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Record Information
Version3.6
Creation Date2006-02-22 10:57:58 UTC
Update Date2016-02-11 01:05:02 UTC
HMDB IDHMDB01859
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetaminophen
DescriptionThe excellent tolerability of therapeutic doses of paracetamol (acetaminophen) is a major factor in the very wide use of the drug. The major problem in the use of paracetamol is its hepatotoxicity after an overdose. Hepatotoxicity has also been reported after therapeutic doses, but critical analysis indicates that most patients with alleged toxicity from therapeutic doses have taken overdoses. Importantly, prospective studies indicate that therapeutic doses of paracetamol are an unlikely cause of hepatotoxicity in patients who ingest moderate to large amounts of alcohol. (PMID 15733027 ). Single doses of paracetamol are effective analgesics for acute postoperative pain and give rise to few adverse effects. (PMID 14974073 ). Acetaminophen (AAP) overdose and the resulting hepatotoxicity is an important clinical problem. In addition, AAP is widely used as a prototype hepatotoxin to study mechanisms of chemical-induced cell injury and to test the hepatoprotective potential of new drugs and herbal medicines. Because of its importance, the mechanisms of AAP-induced liver cell injury have been extensively investigated and controversially discussed for many years. (PMID 16863451 ).
Structure
Thumb
Synonyms
ValueSource
4'-HydroxyacetanilideChEBI
4-(acetylamino)PhenolChEBI
4-AcetamidophenolChEBI
AcenolChEBI
AcetaminofenChEBI
AcetaminopheneChEBI
APAPChEBI
N-Acetyl-P-aminophenolChEBI
P-AcetamidophenolChEBI
P-AcetaminophenolChEBI
P-AcetylaminophenolChEBI
P-HydroxyacetanilideChEBI
P-HydroxyphenolacetamideChEBI
PanadolChEBI
ParacetamolumChEBI
TylenolChEBI
4-AcetaminophenolHMDB
4-HydroxyacetanilideHMDB
4-Hydroxyanilid kyseliny octoveHMDB
a-PerHMDB
A.F. anacinHMDB
AbenolHMDB
AbensanilHMDB
AbrolHMDB
AbroletHMDB
AcamolHMDB
Accu-tapHMDB
AcephenHMDB
AcertolHMDB
Aceta elixirHMDB
Aceta tabletsHMDB
AcetagesicHMDB
AcetalginHMDB
Acetaminophen unisertsHMDB
AcetamolHMDB
AcetofenHMDB
ActaminHMDB
Actamin extraHMDB
Actamin superHMDB
Actifed plusHMDB
Actimol chewable tabletsHMDB
Actimol children's suspensionHMDB
Actimol infants' suspensionHMDB
Actimol junior strength capletsHMDB
ActronHMDB
AfebrinHMDB
AfebrylHMDB
AferadolHMDB
AlgesidalHMDB
AlginaHMDB
AlgomolHMDB
AlgotropylHMDB
AllayHMDB
alpha-PerHMDB
AlpinyHMDB
AlpinylHMDB
AlvedonHMDB
AmadilHMDB
AminofenHMDB
Aminofen maxHMDB
Anacin-3HMDB
Anacin-3 extra strengthHMDB
Anadin dla dzieciHMDB
AnaflonHMDB
AnalterHMDB
AnapapHMDB
AndoxHMDB
AnelixHMDB
AnexsiaHMDB
Anexsia 10/660HMDB
Anexsia 5/325HMDB
Anexsia 7.5/325HMDB
Anexsia 7.5/650HMDB
AnhibaHMDB
AnoquanHMDB
Anti-algosHMDB
AntidolHMDB
ApacetHMDB
Apacet capsulesHMDB
Apacet elixirHMDB
Apacet extra strength capletsHMDB
Apacet extra strength tabletsHMDB
Apacet regular strength tabletsHMDB
ApadonHMDB
