Compounds > valproic acid glucuronide
Page last updated: 2024-11-06

valproic acid glucuronide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

valproic acid glucuronide: major metabolite of valproic acid [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID88111
CHEMBL ID3526941
CHEBI ID168243
SCHEMBL ID17061412
MeSH IDM0122523

Synonyms (31)

Synonym
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(2-propylpentanoyloxy)oxane-2-carboxylic acid
CHEBI:168243
vpag
60113-83-9
valproic acid glucuronide
beta-d-glucopyranuronic acid, 1-(2-propylpentanoate)
unii-sb05j7266c
sb05j7266c ,
valproic acid beta-d-glucuronide
valproate glucuronide
vpa-g
dipropylacetate glucuronide
CHEMBL3526941
valproic acid b-d-glucuronide
SCHEMBL17061412
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid
1-(2-propylpentanoate) beta-delta-glucopyranuronate
1-(2-propylpentanoic acid
1-(2-propylpentanoate
1-o-valproyl-beta-delta-glucopyranuronic acid
3,4,5-trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid
1-(2-propylpentanoate) beta-d-glucopyranuronic acid
1-o-valproyl-b-d-glucopyranuronic acid
1-(2-propylpentanoate) beta-d-glucopyranuronate
3,4,5-trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylate
1-(2-propylpentanoate) beta-delta-glucopyranuronic acid
1-o-valproyl-.beta.-d-glucopyranuronic acid
.beta.-d-glucopyranuronic acid, 1-(2-propylpentanoate)
(2s,3s,4s,5r,6s)-3,4,5-trihydroxy-6-((2-propylpentanoyl)oxy)tetrahydro-2h-pyran-2-carboxylic acid
valproic acid ?-d-glucuronide
DTXSID901311881

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Our results indicate that all three risk factors clearly increase the metabolic conversion of VPA to 4-en, the most toxic VPA metabolite, and that polytherapy and high VPA serum level result in the inhibited beta-oxidative metabolism of VPA to 2-en."( Associations between risk factors for valproate hepatotoxicity and altered valproate metabolism.
Fukushima, Y; Hirano, T; Ishida, M; Kaneko, S; Koide, N; Kondo, T; Muranaka, H; Otani, K; Yokoyama, M, )		0.13
"The aim of this study was to investigate the relationship between hepatotoxicity, levels of glucuronide conjugates of valproic acid (VPA), and the toxic metabolites of VPA (4-ene VPA and 2,4-diene VPA)."( The relationship between glucuronide conjugate levels and hepatotoxicity after oral administration of valproic acid.
Baek, DJ; Chung, BC; Jung, BH; Kim, BJ; Lee, MS; Lee, YJ; Shin, KJ, 2009)		0.35

Pharmacokinetics

ExcerptReferenceRelevance
" A pharmacokinetic model was developed to describe the influence of phenobarbital on the hepatobiliary disposition of VPA and valproate glucuronide (V-G) in the IPL; all processes governing VPA and V-G disposition appeared to be linear."( Hepatobiliary disposition of valproic acid and valproate glucuronide: use of a pharmacokinetic model to examine the rate-limiting steps and potential sites of drug interactions.
Booth, CL; Brouwer, KL; Pollack, GM, 1996)		0.29
" Pharmacokinetic parameters were calculated using noncompartmental methods."( Effects of amoxicillin/clavulanic acid on the pharmacokinetics of valproic acid.
Huh, W; Jung, JA; Kim, JR; Ko, JW; Lee, SY; Yoo, HM, 2015)		0.42

Dosage Studied

ExcerptRelevanceReference
" Urine was collected for one dosage interval (12 h) at steady state for each dose and assayed for 15 VPA metabolites by gas chromatography/mass spectrometry (GCMS)."( Effect of valproate dose on formation of hepatotoxic metabolites.
Acheampong, AA; Anderson, GD; Levy, RH; Wilensky, AJ, )		0.13
" Hepatic and renal APEH activity was negligible even at 24 h after dosing of MEPM to a dog."( In vivo inhibition of acylpeptide hydrolase by carbapenem antibiotics causes the decrease of plasma concentration of valproic acid in dogs.
Fusegawa, K; Goda, R; Ikenaga, H; Izumi, T; Kobayashi, N; Kuga, H; Nakai, D; Suzuki, E, 2016)		0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glucosiduronic acidAny substance produced by linking glucuronic acid to another substance via a glycosidic bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Valproic Acid Metabolism Pathway1132
Valproic acid pathway022

