<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2009-07-05 03:31:24 UTC</creation_date>
  <update_date>2026-05-14 16:25:22 UTC</update_date>
  <accession>T3D2571</accession>
  <common_name>Acetaminophen</common_name>
  <class>SmallMolecule</class>
  <description>Acetaminophen belongs to the 1-hydroxy-2-unsubstituted benzenoids, a subclass of phenols within the organic compounds. It has the chemical formula C8H9NO2 and an average molecular weight of 151.16 g/mol. This exogenous compound is a solid at room temperature. In industrial applications, it is used as a pharmaceutical, a softener and conditioner, and is used in Polyethylene Terephthalate plastics. It is identified as an environmental contaminant (PMC10386104).

Biologically, acetaminophen acts as an analgesic, antipyretic, and anti-inflammatory agent (PMC13130104) (PMC12841746, PMC13298484). It is used as a non-narcotic analgesic and a non-steroidal anti-inflammatory drug (PMC12841746, PMC13298484). It functions as an inhibitor of cyclooxygenase 1, 2, and 3 (PMC12841746, PMC13298484). Its protein targets include Prostaglandin G/H synthase 1 (PTGS1), Prostaglandin G/H synthase 2 (PTGS2), Thioredoxin reductase 1 (cytoplasmic), Thioredoxin reductase 2 (mitochondrial), Sulfotransferase 1A3 (SULT1A3), and Glutathione peroxidase 1 (GPX1), among 26 other proteins. Acetaminophen is thought to act primarily in the CNS to increase the pain threshold by inhibiting COX-1 and COX-2; unlike NSAIDs, it does not inhibit cyclooxygenase in peripheral tissues and thus lacks peripheral anti-inflammatory effects.

Acetaminophen is used to treat fever (PMC10383651, PMC10386104, PMC13342574, PMC6201998, PMC8720699), pain (PMC11859530, PMC13342574, PMC6160138, PMC6201998, PMC8502730), headache (PMC10383651, PMC10386104), hypertension (PMC10893462), inflammation (PMC12085248), and fatigue (PMC12496125). It has a therapeutic effect on pain (PMC12684957). However, it is associated with necrosis (PMC13298484) and an increase in cancer (PMC9454765). It has been detected in all tissues and is released from 53 recorded sources, including drinking water, healthcare products, and various consumer and industrial goods. Exposure routes include oral, intravenous, cutaneous, inhalation, nasal, ophthalmic, rectal, respiratory, and topical.</description>
  <categories>
    <category>Drug</category>
    <category>Food Toxin</category>
    <category>Synthetic Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Amine</type>
    <type>Amide</type>
    <type>Drug</type>
    <type>Food Toxin</type>
    <type>Analgesic, Non-Narcotic</type>
    <type>Antipyretic</type>
    <type>Metabolite</type>
    <type>Synthetic Compound</type>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>4'-Hydroxyacetanilide</synonym>
    <synonym>4-(Acetylamino)phenol</synonym>
    <synonym>4-Acetamidophenol</synonym>
    <synonym>4-Acetaminophenol</synonym>
    <synonym>4-Hydroxyacetanilide</synonym>
    <synonym>4-Hydroxyanilid kyseliny octove</synonym>
    <synonym>A-Per</synonym>
    <synonym>A.F. Anacin</synonym>
    <synonym>Abenol</synonym>
    <synonym>Abensanil</synonym>
    <synonym>Abrol</synonym>
    <synonym>Abrolet</synonym>
    <synonym>Acamol</synonym>
    <synonym>Accu-Tap</synonym>
    <synonym>Acenol</synonym>
    <synonym>Acephen</synonym>
    <synonym>Acertol</synonym>
    <synonym>Aceta Elixir</synonym>
    <synonym>Aceta Tablets</synonym>
    <synonym>Acetagesic</synonym>
    <synonym>Acetalgin</synonym>
    <synonym>Acetaminofen</synonym>
    <synonym>Acetaminophen (see Paracetamol)</synonym>
    <synonym>Acetaminophen Uniserts</synonym>
    <synonym>Acetaminophene</synonym>
    <synonym>Acetamol</synonym>
    <synonym>Acetofen</synonym>
    <synonym>Actamin</synonym>
    <synonym>Actamin Extra</synonym>
    <synonym>Actamin Super</synonym>
    <synonym>Actifed Plus</synonym>
    <synonym>Actimol</synonym>
    <synonym>Actimol Chewable Tablets</synonym>
    <synonym>Actimol Children'S Suspension</synonym>
    <synonym>Actimol Infants' Suspension</synonym>
    <synonym>Actimol Junior Strength Caplets</synonym>
    <synonym>Actron</synonym>
    <synonym>Afebrin</synonym>
    <synonym>Afebryl</synonym>
    <synonym>Aferadol</synonym>
    <synonym>Algesidal</synonym>
    <synonym>Algina</synonym>
    <synonym>Algomol</synonym>
    <synonym>Algotropyl</synonym>
    <synonym>Allay</synonym>
    <synonym>alpha-Per</synonym>
    <synonym>Alpiny</synonym>
    <synonym>Alpinyl</synonym>
    <synonym>Alvedon</synonym>
    <synonym>Amadil</synonym>
    <synonym>Aminofen</synonym>
    <synonym>Aminofen Max</synonym>
    <synonym>Anacin-3</synonym>
    <synonym>Anacin-3 Extra Strength</synonym>
    <synonym>Anadin dla dzieci</synonym>
    <synonym>Anaflon</synonym>
    <synonym>Analter</synonym>
    <synonym>Anapap</synonym>
    <synonym>Andox</synonym>
    <synonym>Anelix</synonym>
    <synonym>Anexsia</synonym>
    <synonym>Anexsia 10/660</synonym>