ApamidHMDB
ApamideHMDB
ApitrelalHMDB
apo-AcetaminophenHMDB
ArfenHMDB
AsetamHMDB
AsomalHMDB
AspacHMDB
Aspirin free anacin maximum strength capletsHMDB
Aspirin free anacin maximum strength gel capletsHMDB
Aspirin free anacin maximum strength tabletsHMDB
Aspirin-free anacinHMDB
Aspirin-free excedrin capletsHMDB
AsplinHMDB
Atasol capletsHMDB
Atasol dropsHMDB
Atasol forte capletsHMDB
Atasol forte tabletsHMDB
Atasol oral solutionHMDB
Atasol tabletsHMDB
AtralidonHMDB
BabikanHMDB
BacetamolHMDB
BancapHMDB
Bancap HCHMDB
BanesinHMDB
Bayer select allergy-sinusHMDB
Bayer select head coldHMDB
Bayer select headache painHMDB
Bayer select maximum strength headache pain relief formulaHMDB
Bayer select menstrual multi-symptomHMDB
Bayer select sinus pain reliefHMDB
Ben-u-ronHMDB
BenmyoHMDB
Bickie-molHMDB
BiocetamolHMDB
BucetHMDB
ButalbitalHMDB
ButapapHMDB
CadafenHMDB
CalapolHMDB
CalmanticoldHMDB
CalpolHMDB
Capital with codeineHMDB
CaptinHMDB
CausalonHMDB
CefalexHMDB
CetadolHMDB
Children'S acetaminophen elixir dropsHMDB
Children'S acetaminophen oral solutionHMDB
Children'S tylenol chewableHMDB
Claradol codeineHMDB
ClixodyneHMDB
CO-GesicHMDB
COD-Acamol forteHMDB
CodabrolHMDB
CodalginHMDB
CodapaneHMDB
CodicetHMDB
CodisalHMDB
Codisal forteHMDB
CodolipraneHMDB
Codral pain reliefHMDB
CofamolHMDB
ConacetolHMDB
Contac cough & sore throat formulaHMDB
Contra-schmerz PHMDB
CoricidinHMDB
Coricidin DHMDB
Coricidin sinusHMDB
CosutoneHMDB
Croix blancheHMDB
CuponolHMDB
CuradonHMDB
CurpolHMDB
CustodialHMDB
Dapa X-SHMDB
DarocetHMDB
DarvocetHMDB
Darvocet-N 50HMDB
DatrilHMDB
Datril extra-strengthHMDB
DaygripHMDB
DemiletsHMDB
DeminofenHMDB
DemocylHMDB
DemogripalHMDB
DesfebreHMDB
DhamolHMDB
DHC PlusHMDB
Dial-a-gesicHMDB
Dial-alpha-gesicHMDB
DimindolHMDB
DiroxHMDB
DisprolHMDB
Dol-stopHMDB
DolcorHMDB
DolefinHMDB
DolegrippinHMDB
Dolene ap-65HMDB
DolgesicHMDB
DolipraneHMDB
DolkoHMDB
DolofuginHMDB
DoloreductHMDB
DolorfugHMDB
Dolorol forteHMDB
DolorstopHMDB
DolotecHMDB
DolproneHMDB
DorocoffHMDB
DresanHMDB
Dristan cold no drowsinessHMDB
DristancitoHMDB
DuracetamolHMDB
Duradyne DHCHMDB
DurapanHMDB
DymadonHMDB
Dymadon coHMDB
Dymadon forteHMDB
DypapHMDB
EcosetolHMDB
ElixodyneHMDB
EmpracetHMDB
EndeconHMDB
EnelfaHMDB
EnerilHMDB
EsgicHMDB
Esgic-plusHMDB
Eu-medHMDB
ExcedrinHMDB
Excedrin capletsHMDB
Excedrin extra strength capletsHMDB
ExcipainHMDB
ExdolHMDB
Exdol strongHMDB
FanalgicHMDB
FarmadolHMDB
FebranineHMDB
FebrectalHMDB
FebrectolHMDB
FebrexHMDB
FebricetHMDB
FebridolHMDB
FebrilixHMDB
FebrinHMDB
FebrinolHMDB
febro-GesicHMDB
FebrolinHMDB
FemcetHMDB
FendonHMDB
FensumHMDB
FepanilHMDB
Feverall junior strengthHMDB
Feverall sprinkle caps junior strengthHMDB
FevorHMDB
FinimalHMDB
FiniwehHMDB
FioricetHMDB
FluparmolHMDB
Fortalidon PHMDB
Freka-cetamolHMDB
Gattaphen THMDB
GelocatilHMDB
GelupraneHMDB
Genapap children's elixirHMDB
Genapap children's tabletsHMDB
Genapap extra strength capletsHMDB
Genapap extra strength tabletsHMDB
Genapap regular strength tabletsHMDB
