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Identification
Name Acetaminophen
Accession Number DB00316 (APRD00252)
Type small molecule
Groups approved
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.

Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Acetaminofen
APAP
Paracetamol
Paracetamolo
Paracetanol
Salts Not Available
Brand names
Name Company
Abenol
Abensanil
Acamol
Accu-Tap
Acephen
Aceta Elixir
Aceta Tablets
Acetagesic
Acetalgin
Actamin
Actimol
Algotropyl
Alpiny
Alpinyl
Alvedon
Amadil
Aminofen
Anacin-3
Anaflon
Anapap
Anelix
Anhiba
Apacet
Apadon
Apamide
Atasol
Banesin
Bayer Select
Bickie-mol
Calpol
Captin
Cetadol
Clixodyne
Conacetol
Dafalgan
Dapa X-S
Darvocet
Datril
Dimindol
Dirox
Disprol
Doliprane
Dolprone
Drixoral Plus
Dularin
Dymadon
Dypap
Elixodyne
Enelfa
Eneril
Eu-Med
Exdol
Febridol
Febrilix
Febrinol
Febro-Gesic
Febrolin
Fendon
Feverall
Fevor
Finimal
Gelocatil
Genapap
Genebs
Hedex
Homoolan
Injectapap
Janupap
Korum
Lestemp
Liquagesic
Liquiprin
Lonarid
Lyteca
Momentum
Multin
Napafen
Naprinol
Nealgyl
Nebs
Neopap
Neotrend
Nobedon
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
Prompt
Pyrinazine
Redutemp
Rivalgyl
Robigesic
Rounox
Salzone
Servigesic
SK-Apap
Snaplets-FR
St. Joseph Fever Reducer
Suppap
Synalgos-Dc-A
Tabalgin
Talacen
Tapanol
Tapar
Tavist Allergy/Sinus/Headache
Temlo
Tempanal
Tempra
Tibinide
Tibizide
Tisin
Tisiodrazida
Tizide
Tralgon
Tussapap
Tylenol
Valadol
Valgesic
Valorin
Valorin Extra
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Brand mixtures
Brand Name Ingredients
Amacodone acetaminophen + hydrocodone bitartrate
Anexsia acetaminophen + hydrocodone bitartrate
Anodynos acetaminophen + hydrocodone bitartrate
Anolor acetaminophen + butalbital + caffeine
Bancap acetaminophen + hydrocodone bitartrate
Co-codamol codeine + acetaminophen
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
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Categories
  • Analgesics, Non-Narcotic
  • Antipyretics
CAS number 103-90-2
Weight Average: 151.1626
Monoisotopic: 151.063328537
Chemical Formula C8H9NO2
InChI Key InChIKey=RZVAJINKPMORJF-UHFFFAOYSA-N
InChI
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
Plain Text
IUPAC Name
N-(4-hydroxyphenyl)acetamide
SMILES
CC(=O)NC1=CC=C(O)C=C1
Plain Text
Mass Spec show (7.63 KB)
Taxonomy
Kingdom Organic
Classes
  • Acetanilides
Substructures
  • Phenols and Derivatives
  • Amino Ketones
  • Benzene and Derivatives
  • Acetanilides
  • Carboxylic Acids and Derivatives
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Phenyl Esters
  • Anilines
Pharmacology
Indication For temporary relief of fever and minor aches and pains.
Pharmacodynamics 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, 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 it is not a member of the class of drugs known as non-steroidal anti-inflammatory drugs or NSAIDs. At therapeutic doses acetaminophen does not irritate the lining of the stomach nor affect blood coagulation, kidney function, 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.
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 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. The antipyretic properties of acetaminophen are likely due to direct effects on the heat-regulating centres of the hypothalamus resulting in peripheral vasodilation, sweating and hence heat dissipation.
Absorption Rapid and almost complete
Volume of distribution Not Available
Protein binding 25%
Metabolism 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
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Ortho mcneil pharmaceutical inc
  • G and w laboratories inc
  • Able laboratories inc
  • Actavis mid atlantic llc
  • Perrigo new york inc
  • Roxane laboratories inc
  • Polymedica industries inc
  • Mcneil consumer healthcare
  • Ohm laboratories inc
