ContaminantDB: Acetaminophen

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (35)XML

Record Information

Version

1.0

Creation Date

2009-07-05 03:31:24 UTC

Update Date

2026-05-14 16:25:22 UTC

Accession Number

CHEM002097

Identification

Common Name

Acetaminophen

Class

Small Molecule

Description

Acetaminophen, also known as paracetamol, is commonly used for its analgesic and antipyretic effects. Its therapeutic effects are similar to salicylates, but it lacks anti-inflammatory, antiplatelet, and gastric ulcerative effects. The 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. (7). Single doses of paracetamol are effective analgesics for acute postoperative pain and give rise to few adverse effects. (8). 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. (9).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens General
IARC Carcinogens Group 3
STOFF IDENT Compounds
Suspected Compounds
Suspected Compounds - Waste Water
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Analgesic, Non-Narcotic
Antipyretic
Drug
Food Toxin
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4'-Hydroxyacetanilide	ChEBI
4-(Acetylamino)phenol	ChEBI
4-Acetamidophenol	ChEBI
Acenol	ChEBI
Acetaminofen	ChEBI
Acetaminophene	ChEBI
APAP	ChEBI
N-Acetyl-p-aminophenol	ChEBI
p-Acetamidophenol	ChEBI
p-Acetaminophenol	ChEBI
p-Acetylaminophenol	ChEBI
p-Hydroxyacetanilide	ChEBI
p-Hydroxyphenolacetamide	ChEBI
Panadol	ChEBI
Paracetamolum	ChEBI
Tylenol	ChEBI
Paracetamol	Kegg
4-Acetaminophenol	HMDB
4-Hydroxyacetanilide	HMDB
4-Hydroxyanilid kyseliny octove	HMDB
a-Per	HMDB
A.F. anacin	HMDB
Abenol	HMDB
Abensanil	HMDB
Abrol	HMDB
Abrolet	HMDB
Acamol	HMDB
Accu-tap	HMDB
Acephen	HMDB
Acertol	HMDB
Aceta elixir	HMDB
Aceta tablets	HMDB
Acetagesic	HMDB
Acetalgin	HMDB
Acetaminophen uniserts	HMDB
Acetamol	HMDB
Acetofen	HMDB
Actamin	HMDB
Actamin extra	HMDB
Actamin super	HMDB
Actifed plus	HMDB
Actimol chewable tablets	HMDB
Actimol children's suspension	HMDB
Actimol infants' suspension	HMDB
Actimol junior strength caplets	HMDB
Actron	HMDB
Afebrin	HMDB
Afebryl	HMDB
Aferadol	HMDB
Algesidal	HMDB
Algina	HMDB
Algomol	HMDB
Algotropyl	HMDB
Allay	HMDB
alpha-Per	HMDB
Alpiny	HMDB
Alpinyl	HMDB
Alvedon	HMDB
Amadil	HMDB
Aminofen	HMDB
Aminofen max	HMDB
Anacin-3	HMDB
Anacin-3 extra strength	HMDB
Anadin dla dzieci	HMDB
Anaflon	HMDB
Analter	HMDB
Anapap	HMDB
Andox	HMDB
Anelix	HMDB
Anexsia	HMDB
Anexsia 10/660	HMDB
Anexsia 5/325	HMDB
Anexsia 7.5/325	HMDB
Anexsia 7.5/650	HMDB
Anhiba	HMDB
Anoquan	HMDB
Anti-algos	HMDB
Antidol	HMDB