Genebs extra strength capletsHMDB
Genebs regular strength tabletsHMDB
Genebs X-traHMDB
Geralgine-PHMDB
Gripin bebeHMDB
GrippostadHMDB
GynospasmineHMDB
HedexHMDB
Helon NHMDB
HomoolanHMDB
Hy-phenHMDB
Hycomine compoundHMDB
HydrocetHMDB
IldamolHMDB
InalgexHMDB
InfadropsHMDB
Infants' feverallHMDB
Influbene NHMDB
InjectapapHMDB
IntensinHMDB
JanupapHMDB
Junior disprolHMDB
KataprinHMDB
Kinder finimalHMDB
KorumHMDB
Kratofin simplexHMDB
LabamolHMDB
LekadolHMDB
LemgripHMDB
LemsipHMDB
LestempHMDB
LiquagesicHMDB
Liquigesic coHMDB
LiquiprinHMDB
Liquiprin children's elixirHMDB
Liquiprin infants" dropsHMDB
LonaridHMDB
Lonarid monoHMDB
Lorcet-HDHMDB
LortabHMDB
LupocetHMDB
LytecaHMDB
Lyteca syrupHMDB
MagnidolHMDB
Malex NHMDB
MalgisHMDB
MalidensHMDB
MaxadolHMDB
Medigesic plusHMDB
Medinol paediatricHMDB
MedocodeneHMDB
Melabon infantilHMDB
MexalenHMDB
Midol maximum strengthHMDB
Midol PM night time formulaHMDB
Midol regular strengthHMDB
Midol teen formulaHMDB
Migraleve yellowHMDB
MinafenHMDB
MinosetHMDB
MiralginHMDB
MomentumHMDB
mono PraecimedHMDB
MultinHMDB
N-(4-Hydroxyphenyl)acetamideHMDB
N-Acetyl-4-aminophenolHMDB
NaldegesicHMDB
NAPAHMDB
NapafenHMDB
NapapHMDB
NaprinolHMDB
NealgylHMDB
NebsHMDB
neo-FepramolHMDB
NeoCitranHMDB
NeodolHMDB
NeodolitoHMDB
NeopapHMDB
NeotrendHMDB
NeuridonHMDB
New cortal for childrenHMDB
NilnOcenHMDB
NinaHMDB
NO-FebrilHMDB
NobedonHMDB
NodolexHMDB
NoralHMDB
NorcetHMDB
NorcoHMDB
O-AcetaminophenolHMDB
OltylHMDB
OralganHMDB
Oraphen-PDHMDB
OrtensanHMDB
OxycetHMDB
OxycocetHMDB
Oxycodone 2.5/apap 500HMDB
Oxycodone 5/apap 500HMDB
P-(acetylamino)PhenolHMDB
PacecoHMDB
PacemoHMDB
PacemolHMDB
PacetHMDB
PacimolHMDB
PaedialgonHMDB
PaedolHMDB
PainexHMDB
PaldesicHMDB
PamolHMDB
PanaceteHMDB
PanadeineHMDB
Panadeine coHMDB
PanadieneHMDB
panado-CoHMDB
panado-co CapletsHMDB
Panadol extra strengthHMDB
Panadol junior strength capletsHMDB
Panadol maximum strength capletsHMDB
Panadol maximum strength tabletsHMDB
PanaleveHMDB
PanamaxHMDB
PanasorbHMDB
PanasorbeHMDB
PanetsHMDB
PanexHMDB
PanodilHMDB
PanofenHMDB
PantalginHMDB
Papa-deine #3HMDB
Papa-deine #4HMDB
Para-suppoHMDB
Para-tabsHMDB
ParacemolHMDB
ParacenolHMDB
ParacetHMDB
ParacetamolHMDB
Paracetamol alHMDB
Paracetamol antipanin PHMDB
Paracetamol basicsHMDB
Paracetamol BCHMDB
Paracetamol DCHMDB
Paracetamol dr. schmidgallHMDB
Paracetamol fecofarHMDB
Paracetamol genericonHMDB
Paracetamol hanselerHMDB
Paracetamol harkleyHMDB
Paracetamol heumannHMDB
Paracetamol hexalHMDB
Paracetamol italfarmacoHMDB
Paracetamol nycomedHMDB
Paracetamol PBHMDB
Paracetamol raffoHMDB
Paracetamol ratiopharmHMDB
Paracetamol roschHMDB
Paracetamol saarHMDB
Paracetamol smithkline beechamHMDB
Paracetamol stadaHMDB
Paracetamol von CTHMDB
Paracetamol winthropHMDB
ParacetamoleHMDB
ParacetamoloHMDB
ParacetanolHMDB
ParacetolHMDB
ParacinHMDB
ParacodHMDB
ParacodolHMDB
ParadorHMDB
ParadropsHMDB
ParakaptonHMDB
ParakeHMDB
ParalenHMDB
ParaliefHMDB
ParalinkHMDB
ParalyocHMDB
ParamolHMDB
ParamolanHMDB
ParanoxHMDB
