You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameAcetaminophen
Accession NumberDB00316  (APRD00252)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
4-(Acetylamino)phenolNot AvailableNot Available
4-acetamidophenolNot AvailableNot Available
4'-hydroxyacetanilideNot AvailableNot Available
AcenolNot AvailableNot Available
AcetaminofenNot AvailableNot Available
AcetaminophenNot AvailableNot Available
AcetaminopheneNot AvailableNot Available
APAPNot AvailableNot Available
N-acetyl-p-aminophenolNot AvailableNot Available
p-acetamidophenolNot AvailableNot Available
p-acetaminophenolNot AvailableNot Available
p-AcetylaminophenolNot AvailableNot Available
p-hydroxyacetanilideNot AvailableNot Available
p-hydroxyphenolacetamideNot AvailableNot Available
PanadolNot AvailableNot Available
ParacetamolNot AvailableINN
ParacetamolumNot AvailableNot Available
TylenolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AbenolNot Available
AcamolTeva
AcephenNot Available
Aceta ElixirNot Available
Aceta TabletsNot Available
AcetalginNot Available
ActaminNot Available
ActimolNot Available
AlgotropylNot Available
AlvedonNot Available
AminofenNot Available
Anacin-3Not Available
AnhibaNot Available
ApacetNot Available
BanesinNot Available
CalpolNot Available
ConacetolNot Available
DafalganNot Available
Dapa X-SNot Available
DisprolNot Available
DolproneNot Available
DymadonNot Available
DypapNot Available
EnelfaNot Available
FebridolNot Available
FebrilixNot Available
FeverallNot Available
FinimalNot Available
GelocatilNot Available
GenapapNot Available
GenebsNot Available
InjectapapNot Available
LiquiprinNot Available
NapafenNot Available
OfirmevNot Available
Oraphen-PDNot Available
PaldesicNot Available
PanadolGlaxoSmithKline
PanofenNot Available
ParaspenNot Available
ParmolNot Available
RedutempNot Available
RounoxNot Available
SalzoneNot Available
Snaplets-FRNot Available
St. Joseph Fever ReducerNot Available
SuppapNot Available
TapanolNot Available
TempraNot Available
TylenolNot Available
ValorinNot Available
Brand mixtures
Brand NameIngredients
AlagesicCaffeine + Butalbital + Acetaminophen
Amacodoneacetaminophen + hydrocodone bitartrate
Anexsiaacetaminophen + hydrocodone bitartrate
Anodynosacetaminophen + hydrocodone bitartrate
Anoloracetaminophen + butalbital + caffeine
Bancapacetaminophen + hydrocodone bitartrate
BUPAPButalbital + Acetaminophen
ButapapButalbital + Acetaminophen
CapacetCaffeine + Butalbital + Acetaminophen
Co-codamolcodeine + acetaminophen
CoGesicacetaminophen + hydrocodone bitartrate
Dolacetacetaminophen + hydrocodone bitartrate
Duradyneacetaminophen + hydrocodone bitartrate
Endoloracetaminophen + butalbital + caffeine
Esgicacetaminophen + butalbital + caffeine
Esgic-PlusCaffeine + Butalbital + Acetaminophen
Fioricetacetaminophen + butalbital + caffeine
HycetAcetaminophen + Hydrocodone
Hydrocetacetaminophen + hydrocodone bitartrate
Hydrogesicacetaminophen + hydrocodone bitartrate
Lorcetacetaminophen + hydrocodone bitartrate
Lortabacetaminophen + hydrocodone bitartrate
MagnacetAcetaminophen + Oxycodone
Margesicacetaminophen + hydrocodone bitartrate
MaxidoneAcetaminophen + Hydrocodone
Norcetacetaminophen + hydrocodone bitartrate
ORBIVANCaffeine + Butalbital + Acetaminophen
Oxycetacetaminophen + oxycodone hydrochloride
Percocetacetaminophen + oxycodone hydrochloride
PhrenilinButalbital + Acetaminophen
PrimlevAcetaminophen + Oxycodone
Roxicetacetaminophen + oxycodone hydrochloride
Roxiloxacetaminophen + oxycodone hydrochloride
Stagesicacetaminophen + hydrocodone bitartrate
TenconAcetaminophen
TGesicacetaminophen + hydrocodone bitartrate
Tyloxacetaminophen + oxycodone hydrochloride
ULTRACETTramadol + Acetaminophen
Vicodinacetaminophen + hydrocodone bitartrate
XartemisAcetaminophen + Oxycodone
XodolAcetaminophen + Hydrocodone
XoloxAcetaminophen + Oxycodone
ZAMICETAcetaminophen + Hydrocodone
Zebutalacetaminophen + butalbital + caffeine
ZolvitAcetaminophen + Hydrocodone
Zydoneacetaminophen + hydrocodone bitartrate
Categories
CAS number103-90-2
WeightAverage: 151.1626
Monoisotopic: 151.063328537
Chemical FormulaC8H9NO2
InChI KeyRZVAJINKPMORJF-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)
IUPAC Name
N-(4-hydroxyphenyl)acetamide
SMILES
CC(=O)NC1=CC=C(O)C=C1
Mass Specshow(7.63 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassAnilides
Direct parentAnilides
Alternative parentsAminophenols; Secondary Carboxylic Acid Amides; Polyamines; Enolates; Carboxylic Acids; Enols
Substituentsaminophenol; phenol derivative; secondary carboxylic acid amide; carboxamide group; polyamine; enol; enolate; carboxylic acid derivative; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
Pharmacology
IndicationFor temporary relief of fever, minor aches, and pains.
PharmacodynamicsAcetaminophen (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 actionAcetaminophen 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.
AbsorptionRapid and almost complete
Volume of distributionNot Available
Protein binding25%
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.