  • L perrigo co
  • Ranbaxy inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral 500 mg
Solution Oral 100 mg/ml
Solution Oral 167 mg/5 ml
Suppository Rectal 120 mg
Suppository Rectal 125 mg
Suppository Rectal 325 mg
Suppository Rectal 650 mg
Suppository Rectal 80 mg
Suspension Oral 160 mg/5 ml
Tablet Oral 325 mg
Tablet Oral 500 mg
Tablet, film coated Oral 500 mg
Tablet, film coated, extended release Oral 650 mg
Tablet, orally disintegrating Oral 160 mg
Tablet, orally disintegrating Oral 80 mg
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Prices
Unit description Cost Unit
Tylenol 100 325 mg tablet Bottle 16.98 USD bottle
Phrenilin Forte 50-650 mg capsule 5.24 USD capsule
Phrenilin forte capsule 4.46 USD capsule
Norco 7.5-325 tablet 2.77 USD tablet
Norco 10-325 tablet 2.76 USD tablet
Propoxyphen-apap 100-325 mg tablet 2.66 USD tablet
Darvocet-N 100 100-650 mg tablet 2.33 USD tablet
Norco 10-325 mg tablet 2.14 USD tablet
Ultracet 37.5-325 mg tablet 1.95 USD tablet
Propoxyphen-apap 100-500 mg tablet 1.85 USD tablet
Ultracet tablet 1.79 USD tablet
Darvocet-n 100 tablet 1.72 USD tablet
Tylenol with Codeine #4 300-60 mg tablet 1.65 USD tablet
Phrenilin 50-325 mg tablet 1.63 USD tablet
Norco 7.5-325 mg tablet 1.61 USD tablet
Darvocet a500 tablet 1.5 USD tablet
Norco 5-325 mg tablet 1.43 USD tablet
Darvocet A500 100-500 mg tablet 1.38 USD tablet
Phrenilin tablet 1.32 USD tablet
Norco 5-325 tablet 1.19 USD tablet
Darvocet-n 50 tablet 1.14 USD tablet
Hydrocodone-apap 10-750 tablet 1.12 USD tablet
Tylenol with Codeine #3 300-30 mg tablet 1.1 USD tablet
Tencon tablet 1.01 USD tablet
Hydrocodone-apap 7.5-650 tablet 0.93 USD tablet
Propoxyphene-apap 50-325 mg tablet 0.93 USD tablet
Co-gesic 5-500 tablet 0.92 USD each
Sedapap 50-650 mg tablet 0.92 USD tablet
Clemastine fum 2.68 mg tablet 0.86 USD tablet
Feverall 120 mg suppository 0.8 USD suppository
Feverall 325 mg suppository 0.8 USD suppository
Feverall 80 mg suppository 0.8 USD suppository
Tavist nd 10 mg tablet 0.74 USD tablet
Darvocet-N 50 50-325 mg tablet 0.73 USD tablet
Hydrocodone-apap 10-325 tablet 0.7 USD tablet
Hydrocodone-apap 7.5-325 tablet 0.62 USD tablet
Hydrocodone-apap 10-660 tablet 0.61 USD tablet
Acephen 650 mg suppository 0.55 USD suppository
Propoxyphen-apap 100-650 mg tablet 0.55 USD tablet
Acephen 120 mg suppository 0.54 USD suppository
Acephen 325 mg suppository 0.54 USD suppository
Hydrocodone-apap 5-325 tablet 0.54 USD tablet
Hydrocodone-apap 10-500 tablet 0.53 USD tablet
Tavist-1 1.34 mg tablet 0.5 USD tablet
Acetaminophen 325 mg suppository 0.44 USD suppository
Feverall 650 mg suppository 0.43 USD suppository
Drixoral cold & allergy tablet sa 0.4 USD tablet
Acetaminophen 650 mg suppository 0.39 USD suppository
Acetaminophen 120 mg suppository 0.38 USD suppository
Apap-butalbital 325-50 tablet 0.38 USD tablet
Hydrocodone-apap 10-650 tablet 0.37 USD each
Hydrocodone-apap 2.5-500 tablet 0.33 USD tablet
Tylenol flu max-strn gelcap 0.24 USD capsule
Momentum caplet 0.23 USD caplet
Tylenol cold gelcap 0.23 USD capsule
Tylenol cold head congestion 0.23 USD each
Tylenol cold multi-symp gelcap 0.23 USD capsule
Tylenol allergy m-s caplet 0.22 USD caplet
Tylenol cold multi-symptom caplet 0.22 USD caplet
Tylenol cold head cong caplet 0.21 USD caplet
Tylenol cold multi-symp caplet 0.21 USD caplet
Tylenol cold severe congestion 0.21 USD each
Tylenol sinus caplet 0.21 USD caplet
Excedrin quicktabs 0.2 USD tablet
Tylenol allergy m-s night caplet 0.2 USD caplet
Tylenol chest congestion caplet 0.2 USD caplet
Tylenol cold head congest caplet 0.2 USD caplet
Tylenol sinus congestion&pain 0.2 USD each
Excedrin menstrual cmplt gelcap 0.19 USD capsule
Jr. tylenol 160 mg meltaways 0.19 USD each
Tylenol allergy complete caplet 0.19 USD caplet
Tylenol allergy complete gelcap 0.19 USD capsule
