Page last updated: 2024-11-06

4-(hydroxyphenyl)acetamide

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

Description

4-(hydroxyphenyl)acetamide, also known as paracetamol or acetaminophen, is a widely used over-the-counter analgesic and antipyretic medication. It is synthesized through a multi-step process involving the reaction of p-aminophenol with acetic anhydride. Paracetamol exerts its analgesic effects by inhibiting the production of prostaglandins, which are inflammatory mediators, in the central nervous system. It is also believed to have antipyretic effects by acting on the hypothalamus, the part of the brain that regulates body temperature. Paracetamol is highly effective in relieving mild to moderate pain, including headaches, muscle aches, and menstrual cramps. It is also commonly used to reduce fever. Due to its widespread use, its safety and efficacy have been extensively studied. While generally considered safe when used as directed, paracetamol can be toxic in high doses or with prolonged use. Its metabolism involves the formation of a reactive metabolite, N-acetyl-p-benzoquinone imine (NAPQI), which can cause liver damage if not detoxified by glutathione. Research continues to explore its mechanisms of action, potential interactions with other drugs, and its long-term effects on health.'

4-(hydroxyphenyl)acetamide: structure given in first source; an impurity found in the HPLC assay for atenolol; do not confuse with acetaminophen [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID86986
CHEMBL ID447310
CHEBI ID194828
SCHEMBL ID661973
MeSH IDM0199982

Synonyms (56)

Synonym
17194-82-0
nsc-187193
nsc187193
(p-hydroxyphenyl)acetamide
einecs 241-235-0
2-(p-hydroxyphenyl)acetamide
4-hydroxybenzeneacetamide
acetamide, 2-(p-hydroxyphenyl)-
brn 2085984
benzeneacetamide, 4-hydroxy-
4-(hydroxyphenyl)acetamide
p-(carbamoylmethyl)phenol
p-hydroxyphenylacetamide
4-hydroxyphenylacetamide
alpha-(p-hydroxyphenyl)acetamide
2-(4-hydroxyphenyl)acetamide
4-hydroxyphenylacetamide, 99%
OPREA1_206241
AC-6787
CHEMBL447310 ,
inchi=1/c8h9no2/c9-8(11)5-6-1-3-7(10)4-2-6/h1-4,10h,5h2,(h2,9,11)
ybpayprludcsey-uhfffaoysa-
H0853
CHEBI:194828
A811367
2-(4-hydroxyphenyl)acetamide;4-hydroxyphenylacetamide
bdbm50339587
2-(4-hydroxyphenyl)-ethylamide
nsc 187193
3-10-00-00434 (beilstein handbook reference)
0hy0n4itn4 ,
unii-0hy0n4itn4
STL163593
BBL012281
AKOS005716492
FT-0618731
FT-0618730
S12297
4-hydroxy phenylacetamide
p-hydroxyphenyl acetamide
SCHEMBL661973
PS-4609
DTXSID4066171
W-107869
(4-hydroxyphenyl)acetamide
hydroxyphenylacetamide, 4-
mfcd00017145
2-(4-hydroxyphenyl)acetamide; atenolol imp. a (ep); atenolol impurity a
p-hydroxy benzylamide
SY001683
4-hydroxyphenylacetamide,(s)
CCG-356424
Q27236794
p-hydroxyphenyl-acetamide
CS-W016314
EN300-219225
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
acetamidesCompounds with the general formula RNHC(=O)CH3.
[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
L-tyrosine degradation IV (to 4-methylphenol)211

