Compounds > 2-ethyl-2-methyl-4-butyrolactone
Page last updated: 2024-12-08

2-ethyl-2-methyl-4-butyrolactone

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

Description

2-ethyl-2-methyl-4-butyrolactone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID169232
CHEMBL ID285171
CHEBI ID35057
SCHEMBL ID132980
MeSH IDM0108850

Synonyms (16)

Synonym
2-ethyl-2-methyl-4-butyrolactone
31004-76-9
alpha-emgbl
chebi:35057 ,
CHEMBL285171
3-ethyl-3-methyldihydrofuran-2(3h)-one
3-ethyl-3-methyloxolan-2-one
2(3h)-furanone, 3-ethyldihydro-3-methyl-
alpha-ethyl-alpha-methyl-gamma-butyrolactone
AC1Q6HQE ,
SCHEMBL132980
3-ethyl-3-methyl-tetrahydrofuran-2-one
surecn132980
Q27116393
DTXSID00953128
PD181384
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
gamma-lactoneA lactone having a five-membered lactone ring.
[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]

Protein Targets (16)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.505710.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.497310.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.498810.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.504610.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.506510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.505710.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
GABA theta subunitRattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)IC50 (µMol)1,151.14000.00010.507510.0000AID159411; AID71294
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID114400Anticonvulsant activity in mice by inhibition of pentylenetetrazole induced seizures.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID118666Compound was evaluated for anticonvulsant activity against PTZ-induced clonic seizures at the 375 mg/kg dose; 0/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID124200Concentration of brain at 40 min was determined after the compound was administered intraperitoneally at a dose 259 mg/kg in mice1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID118664Compound was evaluated for anticonvulsant activity against PTZ-induced clonic seizures at the 250 mg/kg dose; 4/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID124198Concentration of brain at 20 min was determined after the compound was administered intraperitoneally at a dose 259 mg/kg in mice1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID118658Compound was evaluated for anticonvulsant activity against PTZ-induced clonic seizures at 62.5 mg/kg dose; 4/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID124197Concentration of brain at 10 min was determined after the compound was administered intraperitoneally at a dose 259 mg/kg in mice1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID118679Compound was evaluated for anticonvulsant activity against PTZ-induced tonic seizures at the 500 mg/kg dose; 0/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID118682Compound was evaluated for anticonvulsant activity against PTZ-induced tonic seizures at the 62.5 mg/kg dose; 4/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID118661Compound was evaluated for anticonvulsant activity against PTZ-induced clonic seizures at the 125 mg/kg dose; 4/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID124201Concentration of brain at 5 min was determined after the compound was administered intraperitoneally at a dose 259 mg/kg in mice1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID121997Neurotoxic effects by rotarod test in mice.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID118676Compound was evaluated for anticonvulsant activity against PTZ-induced tonic seizures at the 250 mg/kg dose; 4/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID159411Displacement of 35[S]-TBPS from picrotoxinin (GABA-A) receptor of rat neuronal membranes1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
Alpha-spirocyclopentyl- and alpha-spirocyclopropyl-gamma-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant alpha,alpha-disubstituted gamma-butyrolactones.
AID88597Percent response relative to current produced by 10 uM GABA in rat hippocampal cells1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
Alpha-spirocyclopentyl- and alpha-spirocyclopropyl-gamma-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant alpha,alpha-disubstituted gamma-butyrolactones.
AID71294Binding affinity to picrotoxin site of Gamma-aminobutyric acid receptor using [35S]TBPS as radioligand1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID114399Anticonvulsant activity in mice by maximal electroshock test.1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID124199Concentration of brain at 30 min was determined after the compound was administered intraperitoneally at a dose 259 mg/kg in mice1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
Synthesis and structure-activity studies of alkyl-substituted gamma-butyrolactones and gamma-thiobutyrolactones: ligands for the picrotoxin receptor.