Apacet	HMDB
Apacet capsules	HMDB
Apacet elixir	HMDB
Apacet extra strength caplets	HMDB
Apacet extra strength tablets	HMDB
Apacet regular strength tablets	HMDB
Apadon	HMDB
Apamid	HMDB
Apamide	HMDB
Apitrelal	HMDB
Apo-acetaminophen	HMDB
Arfen	HMDB
Asetam	HMDB
Asomal	HMDB
Aspac	HMDB
Aspirin free anacin maximum strength caplets	HMDB
Aspirin free anacin maximum strength gel caplets	HMDB
Aspirin free anacin maximum strength tablets	HMDB
Aspirin-free anacin	HMDB
Aspirin-free excedrin caplets	HMDB
Asplin	HMDB
Atasol caplets	HMDB
Atasol drops	HMDB
Atasol forte caplets	HMDB
Atasol forte tablets	HMDB
Atasol oral solution	HMDB
Atasol tablets	HMDB
Atralidon	HMDB
Babikan	HMDB
Bacetamol	HMDB
Bancap	HMDB
Bancap HC	HMDB
Banesin	HMDB
Bayer select allergy-sinus	HMDB
Bayer select head cold	HMDB
Bayer select headache pain	HMDB
Bayer select maximum strength headache pain relief formula	HMDB
Bayer select menstrual multi-symptom	HMDB
Bayer select sinus pain relief	HMDB
Ben-u-ron	HMDB
Benmyo	HMDB
Bickie-mol	HMDB
Biocetamol	HMDB
Bucet	HMDB
Butalbital	HMDB
Butapap	HMDB
Cadafen	HMDB
Calapol	HMDB
Calmanticold	HMDB
Calpol	HMDB
Capital with codeine	HMDB
Captin	HMDB
Causalon	HMDB
Cefalex	HMDB
Cetadol	HMDB
Children'S acetaminophen elixir drops	HMDB
Children'S acetaminophen oral solution	HMDB
Children'S tylenol chewable	HMDB
Claradol codeine	HMDB
Clixodyne	HMDB
CO-Gesic	HMDB
COD-Acamol forte	HMDB
Codabrol	HMDB
Codalgin	HMDB
Codapane	HMDB
Codicet	HMDB
Codisal	HMDB
Codisal forte	HMDB
Codoliprane	HMDB
Codral pain relief	HMDB
Cofamol	HMDB
Conacetol	HMDB
Contac cough & sore throat formula	HMDB
Contra-schmerz p	HMDB
Coricidin	HMDB
Coricidin D	HMDB
Coricidin sinus	HMDB
Cosutone	HMDB
Croix blanche	HMDB
Cuponol	HMDB
Curadon	HMDB
Curpol	HMDB
Custodial	HMDB
Dapa X-S	HMDB
Darocet	HMDB
Darvocet	HMDB
Darvocet-N 50	HMDB
Datril	HMDB
Datril extra-strength	HMDB
Daygrip	HMDB
Demilets	HMDB
Deminofen	HMDB
Democyl	HMDB
Demogripal	HMDB
Desfebre	HMDB
Dhamol	HMDB
DHC Plus	HMDB
Dial-a-gesic	HMDB
Dial-alpha-gesic	HMDB
Dimindol	HMDB
Dirox	HMDB
Disprol	HMDB
Dol-stop	HMDB
Dolcor	HMDB
Dolefin	HMDB
Dolegrippin	HMDB
Dolene ap-65	HMDB
Dolgesic	HMDB
Doliprane	HMDB
Dolko	HMDB
Dolofugin	HMDB
Doloreduct	HMDB
Dolorfug	HMDB
Dolorol forte	HMDB
Dolorstop	HMDB
Dolotec	HMDB
Dolprone	HMDB
Dorocoff	HMDB
Dresan	HMDB
Dristan cold no drowsiness	HMDB
Dristancito	HMDB
Duracetamol	HMDB
Duradyne DHC	HMDB
Durapan	HMDB
Dymadon	HMDB
Dymadon co	HMDB
Dymadon forte	HMDB
Dypap	HMDB
Ecosetol	HMDB
Elixodyne	HMDB
Empracet	HMDB
Endecon	HMDB
Enelfa	HMDB
Eneril	HMDB
Esgic	HMDB