ParapanHMDB
ParasedolHMDB
ParasinHMDB
ParaspenHMDB
ParcetolHMDB
ParelanHMDB
ParmolHMDB
ParogalHMDB
ParomaHMDB
PasolindHMDB
Pasolind NHMDB
PCM Paracetamol lichtensteinHMDB
Pe-tamHMDB
PediapirinHMDB
PediatrixHMDB
PedricHMDB
PercocetHMDB
Percocet-5HMDB
Percocet-demiHMDB
Percogesic with codeineHMDB
Perdolan monoHMDB
PhenaphenHMDB
Phenaphen capletsHMDB
Phenaphen w/codeineHMDB
PhendonHMDB
PhenipirinHMDB
PhogoglandinHMDB
PhrenilinHMDB
Phrenilin forteHMDB
PinexHMDB
PiraminHMDB
PirinasolHMDB
PlicetHMDB
PolmofenHMDB
PredimolHMDB
PredualitoHMDB
Prestwick_13HMDB
ProdolHMDB
PromptHMDB
ProntinaHMDB
PropacetHMDB
Propacet 100HMDB
Proval #3HMDB
PuernolHMDB
PulmofenHMDB
Pyregesic-CHMDB
PyrigesicHMDB
PyrinazineHMDB
PyromedHMDB
Quiet worldHMDB
RedutempHMDB
RelivHMDB
RemedolHMDB
Rhinex D-lay tabletsHMDB
RivalgylHMDB
RobigesicHMDB
Robitussin night reliefHMDB
Rockamol plusHMDB
RounoxHMDB
RoxicetHMDB
Roxicet 5/500HMDB
RoxiloxHMDB
RubieMolHMDB
RubophenHMDB
RupemolHMDB
SalzoneHMDB
SanicetHMDB
SanicopyrineHMDB
ScanolHMDB
ScentalgylHMDB
Scherzatabletten rezeptur 534HMDB
SchmerzexHMDB
SedalitoHMDB
SedapapHMDB
SemolacinHMDB
ServigesicHMDB
SeskamolHMDB
SetakopHMDB
SetamolHMDB
SetolHMDB
SifenolHMDB
SinasprilHMDB
Sine-OFF sinus medicine capletsHMDB
SinedolHMDB
SinmolHMDB
SinubidHMDB
SK-ApapHMDB
Snaplets-FRHMDB
Spalt fur die nachtHMDB
Spalt NHMDB
ST Joseph aspirin-freeHMDB
ST Joseph aspirin-free for childrenHMDB
St. joseph cold tablets for childrenHMDB
St. joseph fever reducerHMDB
StanbackHMDB
StopainHMDB
Sudafed severe cold formulaHMDB
Sudafed sinusHMDB
SunethetonHMDB
SupacHMDB
Supadol monoHMDB
SupofenHMDB
SuppapHMDB
Suppap-120HMDB
Suppap-325HMDB
Suppap-650HMDB
Supramol-mHMDB
Synalgos-DC-aHMDB
TabalginHMDB
TachiprinaHMDB
TalacenHMDB
Tapanol extra strength capletsHMDB
Tapanol extra strength tabletsHMDB
TaparHMDB
Tavist allergy/sinus/headacheHMDB
TazamolHMDB
TemloHMDB
TempanalHMDB
TempraHMDB
Tempra capletsHMDB
Tempra chewable tabletsHMDB
Tempra d.sHMDB
Tempra dropsHMDB
Tempra syrupHMDB
TenconHMDB
TermacetHMDB
TermalginHMDB
TermalgineHMDB
TermofrenHMDB
TheraFluHMDB
TibinideHMDB
TibizideHMDB
TiffyHMDB
TisinHMDB
TisiodrazidaHMDB
TitralganHMDB
TizideHMDB
Tocris-1706HMDB
Toximer PHMDB
TralgonHMDB
Treupel monHMDB
Treupel NHMDB
TreuphadolHMDB
TriadHMDB
Triaminic sore throat formulaHMDB
TriaprinHMDB
TricotonHMDB
TussapapHMDB
TycoletHMDB
TYLHMDB
Tylenol allergy sinusHMDB
Tylenol arthritis extended reliefHMDB
Tylenol capletsHMDB
Tylenol children's chewable tabletsHMDB
Tylenol children's elixirHMDB
Tylenol children's suspension liquidHMDB
Tylenol dropsHMDB
Tylenol elixirHMDB
Tylenol extra strength adult liquid pain relieverHMDB
Tylenol extra strength capletsHMDB
Tylenol extra strength gelcapsHMDB
Tylenol extra strength tabletsHMDB
Tylenol gelcapsHMDB
Tylenol infants dropsHMDB
Tylenol infants" suspension dropsHMDB
Tylenol junior strength capletsHMDB
Tylenol junior strength chewable tabletsHMDB
Tylenol regular strength capletsHMDB
Tylenol regular strength tabletsHMDB