    <synonym>Anexsia 5/325</synonym>
    <synonym>Anexsia 7.5/325</synonym>
    <synonym>Anexsia 7.5/650</synonym>
    <synonym>Anhiba</synonym>
    <synonym>Anoquan</synonym>
    <synonym>Anti-Algos</synonym>
    <synonym>Antidol</synonym>
    <synonym>Apacet</synonym>
    <synonym>Apacet Capsules</synonym>
    <synonym>Apacet Elixir</synonym>
    <synonym>Apacet Extra Strength Caplets</synonym>
    <synonym>Apacet Extra Strength Tablets</synonym>
    <synonym>Apacet Regular Strength Tablets</synonym>
    <synonym>Apadon</synonym>
    <synonym>Apamid</synonym>
    <synonym>Apamide</synonym>
    <synonym>APAP</synonym>
    <synonym>Apitrelal</synonym>
    <synonym>Apo-Acetaminophen</synonym>
    <synonym>Arfen</synonym>
    <synonym>Asetam</synonym>
    <synonym>Asomal</synonym>
    <synonym>Aspac</synonym>
    <synonym>Aspirin Free Anacin Maximum Strength Caplets</synonym>
    <synonym>Aspirin Free Anacin Maximum Strength Gel Caplets</synonym>
    <synonym>Aspirin Free Anacin Maximum Strength Tablets</synonym>
    <synonym>Aspirin-Free Anacin</synonym>
    <synonym>Aspirin-Free Excedrin Caplets</synonym>
    <synonym>Asplin</synonym>
    <synonym>Atasol Caplets</synonym>
    <synonym>Atasol Drops</synonym>
    <synonym>Atasol Forte Caplets</synonym>
    <synonym>Atasol Forte Tablets</synonym>
    <synonym>Atasol Oral Solution</synonym>
    <synonym>Atasol Tablets</synonym>
    <synonym>Atralidon</synonym>
    <synonym>Babikan</synonym>
    <synonym>Bacetamol</synonym>
    <synonym>Bancap</synonym>
    <synonym>Bancap Hc</synonym>
    <synonym>Banesin</synonym>
    <synonym>Bayer Select Allergy-Sinus</synonym>
    <synonym>Bayer Select Head Cold</synonym>
    <synonym>Bayer Select Headache Pain</synonym>
    <synonym>Bayer Select Maximum Strength Headache Pain Relief Formula</synonym>
    <synonym>Bayer Select Menstrual Multi-Symptom</synonym>
    <synonym>Bayer Select Sinus Pain Relief</synonym>
    <synonym>Ben-u-ron</synonym>
    <synonym>Benmyo</synonym>
    <synonym>Bickie-mol</synonym>
    <synonym>Biocetamol</synonym>
    <synonym>Bucet</synonym>
    <synonym>Butalbital</synonym>
    <synonym>Butapap</synonym>
    <synonym>Cadafen</synonym>
    <synonym>Calapol</synonym>
    <synonym>Calmanticold</synonym>
    <synonym>Calpol</synonym>
    <synonym>Capital with Codeine</synonym>
    <synonym>Captin</synonym>
    <synonym>Causalon</synonym>
    <synonym>Cefalex</synonym>
    <synonym>Cetadol</synonym>
    <synonym>Children'S Acetaminophen Elixir Drops</synonym>
    <synonym>Children'S Acetaminophen Oral Solution</synonym>
    <synonym>Children'S Tylenol Chewable</synonym>
    <synonym>Claradol Codeine</synonym>
    <synonym>Clixodyne</synonym>
    <synonym>Co-Gesic</synonym>
    <synonym>Cod-Acamol Forte</synonym>
    <synonym>Codabrol</synonym>
    <synonym>Codalgin</synonym>
    <synonym>Codapane</synonym>
    <synonym>Codicet</synonym>
    <synonym>Codisal</synonym>
    <synonym>Codisal Forte</synonym>
    <synonym>Codoliprane</synonym>
    <synonym>Codral Pain Relief</synonym>
    <synonym>Cofamol</synonym>
    <synonym>Conacetol</synonym>
    <synonym>Contac Cough &amp; Sore Throat Formula</synonym>
    <synonym>Contra-Schmerz P</synonym>
    <synonym>Coricidin</synonym>
    <synonym>Coricidin D</synonym>
    <synonym>Coricidin Sinus</synonym>
    <synonym>Cosutone</synonym>
    <synonym>Croix Blanche</synonym>
    <synonym>Cuponol</synonym>
    <synonym>Curadon</synonym>
    <synonym>Curpol</synonym>
    <synonym>Custodial</synonym>
    <synonym>Dafalgan</synonym>
    <synonym>Dapa X-S</synonym>
    <synonym>Darocet</synonym>
    <synonym>Darvocet</synonym>
    <synonym>Darvocet-N 50</synonym>
    <synonym>Datril</synonym>
    <synonym>Datril Extra-Strength</synonym>
    <synonym>Daygrip</synonym>
    <synonym>Demilets</synonym>
    <synonym>Deminofen</synonym>
    <synonym>Democyl</synonym>
    <synonym>Demogripal</synonym>
    <synonym>Desfebre</synonym>
    <synonym>Dhamol</synonym>
    <synonym>Dhc Plus</synonym>
    <synonym>Dial-a-gesic</synonym>
    <synonym>Dial-alpha-gesic</synonym>
    <synonym>Dimindol</synonym>
    <synonym>Dirox</synonym>
    <synonym>Disprol</synonym>
    <synonym>Dol-Stop</synonym>
    <synonym>Dolcor</synonym>
    <synonym>Dolefin</synonym>
    <synonym>Dolegrippin</synonym>
    <synonym>Dolene Ap-65</synonym>
    <synonym>Dolgesic</synonym>
    <synonym>Doliprane</synonym>
    <synonym>Dolko</synonym>
    <synonym>Dolofugin</synonym>
    <synonym>Doloreduct</synonym>
    <synonym>Dolorfug</synonym>
    <synonym>Dolorol Forte</synonym>
    <synonym>Dolorstop</synonym>
    <synonym>Dolotec</synonym>
    <synonym>Dolprone</synonym>
    <synonym>Dorocoff</synonym>
    <synonym>Dresan</synonym>
    <synonym>Dristan Cold No Drowsiness</synonym>
    <synonym>Dristancito</synonym>
    <synonym>Duracetamol</synonym>
    <synonym>Duradyne Dhc</synonym>
    <synonym>Durapan</synonym>
    <synonym>Dymadon</synonym>
    <synonym>Dymadon Co</synonym>