Esgic-plus	HMDB
Eu-med	HMDB
Excedrin	HMDB
Excedrin caplets	HMDB
Excedrin extra strength caplets	HMDB
Excipain	HMDB
Exdol	HMDB
Exdol strong	HMDB
Fanalgic	HMDB
Farmadol	HMDB
Febranine	HMDB
Febrectal	HMDB
Febrectol	HMDB
Febrex	HMDB
Febricet	HMDB
Febridol	HMDB
Febrilix	HMDB
Febrin	HMDB
Febrinol	HMDB
Febro-gesic	HMDB
Febrolin	HMDB
Femcet	HMDB
Fendon	HMDB
Fensum	HMDB
Fepanil	HMDB
Feverall junior strength	HMDB
Feverall sprinkle caps junior strength	HMDB
Fevor	HMDB
Finimal	HMDB
Finiweh	HMDB
Fioricet	HMDB
Fluparmol	HMDB
Fortalidon p	HMDB
Freka-cetamol	HMDB
Gattaphen T	HMDB
Gelocatil	HMDB
Geluprane	HMDB
Genapap children's elixir	HMDB
Genapap children's tablets	HMDB
Genapap extra strength caplets	HMDB
Genapap extra strength tablets	HMDB
Genapap regular strength tablets	HMDB
Genebs extra strength caplets	HMDB
Genebs regular strength tablets	HMDB
Genebs X-tra	HMDB
Geralgine-p	HMDB
Gripin bebe	HMDB
Grippostad	HMDB
Gynospasmine	HMDB
Hedex	HMDB
Helon N	HMDB
Homoolan	HMDB
Hy-phen	HMDB
Hycomine compound	HMDB
Hydrocet	HMDB
Ildamol	HMDB
Inalgex	HMDB
Infadrops	HMDB
Infants' feverall	HMDB
Influbene N	HMDB
Injectapap	HMDB
Intensin	HMDB
Janupap	HMDB
Junior disprol	HMDB
Kataprin	HMDB
Kinder finimal	HMDB
Korum	HMDB
Kratofin simplex	HMDB
Labamol	HMDB
Lekadol	HMDB
Lemgrip	HMDB
Lemsip	HMDB
Lestemp	HMDB
Liquagesic	HMDB
Liquigesic co	HMDB
Liquiprin	HMDB
Liquiprin children's elixir	HMDB
Liquiprin infants" drops	HMDB
Lonarid	HMDB
Lonarid mono	HMDB
Lorcet-HD	HMDB
Lortab	HMDB
Lupocet	HMDB
Lyteca	HMDB
Lyteca syrup	HMDB
Magnidol	HMDB
Malex N	HMDB
Malgis	HMDB
Malidens	HMDB
Maxadol	HMDB
Medigesic plus	HMDB
Medinol paediatric	HMDB
Medocodene	HMDB
Melabon infantil	HMDB
Mexalen	HMDB
Midol maximum strength	HMDB
Midol PM night time formula	HMDB
Midol regular strength	HMDB
Midol teen formula	HMDB
Migraleve yellow	HMDB
Minafen	HMDB
Minoset	HMDB
Miralgin	HMDB
Momentum	HMDB
mono Praecimed	HMDB
Multin	HMDB
N-(4-Hydroxyphenyl)acetamide	HMDB
N-Acetyl-4-aminophenol	HMDB
Naldegesic	HMDB
NAPA	HMDB
Napafen	HMDB
Napap	HMDB
Naprinol	HMDB
Nealgyl	HMDB
Nebs	HMDB
Neo-fepramol	HMDB
NeoCitran	HMDB
Neodol	HMDB
Neodolito	HMDB
Neopap	HMDB
Neotrend	HMDB
Neuridon	HMDB
New cortal for children	HMDB
NilnOcen	HMDB
Nina	HMDB
NO-Febril	HMDB
Nobedon	HMDB
Nodolex	HMDB
Noral	HMDB
Norcet	HMDB
Norco	HMDB
O-Acetaminophenol	HMDB
Oltyl	HMDB
Oralgan	HMDB
Oraphen-PD	HMDB
Ortensan	HMDB
Oxycet	HMDB
Oxycocet	HMDB
Oxycodone 2.5/apap 500	HMDB
Oxycodone 5/apap 500	HMDB
p-(Acetylamino)phenol	HMDB
Paceco	HMDB
Pacemo	HMDB
Pacemol	HMDB
Pacet	HMDB
Pacimol	HMDB
Paedialgon	HMDB