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1222890Activity of human CES1 assessed as compound hydrolysis at 100 uM measured up to 60 mins by LC/TOF-MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222889Half life of the compound2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222884Inhibition of human CES1 assessed as hydrolysis of 4NPA to 4NP at 1 mM by spectrophotometric analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222897Activity of human CES2 assessed as compound hydrolysis at 100 uM measured up to 60 mins by LC/TOF-MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222885Half life in phosphate buffer at 10 uM at pH 7.4 by LC/TOF-MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
AID1222886Inhibition of human CES2 assessed as hydrolysis of 4NPA to 4NP at 1 mM by spectrophotometric analysis2013Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 41, Issue:4
Reversible inhibition of human carboxylesterases by acyl glucuronides.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (16.67)18.7374
1990's1 (4.17)18.2507
2000's9 (37.50)29.6817
2010's7 (29.17)24.3611
2020's3 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.34

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.34 (24.57)
Research Supply Index3.47 (2.92)
Research Growth Index4.81 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.34)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.33%)5.53%
Reviews1 (3.33%)6.00%
Case Studies2 (6.67%)4.05%
Observational0 (0.00%)0.25%
Other26 (86.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gamma-aminobutyric acid
gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.		2.5820amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		210elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
valproic acid
Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.		6.9211branched-chain fatty acid;
branched-chain saturated fatty acid		anticonvulsant;
antimanic drug;
EC 3.5.1.98 (histone deacetylase) inhibitor;
GABA agent;
neuroprotective agent;
psychotropic drug;
teratogenic agent
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		1.9910barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
uridine diphosphate glucuronic acid
Uridine Diphosphate Glucuronic Acid: A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.. UDP-alpha-D-glucuronic acid : A UDP-sugar having alpha-D-glucuronic acid as the sugar component.		3.1310UDP-D-glucuronic acidEscherichia coli metabolite;
human metabolite;
mouse metabolite
glucuronic acid
Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.		210D-glucuronic acidalgal metabolite
2-propyl-4-pentenoic acid
2-propyl-4-pentenoic acid: putative toxic metabolite of valproic acid		2.0510methyl-branched fatty acid
carbapenems
[no description available]		4.2750
ibuprofen acyl glucuronide
ibuprofen acyl glucuronide: structure given in first source; metabolite of ibuprofen; 13% of ibuprofen administered to humans is excreted in urine as its acyl glucuronide		2.0810terpene glycoside
naproxen glucuronide
naproxen glucuronide: structure in first source		2.0810
erythritol
[no description available]		1.9610butane-1,2,3,4-tetrolantioxidant;
human metabolite;
plant metabolite
meropenem
Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.		2.1310alpha,beta-unsaturated monocarboxylic acid;
carbapenemcarboxylic acid;
organic sulfide;
pyrrolidinecarboxamide		antibacterial agent;
antibacterial drug;
drug allergen
trans-2-en-valproate
2-propyl-2-pentenoic acid: valproate metabolite; RN given refers to parent cpd		210methyl-branched fatty acid
amoxicillin-potassium clavulanate combination
Amoxicillin-Potassium Clavulanate Combination: A fixed-ratio combination of amoxicillin trihydrate and potassium clavulanate.		3.511
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Post-Traumatic Stress Disorder
[description not available]		02.610
Stress Disorders, Post-Traumatic
A class of traumatic stress disorders with symptoms that last more than one month.		02.610
Fatty Liver, Nonalcoholic
[description not available]		02.0810
Liver Steatosis
[description not available]		02.0810
Fatty Liver
Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.		02.0810
Non-alcoholic Fatty Liver Disease
Fatty liver finding without excessive ALCOHOL CONSUMPTION.		02.0810
Acute Liver Injury, Drug-Induced
[description not available]		02.0510
Liver Dysfunction
[description not available]		02.0510
Liver Diseases
Pathological processes of the LIVER.		02.0510
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.0510
Drug Overdose
Accidental or deliberate use of a medication or street drug in excess of normal dosage.		0210
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		01.9710
Aura
[description not available]		01.9710
Epilepsy
A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)		01.9710