Tylenol allergy sinus gelcap 0.19 USD capsule
Tylenol allergy sinus geltab 0.19 USD tablet
Tylenol flu nighttime gelcap 0.19 USD capsule
Tylenol sinus congest-pain caplet 0.19 USD caplet
Tylenol sinus gelcap 0.19 USD capsule
Tylenol sinus geltab 0.19 USD tablet
Tylenol sinus nighttime caplet 0.19 USD caplet
Tylenol arthritis geltab 0.18 USD tablet
Child tylenol cold/cough tablet 0.17 USD tablet
Childrens apap 80 mg tablet chew 0.17 USD tablet
Tavist max-str sinus caplet 0.17 USD caplet
Tylenol allergy sinus caplet 0.17 USD caplet
Tylenol cold caplet 0.17 USD caplet
Tylenol severe allergy caplet 0.17 USD caplet
Tylenol allergy multi-symptom 0.16 USD each
Tylenol cold relief nightime 0.16 USD each
Tylenol pm ex-strength gelcap 0.16 USD capsule
Women's tylenol 500-25 capsule 0.16 USD capsule
Excedrin migraine geltabs 0.15 USD tablet
Tylenol cold relief caplet 0.15 USD caplet
Excedrin extra strength caplet 0.14 USD caplet
Excedrin migraine caplet 0.14 USD caplet
Excedrin sinus headache tablet 0.14 USD tablet
Excedrin tension headache tablet 0.14 USD tablet
Hydrocodone-apap 7.5-750 tablet 0.13 USD tablet
Tylenol arthritis caplet sa 0.13 USD caplet
Tylenol ex-str 500 mg tablet 0.13 USD tablet
Acetaminophen 650 mg caplet 0.12 USD caplet
Apap jr str 160 mg tablet chew 0.12 USD tablet
Hydrocodone-apap 7.5-500 tablet 0.12 USD tablet
Tylenol day & night value pack 0.12 USD each
Acetaminophen 500 mg geltab 0.11 USD tablet
Acetaminophen 500 mg tablet 0.11 USD tablet
Child's tylenol 80 mg meltaway 0.11 USD each
Eql pain relief 500 mg caplet 0.1 USD caplet
Eql pain relief 500 mg geltab 0.1 USD tablet
Excedrin back & body caplet 0.1 USD caplet
Excedrin sinus headache caplet 0.1 USD caplet
Excedrin tension headache caplet 0.1 USD caplet
Soba pain rel 500 mg gelcap 0.1 USD capsule
Tylenol 8 hour 650 mg caplet 0.1 USD caplet
Tylenol p.m. ex-str geltab 0.1 USD tablet
Tylenol pm ex-strength caplet 0.1 USD caplet
Acetaminophen 160 mg tablet chw 0.09 USD tablet
Pain reliever 500 mg caplet 0.09 USD caplet
Tylenol ex-str 500 mg geltab 0.09 USD tablet
Acetaminophen pm caplet 0.08 USD caplet
Excedrin pm 500-38 mg tablet 0.08 USD tablet
Pain reliever 160 mg tablet 0.08 USD tablet
Tylenol es for arthritis pain 0.08 USD each
Tylenol ex-str 500 mg caplet 0.08 USD caplet
Tylenol pm ex-strength geltab 0.08 USD tablet
Acetaminophen 80 mg tablet chew 0.07 USD tablet
Acetaminophen powder dense 0.07 USD g
Apap 325 mg tablet 0.07 USD tablet
Apap child's 80 mg tablet chew 0.07 USD tablet
Soba pain rel xs 500 mg tablet 0.07 USD tablet
Tylenol 325 mg tablet 0.07 USD tablet
Acetaminophen 500 mg gelcap 0.06 USD tablet
CVS Pharmacy non-aspirin 500 mg caplet 0.06 USD caplet
CVS Pharmacy non-aspirin 500 mg tablet 0.06 USD tablet
CVS Pharmacy pain relief 500 mg gelcap 0.06 USD capsule
CVS Pharmacy pain rlf cool ice caplet 0.06 USD caplet
Eql pain relief 325 mg tablet 0.06 USD tablet
Pain relief 500 mg caplet 0.06 USD caplet
Pain reliever 325 mg tablet 0.06 USD tablet
Soba pain reliever 500 mg tablet 0.06 USD tablet
Child tylenol cough-runny nose 0.05 USD ml
Child tylenol cough-sore thrt 0.05 USD ml
Childs tylenol cold-cough susp 0.05 USD ml
Mapap 325 mg tablet 0.05 USD tablet
Non-aspirin 500 mg geltab 0.05 USD tablet
Pain relief without asa tablet 0.05 USD tablet
Tylenol ex-str 500 mg gelcap 0.05 USD capsule
Childs tylenol cold-aller susp 0.04 USD ml
Childs tylenol plus cold susp 0.04 USD ml
Childs tylenol plus flu susp 0.04 USD ml
CVS Pharmacy acetaminophen 325 mg tablet 0.04 USD tablet
Non-aspirin 500 mg tablet 0.04 USD tablet
Pain reliever 500 mg geltab 0.04 USD tablet
Q-pap ex-str 500 mg tablet 0.04 USD tablet
Ra acetaminophen pm caplet 0.04 USD caplet
Acetaminophen 325 mg tablet 0.03 USD tablet
Acetaminophen 500 mg caplet 0.03 USD caplet
Genapap 325 mg tablet 0.03 USD tablet
Genapap 500 mg tablet 0.03 USD tablet