Paedol	HMDB
Painex	HMDB
Paldesic	HMDB
Pamol	HMDB
Panacete	HMDB
Panadeine	HMDB
Panadeine co	HMDB
Panadiene	HMDB
Panado-co	HMDB
Panado-co caplets	HMDB
Panadol extra strength	HMDB
Panadol junior strength caplets	HMDB
Panadol maximum strength caplets	HMDB
Panadol maximum strength tablets	HMDB
Panaleve	HMDB
Panamax	HMDB
Panasorb	HMDB
Panasorbe	HMDB
Panets	HMDB
Panex	HMDB
Panodil	HMDB
Panofen	HMDB
Pantalgin	HMDB
Papa-deine #3	HMDB
Papa-deine #4	HMDB
Para-suppo	HMDB
Para-tabs	HMDB
Paracemol	HMDB
Paracenol	HMDB
Paracet	HMDB
Paracetamol al	HMDB
Paracetamol antipanin p	HMDB
Paracetamol basics	HMDB
Paracetamol BC	HMDB
Paracetamol DC	HMDB
Paracetamol dr. schmidgall	HMDB
Paracetamol fecofar	HMDB
Paracetamol genericon	HMDB
Paracetamol hanseler	HMDB
Paracetamol harkley	HMDB
Paracetamol heumann	HMDB
Paracetamol hexal	HMDB
Paracetamol italfarmaco	HMDB
Paracetamol nycomed	HMDB
Paracetamol PB	HMDB
Paracetamol raffo	HMDB
Paracetamol ratiopharm	HMDB
Paracetamol rosch	HMDB
Paracetamol saar	HMDB
Paracetamol smithkline beecham	HMDB
Paracetamol stada	HMDB
Paracetamol von CT	HMDB
Paracetamol winthrop	HMDB
Paracetamole	HMDB
Paracetamolo	HMDB
Paracetanol	HMDB
Paracetol	HMDB
Paracin	HMDB
Paracod	HMDB
Paracodol	HMDB
Parador	HMDB
Paradrops	HMDB
Parakapton	HMDB
Parake	HMDB
Paralen	HMDB
Paralief	HMDB
Paralink	HMDB
Paralyoc	HMDB
Paramol	HMDB
Paramolan	HMDB
Paranox	HMDB
Parapan	HMDB
Parasedol	HMDB
Parasin	HMDB
Paraspen	HMDB
Parcetol	HMDB
Parelan	HMDB
Parmol	HMDB
Parogal	HMDB
Paroma	HMDB
Pasolind	HMDB
Pasolind N	HMDB
PCM Paracetamol lichtenstein	HMDB
Pe-tam	HMDB
Pediapirin	HMDB
Pediatrix	HMDB
Pedric	HMDB
Percocet	HMDB
Percocet-5	HMDB
Percocet-demi	HMDB
Percogesic with codeine	HMDB
Perdolan mono	HMDB
Phenaphen	HMDB
Phenaphen caplets	HMDB
Phenaphen w/codeine	HMDB
Phendon	HMDB
Phenipirin	HMDB
Phogoglandin	HMDB
Phrenilin	HMDB
Phrenilin forte	HMDB
Pinex	HMDB
Piramin	HMDB
Pirinasol	HMDB
Plicet	HMDB
Polmofen	HMDB
Predimol	HMDB
Predualito	HMDB
Prestwick_13	HMDB
Prodol	HMDB
Prompt	HMDB
Prontina	HMDB
Propacet	HMDB
Propacet 100	HMDB
Proval #3	HMDB
Puernol	HMDB
Pulmofen	HMDB
Pyregesic-C	HMDB
Pyrigesic	HMDB
Pyrinazine	HMDB
Pyromed	HMDB
Quiet world	HMDB
Redutemp	HMDB
Reliv	HMDB
Remedol	HMDB
Rhinex D-lay tablets	HMDB
Rivalgyl	HMDB
Robigesic	HMDB
Robitussin night relief	HMDB
Rockamol plus	HMDB
Rounox	HMDB
Roxicet	HMDB
Roxicet 5/500	HMDB
Roxilox	HMDB
RubieMol	HMDB
Rubophen	HMDB
Rupemol	HMDB
Salzone	HMDB
Sanicet	HMDB
Sanicopyrine	HMDB
Scanol	HMDB
Scentalgyl	HMDB
Scherzatabletten rezeptur 534	HMDB
Schmerzex	HMDB
Sedalito	HMDB
