Page last updated: 2024-11-05

n-ethyl-2-pyrrolidone

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

Description

N-ethyl-2-pyrrolidone (NEP) is a colorless, transparent liquid with a characteristic odor. It is a highly polar, aprotic solvent with a high boiling point and excellent solvency properties. It is commonly used as a solvent for various organic and inorganic compounds, including polymers, resins, and pharmaceuticals. NEP is produced industrially by the reaction of 2-pyrrolidone with ethyl chloride or ethyl bromide in the presence of a base. It is used in various applications, including as a solvent for paints, coatings, and adhesives; as a reaction medium in chemical synthesis; as an extractant in the pharmaceutical and food industries; and as a component in lithium-ion batteries. The high polarity and solvency properties of NEP make it a versatile solvent in various industrial applications. Its low toxicity and biodegradability make it an environmentally friendly alternative to other solvents. NEP is also used in research as a model compound to study the properties and behavior of other polar aprotic solvents. The synthesis of NEP involves the reaction of 2-pyrrolidone with ethyl halide in the presence of a base. The reaction is typically carried out at elevated temperatures and pressures. NEP is a highly effective solvent for various organic and inorganic compounds. It has a high boiling point and is miscible with water and many organic solvents. It is also a good extractant for various substances, including pharmaceuticals and food ingredients. The importance of NEP lies in its versatility as a solvent and extractant. It is used in a wide range of industrial applications, including the production of paints, coatings, adhesives, pharmaceuticals, and food products. Its low toxicity and biodegradability make it an environmentally friendly alternative to other solvents. NEP is also used in research to study the properties and behavior of polar aprotic solvents.'

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

Cross-References

ID SourceID
PubMed CID17595
CHEMBL ID12221
CHEBI ID173690
SCHEMBL ID18635
MeSH IDM0514783

Synonyms (56)

Synonym
einecs 220-250-6
brn 0107971
n-ethylpyrrolidinone
CHEBI:173690
1-ethyl-2-pyrrolidone
1-ethyl-2-pyrrolidinone
n-ethylpyrrolidone
1-ethylpyrrolidin-2-one
inchi=1/c6h11no/c1-2-7-5-3-4-6(7)8/h2-5h2,1h
2-pyrrolidinone, 1-ethyl-
NCGC00160611-02
NCGC00160611-01
1-ethyl-2-pyrrolidone, 98%
n-ethyl-2-pyrrolidone
CHEMBL12221
E0358
n-ethyl-2-azapentanone
2687-91-4
5-21-06-00328 (beilstein handbook reference)
ec 220-250-6
ethyl pyrrolidone
h0229sx1cw ,
unii-h0229sx1cw
dtxsid3044413 ,
tox21_302140
dtxcid1024413
NCGC00255747-01
cas-2687-91-4
tox21_111935
A818647
1-ethyl-2-pyrrolidinone, 98%
smr001561581
MLS004734624
n-ethyl-|a-pyrrolidone
FT-0607741
AKOS015915384
n-ethylbutyrolactam
ethylazacyclopentan-2-one
n-ethyl-.alpha.-pyrrolidinone
n-ethyl-.gamma.-butyrolactam
ethyl pyrrolidone [inci]
n-ethyl-2-pyrrolidinone
SCHEMBL18635
NCGC00160611-03
tox21_111935_1
agsol ex 2
W-107143
pyrrolidinone, 1-ethyl-
mfcd00003199
CS-W013650
AS-12228
2-pyrrolidinone, 1-ethyl-;1-ethylpyrrolidin-2-one;2-pyrrolidinone, 1-ethyl- 1-ethylpyrrolidin-2-one
Q27279388
1-ethyl-pyrrolidin-2-one
EN300-7375258
Z1255438420

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In conclusion, NEP administered by gavage is embryotoxic and teratogenic at maternal toxic doses."( Developmental toxic effects of N-ethyl-2-pyrrolidone administered orally to rats.
Gallissot, F; Sabaté, JP; Saillenfait, AM,
)
0.42

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-alkylpyrrolidine
[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 (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency36.16480.000714.592883.7951AID1259369; AID1259392
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency38.33560.001723.839378.1014AID743083
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (38)

Assay IDTitleYearJournalArticle
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID70691Concentration producing the maximum percentage of benzidine-positive cells after 6-days of continuous exposure in murine leukemia cells.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID70689Cell growth was measured on day 3, after murine erythroleukemia cells were exposed at a cell concentration of 1*10e5 cells/mL.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID70690Cell growth was measured on day 6 after murine erythroleukemia cells were exposed at a cell concentration of 1*10e5 cells/mL.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
AID70688Percentage of benzidine-positive murine erythroleukemia cells on day 6.1981Journal of medicinal chemistry, Sep, Volume: 24, Issue:9
Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.76)18.7374
1990's0 (0.00)18.2507
2000's1 (4.76)29.6817
2010's12 (57.14)24.3611
2020's7 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.45

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index44.45 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index6.05 (4.65)
Search Engine Demand Index52.86 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.45)

All Compounds (24.57)

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%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]