Pain relief 500 mg tablet 0.03 USD each
Pain reliever 500 mg gelcap 0.03 USD capsule
Pain reliever 500 mg tablet 0.03 USD tablet
Pain relief 325 mg tablet 0.02 USD tablet
Pain reliever w-o asa 325 mg 0.02 USD each
Tylenol cold & flu severe liq 0.02 USD ml
Tylenol cold m-s severe day liquid 0.02 USD ml
Tylenol cough & sore throat lq 0.02 USD ml
Tylenol nighttime liquid 0.02 USD ml
Tylenol pm liquid 0.02 USD ml
Tylenol sore throat liquid 0.02 USD ml
Maxapap 325 mg tablet 0.01 USD tablet
Maxapap 500 mg caplet 0.01 USD each
Maxapap 500 mg tablet 0.01 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States RE39221 1994-08-09 2011-08-09
Properties
State solid
Experimental Properties
Property Value Source
melting point 170 °C PhysProp
water solubility 1.4E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 0.46 SANGSTER (1994)
logS -1.03 ADME Research, USCD
pKa 9.38 DASTMALCHI,S ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 4.15e+00 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 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 42.9 ChemAxon
polarizability 15.52 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Kis B, Snipes JA, Busija DW: Acetaminophen and the cyclooxygenase-3 puzzle: sorting out facts, fictions, and uncertainties. J Pharmacol Exp Ther. 2005 Oct;315(1):1-7. Epub 2005 May 6. Pubmed
  2. Aronoff DM, Oates JA, Boutaud O: New insights into the mechanism of action of acetaminophen: Its clinical pharmacologic characteristics reflect its inhibition of the two prostaglandin H2 synthases. Clin Pharmacol Ther. 2006 Jan;79(1):9-19. Pubmed
  3. Bertolini A, Ferrari A, Ottani A, Guerzoni S, Tacchi R, Leone S: Paracetamol: new vistas of an old drug. CNS Drug Rev. 2006 Fall-Winter;12(3-4):250-75. Pubmed
  4. Graham GG, Scott KF: Mechanism of action of paracetamol. Am J Ther. 2005 Jan-Feb;12(1):46-55. Pubmed
  5. Ohki S, Ogino N, Yamamoto S, Hayaishi O: Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. J Biol Chem. 1979 Feb 10;254(3):829-36. Pubmed
  6. Bertolini A, Ferrari A, Ottani A, Guerzoni S, Tacchi R, Leone S: Paracetamol: new vistas of an old drug. CNS Drug Rev. 2006 Fall-Winter;12(3-4):250-75. Pubmed
  7. Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS, Simmons DL: COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31. Epub 2002 Sep 19. Pubmed
External Links
Resource Link
KEGG Drug D00217 Link_out
KEGG Compound C06804 Link_out
PubChem Compound 1983 Link_out
PubChem Substance 46506142 Link_out
ChemSpider 1906 Link_out
BindingDB 26197 Link_out
ChEBI 2386 Link_out
ChEMBL 2386 Link_out
Therapeutic Targets Database DAP001436 Link_out
PharmGKB PA448015 Link_out
Drug Product Database 2269120 Link_out
RxList http://www.rxlist.com/cgi/generic/apap.htm Link_out
Drugs.com http://www.drugs.com/acetaminophen.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Acetaminophen Link_out
ATC Codes
  • N02BE01
AHFS Codes
  • 28:08.92
PDB Entries Not Available
FDA label show (173 KB)
MSDS show (71.9 KB)
Interactions
Drug Interactions
Drug Interaction
Acenocoumarol Acetaminophen may increase the anticoagulant effect of acenocoumarol. Monitor for changes in the therapeutic and adverse effects of acenocoumarol if acetaminophen is initiated, discontinued or dose changed.
Anisindione Acetaminophen 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.
Dicumarol Acetaminophen 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.
Eltrombopag Eltrombopag increases acetaminophen levels via decreasing metabolism. UDP-glucuronosyltransferase inhibition with unclear significance.
Imatinib Increased hepatic toxicity of both agents
Isoniazid Risk of hepatotoxicity
Warfarin Acetaminophen 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.
Food Interactions
  • Avoid alcohol (may increase risk of hepatotoxicity).
  • Take without regard to meals.
Targets

