard polar	33892256
Vigabatrin,3TMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1560.1	Semi standard non polar	33892256
Vigabatrin,3TMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1544.3	Standard non polar	33892256
Vigabatrin,3TMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1565.9	Standard polar	33892256
Vigabatrin,1TBDMS,isomer #1	C=CC(N)CCC(=O)O[Si](C)(C)C(C)(C)C	1466.0	Semi standard non polar	33892256
Vigabatrin,1TBDMS,isomer #2	C=CC(CCC(=O)O)N[Si](C)(C)C(C)(C)C	1612.0	Semi standard non polar	33892256
Vigabatrin,2TBDMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1833.8	Semi standard non polar	33892256
Vigabatrin,2TBDMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1832.2	Standard non polar	33892256
Vigabatrin,2TBDMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1827.6	Standard polar	33892256
Vigabatrin,2TBDMS,isomer #2	C=CC(CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1997.9	Semi standard non polar	33892256
Vigabatrin,2TBDMS,isomer #2	C=CC(CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1888.4	Standard non polar	33892256
Vigabatrin,2TBDMS,isomer #2	C=CC(CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1959.4	Standard polar	33892256
Vigabatrin,3TBDMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2231.3	Semi standard non polar	33892256
Vigabatrin,3TBDMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2163.4	Standard non polar	33892256
Vigabatrin,3TBDMS,isomer #1	C=CC(CCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1926.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-ed9483c326234125f4ad	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (1 TMS) - 70eV, Positive	splash10-004i-3900000000-6c317e49ab8cc532a558	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vigabatrin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-00di-9400000000-0215823a9ba364cc48cb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-00di-9400000000-c7d21d36dfb8e7079ee2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-00di-9200000000-e0c504f980ef5bbc0501	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-00di-9000000000-e1b2ea8d5a2da84a5a64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-00di-9000000000-52958176067fd9bae916	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-00di-9000000000-263da4b132ca66986967	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-01b9-9000000000-1f8826cc32ef269c1a7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-014i-9000000000-32306e2f90cd529accc7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin LC-ESI-QFT , positive-QTOF	splash10-0gb9-9000000000-aefa9f2682087c7b78ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 90V, Positive-QTOF	splash10-00di-9000000000-2e8122bd9fa086c48c81	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 60V, Positive-QTOF	splash10-00di-9000000000-c89fa23e4a66cb1fda0e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 75V, Positive-QTOF	splash10-00di-9000000000-ee55e365ddd88597a424	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 120V, Positive-QTOF	splash10-01b9-9000000000-59ee75afd49600cf9595	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 150V, Positive-QTOF	splash10-014i-9000000000-32306e2f90cd529accc7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 45V, Positive-QTOF	splash10-00di-9200000000-6c0ed7a9357b20c8ddec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 30V, Positive-QTOF	splash10-00di-9400000000-67f3710d9b1a8968c528	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vigabatrin 180V, Positive-QTOF	splash10-0gb9-9000000000-aefa9f2682087c7b78ed	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 10V, Positive-QTOF	splash10-01q9-3900000000-5bf6d0079fa19a719d28	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 20V, Positive-QTOF	splash10-01q9-9400000000-1d89cce66d591018b8b6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 40V, Positive-QTOF	splash10-0gb9-9000000000-25ce972a542597293a60	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 10V, Negative-QTOF	splash10-004i-2900000000-14e6a479b3001860431b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 20V, Negative-QTOF	splash10-004i-7900000000-fd7f3b3f074734314a87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 40V, Negative-QTOF	splash10-0a4l-9100000000-db0d4ab6ed018a7e6a3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 10V, Positive-QTOF	splash10-001i-9400000000-6179584a37d7e78d7234	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vigabatrin 20V, Positive-QTOF	splash10-014i-9000000000-ff84f320ba47dd80531b	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	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
Extracellular
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 DB01080	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01080	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