Protein Targets (9)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Ki309.00000.00001.372610.0000AID588186
Carbonic anhydrase 2Homo sapiens (human)Ki11.20000.00000.72369.9200AID588187
Carbonic anhydrase Mycobacterium tuberculosis H37RvKi9.12000.01202.72389.1200AID588182
Beta-carbonic anhydrase 1Mycobacterium tuberculosis H37RvKi0.85000.00483.38419.8400AID588183
Carbonic anhydrase Cryptococcus neoformans var. grubiiKi0.84000.01000.73648.3470AID588185
Carbonic anhydraseCandida albicans SC5314Ki0.91000.01051.44448.3470AID588184
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Olfactory receptor class A-like protein 1Danio rerio (zebrafish)EC50 (µMol)199.90001.90001.90001.9000AID1802885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Kinact309.00000.01000.93878.6000AID456398
Carbonic anhydrase 2Homo sapiens (human)Kinact11.20000.00300.794610.0000AID456397
Carbonic anhydrase 5A, mitochondrialHomo sapiens (human)Kinact0.09200.02000.85809.4000AID456399
Carbonic anhydrase 5B, mitochondrialHomo sapiens (human)Kinact0.08100.00900.92319.0400AID456400
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
response to bacteriumCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
zinc ion bindingCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5A, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
mitochondrial matrixCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
mitochondrionCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
cytoplasmCarbonic anhydrase 5B, mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID456403Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5B2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588186Inhibition of human recombinant alpha-carbonic anhydrase 1 after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588188Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay relative to phenol2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588190Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID361417Antimicrobial activity against Escherichia coli by agar diffusion method2002Journal of natural products, Nov, Volume: 65, Issue:11
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
AID588195Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID361414Antimicrobial activity against Candida albicans by agar diffusion method2002Journal of natural products, Nov, Volume: 65, Issue:11
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
AID361413Antimicrobial activity against Mucor miehei by agar diffusion method2002Journal of natural products, Nov, Volume: 65, Issue:11
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
AID456399Inhibition of human recombinant carbonic anhydrase 5A by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID456397Inhibition of human recombinant carbonic anhydrase 2 by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID456401Selectivity ratio of Kinact for human recombinant carbonic anhydrase 1 to Kinact for human recombinant carbonic anhydrase 5A2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588197Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588191Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID361415Antimicrobial activity against Staphylococcus aureus by agar diffusion method2002Journal of natural products, Nov, Volume: 65, Issue:11
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
AID588194Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588183Inhibition of Mycobacterium tuberculosis recombinant Rv1284 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588196Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 2 to Ki for Candida albicans recombinant Nce103 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456400Inhibition of human recombinant carbonic anhydrase 5B by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588187Inhibition of human recombinant alpha-carbonic anhydrase 2 after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID361418Antimicrobial activity against Streptomyces viridochromogenes by agar diffusion method2002Journal of natural products, Nov, Volume: 65, Issue:11
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
AID588182Inhibition of Mycobacterium tuberculosis recombinant Rv3273 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456402Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5A2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID588184Inhibition of Candida albicans recombinant Nce103 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588192Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Candida albicans recombinant Nce103 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID588193Selectivity ratio of Ki for human recombinant alpha-carbonic anhydrase 1 to Ki for Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456398Inhibition of human recombinant carbonic anhydrase 1 by stopped flow CO2 hydration method2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID361416Antimicrobial activity against Bacillus subtilis by agar diffusion method2002Journal of natural products, Nov, Volume: 65, Issue:11
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.
AID588185Inhibition of Cryptococcus neoformans recombinant Can2 beta-carbonic anhydrase after 15 mins by stopped flow CO2 hydration assay2011Journal of medicinal chemistry, Mar-24, Volume: 54, Issue:6
Natural product-based phenols as novel probes for mycobacterial and fungal carbonic anhydrases.
AID456404Selectivity ratio of Kinact for human recombinant carbonic anhydrase 2 to Kinact for human recombinant carbonic anhydrase 5B2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.
AID1802885Functional Calcium Imaging Assay from Article 10.1074/jbc.M114.573162: \\ORA1, a zebrafish olfactory receptor ancestral to all mammalian V1R genes, recognizes 4-hydroxyphenylacetic acid, a putative reproductive pheromone.\\2014The Journal of biological chemistry, Jul-11, Volume: 289, Issue:28
ORA1, a zebrafish olfactory receptor ancestral to all mammalian V1R genes, recognizes 4-hydroxyphenylacetic acid, a putative reproductive pheromone.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (12.50)18.2507
2000's2 (25.00)29.6817
2010's5 (62.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.34

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

MetricThis Compound (vs All)
Research Demand Index41.34 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.86 (4.65)
Search Engine Demand Index55.32 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.34)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]