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Overview
| Generic Names: | APAP; Acetaminofen; Paracetamol; Paracetamolo; Paracetanol |
|---|---|
| Trade Names: | Abenol; Abensanil; Acamol; Accu-Tap; Acephen; Aceta Elixir; Aceta Tablets; Acetagesic; Acetalgin; Actamin; Actimol; Algotropyl; Allay; Alpiny; Alpinyl; Alvedon; Amadil; Aminofen; Anacin; Anacin-3; Anaflon; Anapap; Anelix; Anhiba; Apacet; Apadon; Apamid; Apamide; Atasol; Banesin; Bayer Select; Bickie-mol; Bucet; Butapap; Calpol; Captin; Cetadol; Clixodyne; Co-Gesic; Conacetol; Dafalgan; Dapa; Dapa X-S; Darvocet; Datril; Dimindol; Dirox; Disprol; Dolene AP-65; Doliprane; Dolprone; Drixoral Plus; Dularin; Dymadon; Dypap; Elixodyne; Enelfa; Eneril; Eu-Med; Excedrin; Exdol; Febridol; Febrilix; Febrinol; Febro-Gesic; Febrolin; Fendon; Feverall; Fevor; Finimal; Gelocatil; Genapap; Genebs; Hedex; Homoolan; Hy-Phen; Injectapap; Janupap; Korum; Lestemp; Liquagesic; Liquiprin; Lonarid; Lyteca; Momentum; Multin; NAPA; Napafen; Napap; Naprinol; Nealgyl; Nebs; Neopap; Neotrend; Nobedon; Norco; Oraphen-PD; Ortensan; Pacemo; Painex; Paldesic; Panadol; Panaleve; Panasorb; Panets; Panex; Panofen; Papa-Deine; Paracet; Parapan; Paraspen; Parelan; Parmol; Pasolind; Pasolind N; Pedric; Phenaphen; Phenaphen Caplets; Phendon; Phrenilin; Phrenilin Forte; Prompt; Propacet 100; Proval #3; Pyrinazine; Redutemp; Rivalgyl; Robigesic; Rounox; SK-Apap; Salzone; Sedapap; Servigesic; Snaplets-FR; St. Joseph Fever Reducer; Suppap; Synalgos-Dc-A; Tabalgin; Talacen; Tapanol; Tapar; Tavist Allergy/Sinus/Headache; Temlo; Tempanal; Tempra; Tencon; Tibinide; Tibizide; Tisin; Tisiodrazida; Tizide; Tralgon; Triaprin; Tussapap; Tycolet; Tylenol; Ultracet; Valadol; Valgesic; Valorin; Valorin Extra; Wygesic |
| Brand Mixtures: | Amacodone (acetaminophen + hydrocodone bitartrate); Anexsia (acetaminophen + hydrocodone bitartrate); Anodynos (acetaminophen + hydrocodone bitartrate); Anolor (acetaminophen + butalbital + caffeine); Bancap (acetaminophen + hydrocodone bitartrate); CoGesic (acetaminophen + hydrocodone bitartrate); Dolacet (acetaminophen + hydrocodone bitartrate); Duradyne (acetaminophen + hydrocodone bitartrate); Endolor (acetaminophen + butalbital + caffeine); Esgic (acetaminophen + butalbital + caffeine); Fioricet (acetaminophen + butalbital + caffeine); Hydrocet (acetaminophen + hydrocodone bitartrate); Hydrogesic (acetaminophen + hydrocodone bitartrate); Lorcet (acetaminophen + hydrocodone bitartrate); Lortab (acetaminophen + hydrocodone bitartrate); Margesic (acetaminophen + hydrocodone bitartrate); Norcet (acetaminophen + hydrocodone bitartrate); Oxycet (acetaminophen + oxycodone hydrochloride); Percocet (acetaminophen + oxycodone hydrochloride); Roxicet (acetaminophen + oxycodone hydrochloride); Roxilox (acetaminophen + oxycodone hydrochloride); Stagesic (acetaminophen + hydrocodone bitartrate); TGesic (acetaminophen + hydrocodone bitartrate); Tylox (acetaminophen + oxycodone hydrochloride); Vicodin (acetaminophen + hydrocodone bitartrate); Zebutal (acetaminophen + butalbital + caffeine); Zydone (acetaminophen + hydrocodone bitartrate) |
| PharmGKB Accession Id: | PA448015 |
Description
Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage. PubChem (source: Drug Bank)
Indication
For temporary relief of fever and minor aches and pains. (source: Drug Bank)
ATC Therapeutic Category
- N02BE:Anilides
Pharmacology, Interactions, and Contraindications
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. (source: Drug Bank)
Pharmacology
Acetaminophen (USAN) or Paracetamol (INN) is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. It is a major ingredient in numerous cold and flu medications and many prescription analgesics. It is extremely safe in standard doses, but because of its wide availability, deliberate or accidental overdoses are not uncommon. Acetaminophen, unlike other common analgesics such as aspirin and ibuprofen, has no anti-inflammatory properties or effects on platelet function, and so it is not a member of the class of drugs known as non-steroidal anti-inflammatory drugs or NSAIDs. In normal doses acetaminophen does not irritate the lining of the stomach nor affect blood coagulation, the kidneys, or the fetal ductus arteriosus (as NSAIDs can). Like NSAIDs and unlike opioid analgesics, acetaminophen does not cause euphoria or alter mood in any way. Acetaminophen and NSAIDs have the benefit of being completely free of problems with addiction, dependence, tolerance and withdrawal. Acetaminophen is used on its own or in combination with pseudoephedrine, dextromethorphan, chlorpheniramine, diphenhydramine, doxylamine, codeine, hydrocodone, or oxycodone. (source: Drug Bank)
