Page last updated: 2024-11-05

2-hydroxyacetanilide

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

Description

2-Hydroxyacetanilide, also known as paracetamol or acetaminophen, is a widely used analgesic and antipyretic drug. It is synthesized by reacting p-aminophenol with acetic anhydride. Paracetamol is effective in relieving mild to moderate pain and reducing fever. It is believed to work by inhibiting the production of prostaglandins, which are chemicals that cause pain and inflammation. Paracetamol is generally safe for most adults when taken as directed. However, overdose can lead to liver damage and even death. It is important to note that paracetamol can interact with other medications, so it is crucial to consult with a healthcare professional before taking it. Paracetamol is studied extensively due to its widespread use and potential for adverse effects. Researchers continue to investigate its mechanisms of action, pharmacokinetic properties, and potential for drug interactions. Understanding these aspects is essential for optimizing its therapeutic use and ensuring patient safety.'

2-acetamidophenol : A member of the class of phenols that is 2-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group. A positional isomer of paracetamol which possesses anti-inflammatory, anti-arthritic and anti-platelet aggregation properties. [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 CID11972
CHEMBL ID1456301
CHEBI ID143107
CHEBI ID88870
SCHEMBL ID79487
MeSH IDM0137846

Synonyms (96)

Synonym
MLS001066417
AC-13288
2-hydroxyanilid kyseliny octove
unii-4as8989rni
3-13-00-00778 (beilstein handbook reference)
4as8989rni ,
EN300-17802
o-(acetylamino)phenol
nsc-3989
614-80-2
2-acetaminophenol
o-acetamidophenol
n-acetyl-2-aminophenol
n-acetyl-o-aminophenol
2-(acetylamino)phenol
acetamide, n-(2-hydroxyphenyl)-
2-acetamidophenol
o-hydroxyacetanilide
acet-o-aminofenol
phenol, 2-acetamido-
nsc3989
acetanilide, 2'-hydroxy-
wln: qr bmv1
2'-hydroxyacetanilide
2-hydroxyacetanilide
brn 0607592
n-phenylglycolamide
brn 1210581
ai3-01928
nsc 99271
o-acetylaminofenol [czech]
2-hydroxyanilid kyseliny octove [czech]
einecs 210-396-9
glycolic acid anilide
nsc 3989
acet-o-aminofenol [czech]
n-(2-hydroxyphenyl)acetamide
o-acetaminophenol
inchi=1/c8h9no2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11h,1h3,(h,9,10
2-acetamidophenol, 97%
MLS000069599 ,
smr000059037
AKOS000319633
H0189
HMS1715J07
2-(n-acetylamino)phenol
o-acetylaminofenol
CHEBI:143107
A833255
n-(2-hydroxyphenyl)ethanamide
A21438
ar-hydroxyacetanilide
acetylaminophenol
57047-65-1
acetamide, n-(hydroxyphenyl)-
2-acetamido phenol
cas-614-80-2
tox21_302185
dtxcid402082
dtxsid8022082 ,
NCGC00257536-01
AG-996/01589028
HMS2235M05
4-12-00-00879 (beilstein handbook reference)
FT-0610936
AB00212
HMS3370F05
acetanilide, o-hydroxy-
hydroxyacetanilide, o-
paracetamol impurity a [ep impurity]
SCHEMBL79487
chebi:88870 ,
CHEMBL1456301
2-acetamido-phenol
2-(n-acetylamino)-phenol
W-105151
cid_11972
bdbm60355
n-(2-hydroxyphenyl)acetamide #
OPERA_ID_1257
mfcd00002181
F1962-0202
2-acetamidophenol, pharmaceutical secondary standard; certified reference material
n-(2-hydroxyphenyl)acetamide (2-acetamidophenol)
SY004721
paracetamol impurity a
Q27160885
AS-15275
9ks ,
STL182726
O11987
CS-W016316
HY-W015600
(r)-3-amino-3-(4-trifluoromethyl-phenyl)-propionicacid
Z57040482
orthocetamol

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The bioavailability of whole-grain rye-derived phytochemicals has not yet been comprehensively characterized, and different baking and manufacturing processes can modulate the phytochemical composition of breads and other rye products."( The postprandial plasma rye fingerprint includes benzoxazinoid-derived phenylacetamide sulfates.
Hanhineva, K; Katina, K; Keski-Rahkonen, P; Lappi, J; Mykkänen, H; Paananen, J; Pekkinen, J; Poutanen, K; Savolainen, O; Timonen, O, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (6)

RoleDescription
platelet aggregation inhibitorA drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound.
apoptosis inducerAny substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antirheumatic drugA drug used to treat rheumatoid arthritis.
[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 (2)

ClassDescription
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
acetamidesCompounds with the general formula RNHC(=O)CH3.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene 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 (9)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency44.66840.003245.467312,589.2998AID2517
Chain A, Beta-lactamaseEscherichia coli K-12Potency44.66840.044717.8581100.0000AID485294
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency55.79400.001022.650876.6163AID1224838; AID1224893
retinoid X nuclear receptor alphaHomo sapiens (human)Potency1.09620.000817.505159.3239AID1159527
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency6.85900.001530.607315,848.9004AID1224841; AID1224842
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency100.00000.707936.904389.1251AID504333
aryl hydrocarbon receptorHomo sapiens (human)Potency49.85070.000723.06741,258.9301AID743085; AID743122
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency25.82120.000627.21521,122.0200AID743202; AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
large T antigenBetapolyomavirus macacaeIC50 (µMol)6.20000.160024.9724100.0000AID1903
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (28)

Assay IDTitleYearJournalArticle
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.
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.
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.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.00)18.2507
2000's2 (10.00)29.6817
2010's15 (75.00)24.3611
2020's2 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.30

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 Index36.30 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index5.28 (4.65)
Search Engine Demand Index45.20 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.30)

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%
Other21 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]