SubstrateEnzymesProduct
Acetaminophen
NAPQIDetails
Acetaminophen
Acetaminophen glucuronideDetails
Acetaminophen
Acetaminophen sulfateDetails
NAPQI
Acetaminophen cysteinDetails
Route of eliminationApproximately 80% of acetaminophen is excreted in the urine after conjugation and about 3% is excreted unchanged.
Half life1 to 4 hours
ClearanceNot Available
ToxicityOral, 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
PathwayCategorySMPDB ID
Acetaminophen Metabolism PathwayDrug metabolismSMP00640
Acetaminophen Action PathwayDrug actionSMP00710
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9921
Blood Brain Barrier + 0.9544
Caco-2 permeable + 0.8285
P-glycoprotein substrate Non-substrate 0.8202
P-glycoprotein inhibitor I Non-inhibitor 0.982
P-glycoprotein inhibitor II Non-inhibitor 0.9781
Renal organic cation transporter Non-inhibitor 0.9292
CYP450 2C9 substrate Non-substrate 0.7259
CYP450 2D6 substrate Substrate 0.8918
CYP450 3A4 substrate Non-substrate 0.5554
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9755
CYP450 2C19 substrate Non-inhibitor 0.9161
CYP450 3A4 substrate Non-inhibitor 0.8496
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8842
Ames test Non AMES toxic 0.8767
Carcinogenicity Non-carcinogens 0.7654
Biodegradation Ready biodegradable 0.6342
Rat acute toxicity 1.8596 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9717
hERG inhibition (predictor II) Non-inhibitor 0.9597
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
FormRouteStrength
CapsuleOral500 mg
SolutionOral100 mg/ml
SolutionOral167 mg/5 ml
SuppositoryRectal120 mg
SuppositoryRectal125 mg
SuppositoryRectal325 mg
SuppositoryRectal650 mg
SuppositoryRectal80 mg
SuspensionOral160 mg/5 ml
TabletOral325 mg
TabletOral500 mg
Tablet, film coatedOral500 mg
Tablet, film coated, extended releaseOral650 mg
Tablet, orally disintegratingOral160 mg
Tablet, orally disintegratingOral80 mg
Prices
Unit descriptionCostUnit
Tylenol 100 325 mg tablet Bottle16.98USDbottle
Phrenilin Forte 50-650 mg capsule5.24USDcapsule
Phrenilin forte capsule4.46USDcapsule
Norco 7.5-325 tablet2.77USDtablet
Norco 10-325 tablet2.76USDtablet
Propoxyphen-apap 100-325 mg tablet2.66USDtablet
Darvocet-N 100 100-650 mg tablet2.33USDtablet
Norco 10-325 mg tablet2.14USDtablet
Ultracet 37.5-325 mg tablet1.95USDtablet
Propoxyphen-apap 100-500 mg tablet1.85USDtablet
Ultracet tablet1.79USDtablet
Darvocet-n 100 tablet1.72USDtablet
Tylenol with Codeine #4 300-60 mg tablet1.65USDtablet
Phrenilin 50-325 mg tablet1.63USDtablet
Norco 7.5-325 mg tablet1.61USDtablet
Darvocet a500 tablet1.5USDtablet
Norco 5-325 mg tablet1.43USDtablet
Darvocet A500 100-500 mg tablet1.38USDtablet
Phrenilin tablet1.32USDtablet
Norco 5-325 tablet1.19USDtablet
Darvocet-n 50 tablet1.14USDtablet
Hydrocodone-apap 10-750 tablet1.12USDtablet
Tylenol with Codeine #3 300-30 mg tablet1.1USDtablet
Tencon tablet1.01USDtablet
Hydrocodone-apap 7.5-650 tablet0.93USDtablet
Propoxyphene-apap 50-325 mg tablet0.93USDtablet
Co-gesic 5-500 tablet0.92USDeach
Sedapap 50-650 mg tablet0.92USDtablet
Clemastine fum 2.68 mg tablet0.86USDtablet
Feverall 120 mg suppository0.8USDsuppository
Feverall 325 mg suppository0.8USDsuppository
Feverall 80 mg suppository0.8USDsuppository
Tavist nd 10 mg tablet0.74USDtablet
Darvocet-N 50 50-325 mg tablet0.73USDtablet
Hydrocodone-apap 10-325 tablet0.7USDtablet
Hydrocodone-apap 7.5-325 tablet0.62USDtablet
Hydrocodone-apap 10-660 tablet0.61USDtablet
Acephen 650 mg suppository0.55USDsuppository
Propoxyphen-apap 100-650 mg tablet0.55USDtablet
Acephen 120 mg suppository0.54USDsuppository
Acephen 325 mg suppository0.54USDsuppository
Hydrocodone-apap 5-325 tablet0.54USDtablet
Hydrocodone-apap 10-500 tablet0.53USDtablet
Tavist-1 1.34 mg tablet0.5USDtablet
Acetaminophen 325 mg suppository0.44USDsuppository
Feverall 650 mg suppository0.43USDsuppository
Drixoral cold & allergy tablet sa0.4USDtablet
Acetaminophen 650 mg suppository0.39USDsuppository
Acetaminophen 120 mg suppository0.38USDsuppository
Apap-butalbital 325-50 tablet0.38USDtablet
Hydrocodone-apap 10-650 tablet0.37USDeach
Hydrocodone-apap 2.5-500 tablet0.33USDtablet
Tylenol flu max-strn gelcap0.24USDcapsule
Momentum caplet0.23USDcaplet
Tylenol cold gelcap0.23USDcapsule
Tylenol cold head congestion0.23USDeach
Tylenol cold multi-symp gelcap0.23USDcapsule
Tylenol allergy m-s caplet0.22USDcaplet
Tylenol cold multi-symptom caplet0.22USDcaplet
Tylenol cold head cong caplet0.21USDcaplet
Tylenol cold multi-symp caplet0.21USDcaplet
Tylenol cold severe congestion0.21USDeach
Tylenol sinus caplet0.21USDcaplet
Excedrin quicktabs0.2USDtablet
Tylenol allergy m-s night caplet0.2USDcaplet
Tylenol chest congestion caplet0.2USDcaplet
Tylenol cold head congest caplet0.2USDcaplet
Tylenol sinus congestion&pain0.2USDeach
Excedrin menstrual cmplt gelcap0.19USDcapsule
