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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... show more » |
| 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
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