    <synonym>Dymadon Forte</synonym>
    <synonym>Dypap</synonym>
    <synonym>Ecosetol</synonym>
    <synonym>Elixodyne</synonym>
    <synonym>Empracet</synonym>
    <synonym>Endecon</synonym>
    <synonym>Enelfa</synonym>
    <synonym>Eneril</synonym>
    <synonym>Esgic</synonym>
    <synonym>Esgic-Plus</synonym>
    <synonym>Eu-Med</synonym>
    <synonym>Excedrin</synonym>
    <synonym>Excedrin Caplets</synonym>
    <synonym>Excedrin Extra Strength Caplets</synonym>
    <synonym>Excipain</synonym>
    <synonym>Exdol</synonym>
    <synonym>Exdol Strong</synonym>
    <synonym>Fanalgic</synonym>
    <synonym>Farmadol</synonym>
    <synonym>Febranine</synonym>
    <synonym>Febrectal</synonym>
    <synonym>Febrectol</synonym>
    <synonym>Febrex</synonym>
    <synonym>Febricet</synonym>
    <synonym>Febridol</synonym>
    <synonym>Febrilix</synonym>
    <synonym>Febrin</synonym>
    <synonym>Febrinol</synonym>
    <synonym>Febro-Gesic</synonym>
    <synonym>Febrolin</synonym>
    <synonym>Femcet</synonym>
    <synonym>Fendon</synonym>
    <synonym>Fensum</synonym>
    <synonym>Fepanil</synonym>
    <synonym>Feverall</synonym>
    <synonym>Feverall Junior Strength</synonym>
    <synonym>Feverall Sprinkle Caps Junior Strength</synonym>
    <synonym>Fevor</synonym>
    <synonym>Finimal</synonym>
    <synonym>Finiweh</synonym>
    <synonym>Fioricet</synonym>
    <synonym>Fluparmol</synonym>
    <synonym>Fortalidon P</synonym>
    <synonym>Freka-cetamol</synonym>
    <synonym>Gattaphen T</synonym>
    <synonym>Gelocatil</synonym>
    <synonym>Geluprane</synonym>
    <synonym>Genapap</synonym>
    <synonym>Genapap Children'S Elixir</synonym>
    <synonym>Genapap Children'S Tablets</synonym>
    <synonym>Genapap Extra Strength Caplets</synonym>
    <synonym>Genapap Extra Strength Tablets</synonym>
    <synonym>Genapap Regular Strength Tablets</synonym>
    <synonym>Genebs</synonym>
    <synonym>Genebs Extra Strength Caplets</synonym>
    <synonym>Genebs Regular Strength Tablets</synonym>
    <synonym>Genebs X-Tra</synonym>
    <synonym>Geralgine-P</synonym>
    <synonym>Gripin Bebe</synonym>
    <synonym>Grippostad</synonym>
    <synonym>Gynospasmine</synonym>
    <synonym>Hedex</synonym>
    <synonym>Helon N</synonym>
    <synonym>Homoolan</synonym>
    <synonym>Hy-Phen</synonym>
    <synonym>Hycomine Compound</synonym>
    <synonym>Hydrocet</synonym>
    <synonym>Ildamol</synonym>
    <synonym>Inalgex</synonym>
    <synonym>Infadrops</synonym>
    <synonym>Infants' Feverall</synonym>
    <synonym>Influbene N</synonym>
    <synonym>Injectapap</synonym>
    <synonym>Intensin</synonym>
    <synonym>Janupap</synonym>
    <synonym>Junior Disprol</synonym>
    <synonym>Kataprin</synonym>
    <synonym>Kinder Finimal</synonym>
    <synonym>Korum</synonym>
    <synonym>Kratofin simplex</synonym>
    <synonym>Labamol</synonym>
    <synonym>Lekadol</synonym>
    <synonym>Lemgrip</synonym>
    <synonym>Lemsip</synonym>
    <synonym>Lestemp</synonym>
    <synonym>Liquagesic</synonym>
    <synonym>Liquigesic Co</synonym>
    <synonym>Liquiprin</synonym>
    <synonym>Liquiprin Children'S Elixir</synonym>
    <synonym>Liquiprin Infants Drops</synonym>
    <synonym>Lonarid</synonym>
    <synonym>Lonarid Mono</synonym>
    <synonym>Lorcet-Hd</synonym>
    <synonym>Lortab</synonym>
    <synonym>Lupocet</synonym>
    <synonym>Lyteca</synonym>
    <synonym>Lyteca Syrup</synonym>
    <synonym>Magnidol</synonym>
    <synonym>Malex N</synonym>
    <synonym>Malgis</synonym>
    <synonym>Malidens</synonym>
    <synonym>Maxadol</synonym>
    <synonym>Medigesic Plus</synonym>
    <synonym>Medinol Paediatric</synonym>
    <synonym>Medocodene</synonym>
    <synonym>Melabon Infantil</synonym>
    <synonym>Mexalen</synonym>
    <synonym>Midol Maximum Strength</synonym>
    <synonym>Midol PM Night Time Formula</synonym>
    <synonym>Midol Regular Strength</synonym>
    <synonym>Midol Teen Formula</synonym>
    <synonym>Migraleve Yellow</synonym>
    <synonym>Minafen</synonym>
    <synonym>Minoset</synonym>
    <synonym>Miralgin</synonym>
    <synonym>Momentum</synonym>
    <synonym>Mono Praecimed</synonym>
    <synonym>Multin</synonym>
    <synonym>N-(4-hydroxyphenyl)acetamide</synonym>
    <synonym>N-(4-Hydroxyphenyl)acetamide</synonym>
    <synonym>N-Acetyl-4-aminophenol</synonym>
    <synonym>N-Acetyl-p-aminophenol</synonym>
    <synonym>Naldegesic</synonym>
    <synonym>NAPA</synonym>
    <synonym>Napafen</synonym>
    <synonym>Napap</synonym>
    <synonym>Naprinol</synonym>
    <synonym>Nealgyl</synonym>
    <synonym>Nebs</synonym>
    <synonym>Neo-Fepramol</synonym>
    <synonym>NeoCitran</synonym>
    <synonym>Neodol</synonym>
    <synonym>Neodolito</synonym>
    <synonym>Neopap</synonym>
    <synonym>Neotrend</synonym>
    <synonym>Neuridon</synonym>
    <synonym>New Cortal for Children</synonym>
    <synonym>NilnOcen</synonym>
    <synonym>Nina</synonym>
    <synonym>No-Febril</synonym>
    <synonym>Nobedon</synonym>