Tylenol tabletsHMDB
TylexHMDB
Tylex CDHMDB
TylolHMDB
TyloxHMDB
Tylox-325HMDB
TymolHMDB
UltracetHMDB
UpsanolHMDB
UtraginHMDB
ValadolHMDB
ValgesicHMDB
ValorinHMDB
Valorin extraHMDB
VanquishHMDB
VeralginaHMDB
VermidonHMDB
VerpolHMDB
Viclor richetHMDB
VicodinHMDB
Vicodin esHMDB
Vicodin HPHMDB
VipsHMDB
VirufluHMDB
VivimedHMDB
VolpanHMDB
WygesicHMDB
ZatinolHMDB
ZolbenHMDB
Chemical FormulaC8H9NO2
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC NameN-(4-hydroxyphenyl)acetamide
Traditional Nameacetaminophen
CAS Registry Number103-90-2
SMILES
CC(=O)NC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
InChI KeyInChIKey=RZVAJINKPMORJF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAcetanilides
Alternative Parents
Substituents
  • N-arylamide
  • Acetanilide
  • Phenol
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Drug metabolite
Biofunction
  • Enzyme cofactor
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility14 mg/mL at 25 °CNot Available
LogP0.46SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility4.15 mg/mLALOGPS
logP0.51ALOGPS
logP0.91ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.9 m3·mol-1ChemAxon
Polarizability15.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-4971200000-17e6e1373f10ba4ec138View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0w29-3900000000-97741eddc3be9c7eaea8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ik9-1900000000-1ddd59340d1db920fa66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9000000000-148fa91ce08e13165712View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0a4i-1900000000-5997c3f6cdebc5326b65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a4i-4900000000-ef277124e1b50b5f010eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-0udi-0900000000-7aa6a54b74b345d91e37View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-4900000000-ffdd0f8a1e6e450fc162View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Acetaminophen Action PathwaySMP00710Not Available
Acetaminophen Metabolism PathwaySMP00640Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified11 +/- 6 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified5.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified11.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified33.5 +/- 22.3 uMAdult (>18 years old)BothHeart Transplant details
UrineDetected and Quantified50.71 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-7 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00316
DrugBank Metabolite IDDBMET00266
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022713
KNApSAcK IDNot Available
Chemspider ID1906
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetaminophen
NuGOwiki LinkHMDB01859
Metagene LinkHMDB01859
METLIN ID6353
PubChem Compound1983
PDB IDTYL
ChEBI ID46195
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. de Morais SM, Uetrecht JP, Wells PG: Decreased glucuronidation and increased bioactivation of acetaminophen in Gilbert's syndrome. Gastroenterology. 1992 Feb;102(2):577-86. [1732127 ]