Sedapap	HMDB
Semolacin	HMDB
Servigesic	HMDB
Seskamol	HMDB
Setakop	HMDB
Setamol	HMDB
Setol	HMDB
Sifenol	HMDB
Sinaspril	HMDB
Sine-OFF sinus medicine caplets	HMDB
Sinedol	HMDB
Sinmol	HMDB
Sinubid	HMDB
SK-Apap	HMDB
Snaplets-FR	HMDB
Spalt fur die nacht	HMDB
Spalt N	HMDB
ST Joseph aspirin-free	HMDB
ST Joseph aspirin-free for children	HMDB
St. joseph cold tablets for children	HMDB
St. joseph fever reducer	HMDB
Stanback	HMDB
Stopain	HMDB
Sudafed severe cold formula	HMDB
Sudafed sinus	HMDB
Sunetheton	HMDB
Supac	HMDB
Supadol mono	HMDB
Supofen	HMDB
Suppap	HMDB
Suppap-120	HMDB
Suppap-325	HMDB
Suppap-650	HMDB
Supramol-m	HMDB
Synalgos-DC-a	HMDB
Tabalgin	HMDB
Tachiprina	HMDB
Talacen	HMDB
Tapanol extra strength caplets	HMDB
Tapanol extra strength tablets	HMDB
Tapar	HMDB
Tavist allergy/sinus/headache	HMDB
Tazamol	HMDB
Temlo	HMDB
Tempanal	HMDB
Tempra	HMDB
Tempra caplets	HMDB
Tempra chewable tablets	HMDB
Tempra d.s	HMDB
Tempra drops	HMDB
Tempra syrup	HMDB
Tencon	HMDB
Termacet	HMDB
Termalgin	HMDB
Termalgine	HMDB
Termofren	HMDB
TheraFlu	HMDB
Tibinide	HMDB
Tibizide	HMDB
Tiffy	HMDB
Tisin	HMDB
Tisiodrazida	HMDB
Titralgan	HMDB
Tizide	HMDB
Tocris-1706	HMDB
Toximer p	HMDB
Tralgon	HMDB
Treupel mon	HMDB
Treupel N	HMDB
Treuphadol	HMDB
Triad	HMDB
Triaminic sore throat formula	HMDB
Triaprin	HMDB
Tricoton	HMDB
Tussapap	HMDB
Tycolet	HMDB
TYL	HMDB
Tylenol allergy sinus	HMDB
Tylenol arthritis extended relief	HMDB
Tylenol caplets	HMDB
Tylenol children's chewable tablets	HMDB
Tylenol children's elixir	HMDB
Tylenol children's suspension liquid	HMDB
Tylenol drops	HMDB
Tylenol elixir	HMDB
Tylenol extra strength adult liquid pain reliever	HMDB
Tylenol extra strength caplets	HMDB
Tylenol extra strength gelcaps	HMDB
Tylenol extra strength tablets	HMDB
Tylenol gelcaps	HMDB
Tylenol infants drops	HMDB
Tylenol infants" suspension drops	HMDB
Tylenol junior strength caplets	HMDB
Tylenol junior strength chewable tablets	HMDB
Tylenol regular strength caplets	HMDB
Tylenol regular strength tablets	HMDB
Tylenol tablets	HMDB
Tylex	HMDB
Tylex CD	HMDB
Tylol	HMDB
Tylox	HMDB
Tylox-325	HMDB
Tymol	HMDB
Ultracet	HMDB
Upsanol	HMDB
Utragin	HMDB
Valadol	HMDB
Valgesic	HMDB
Valorin	HMDB
Valorin extra	HMDB
Vanquish	HMDB
Veralgina	HMDB
Vermidon	HMDB
Verpol	HMDB
Viclor richet	HMDB
Vicodin	HMDB
Vicodin es	HMDB
Vicodin HP	HMDB
Vips	HMDB
Viruflu	HMDB
Vivimed	HMDB
Volpan	HMDB
Wygesic	HMDB
Zatinol	HMDB
Zolben	HMDB
Acetaco	HMDB
Anacin3	HMDB
N-(4-Hydroxyphenyl)acetanilide	HMDB
Acetominophen	HMDB
Hydroxyacetanilide	HMDB
Acetamidophenol	HMDB
Anacin 3	HMDB