    <synonym>Nodolex</synonym>
    <synonym>Noral</synonym>
    <synonym>Norcet</synonym>
    <synonym>Norco</synonym>
    <synonym>O-Acetaminophenol</synonym>
    <synonym>Ofirmev</synonym>
    <synonym>Oltyl</synonym>
    <synonym>Oralgan</synonym>
    <synonym>Oraphen-PD</synonym>
    <synonym>Ortensan</synonym>
    <synonym>Oxycet</synonym>
    <synonym>Oxycocet</synonym>
    <synonym>Oxycodone 2.5/Apap 500</synonym>
    <synonym>Oxycodone 5/Apap 500</synonym>
    <synonym>p-(Acetylamino)phenol</synonym>
    <synonym>p-Acetamidophenol</synonym>
    <synonym>p-Acetaminophenol</synonym>
    <synonym>p-Acetylaminophenol</synonym>
    <synonym>p-Hydroxyacetanilide</synonym>
    <synonym>p-Hydroxyphenolacetamide</synonym>
    <synonym>Paceco</synonym>
    <synonym>Pacemo</synonym>
    <synonym>Pacemol</synonym>
    <synonym>Pacet</synonym>
    <synonym>Pacimol</synonym>
    <synonym>Paedialgon</synonym>
    <synonym>Paedol</synonym>
    <synonym>Painex</synonym>
    <synonym>Paldesic</synonym>
    <synonym>Pamol</synonym>
    <synonym>Panacete</synonym>
    <synonym>Panadeine</synonym>
    <synonym>Panadeine Co</synonym>
    <synonym>Panadiene</synonym>
    <synonym>Panado-Co</synonym>
    <synonym>Panado-Co Caplets</synonym>
    <synonym>Panadol</synonym>
    <synonym>Panadol Extra Strength</synonym>
    <synonym>Panadol Junior Strength Caplets</synonym>
    <synonym>Panadol Maximum Strength Caplets</synonym>
    <synonym>Panadol Maximum Strength Tablets</synonym>
    <synonym>Panaleve</synonym>
    <synonym>Panamax</synonym>
    <synonym>Panasorb</synonym>
    <synonym>Panasorbe</synonym>
    <synonym>Panets</synonym>
    <synonym>Panex</synonym>
    <synonym>Panodil</synonym>
    <synonym>Panofen</synonym>
    <synonym>Pantalgin</synonym>
    <synonym>Papa-Deine #3</synonym>
    <synonym>Papa-Deine #4</synonym>
    <synonym>Para-Suppo</synonym>
    <synonym>Para-Tabs</synonym>
    <synonym>Paracemol</synonym>
    <synonym>Paracenol</synonym>
    <synonym>Paracet</synonym>
    <synonym>paracetamol</synonym>
    <synonym>Paracetamol</synonym>
    <synonym>Paracetamol (Acetaminophen)</synonym>
    <synonym>Paracetamol AL</synonym>
    <synonym>Paracetamol Antipanin P</synonym>
    <synonym>Paracetamol Basics</synonym>
    <synonym>Paracetamol BC</synonym>
    <synonym>Paracetamol DC</synonym>
    <synonym>Paracetamol Dr. Schmidgall</synonym>
    <synonym>Paracetamol Fecofar</synonym>
    <synonym>Paracetamol Genericon</synonym>
    <synonym>Paracetamol Hanseler</synonym>
    <synonym>Paracetamol Harkley</synonym>
    <synonym>Paracetamol Heumann</synonym>
    <synonym>Paracetamol Hexal</synonym>
    <synonym>Paracetamol Italfarmaco</synonym>
    <synonym>Paracetamol Nycomed</synonym>
    <synonym>Paracetamol PB</synonym>
    <synonym>Paracetamol Raffo</synonym>
    <synonym>Paracetamol Ratiopharm</synonym>
    <synonym>Paracetamol Rosch</synonym>
    <synonym>Paracetamol Saar</synonym>
    <synonym>Paracetamol SmithKline Beecham</synonym>
    <synonym>Paracetamol Stada</synonym>
    <synonym>Paracetamol von ct</synonym>
    <synonym>Paracetamol Winthrop</synonym>
    <synonym>Paracetamole</synonym>
    <synonym>Paracetamolo</synonym>
    <synonym>Paracetamolum</synonym>
    <synonym>Paracetanol</synonym>
    <synonym>Paracetol</synonym>
    <synonym>Paracin</synonym>
    <synonym>Paracod</synonym>
    <synonym>Paracodol</synonym>
    <synonym>Parador</synonym>
    <synonym>Paradrops</synonym>
    <synonym>Parakapton</synonym>
    <synonym>Parake</synonym>
    <synonym>Paralen</synonym>
    <synonym>Paralief</synonym>
    <synonym>Paralink</synonym>
    <synonym>Paralyoc</synonym>
    <synonym>Paramol</synonym>
    <synonym>Paramolan</synonym>
    <synonym>Paranox</synonym>
    <synonym>Parapan</synonym>
    <synonym>Parasedol</synonym>
    <synonym>Parasin</synonym>
    <synonym>Paraspen</synonym>
    <synonym>Parcetol</synonym>
    <synonym>Parelan</synonym>
    <synonym>Parmol</synonym>
    <synonym>Parogal</synonym>
    <synonym>Paroma</synonym>
    <synonym>Pasolind</synonym>
    <synonym>Pasolind N</synonym>
    <synonym>PCM Paracetamol Lichtenstein</synonym>
    <synonym>Pe-Tam</synonym>
    <synonym>Pediapirin</synonym>
    <synonym>Pediatrix</synonym>
    <synonym>Pedric</synonym>
    <synonym>Percocet</synonym>
    <synonym>Percocet-5</synonym>
    <synonym>Percocet-Demi</synonym>
    <synonym>Percogesic with Codeine</synonym>
    <synonym>Perdolan Mono</synonym>
    <synonym>Phenaphen</synonym>
    <synonym>Phenaphen Caplets</synonym>
    <synonym>Phenaphen W/Codeine</synonym>
    <synonym>Phendon</synonym>
    <synonym>Phenipirin</synonym>
    <synonym>Phogoglandin</synonym>
    <synonym>Phrenilin</synonym>
    <synonym>Phrenilin Forte</synonym>
    <synonym>Pinex</synonym>
    <synonym>Piramin</synonym>
    <synonym>Pirinasol</synonym>
    <synonym>Plicet</synonym>
    <synonym>Polmofen</synonym>
    <synonym>Predimol</synonym>
    <synonym>Predualito</synonym>