AID118668Compound was evaluated for anticonvulsant activity against PTZ-induced clonic seizures at the 500 mg/kg dose; 0/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID212344Toxic dose at which 50% of the mice failed the rotarod neurotoxicity test1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
Alpha-spirocyclopentyl- and alpha-spirocyclopropyl-gamma-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant alpha,alpha-disubstituted gamma-butyrolactones.
AID159410Maximum Binding affinity for picrotoxinin (GABA-A) receptor of rat cerebral cortex1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
Alpha-spirocyclopentyl- and alpha-spirocyclopropyl-gamma-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant alpha,alpha-disubstituted gamma-butyrolactones.
AID118677Compound was evaluated for anticonvulsant activity against PTZ-induced tonic seizures at the 375 mg/kg dose; 0/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID159413Dissociation constant from displacement of 35[S]-TBPS binding from picrotoxinin (GABA-A) receptor of rat cerebral cortex1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
Alpha-spirocyclopentyl- and alpha-spirocyclopropyl-gamma-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant alpha,alpha-disubstituted gamma-butyrolactones.
AID118684Compound was evaluated for anticonvulsant activity against PTZ-induced tonic seizures at the 125 mg/kg dose; 4/41986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Alkyl-substituted thiolo-, thiono-, and dithio-gamma-butyrolactones: new classes of convulsant and anticonvulsant agents.
AID131531Effective dose at which 50% of the mice were protected from clonic seizures induced by pentylenetetrazole (85 mg/kg)1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
Alpha-spirocyclopentyl- and alpha-spirocyclopropyl-gamma-butyrolactones: conformationally constrained derivatives of anticonvulsant and convulsant alpha,alpha-disubstituted gamma-butyrolactones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (44.44)18.7374
1990's5 (55.56)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)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.		2.3820amino acid zwitterion;
gamma-amino acid;
monocarboxylic acid		human metabolite;
neurotransmitter;
Saccharomyces cerevisiae metabolite;
signalling molecule
chlorine
chloride : A halide anion formed when chlorine picks up an electron to form an an anion.		1.9810halide anion;
monoatomic chlorine		cofactor;
Escherichia coli metabolite;
human metabolite
ethosuximide
Ethosuximide: An anticonvulsant especially useful in the treatment of absence seizures unaccompanied by other types of seizures.. ethosuximide : A dicarboximide that is pyrrolidine-2,5-dione in which the hydrogens at position 3 are substituted by one methyl and one ethyl group. An antiepileptic, it is used in the treatment of absence seizures and may be used for myoclonic seizures, but is ineffective against tonic-clonic seizures.		2.3820dicarboximide;
pyrrolidinone		anticonvulsant;
geroprotector;
T-type calcium channel blocker
trimethadione
Trimethadione: An anticonvulsant effective in absence seizures, but generally reserved for refractory cases because of its toxicity. (From AMA Drug Evaluations Annual, 1994, p378). trimethadione : An oxazolidinone that is 1,3-oxazolidine-2,4-dione substituted by methyl groups at positions 3, 5 and 5. It is an antiepileptic agent.		1.9610oxazolidinoneanticonvulsant;
geroprotector
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		3.2260butan-4-olidemetabolite;
neurotoxin
tert-butylbicyclophosphorothionate
tert-butylbicyclophosphorothionate: binds to GABA & ion recognition sites; structure given in first source		1.9610organic thiophosphate
alpha-ethyl, alpha-methyl-thiobutyrolactone
[no description available]		2.8940tetrahydrothiophenes
beta-ethyl, beta-methyl-thiobutyrolactone
[no description available]		2.6730
alpha-isopropyl-alpha-methyl-gamma-butyrolactone
alpha-isopropyl-alpha-methyl-gamma-butyrolactone: structure given in first source; picrotoxin receptor antagonist		2.8940
sodium oxybate
Sodium Oxybate: The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.		1.9610
picrotoxin
Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Absence Seizure
[description not available]		02.3820
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		02.3820
Absence Seizure Disorder
[description not available]		01.9610
Epilepsy, Absence
A seizure disorder usually occurring in childhood characterized by rhythmic electrical brain discharges of generalized onset. Clinical features include a sudden cessation of ongoing activity usually without loss of postural tone. Rhythmic blinking of the eyelids or lip smacking frequently accompanies the SEIZURES. The usual duration is 5-10 seconds, and multiple episodes may occur daily. Juvenile absence epilepsy is characterized by the juvenile onset of absence seizures and an increased incidence of myoclonus and tonic-clonic seizures. (Menkes, Textbook of Child Neurology, 5th ed, p736)		01.9610