Jr. tylenol 160 mg meltaways0.19USDeach
Tylenol allergy complete caplet0.19USDcaplet
Tylenol allergy complete gelcap0.19USDcapsule
Tylenol allergy sinus gelcap0.19USDcapsule
Tylenol allergy sinus geltab0.19USDtablet
Tylenol flu nighttime gelcap0.19USDcapsule
Tylenol sinus congest-pain caplet0.19USDcaplet
Tylenol sinus gelcap0.19USDcapsule
Tylenol sinus geltab0.19USDtablet
Tylenol sinus nighttime caplet0.19USDcaplet
Tylenol arthritis geltab0.18USDtablet
Child tylenol cold/cough tablet0.17USDtablet
Childrens apap 80 mg tablet chew0.17USDtablet
Tavist max-str sinus caplet0.17USDcaplet
Tylenol allergy sinus caplet0.17USDcaplet
Tylenol cold caplet0.17USDcaplet
Tylenol severe allergy caplet0.17USDcaplet
Tylenol allergy multi-symptom0.16USDeach
Tylenol cold relief nightime0.16USDeach
Tylenol pm ex-strength gelcap0.16USDcapsule
Women's tylenol 500-25 capsule0.16USDcapsule
Excedrin migraine geltabs0.15USDtablet
Tylenol cold relief caplet0.15USDcaplet
Excedrin extra strength caplet0.14USDcaplet
Excedrin migraine caplet0.14USDcaplet
Excedrin sinus headache tablet0.14USDtablet
Excedrin tension headache tablet0.14USDtablet
Hydrocodone-apap 7.5-750 tablet0.13USDtablet
Tylenol arthritis caplet sa0.13USDcaplet
Tylenol ex-str 500 mg tablet0.13USDtablet
Acetaminophen 650 mg caplet0.12USDcaplet
Apap jr str 160 mg tablet chew0.12USDtablet
Hydrocodone-apap 7.5-500 tablet0.12USDtablet
Tylenol day & night value pack0.12USDeach
Acetaminophen 500 mg geltab0.11USDtablet
Acetaminophen 500 mg tablet0.11USDtablet
Child's tylenol 80 mg meltaway0.11USDeach
Eql pain relief 500 mg caplet0.1USDcaplet
Eql pain relief 500 mg geltab0.1USDtablet
Excedrin back & body caplet0.1USDcaplet
Excedrin sinus headache caplet0.1USDcaplet
Excedrin tension headache caplet0.1USDcaplet
Soba pain rel 500 mg gelcap0.1USDcapsule
Tylenol 8 hour 650 mg caplet0.1USDcaplet
Tylenol p.m. ex-str geltab0.1USDtablet
Tylenol pm ex-strength caplet0.1USDcaplet
Acetaminophen 160 mg tablet chw0.09USDtablet
Pain reliever 500 mg caplet0.09USDcaplet
Tylenol ex-str 500 mg geltab0.09USDtablet
Acetaminophen pm caplet0.08USDcaplet
Excedrin pm 500-38 mg tablet0.08USDtablet
Pain reliever 160 mg tablet0.08USDtablet
Tylenol es for arthritis pain0.08USDeach
Tylenol ex-str 500 mg caplet0.08USDcaplet
Tylenol pm ex-strength geltab0.08USDtablet
Acetaminophen 80 mg tablet chew0.07USDtablet
Acetaminophen powder dense0.07USDg
Apap 325 mg tablet0.07USDtablet
Apap child's 80 mg tablet chew0.07USDtablet
Soba pain rel xs 500 mg tablet0.07USDtablet
Tylenol 325 mg tablet0.07USDtablet
Acetaminophen 500 mg gelcap0.06USDtablet
CVS Pharmacy non-aspirin 500 mg caplet0.06USDcaplet
CVS Pharmacy non-aspirin 500 mg tablet0.06USDtablet
CVS Pharmacy pain relief 500 mg gelcap0.06USDcapsule
CVS Pharmacy pain rlf cool ice caplet0.06USDcaplet
Eql pain relief 325 mg tablet0.06USDtablet
Pain relief 500 mg caplet0.06USDcaplet
Pain reliever 325 mg tablet0.06USDtablet
Soba pain reliever 500 mg tablet0.06USDtablet
Child tylenol cough-runny nose0.05USDml
Child tylenol cough-sore thrt0.05USDml
Childs tylenol cold-cough susp0.05USDml
Mapap 325 mg tablet0.05USDtablet
Non-aspirin 500 mg geltab0.05USDtablet
Pain relief without asa tablet0.05USDtablet
Tylenol ex-str 500 mg gelcap0.05USDcapsule
Childs tylenol cold-aller susp0.04USDml
Childs tylenol plus cold susp0.04USDml
Childs tylenol plus flu susp0.04USDml
CVS Pharmacy acetaminophen 325 mg tablet0.04USDtablet
Non-aspirin 500 mg tablet0.04USDtablet
Pain reliever 500 mg geltab0.04USDtablet
Q-pap ex-str 500 mg tablet0.04USDtablet
Ra acetaminophen pm caplet0.04USDcaplet
Acetaminophen 325 mg tablet0.03USDtablet
Acetaminophen 500 mg caplet0.03USDcaplet
Genapap 325 mg tablet0.03USDtablet
Genapap 500 mg tablet0.03USDtablet
Pain relief 500 mg tablet0.03USDeach
Pain reliever 500 mg gelcap0.03USDcapsule
Pain reliever 500 mg tablet0.03USDtablet
Pain relief 325 mg tablet0.02USDtablet
Pain reliever w-o asa 325 mg0.02USDeach
Tylenol cold & flu severe liq0.02USDml
Tylenol cold m-s severe day liquid0.02USDml
Tylenol cough & sore throat lq0.02USDml
Tylenol nighttime liquid0.02USDml
Tylenol pm liquid0.02USDml
Tylenol sore throat liquid0.02USDml
Maxapap 325 mg tablet0.01USDtablet
Maxapap 500 mg caplet0.01USDeach
Maxapap 500 mg tablet0.01USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United StatesRE392211994-08-092011-08-09
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point169-171Merck Index 39
water solubility1.4E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.46SANGSTER (1994)
logS-1.03ADME Research, USCD
pKa9.38DASTMALCHI,S ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility4.15ALOGPS
logP0.51ALOGPS
logP0.91ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.9 m3·mol-1ChemAxon
Polarizability15.52 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis Reference

Jeffrey L. Finnan, Rudolph E. Lisa, Douglass N. Schmidt, “Process for preparing spray dried acetaminophen powder and the powder prepared thereby.” U.S. Patent US4710519, issued October, 1975.

US4710519
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
  8. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. Pubmed
  9. Hazai E, Vereczkey L, Monostory K: Reduction of toxic metabolite formation of acetaminophen. Biochem Biophys Res Commun. 2002 Mar 8;291(4):1089-94. Pubmed
External Links
ResourceLink
KEGG DrugD00217
KEGG CompoundC06804
PubChem Compound1983
PubChem Substance46506142
ChemSpider1906
BindingDB26197
ChEBI2386
ChEMBLCHEMBL112
Therapeutic Targets DatabaseDAP001436
PharmGKBPA448015
Drug Product Database2269120
RxListhttp://www.rxlist.com/cgi/generic/apap.htm
Drugs.comhttp://www.drugs.com/acetaminophen.html
WikipediaAcetaminophen
ATC CodesNot Available
AHFS Codes
  • 28:08.92
PDB EntriesNot Available
FDA labelshow(173 KB)
MSDSshow(71.9 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolAcetaminophen 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.
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.
DicoumarolAcetaminophen 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.
EltrombopagEltrombopag increases acetaminophen levels via decreasing metabolism. UDP-glucuronosyltransferase inhibition with unclear significance.
ImatinibIncreased hepatic toxicity of both agents
IsoniazidRisk of hepatotoxicity
LiraglutideThese agents may have decreased C max and a delayed T max during coadministration.
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.
Food Interactions
  • Avoid alcohol (may increase risk of hepatotoxicity).
  • Take without regard to meals.

Targets

1. Prostaglandin G/H synthase 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

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

3. Prostaglandin G/H synthase 3

Kind: protein

Organism: Mouse

Pharmacological action: unknown

Components

Name UniProt ID Details

References:

  1. Botting R, Ayoub SS: COX-3 and the mechanism of action of paracetamol/acetaminophen. Prostaglandins Leukot Essent Fatty Acids. 2005 Feb;72(2):85-7. Pubmed

Enzymes

1. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

9. UDP-glucuronosyltransferase 1-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-1 P22309 Details

References:

  1. Bock KW, Forster A, Gschaidmeier H, Bruck M, Munzel P, Schareck W, Fournel-Gigleux S, Burchell B: Paracetamol glucuronidation by recombinant rat and human phenol UDP-glucuronosyltransferases. Biochem Pharmacol. 1993 May 5;45(9):1809-14. Pubmed

10. UDP-glucuronosyltransferase 1-6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-6 P19224 Details

References:

  1. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. Pubmed

11. UDP-glucuronosyltransferase 1-9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-9 O60656 Details

References:

  1. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. Pubmed

12. UDP-glucuronosyltransferase 2B15

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B15 P54855 Details

References:

  1. Navarro SL, Chen Y, Li L, Li SS, Chang JL, Schwarz Y, King IB, Potter JD, Bigler J, Lampe JW: UGT1A6 and UGT2B15 polymorphisms and acetaminophen conjugation in response to a randomized, controlled diet of select fruits and vegetables. Drug Metab Dispos. 2011 Sep;39(9):1650-7. doi: 10.1124/dmd.111.039149. Epub 2011 Jun 10. Pubmed

13. UDP-glucuronosyltransferase 1-10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-10 Q9HAW8 Details

References:

  1. Kiang TK, Ensom MH, Chang TK: UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther. 2005 Apr;106(1):97-132. Epub 2005 Jan 12. Pubmed

14. Sulfotransferase 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Sulfotransferase 1A1 P50225 Details

References:

  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. Pubmed

15. Sulfotransferase 1A3/1A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Sulfotransferase 1A3/1A4 P50224 Details

References:

  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. Pubmed

16. Estrogen sulfotransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Estrogen sulfotransferase P49888 Details

References:

  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. Pubmed

17. Bile salt sulfotransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Bile salt sulfotransferase Q06520 Details

References:

  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. Pubmed

18. Arylamine N-acetyltransferase 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Arylamine N-acetyltransferase 2 P11245 Details

References:

  1. Rothen JP, Haefeli WE, Meyer UA, Todesco L, Wenk M: Acetaminophen is an inhibitor of hepatic N-acetyltransferase 2 in vitro and in vivo. Pharmacogenetics. 1998 Dec;8(6):553-9. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09