    <synonym>Prestwick_13</synonym>
    <synonym>Prodol</synonym>
    <synonym>Prompt</synonym>
    <synonym>Prontina</synonym>
    <synonym>Propacet</synonym>
    <synonym>Propacet 100</synonym>
    <synonym>Proval #3</synonym>
    <synonym>Puernol</synonym>
    <synonym>Pulmofen</synonym>
    <synonym>Pyregesic-C</synonym>
    <synonym>Pyrigesic</synonym>
    <synonym>Pyrinazine</synonym>
    <synonym>Pyromed</synonym>
    <synonym>Quiet World</synonym>
    <synonym>Redutemp</synonym>
    <synonym>Reliv</synonym>
    <synonym>Remedol</synonym>
    <synonym>Rhinex D-Lay Tablets</synonym>
    <synonym>Rivalgyl</synonym>
    <synonym>Robigesic</synonym>
    <synonym>Robitussin Night Relief</synonym>
    <synonym>Rockamol Plus</synonym>
    <synonym>Rounox</synonym>
    <synonym>Roxicet</synonym>
    <synonym>Roxicet 5/500</synonym>
    <synonym>Roxilox</synonym>
    <synonym>RubieMol</synonym>
    <synonym>Rubophen</synonym>
    <synonym>Rupemol</synonym>
    <synonym>Salzone</synonym>
    <synonym>Sanicet</synonym>
    <synonym>Sanicopyrine</synonym>
    <synonym>Scanol</synonym>
    <synonym>Scentalgyl</synonym>
    <synonym>Scherzatabletten Rezeptur 534</synonym>
    <synonym>Schmerzex</synonym>
    <synonym>Sedalito</synonym>
    <synonym>Sedapap</synonym>
    <synonym>Semolacin</synonym>
    <synonym>Servigesic</synonym>
    <synonym>Seskamol</synonym>
    <synonym>Setakop</synonym>
    <synonym>Setamol</synonym>
    <synonym>Setol</synonym>
    <synonym>Sifenol</synonym>
    <synonym>Sinaspril</synonym>
    <synonym>Sine-Off Sinus Medicine Caplets</synonym>
    <synonym>Sinedol</synonym>
    <synonym>Sinmol</synonym>
    <synonym>Sinubid</synonym>
    <synonym>SK-Apap</synonym>
    <synonym>Snaplets-FR</synonym>
    <synonym>Spalt fur die nacht</synonym>
    <synonym>Spalt N</synonym>
    <synonym>St Joseph Aspirin-Free</synonym>
    <synonym>St Joseph Aspirin-Free for Children</synonym>
    <synonym>St. Joseph Cold Tablets for Children</synonym>
    <synonym>St. Joseph Fever Reducer</synonym>
    <synonym>Stanback</synonym>
    <synonym>Stopain</synonym>
    <synonym>Sudafed Severe Cold Formula</synonym>
    <synonym>Sudafed Sinus</synonym>
    <synonym>Sunetheton</synonym>
    <synonym>Supac</synonym>
    <synonym>Supadol mono</synonym>
    <synonym>Supofen</synonym>
    <synonym>Suppap</synonym>
    <synonym>Suppap-120</synonym>
    <synonym>Suppap-325</synonym>
    <synonym>Suppap-650</synonym>
    <synonym>Supramol-M</synonym>
    <synonym>Synalgos-Dc-A</synonym>
    <synonym>Tabalgin</synonym>
    <synonym>Tachiprina</synonym>
    <synonym>Talacen</synonym>
    <synonym>Tapanol</synonym>
    <synonym>Tapanol Extra Strength Caplets</synonym>
    <synonym>Tapanol Extra Strength Tablets</synonym>
    <synonym>Tapar</synonym>
    <synonym>Tavist Allergy/Sinus/Headache</synonym>
    <synonym>Tazamol</synonym>
    <synonym>Temlo</synonym>
    <synonym>Tempanal</synonym>
    <synonym>Tempra</synonym>
    <synonym>Tempra Caplets</synonym>
    <synonym>Tempra Chewable Tablets</synonym>
    <synonym>Tempra D.S</synonym>
    <synonym>Tempra Drops</synonym>
    <synonym>Tempra Syrup</synonym>
    <synonym>Tencon</synonym>
    <synonym>Termacet</synonym>
    <synonym>Termalgin</synonym>
    <synonym>Termalgine</synonym>
    <synonym>Termofren</synonym>
    <synonym>TheraFlu</synonym>
    <synonym>Tibinide</synonym>
    <synonym>Tibizide</synonym>
    <synonym>Tiffy</synonym>
    <synonym>Tisin</synonym>
    <synonym>Tisiodrazida</synonym>
    <synonym>Titralgan</synonym>
    <synonym>Tizide</synonym>
    <synonym>Tocris-1706</synonym>
    <synonym>Toximer P</synonym>
    <synonym>Tralgon</synonym>
    <synonym>Treupel mon</synonym>
    <synonym>Treupel N</synonym>
    <synonym>Treuphadol</synonym>
    <synonym>Triad</synonym>
    <synonym>Triaminic Sore Throat Formula</synonym>
    <synonym>Triaprin</synonym>
    <synonym>Tricoton</synonym>
    <synonym>Tussapap</synonym>
    <synonym>Tycolet</synonym>
    <synonym>TYL</synonym>
    <synonym>Tylenol</synonym>
    <synonym>Tylenol Allergy Sinus</synonym>
    <synonym>Tylenol Arthritis Extended Relief</synonym>
    <synonym>Tylenol Caplets</synonym>
    <synonym>Tylenol Children'S Chewable Tablets</synonym>
    <synonym>Tylenol Children'S Elixir</synonym>
    <synonym>Tylenol Children'S Suspension Liquid</synonym>
    <synonym>Tylenol Drops</synonym>
    <synonym>Tylenol Elixir</synonym>
    <synonym>Tylenol Extra Strength Adult Liquid Pain Reliever</synonym>
    <synonym>Tylenol Extra Strength Caplets</synonym>
    <synonym>Tylenol Extra Strength Gelcaps</synonym>
    <synonym>Tylenol Extra Strength Tablets</synonym>
    <synonym>Tylenol Gelcaps</synonym>
    <synonym>Tylenol Infants Drops</synonym>
    <synonym>Tylenol Infants Suspension Drops</synonym>
    <synonym>Tylenol Junior Strength Caplets</synonym>
    <synonym>Tylenol Junior Strength Chewable Tablets</synonym>
    <synonym>Tylenol Regular Strength Caplets</synonym>