1. Prostaglandin G/H synthase 2

Pharmacological action: yes
Actions: inhibitor

May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

Organism class: human
UniProt ID: P35354 Link_out
Gene: PTGS2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Lee YS, Kim H, Brahim JS, Rowan J, Lee G, Dionne RA: Acetaminophen selectively suppresses peripheral prostaglandin E2 release and increases COX-2 gene expression in a clinical model of acute inflammation. Pain. 2007 Jun;129(3):279-86. Epub 2006 Dec 18. Pubmed
  3. Hinz B, Cheremina O, Brune K: Acetaminophen (paracetamol) is a selective cyclooxygenase-2 inhibitor in man. FASEB J. 2007 Sep 20;. Pubmed
  4. Weinheimer EM, Jemiolo B, Carroll CC, Harber MP, Haus JM, Burd NA, LeMoine JK, Trappe SW, Trappe TA: Resistance exercise and cyclooxygenase (COX) expression in human skeletal muscle: implications for COX-inhibiting drugs and protein synthesis. Am J Physiol Regul Integr Comp Physiol. 2007 Jun;292(6):R2241-8. Epub 2007 Feb 22. Pubmed

2. Prostaglandin G/H synthase 1

Pharmacological action: yes
Actions: inhibitor

May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

Organism class: human
UniProt ID: P23219 Link_out
Gene: PTGS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 1A2

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Raucy JL, Lasker JM, Lieber CS, Black M: Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys. 1989 Jun;271(2):270-83. Pubmed

2. Cytochrome P450 2E1

Actions: substrate

Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms

UniProt ID: P05181 Link_out
Gene: CYP2E1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Dong H, Haining RL, Thummel KE, Rettie AE, Nelson SD: Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400. Pubmed

3. Cytochrome P450 2D6

Actions: substrate

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  2. Dong H, Haining RL, Thummel KE, Rettie AE, Nelson SD: Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400. Pubmed

4. Cytochrome P450 1A1

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2A6

Actions: substrate

Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase

UniProt ID: P11509 Link_out
Gene: CYP2A6
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2C8

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2C9

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan

UniProt ID: P11712 Link_out
Gene: CYP2C9
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 3A4

Actions: substrate, inhibitor, inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Actions: substrate, inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. Pubmed
  2. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. Pubmed

2. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out
Gene: hROAT1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19