  2. Muldrew KL, James LP, Coop L, McCullough SS, Hendrickson HP, Hinson JA, Mayeux PR: Determination of acetaminophen-protein adducts in mouse liver and serum and human serum after hepatotoxic doses of acetaminophen using high-performance liquid chromatography with electrochemical detection. Drug Metab Dispos. 2002 Apr;30(4):446-51. [11901099 ]
  3. Bales JR, Nicholson JK, Sadler PJ: Two-dimensional proton nuclear magnetic resonance "maps" of acetaminophen metabolites in human urine. Clin Chem. 1985 May;31(5):757-62. [3987005 ]
  4. van der Marel CD, Anderson BJ, Pluim MA, de Jong TH, Gonzalez A, Tibboel D: Acetaminophen in cerebrospinal fluid in children. Eur J Clin Pharmacol. 2003 Aug;59(4):297-302. Epub 2003 Jul 4. [12845506 ]
  5. Watari N, Iwai M, Kaneniwa N: Pharmacokinetic study of the fate of acetaminophen and its conjugates in rats. J Pharmacokinet Biopharm. 1983 Jun;11(3):245-72. [6644552 ]
  6. Kunkel A, Watzig H: Micellar electrokinetic capillary chromatography as a powerful tool for pharmacological investigations without sample pretreatment: a precise technique providing cost advantages and limits of detection to the low nanomolar range. Electrophoresis. 1999 Sep;20(12):2379-89. [10499329 ]
  7. Vanbinst R, Koenig J, Di Fazio V, Hassoun A: Bile analysis of drugs in postmortem cases. Forensic Sci Int. 2002 Aug 14;128(1-2):35-40. [12208019 ]
  8. Quattrone AJ, Putnam RS: A single liquid-chromatographic procedure for therapeutic monitoring of theophylline, acetaminophen, or ethosuximide. Clin Chem. 1981 Jan;27(1):129-32. [7004665 ]
  9. Smilgin Z, Drozdzik M, Gawronska-Szklarz B, Wojcicki J, Tustanowski S, Gornik W: [Pharmacokinetics of acetaminophen in individuals occupationally exposed to polyvinyl chloride modified with plasticizers] Med Pr. 1993;44(5):423-9. [8107555 ]
  10. Griener JC, Msall ME, Cooke RE, Corcoran GB: Noninvasive determination of acetaminophen disposition in Down's syndrome. Clin Pharmacol Ther. 1990 Nov;48(5):520-8. [2146059 ]
  11. Mohammadi M, Mohebbi MR, Naderi F: CSF Glucose Concentrations in Infants with Febrile Convulsions and the Possible Effect of Acetaminophen. Indian Pediatr. 2003 Dec;40(12):1183-6. [14722369 ]
  12. Munsterhjelm E, Munsterhjelm NM, Niemi TT, Ylikorkala O, Neuvonen PJ, Rosenberg PH: Dose-dependent inhibition of platelet function by acetaminophen in healthy volunteers. Anesthesiology. 2005 Oct;103(4):712-7. [16192763 ]
  13. Findlay JW, DeAngelis RL, Kearney MF, Welch RM, Findlay JM: Analgesic drugs in breast milk and plasma. Clin Pharmacol Ther. 1981 May;29(5):625-33. [7214793 ]
  14. Lifshitz M, Weinstein O, Gavrilov V, Rosenthal G, Lifshitz T: Acetaminophen (paracetamol) levels in human tears. Ther Drug Monit. 1999 Oct;21(5):544-6. [10519453 ]
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Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915