Food Interactions
Avoid alcohol (may increase risk of hepatotoxicity).
Take without regard to meals.
(source:
Drug Bank)
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Approximately 90 to 95% of a dose is metabolized in the liver via the cytochrome P450 enzyme pathways (primarily by conjugation with glucuronic acid, sulfuric acid, and cysteine). An intermediate metabolite is hepatotoxic and most likely nephrotoxic and can accumulate after the primary metabolic pathways have been saturated. (source: Drug Bank)
Protein Binding
25% (source: Drug Bank)
Absorption
Rapid and almost complete (source: Drug Bank)
Toxicity
Oral, mouse: LD<sub>50</sub> = 338 mg/kg; Oral, rat: LD<sub>50</sub> = 1944 mg/kg. 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. In adults, single doses above 10 grams or 140 mg/kg have a reasonable likelihood of causing toxicity. In adults, single doses of more than 25 grams have a high risk of lethality. (source: Drug Bank)
Isomeric SMILES Code:
CC(=O)Nc1ccc(cc1)O (source: Drug Bank)
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
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ABCB1 |
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BHMT2 |
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CYP2D6 |
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CYP2E1 |
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CYP3A |
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CYP3A4 |
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CYP3A5 |
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SULT1A1 |
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SULT1A3 |
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SULT1A4 |
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UGT1A1 |
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UGT1A6 |
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UGT1A9 |
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Publications |
A list of non-curated publications that mention this drug along with other genes is available.
Drug Targets
| Gene | Description | |
|---|---|---|
| PTGS1 |
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(source: Drug Bank) |
| PTGS2 |
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(source: Drug Bank) |
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
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acetylcysteine |
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tropisetron |
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warfarin |
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Publications |
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| Drug | Description | |
|---|---|---|
| acenocoumarol |
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Increases the anticoagulant effect (source: Drug Bank) |
| dicumarol |
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Increases the anticoagulant effect (source: Drug Bank) |
| imatinib |
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Increased hepatic toxicity of both agents (source: Drug Bank) |
| isoniazid |
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Risk of hepatotoxicity (source: Drug Bank) |
| warfarin |
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Acetaminophen increases the anticoagulant effect (source: Drug Bank) |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
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Bradycardia |
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Drug interaction with drug |
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Drug Toxicity |
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Gastroschisis |
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Liver Failure, Acute |
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Pain |
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Toxic liver disease |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
Common Searches
Search PubMed
Search Medline Plus
Search PubChem
Search CTD
Non-Curated Publications
A list of non-curated publications that mention this drug is available.