    <synonym>Tylenol Regular Strength Tablets</synonym>
    <synonym>Tylenol Tablets</synonym>
    <synonym>Tylex</synonym>
    <synonym>Tylex CD</synonym>
    <synonym>Tylol</synonym>
    <synonym>Tylox</synonym>
    <synonym>Tylox-325</synonym>
    <synonym>Tymol</synonym>
    <synonym>Ukonan D</synonym>
    <synonym>Ultracet</synonym>
    <synonym>Upsanol</synonym>
    <synonym>Utragin</synonym>
    <synonym>Valadol</synonym>
    <synonym>Valgesic</synonym>
    <synonym>Valorin</synonym>
    <synonym>Valorin Extra</synonym>
    <synonym>Vanquish</synonym>
    <synonym>Veralgina</synonym>
    <synonym>Vermidon</synonym>
    <synonym>Verpol</synonym>
    <synonym>Viclor Richet</synonym>
    <synonym>Vicodin</synonym>
    <synonym>Vicodin Es</synonym>
    <synonym>Vicodin Hp</synonym>
    <synonym>Vips</synonym>
    <synonym>Viruflu</synonym>
    <synonym>Vivimed</synonym>
    <synonym>Volpan</synonym>
    <synonym>Wygesic</synonym>
    <synonym>Zatinol</synonym>
    <synonym>Zolben</synonym>
  </synonyms>
  <chemical_formula>C8H9NO2</chemical_formula>
  <average_molecular_weight>151.1626</average_molecular_weight>
  <monisotopic_moleculate_weight>151.063328537</monisotopic_moleculate_weight>
  <iupac_name>N-(4-hydroxyphenyl)acetamide</iupac_name>
  <traditional_iupac>acetaminophen</traditional_iupac>
  <cas_registry_number>103-90-2</cas_registry_number>
  <smiles>CC(=O)NC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)</inchi>
  <inchikey>RZVAJINKPMORJF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>a small molecule</descriptor>
      <descriptor>acetamides</descriptor>
      <descriptor>phenols</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Exogenous</origin>
  <cellular_locations>
    <cellular_location>Cytoplasm</cellular_location>
    <cellular_location>Extracellular</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations>
    <tissue>All Tissues</tissue>
  </tissue_locations>
  <pathways>
    <pathway>
      <name>Acetaminophen Metabolism Pathway</name>
      <smpdb_id>SMP0000640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Acetaminophen Action Pathway</name>
      <smpdb_id>SMP0000710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Acetaminophen Action Pathway (New)</name>
      <smpdb_id>SMP0122823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Acetaminophen Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142775</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>169-171°C</value>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.4E+004 mg/L (at 25°C)</value>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.46</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.15e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(4-hydroxyphenyl)acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>151.1626</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RZVAJINKPMORJF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure>Oral, rapid and almost complete.</route_of_exposure>
  <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. 

In adults, single doses above 10 grams or 200 mg/kg of bodyweight, whichever is lower, have a reasonable likelihood of causing toxicity.</mechanism_of_toxicity>
  <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.&#13;
Route of Elimination: Approximately 80% of acetaminophen is excreted in the urine after conjugation and about 3% is excreted unchanged.&#13;
Half Life: 1 to 4 hours</metabolism>
  <toxicity>LD50: 338 mg/kg (Oral, Mouse) (A308)&#13;
LD50: 1944 mg/kg (Oral, Rat) (A308)&#13;
In adults, single doses above 10 grams or 200 mg/kg of bodyweight, whichever is lower, have a reasonable likelihood of causing toxicity.</toxicity>
  <lethaldose>25 g for an adult human. (A308)</lethaldose>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use_source>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.</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f721f8fd8e0&gt;</health_effects>
  <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.</symptoms>
  <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. (L1712) In patients who develop fulminant hepatic failure or who are otherwise expected to die from liver failure, the mainstay of management is liver transplantation.</treatment>
  <drugbank_id>DB00316</drugbank_id>
  <hmdb_id>HMDB01859</hmdb_id>
  <pubchem_compound_id>1983</pubchem_compound_id>
  <chembl_id>CHEMBL112</chembl_id>
  <chemspider_id>1906</chemspider_id>
  <kegg_id>C06804</kegg_id>
  <uniprot_id/>
  <omim_id/>
  <chebi_id>2386</chebi_id>
  <biocyc_id>CPD-7669</biocyc_id>
  <ctd_id>D000082</ctd_id>
  <stitch_id>Paracetamol </stitch_id>
  <actor_id>7</actor_id>
  <pdb_id>TYL</pdb_id>
  <wikipidia>Acetaminophen</wikipidia>
  <general_references>
    <reference>
      <pubmed_id>18048412</pubmed_id>
    </reference>
    <reference>
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    <reference>
