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QuickView for paracetamol (compound)


PubChem
Name: Acetaminophen
PubChem Compound ID: 10441890
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.
Molecular formula: C8H9NO2
Molecular weight: 154.141 g/mol
DrugBank
Identification
Name: Acetaminophen
Name (isomeric): DB00316
Drug Type: small molecule
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.
Synonyms:
APAP; Acetaminofen; Paracetamol; Paracetanol; Paracetamolo
Brand: Febrinol, Dolene AP-65, Captin, Snaplets-FR, Pyrinazine, Ultracet, Tempanal, Gelocatil, Phrenilin, Ortensan, Servigesic, Febrolin, Phenaphen Caplets, Dimindol, Enelfa, Atasol, Dirox, Acamol, Multin, Cetadol, Anacin, Paraspen, Amadil, Apacet, Lestemp, Liquagesic, Nealgyl, SK-Apap, Pasolind, Tibizide, Napap, Nobedon, Conacetol, Tapar, Actamin, Dularin, Fevor, Dypap, Doliprane, Nebs, Painex, Drixoral Plus, Febro-Gesic, Panaleve, Korum, Panex, Pacemo, Lyteca, NAPA, Anapap, Proval #3, Parmol, Panasorb, Acephen, Alvedon, Homoolan, Apadon, Clixodyne, Abenol, Neopap, Norco, Fendon, Panets, Actimol, Feverall, Tavist Allergy/Sinus/Headache, Talacen, Aceta Tablets, Lonarid, Algotropyl, Tempra, Anhiba, Dapa X-S, Bucet, Wygesic, Tussapap, Temlo, Pedric, Eneril, Momentum, Napafen, Sedapap, Acetalgin, Injectapap, Acetagesic, Aceta Elixir, Bickie-mol, Febridol, Synalgos-Dc-A, Rounox, Finimal, Tapanol, Redutemp, Tisin, Valorin Extra, Naprinol, Butapap, Phendon, Panofen, Propacet 100, Dapa, Apamid, Tizide, Alpinyl, Bayer Select, Genebs, Papa-Deine, Abensanil, Febrilix, Valorin, Pasolind N, Valgesic, Janupap, Paldesic, Eu-Med, Dafalgan, Valadol, Datril, Co-Gesic, Aminofen, Disprol, Anacin-3, Exdol, Tralgon, Anaflon, Neotrend, Tabalgin, Salzone, Accu-Tap, Oraphen-PD, Triaprin, Phenaphen, Apamide, Genapap, Hedex, Tibinide, Rivalgyl, Paracet, Panadol, Anelix, Suppap, Tylenol, Alpiny, Tycolet, Tisiodrazida, Banesin, Prompt, Calpol, Parelan, Phrenilin Forte, Allay, Tencon, St. Joseph Fever Reducer, Robigesic, Elixodyne, Liquiprin, Dymadon, Parapan, Hy-Phen, Excedrin, Dolprone, Darvocet
Brand name mixture:
Oxycet(acetaminophen + oxycodone hydrochloride), Anodynos(acetaminophen + hydrocodone bitartrate), Hydrogesic(acetaminophen + hydrocodone bitartrate), Endolor(acetaminophen + butalbital + caffeine), Bancap(acetaminophen + hydrocodone bitartrate), Margesic(acetaminophen + hydrocodone bitartrate), CoGesic(acetaminophen + hydrocodone bitartrate), V...
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Category: Analgesics, Non-Narcotic, Antipyretics
CAS number: 103-90-2
Pharmacology
Indication: For temporary relief of fever and minor aches and pains.
Pharmacology:
Acetaminophen (USAN) or Paracetamol (INN) is a widely used 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, deli...
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Mechanism of Action:
Acetaminophen is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1, COX-2, and COX-3 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 ...
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Absorption: Rapid and almost complete
Protein binding: 25%
Biotransformation: Approximately 90 to 95% of a dose is conjugated in the liver with glucuronic acid and sulfuric acid. 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. Accumulation of NAPQI may occur if primary metabolic pathways are saturated.
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: Oral, mouse: LD50 = 338 mg/kg; Oral, rat: LD50 = 1944 mg/kg. Acetaminophen is metabolized primarily in the liver, where most of it is converted to inactive compounds by conjugation with glucuronic acid and, to a lesser extent, sulfuric acid. Conjugates are then excreted by the kidneys. Only a small portion is excreted in unchanged in urine or oxidized via the hepatic cytochrome P450 enzyme system (CYP2E1). Metabolism via CYP2E1 produces a toxic metabolite, N-acetyl-p-benzoquinoneimine (NAPQI). The toxic effects of acetaminophen are due to NAPQI, not acetaminophen itself nor any of the major metabolites. At therapeutic doses, NAPQI reacts with the sulfhydryl group of glutathione to produce a non-toxic conjugate that is excreted by the kidneys. High doses of acetaminophen may cause glutathione depletion, accumulation of NAPQI and hepatic necrosis. The maximum daily dose of acetaminophen is 4 g. Liver failure has been observed at doses as low as 6 g per day. As such, the maximum daily and single dose of acetaminophen is currently being reviewed in some countries. N-acetyl-cysteine, a precursor of glutathione, may be administered in the event of acetaminophen toxicity.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Avoid alcohol (may increase risk of hepatotoxicity).
Take without regard to meals.
Drug interaction:
DicumarolAcetaminophen may increase the anticoagulant effect of dicumarol. Monitor for changes in the therapeutic and adverse effects of dicumarol if acetaminophen is initiated, discontinued or dose changed.
ImatinibIncreased hepatic toxicity of both agents
AnisindioneAcetaminophen increases the anticoagulant effect of anisindione. Monitor for changes in the therapeutic and adverse effects of anisindione if acetaminophen is initiated, discontinued or dose changed.
WarfarinAcetaminophen increases the anticoagulant effect of warfarin. Monitor for changes in the therapeutic and adverse effects of warfarin if acetaminophen is initiated, discontinued or dose changed.
IsoniazidRisk of hepatotoxicity
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