Page last updated: 2024-12-05

2-phenylacetamide

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

Description

2-Phenylacetamide, also known as N-phenylacetamide, is a white crystalline solid with a sweet, aromatic odor. It is synthesized by the reaction of phenylamine (aniline) with acetic anhydride. 2-phenylacetamide exhibits analgesic and antipyretic properties. It is also a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its importance lies in its ability to act as a building block for more complex molecules. Research into 2-phenylacetamide focuses on its pharmacological properties, its potential as a precursor in organic synthesis, and its environmental fate.'

2-phenylacetamide: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-phenylacetamide : A monocarboxylic acid amide that is acetamide substituted by a phenyl group at position 2. [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]

Cross-References

ID SourceID
PubMed CID7680
CHEMBL ID347645
CHEBI ID16562
SCHEMBL ID25676
MeSH IDM0046744

Synonyms (63)

Synonym
2-phenyl-acetamide
phenylacetamide
phenylacetic acid amide
.alpha.-toluamide
nsc-1877
phenyl-.beta.-acetylamine
.alpha.-phenylacetamide
nsc1877
benzeneacetamide
acetamide, 2-phenyl-
.alpha.-toluimidic acid
phenyl-beta-acetylamine
CHEBI:16562 ,
alpha-toluamide
2-phenylacetamide(alpha-)
alpha-toluimidic acid
nsc 1877
ai3-19421
einecs 203-147-0
inchi=1/c8h9no/c9-8(10)6-7-4-2-1-3-5-7/h1-5h,6h2,(h2,9,10
103-81-1
2-phenylacetamide
alpha-phenylacetamide
C02505
46AFC744-1FF7-4816-B1C1-7C9995F369E8
acetamide, 2-phenyl
AKOS001215073
CHEMBL347645 ,
gnf-pf-1199 ,
P0120
A1882
5r219m9tjf ,
unii-5r219m9tjf
S4440
FT-0613318
.alpha.-phenylacetamide [mi]
benzenediacetamide
phenacetamide
SCHEMBL25676
(+/-)-benzeneacetamide
phenyl acetamide
(-)-benzeneacetamide
benzene-acetamide
(+)-benzeneacetamide
DTXSID1059282
Q-200316
AC-24581
F1084-0941
mfcd00059193
Z33546508
(alpha-)2-phenylacetamide
beta-phenyl-acetylamine
SY017094
CS-W018983
phenylacetimidic acid
Q27101974
BCP10408
bdbm50226209
n-o-nitrophenylsulfenyl-l-prolinedi(cyclohexyl)ammoniumsalt
phenylacetamide;alpha-toluamide
HY-W018197
EN300-15619
PD155928

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The orally bioavailable lead imidazolopiperazine confers complete causal prophylactic protection (15 milligrams/kilogram) in rodent models of malaria and shows potent in vivo blood-stage therapeutic activity."( Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery.
Barnes, SW; Bonamy, GM; Bopp, SE; Borboa, R; Bright, AT; Chatterjee, A; Che, J; Cohen, S; Dharia, NV; Diagana, TT; Fidock, DA; Froissard, P; Gagaring, K; Gettayacamin, M; Glynne, RJ; Gordon, P; Groessl, T; Kato, N; Kuhen, KL; Lee, MC; Mazier, D; McNamara, CW; Meister, S; Nagle, A; Nam, TG; Plouffe, DM; Richmond, W; Roland, J; Rottmann, M; Sattabongkot, J; Schultz, PG; Tuntland, T; Walker, JR; Winzeler, EA; Wu, T; Zhou, B; Zhou, Y, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role 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]

Drug Classes (1)

ClassDescription
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
[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 (1)

PathwayProteinsCompounds
Phenylalanine Metabolism1013

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alcohol dehydrogenase E chainEquus caballus (horse)Ki141.25400.14122.89278.7000AID33855
Alcohol dehydrogenase S chainEquus caballus (horse)Ki141.25400.14122.89278.7000AID33855
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID449705NOVARTIS: Cytotoxicity against human hepatocellular carcinoma cell line (Huh7)2008Proceedings of the National Academy of Sciences of the United States of America, Jul-01, Volume: 105, Issue:26
In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.
AID449706NOVARTIS: Inhibition Frequency Index (IFI) - the number of HTS assays where a compound showed > 50% inhibition/induction, expressed as a percentage of the number of assays in which the compound was tested.2008Proceedings of the National Academy of Sciences of the United States of America, Jul-01, Volume: 105, Issue:26
In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.
AID1437561Antifungal activity against Saccharomyces cerevisiae ATCC 204508 up to 60 uM after 16 to 48 hrs2017Journal of natural products, 01-27, Volume: 80, Issue:1
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.
AID1437557Antibacterial activity against Staphylococcus aureus ATCC 6538 up to 60 uM after 16 to 48 hrs2017Journal of natural products, 01-27, Volume: 80, Issue:1
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.
AID33855Inhibitory activity against horse liver alcohol dehydrogenase (ADH)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
A quantitative structure-activity relationship and molecular graphics analysis of hydrophobic effects in the interactions of inhibitors with alcohol dehydrogenase.
AID1437558Antibacterial activity against Micrococcus luteus NRRL B-287 up to 60 uM after 16 to 48 hrs2017Journal of natural products, 01-27, Volume: 80, Issue:1
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.
AID1332258Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced NO production after 24 hrs in presence of LPS by Griess reaction based assay2017Bioorganic & medicinal chemistry letters, 01-15, Volume: 27, Issue:2
Biotransformation of isofraxetin-6-O-β-d-glucopyranoside by Angelica sinensis (Oliv.) Diels callus.
AID1437567Cytotoxicity against human A549 cells assessed as decrease in cell viability up to 20 uM after 48 hrs by resazurin assay2017Journal of natural products, 01-27, Volume: 80, Issue:1
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.
AID449704NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation in erythrocyte-based infection assay2008Proceedings of the National Academy of Sciences of the United States of America, Jul-01, Volume: 105, Issue:26
In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.
AID23467Partition coefficient (logP)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
A quantitative structure-activity relationship and molecular graphics analysis of hydrophobic effects in the interactions of inhibitors with alcohol dehydrogenase.
AID1134000Inhibition of chymotrypsin (unknown origin)1977Journal of medicinal chemistry, Apr, Volume: 20, Issue:4
Quantitative structure-activity relationships of chymotrypsin. On the predictive value of correlation equations.
AID1437559Antibacterial activity against Escherichia coli NRRL B-3708 up to 60 uM after 16 to 48 hrs2017Journal of natural products, 01-27, Volume: 80, Issue:1
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.
AID449703NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferation in erythrocyte-based infection assay 2008Proceedings of the National Academy of Sciences of the United States of America, Jul-01, Volume: 105, Issue:26
In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.
AID1437560Antibacterial activity against Salmonella enterica ATCC 10708 up to 60 uM after 16 to 48 hrs2017Journal of natural products, 01-27, Volume: 80, Issue:1
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.
AID602156Novartis GNF Liver Stage Dataset: Malariabox Annotation2011Science (New York, N.Y.), Dec-09, Volume: 334, Issue:6061
Imaging of Plasmodium liver stages to drive next-generation antimalarial drug discovery.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (21.43)18.7374
1990's0 (0.00)18.2507
2000's3 (21.43)29.6817
2010's7 (50.00)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.02

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 Index44.02 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index61.30 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]