      <reference_text>McEvoy GK (ed) (2007). American Hospital Formulary Service - Drug Information 2007. Bethesda, MD: American Society of Health-System Pharmacists.</reference_text>
    </reference>
    <reference>
      <reference_text>International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php</reference_text>
    </reference>
    <reference>
      <reference_text>Beaufort-Jasper Water &amp; Sewer Authority (2008). UL Drinking Water Laboratory.: http://media.islandpacket.com/smedia/2008/05/16/17/pharma_list.source.prod_affiliate.9.pdf</reference_text>
    </reference>
    <reference>
      <reference_text>Wikipedia. Acetaminophen. Last Updated 8 August 2009.: http://en.wikipedia.org/wiki/Acetaminophen</reference_text>
    </reference>
    <reference>
      <reference_text>Drugs.com: http://www.drugs.com/cons/Acetaminophen.html</reference_text>
    </reference>
    <reference>
      <reference_text>RxList: The Internet Drug Index (2009).: http://www.rxlist.com/</reference_text>
    </reference>
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    <target>
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    <target>
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    <target>
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    <target>
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    <target>
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    <target>
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    <target>
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    <target>
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    <target>
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      <references/>
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    <target>
      <target_id/>
      <mechanism_of_action/>
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      <references/>
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    <target>
      <target_id/>
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      <references/>
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    <target>
      <target_id/>
      <mechanism_of_action/>
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      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
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    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
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    <target>
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      <constants/>
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    <target>
      <target_id>BE0000262</target_id>
      <mechanism_of_action>Acetaminophen is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1 and COX-2, enzymes involved in prostaglandin (PG) synthesis. Unlike NSAIDs, acetaminophen does not inhibit cyclooxygenase in peripheral tissues and, thus, has no peripheral anti-inflammatory affects. While aspirin acts as an irreversible inhibitor of COX and directly blocks the enzyme's active site, studies have found that acetaminophen indirectly blocks COX, and that this blockade is ineffective in the presence of peroxides. This might explain why acetaminophen is effective in the central nervous system and in endothelial cells but not in platelets and immune cells which have high levels of peroxides. Studies also report data suggesting that acetaminophen selectively blocks a variant of the COX enzyme that is different from the known variants COX-1 and COX-2. This enzyme is now referred to as COX-3. Its exact mechanism of action is still poorly understood, but future research may provide further insight into how it works.</mechanism_of_action>
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          <constant_type>Inhibitory</constant_type>
          <value>&gt;10</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
        <constant>
          <constant_type>IC50</constant_type>
          <value>141</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0000267</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>10</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
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      <references/>
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      <target_id>BE0000322</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>6.2</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
    </target>
    <target>
      <target_id>BE0000017</target_id>