Chemical Formula

C₈H₉NO₂

Average Molecular Mass

151.163 g/mol

Monoisotopic Mass

151.063 g/mol

CAS Registry Number

103-90-2

IUPAC Name

N-(4-hydroxyphenyl)acetamide

Traditional Name

acetaminophen

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 Key

RZVAJINKPMORJF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:46195 )
acetamides (CHEBI:46195 )
a small molecule (CPD-7669 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

All Tissues

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	169-171°C
Boiling Point	Not Available
Solubility	1.4E+004 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	4.15 g/L	ALOGPS
logP	0.51	ALOGPS
logP	0.91	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.9 m³·mol⁻¹	ChemAxon
Polarizability	15.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0a4i-4971200000-17e6e1373f10ba4ec138	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-1900000000-df97f74a81da3a46a697	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-4900000000-ef277124e1b50b5f010e	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0900000000-7aa6a54b74b345d91e37	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a4i-4971200000-17e6e1373f10ba4ec138	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3900000000-070b8ab49f93898e0aa4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05gl-8930000000-76d6dca6afdf5945dba1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0w29-3900000000-97741eddc3be9c7eaea8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ik9-1900000000-1ddd59340d1db920fa66	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kf-9000000000-148fa91ce08e13165712	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0a4i-1900000000-5997c3f6cdebc5326b65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a4i-4900000000-ef277124e1b50b5f010e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (Unknown) , Positive	splash10-0udi-0900000000-7aa6a54b74b345d91e37	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0zfr-0900000000-125e44ce332576a1e155	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-7e46df4b4b653c90c258	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-bb6e34d2d574a249d721	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-2f45dd7efce38361f806	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0pb9-0900000000-e48b48d64b6b985ab455	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-b72b0e33fd35512fe6de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-97bcaa95f26159307d03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-c50b4b79792e2c2e68f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-7e46df4b4b653c90c258	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-2b07cd2813d3f23e88f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0pb9-0900000000-5b92f09589afe838f23a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0900000000-f0ca5ff6526b9f005034	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0udi-0900000000-7e45ef71674dcdde9068	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-0900000000-0145273b7145728775e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-00e12b1805f379cd3062	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7i-9600000000-3a0dd97400bd7ecff7d0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-92761f5b18a4de851da8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-1900000000-5f270ee30747595c5483	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-2097a693ba6db334acec	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-4900000000-ffdd0f8a1e6e450fc162	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, rapid and almost complete.

Mechanism of Toxicity

Paracetamol toxicity is one of the most common causes of poisoning worldwide. The toxic effects of acetaminophen are due to a minor alkylating metabolite (N-acetyl-p-benzo-quinone imine – also known as NAPQI), not acetaminophen itself nor any of the other major metabolites. Cytochromes P450 2E1 and 3A4 convert approximately 5% of paracetamol to NAPQI. This toxic metabolite reacts with sulfhydryl groups on proteins and with glutathione (GSH). NAPQI depletes the liver's natural antioxidant glutathione and directly damages cells in the liver, leading to liver failure. In animal studies, hepatic glutathione must be depleted to less than 70% of normal levels before hepatotoxicity occurs. More specifically, oxidation by NAPQI of GSH to GSSG (oxidized glutathione) and the reduction of GSSG back to GSH by the NADPH-dependent glutathione reductase appear to be responsible for the rapid oxidation of NADPH that occurs in hepatocytes incubated with NAPQI. Risk factors for toxicity include excessive chronic alcohol intake, fasting or anorexia nervosa, and the use of certain drugs such as isoniazid. At usual doses, paracetamol is quickly detoxified by combining irreversibly with the sulfhydryl group of glutathione to produce a non-toxic conjugate that is eventually excreted by the kidneys. The toxic dose of paracetamol is highly variable.