DB01080

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5463

KEGG Compound ID

C07500

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vigabatrin

METLIN ID

Not Available

PubChem Compound

5665

PDB ID

Not Available

ChEBI ID

63638

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

Lindberger M, Luhr O, Johannessen SI, Larsson S, Tomson T: Serum concentrations and effects of gabapentin and vigabatrin: observations from a dose titration study. Ther Drug Monit. 2003 Aug;25(4):457-62. [PubMed:12883229 ]
Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. [PubMed:2757904 ]
Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. [PubMed:9818917 ]
Zwanzger P, Baghai TC, Schuele C, Strohle A, Padberg F, Kathmann N, Schwarz M, Moller HJ, Rupprecht R: Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers. Neuropsychopharmacology. 2001 Nov;25(5):699-703. [PubMed:11682253 ]
Hawker DD, Silverman RB: Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase. Bioorg Med Chem. 2012 Oct 1;20(19):5763-73. doi: 10.1016/j.bmc.2012.08.009. Epub 2012 Aug 16. [PubMed:22944334 ]
Tulloch JK, Carr RR, Ensom MH: A systematic review of the pharmacokinetics of antiepileptic drugs in neonates with refractory seizures. J Pediatr Pharmacol Ther. 2012 Jan;17(1):31-44. doi: 10.5863/1551-6776-17.1.31. [PubMed:23118657 ]
Clayton LM, Stern WM, Newman WD, Sander JW, Acheson J, Sisodiya SM: Evolution of visual field loss over ten years in individuals taking vigabatrin. Epilepsy Res. 2013 Aug;105(3):262-71. doi: 10.1016/j.eplepsyres.2013.02.014. Epub 2013 Mar 28. [PubMed:23541931 ]

Enzymes

Enzyme Details

1. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Involved in 4-aminobutyrate transaminase activity
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular weight:: 56438.405

References

Weber OM, Verhagen A, Duc CO, Meier D, Leenders KL, Boesiger P: Effects of vigabatrin intake on brain GABA activity as monitored by spectrally edited magnetic resonance spectroscopy and positron emission tomography. Magn Reson Imaging. 1999 Apr;17(3):417-25. [PubMed:10195585 ]
Valdizan EM, Garcia AP, Armijo JA: Effects of increasing doses of vigabatrin on platelet gamma-aminobutyric acid-transaminase and brain gamma-aminobutyric acid in rats. Eur J Pharmacol. 1999 Mar 19;369(2):169-73. [PubMed:10206175 ]
Arndt CF, Derambure P, Defoort-Dhellemmes S, Hache JC: Outer retinal dysfunction in patients treated with vigabatrin. Neurology. 1999 Apr 12;52(6):1201-5. [PubMed:10214744 ]
Molina PE, Ahmed N, Ajmal M, Dewey S, Volkow N, Fowler J, Abumrad N: Co-administration of gamma-vinyl GABA and cocaine: preclinical assessment of safety. Life Sci. 1999;65(11):1175-82. [PubMed:10503933 ]
French JA: Vigabatrin. Epilepsia. 1999;40 Suppl 5:S11-6. [PubMed:10530689 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Gamma-aminobutyric acid type B receptor subunit 1

General function:: Involved in G-protein coupled receptor activity
Specific function:: Isoform 1E function may be to regulate the availability of functional GABA-B-R1A/GABA-B-R2 heterodimers by competing for GABA-B-R2 dimerization. This could explain the observation that certain small molecule ligands exhibit differential affinity for central versus peripheral sites
Gene Name:: GABBR1
Uniprot ID:: Q9UBS5
Molecular weight:: 108319.4

References

Tyacke RJ, Lingford-Hughes A, Reed LJ, Nutt DJ: GABAB receptors in addiction and its treatment. Adv Pharmacol. 2010;58:373-96. doi: 10.1016/S1054-3589(10)58014-1. [PubMed:20655489 ]

Showing metabocard for Vigabatrin (HMDB0015212)

MOL for HMDB0015212 (Vigabatrin)

3D MOL for HMDB0015212 (Vigabatrin)

3D SDF for HMDB0015212 (Vigabatrin)

3D-SDF for HMDB0015212 (Vigabatrin)

PDB for HMDB0015212 (Vigabatrin)

3D PDB for HMDB0015212 (Vigabatrin)

SMILES for HMDB0015212 (Vigabatrin)

INCHI for HMDB0015212 (Vigabatrin)

Structure for HMDB0015212 (Vigabatrin)

3D Structure for HMDB0015212 (Vigabatrin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References