      <mechanism_of_action>Acetaminophen is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1 and COX-2, enzymes involved in prostaglandin (PG) synthesis. Unlike NSAIDs, acetaminophen does not inhibit cyclooxygenase in peripheral tissues and, thus, has no peripheral anti-inflammatory affects. While aspirin acts as an irreversible inhibitor of COX and directly blocks the enzyme's active site, studies have found that acetaminophen indirectly blocks COX, and that this blockade is ineffective in the presence of peroxides. This might explain why acetaminophen is effective in the central nervous system and in endothelial cells but not in platelets and immune cells which have high levels of peroxides. Studies also report data suggesting that acetaminophen selectively blocks a variant of the COX enzyme that is different from the known variants COX-1 and COX-2. This enzyme is now referred to as COX-3. Its exact mechanism of action is still poorly understood, but future research may provide further insight into how it works.</mechanism_of_action>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002382</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>IC50</constant_type>
          <value>44</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
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      <references/>
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    <target>
      <target_id>BE0001653</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>4.1</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0003634</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>10.6</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0003625</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>7.1</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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      <target_id>BE0000535</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>11.4</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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      <target_id>BE0003626</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>802</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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      <target_id>BE0003627</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>296</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0003628</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>658</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0003629</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>9.1</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0002437</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Inhibitory</constant_type>
          <value>70.7</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
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      <target_id>BE0003543</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>Dissociation</constant_type>
          <value>19.1</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
    </target>
    <target>
      <target_id>BE0004467</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>IC50</constant_type>
          <value>2.3</value>
          <units>uM</units>
          <assay_type/>
          <assay_source>BindingDB 26197</assay_source>
        </constant>
      </constants>
      <references/>
    </target>
    <target>
      <target_id>BE0000133</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0003533</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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    <target>
      <target_id>BE0002638</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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    <target>
      <target_id>BE0000933</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000180</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002240</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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    <target>
      <target_id>BE0000816</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000208</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0005581</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0005565</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000530</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0004767</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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      <target_id>BE0001979</target_id>
      <mechanism_of_action/>
      <constants>
        <constant>
          <constant_type>IC50</constant_type>
          <value>0.023</value>
          <units>uM</units>
          <assay_type/>
          <assay_source/>
        </constant>
      </constants>
      <references/>
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    <target>
      <target_id>BE0003388</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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      <target_id>BE0004992</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
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    <target>
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      <mechanism_of_action/>
      <constants/>
      <references/>
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      <target_id>BE0001023</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000486</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000749</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
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</compound>