Metabolism

Acetaminophen primarily undergoes glucuronidation (45-55% of the dose) in which this process is facilitated by UGT1A1, UGT1A6, UGT1A9, UGT2B15 in the liver or UGT1A10 in the gut. 30-35% of the dose undergoes sulfation. This biotransformation is facilitated by SULT1A1, SULT1A3, SULT1A4, SULT1E1 and SULT2A1. A small percentage of acetaminophen is oxidized by CYP2E1 to form N-acetyl-p-benzo-quinone imine (NAPQI), a toxic metabolite which is then conjugated to glutathione and excreted renally. Studies suggest that CYP3A4 and CYP2E1 are the primary cytochrome P450 isozymes responsible for the generation of toxic metabolites. Accumulation of NAPQI may occur if primary metabolic pathways are saturated. Acetaminophen is metabolized primarily in the liver, where most of it is converted to inactive compounds by conjugation with sulfate and glucuronide, and then excreted by the kidneys. Only a small portion is metabolized via the hepatic cytochrome P450 enzyme system. The toxic effects of acetaminophen are due to a minor alkylating metabolite (N-acetyl-p-benzo-quinone imine), not acetaminophen itself nor any of the major metabolites. This toxic metabolite reacts with sulfhydryl groups. At usual doses, it is quickly detoxified by combining irreversibly with the sulfhydryl group of glutathione to produce a non-toxic conjugate that is eventually excreted by the kidneys. The toxic dose of paracetamol is highly variable. Route of Elimination: Approximately 80% of acetaminophen is excreted in the urine after conjugation and about 3% is excreted unchanged. Half Life: 1 to 4 hours

Toxicity Values

LD50: 338 mg/kg (Oral, Mouse) (1) LD50: 1944 mg/kg (Oral, Rat) (1) In adults, single doses above 10 grams or 200 mg/kg of bodyweight, whichever is lower, have a reasonable likelihood of causing toxicity.

Lethal Dose

25 g for an adult human. (1)

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (32)

Uses/Sources

An over-the-counter analgesic (pain reliever) and antipyretic (fever reducer). It is commonly used for the relief of fever, headaches, and other minor aches and pains, and is a major ingredient in numerous cold and flu remedies.

Minimum Risk Level

Not Available

Health Effects

Skin rashes, blood disorders and a swollen pancreas have occasionally happened in people taking the drug on a regular basis for a long time.

Symptoms

When taken at the recommended dose, side-effects of paracetamol are rare. Skin rashes, blood disorders and a swollen pancreas have occasionally happened in people taking the drug on a regular basis for a long time. The signs and symptoms of paracetamol toxicity occur in three phases. The first phase begins within hours of overdose, and consists of nausea, vomiting, pallor, and sweating. Rarely, after massive overdoses, patients may develop symptoms of metabolic acidosis and coma early in the course of poisoning.The second phase occurs between 24 and 72 hours following overdose and consists of signs of increasing liver damage. In general, damage occurs in hepatocytes as they metabolize the paracetamol. The individual may experience right upper quadrant pain. Acute kidney failure may also occur during this phase, typically caused by either hepatorenal syndrome or multiple organ dysfunction syndrome. The third phase follows at 3 to 5 days, and is marked by complications of massive hepatic necrosis leading to fulminant hepatic failure with complications of coagulation defects, hypoglycemia, kidney failure, hepatic encephalopathy, cerebral edema, sepsis, multiple organ failure, and death.

Treatment

In adults, the initial treatment for paracetamol overdose is gastrointestinal decontamination. Paracetamol absorption from the gastrointestinal tract is complete within two hours under normal circumstances, so decontamination is most helpful if performed within this timeframe. Gastric lavage, better known as stomach pumping, may be considered if the amount ingested is potentially life-threatening and the procedure can be performed within 60 minutes of ingestion. Acetylcysteine, when used early in the course of treatment, reduces morbidity and virtually eliminating mortality associated with even a massive acetaminophen overdose. (36) In patients who develop fulminant hepatic failure or who are otherwise expected to die from liver failure, the mainstay of management is liver transplantation.

Concentrations

Not Available

External Links

DrugBank ID

DB00316

HMDB ID

HMDB0001859

FooDB ID

FDB022713

Phenol Explorer ID

Not Available

KNApSAcK ID

C00044491

BiGG ID

Not Available

BioCyc ID

CPD-7669

METLIN ID

6353

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Jeffrey L. Finnan, Rudolph E. Lisa, Douglass N. Schmidt, “Process for preparing spray dried acetaminophen powder and the powder prepared thereby.” U.S. Patent US4710519, issued October, 1975.

MSDS

Link

General References

1. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.

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.

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.

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.

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.

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.

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.

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.

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.