Compounds > n-hydroxyacetaminophen
Page last updated: 2024-12-06

n-hydroxyacetaminophen

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Description

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

Cross-References

ID SourceID
PubMed CID45750
CHEMBL ID107641
SCHEMBL ID874035
MeSH IDM0068098

Synonyms (13)

Synonym
ccris 9182
brn 2833948
acetamide, n-hydroxy-n-(4-hydroxyphenyl)-
n-hydroxyparacetamol
n,4'-dihydroxyacetanilide
n-hydroxyacetaminophen
n-hydroxy-n-(4-hydroxyphenyl)acetamide
CHEMBL107641
AKOS006278702
63975-21-3
SCHEMBL874035
DTXSID00213810
n-hydroxy-paracetamol

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In contrast, no toxic effects of pHAA (less than or equal to 20 mM) could be demonstrated."( Cytotoxic effects of N-acetyl-p-benzoquinone imine, a common arylating intermediate of paracetamol and N-hydroxyparacetamol.
Dahlin, DC; Dybing, E; Holme, JA; Nelson, SD, 1984)		0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (53)

Assay IDTitleYearJournalArticle
AID24935Percent total excretion of N-methoxyacetaminophen sulfate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24936Percent total excretion of acetaminophen1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID1146393Aqueous stability of the compound in 100 mM Na2HPO4 buffer assessed as half life at 2 mM at pH 6.6 at 37 degC by ferric chloride assay1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate.
AID24012The compound was tested for half life in presence of N-acetyl cysteine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID22481Percent dose excreted in 0-48 hours administered ip to male rat1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24019The compound was tested for half life in presence of cysteine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID1146398Aqueous stability of the compound in 100 mM NaOH buffer at 2 mM at pH 12.7 at 37 degC by ferric chloride assay1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate.
AID24020The compound was tested for half life in presence of dithionite as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID24026The compound was tested for half life in presence of phenol as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID13267Percent total excretion of acetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID1146396Aqueous stability of the compound in 100 mM Na2HPO4 buffer assessed as half life at 2 mM at pH 8.0 at 37 degC by ferric chloride assay1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate.
AID24027The compound was tested for half life in presence of pyrogallol as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID13111Percent total excretion of acetaminophen1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24937Percent total excretion of acetaminophen cysteine conjugate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24940Percent total excretion of acetaminophen-mercapturic acid1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24013The compound was tested for half life in presence of acetaminophen as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID22480Percent dose excreted in 0-48 hours administered ip to male mouse1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24934Percent total excretion of N-methoxyacetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24931Percent total excretion of 3-(thiomethyl)acetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID31113The compound tested for toxicity in liver against male rat after intraperitoneal administration of 2.0 mmol/kg1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24938Percent total excretion of acetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID30992The compound tested for toxicity in kidney against male mouse after intraperitoneal administration of 2.0 mmol/kg1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID1146392Aqueous stability of the compound in 100 mM HCl buffer assessed as half life at 2 mM at pH 1.5 at 37 degC by ferric chloride assay1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate.
AID24029The compound was tested for half life in presence of thiosulphate as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID24939Percent total excretion of acetaminophen sulfate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24932Percent total excretion of 3-(thiomethyl)acetaminophen sulfate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID31112The compound tested for toxicity in liver against male rat after intraperitoneal administration of 1.0 mmol/kg1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID31111The compound tested for toxicity in liver against male mouse after intraperitoneal administration of 2.0 mmol/kg1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24028The compound was tested for half life in presence of salicylate as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID13106Percent total excretion of 3-(thiomethyl)acetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24023The compound was tested for half life in presence of lysine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID24025The compound was tested for half life in presence of p-Nitrosophenol as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID30993The compound tested for toxicity in kidney against male rat after intraperitoneal administration of 1.0 mmol/kg1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID13110Percent total excretion of N-methoxyacetaminophen sulfate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24015The compound was tested for half life in presence of aspirin as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID30994The compound tested for toxicity in kidney against male rat after intraperitoneal administration of 2.0 mmol/kg; Positive1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24017The compound was tested for half life in presence of cystamine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID1146394Aqueous stability of the compound in 100 mM Na2HPO4 buffer assessed as half life at 2 mM at pH 7.0 at 37 degC by ferric chloride assay1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate.
AID24933Percent total excretion of 3-methoxyacetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24022The compound was tested for half life in presence of glycine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID1146395Aqueous stability of the compound in 100 mM Na2HPO4 buffer assessed as half life at 2 mM at pH 7.2 at 37 degC by ferric chloride assay1978Journal of medicinal chemistry, Jul, Volume: 21, Issue:7
Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate.
AID13266Percent total excretion of acetaminophen cysteine conjugate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID13107Percent total excretion of 3-(thiomethyl)acetaminophen sulfate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID13108Percent total excretion of 3-methoxyacetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24021The compound was tested for half life in presence of ethanol as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID13269Percent total excretion of acetaminophen-mercapturic acid1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID11520Percent dose excreted in 0-48 hours administered ip to male rat1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID13109Percent total excretion of N-methoxyacetaminophen glucuronide1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
AID24014The compound was tested for half life in presence of ascorbic acid as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID24018The compound was tested for half life in presence of cysteamine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID24016The compound was tested for half life in presence of control1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID24024The compound was tested for half life in presence of methionine as additive (20 mM)1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen.
AID13268Percent total excretion of acetaminophen sulfate1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
N-hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen.
[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-199013 (92.86)18.7374
1990's1 (7.14)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]

Market Indicators

Research Demand Index: 11.56

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

MetricThis Compound (vs All)
Research Demand Index11.56 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.56)

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]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetic acid
Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.		3.0810monocarboxylic acidantimicrobial food preservative;
Daphnia magna metabolite;
food acidity regulator;
protic solvent
4-aminophenol
4-aminophenol: RN given refers to parent cpd. 4-aminophenol : An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.		3.0810aminophenolallergen;
metabolite
acetaminophen
Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.		5.07140acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
phenacetin
Saridon: contains phenacetin, caffeine, propyphenazone & pyrithyldione		2.3620acetamides;
aromatic ether		cyclooxygenase 3 inhibitor;
non-narcotic analgesic;
peripheral nervous system drug
hydroxyacetylaminofluorene
Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.		1.95102-acetamidofluorenes
2-acetylaminofluorene
2-Acetylaminofluorene: A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.		1.95102-acetamidofluorenesantimitotic;
carcinogenic agent;
epitope;
mutagen
4-nitrosophenol
4-nitrosophenol: RN given refers to unlabeled parent cpd		1.9510
paraoxon
[no description available]		1.9510aryl dialkyl phosphate;
organophosphate insecticide		EC 3.1.1.7 (acetylcholinesterase) inhibitor;
mouse metabolite
n-hydroxyphenacetin
N-hydroxyphenacetin: RN given refers to parent cpd; structure		2.3620
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		3.0810benzenes;
phenyl acetates
n-acetyl-4-benzoquinoneimine
N-acetyl-4-benzoquinoneimine: reactive arylating intermediate from acetaminophen & N-hydroxyacetaminophen; structure given in first source		3.7630ketoimine;
quinone imine
nadp
[no description available]		1.9510
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9510cysteiniumfundamental metabolite
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.3620ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials