Chemical Component Summary

NameN-(4-HYDROXYPHENYL)ACETAMIDE (TYLENOL)
IdentifiersN-(4-hydroxyphenyl)ethanamide
FormulaC8 H9 N O2
Molecular Weight151.163
TypeNON-POLYMER
Isomeric SMILESCC(=O)Nc1ccc(cc1)O
InChIInChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
InChIKeyRZVAJINKPMORJF-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count20
Chiral Atom Count0
Bond Count20
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00316 
NameAcetaminophen
Groups approved
DescriptionAcetaminophen (paracetamol), also commonly known as _Tylenol_, is the most commonly taken analgesic worldwide and is recommended as first-line therapy in pain conditions by the World Health Organization (WHO).[A176318] It is also used for its antipyretic effects, helping to reduce fever.[F4124] This drug was initially approved by the U.S. FDA in 1951 and is available in a variety of forms including syrup form, regular tablets, effervescent tablets, injection, suppository, and other forms.[L5756,L5774,F4124,Label] Acetaminophen is often found combined with other drugs in more than 600 over the counter (OTC) allergy medications, cold medications, sleep medications, pain relievers, and other products.[L5783] Confusion about dosing of this drug may be caused by the availability of different formulas, strengths, and dosage instructions for children of different ages.[L5783] Due to the possibility of fatal overdose and liver failure associated with the incorrect use of acetaminophen, it is important to follow current and available national and manufacturer dosing guidelines while this drug is taken or prescribed.[L5786,L5789,Label]
Synonyms
  • 4-(Acetylamino)phenol
  • Paracétamol
  • N-acetyl-p-aminophenol
  • 4'-hydroxyacetanilide
  • p-hydroxyacetanilide
Brand Names
  • Day Time PE cold and flu relief
  • Walgreens High Blood Pressure Cold and Flu
  • Day Time Cold and Flu Relief
  • Healthy Accents infants pain and fever
  • Theraflu Flu Relief Max Strength Daytime Nighttime Value Pack
IndicationIn general, acetaminophen is used for the treatment of mild to moderate pain and reduction of fever.[F4124] It is available over the counter in various forms, the most common being oral forms. Acetaminophen _injection_ is indicated for the management of mild to moderate pain, the management of moderate to severe pain with adjunctive opioid analgesics, and the reduction of fever.[Label] Because of its low risk of causing allergic reactions, this drug can be administered in patients who are intolerant to salicylates and those with allergic tendencies, including bronchial asthmatics.[F4124] Specific dosing guidelines should be followed when administering acetaminophen to children.[L5780]
Categories
  • Acetaminophen and Prodrugs
  • Amides
  • Amines
  • Analgesics
  • Analgesics, Non-Narcotic
ATC-Code
  • N02BE71
  • N02BE01
  • N02AJ13
  • N02AJ17
  • N02BE51
CAS number103-90-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
Prostaglandin E synthase 3MQPASAKWYDRRDYVFIEFCVEDSKDVNVNFEKSKLTFSCLGGSDNFKHL...unknowninhibitor
Transient receptor potential cation channel subfamily V member 1MKKWSSTDLGAAADPLQKDTCPDPLDGDPNSRPPPAKPQLSTAKSRTRLF...unknownactivator
Cytochrome P450 2E1MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL112
PubChem 1983
ChEMBL CHEMBL112
ChEBI CHEBI:46195
CCDC/CSD HXACAN27, HXACAN47, HXACAN28, HXACAN31, HXACAN30, CUQKAC, HXACAN40, HXACAN11, HXACAN12, HXACAN10, HXACAN07, HXACAN09, HXACAN38, HXACAN37, HXACAN33, HXACAN36, HXACAN25, HXACAN08, HXACAN49, HXACAN35, HXACAN39, HXACAN46, BODSUL, HXACAN32, AMUBAM, HXACAN21, HXACAN14, HXACAN04, HXACAN22, HXACAN44, HXACAN23, COKCEL, HUMJEE, HXACAN06, HXACAN48, HXACAN13, HXACAN16, HXACAN18, HXACAN17, HXACAN45, HXACAN19, HXACAN01, HXACAN, HXACAN15, HXACAN24, HXACAN41, HXACAN42, ARAFOR, HXACAN52, HXACAN53
COD 7221912, 7221913, 7221914, 7221915, 7221917, 7221916, 7221918, 7221919, 4510931, 2102013, 2102014, 2102015, 2102016, 2201530, 2103464, 2103465, 2103466, 2103467, 2104364, 2007205, 1548348, 2105052, 2300230, 2300229, 2300232, 2300233, 2300234, 2300231, 2300236, 2300235, 2300237, 2300238, 2300241, 2300239, 2300242, 2300455, 7208248, 7103910, 7113592