Acetaminophen

HCID 1983CAS 103-90-2

Basic information

Standard SMILES
CC(=O)Nc1ccc(O)cc1
InChIKey
RZVAJINKPMORJF-UHFFFAOYSA-N
Molecular formula
C8H9NO2
Average molar mass
151.16 g/mol
Monoisotopic mass
151.06332853

Names & identifiers

Preferred name
Acetaminophen
IUPAC
N-(4-hydroxyphenyl)acetamide
English name
Acetaminophen
Molecular formula
C8H9NO2
Molecular weight
151.16

Names & synonyms

acetaminophenParacetamol4-Acetamidophenol103-90-2N-(4-Hydroxyphenyl)acetamideTylenolAPAP4'-HydroxyacetanilideDatrilPanadolN-Acetyl-p-aminophenolAcetaminofen
Show more names
PARACETAMOL POWDER4-ACETAMINOPHENOLexcedrin
Algotropylp-Acetamidophenolp-HydroxyacetanilideDolipraneAcamolAnelixLonaridNaprinol

Database identifiers

CAS
103-90-2
PubChem CID
1983
DTXSID
DTXSID2020006
ChEMBL
CHEMBL112
ChEBI
CHEBI:46195
UNII
362O9ITL9D
EC Number
203-157-5
Nikkaji
J4.025H

Properties

Computed structural properties

XLogP
0.5
Topological polar surface area
49.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
11

Physicochemical properties

Melting point
168 · 168-172 °C(lit.)
Boiling point
273.17 °C · 273.17°C (rough estimate)
Density
1 · 1,293 g/cm3
vapor pressure
0.008 Pa · 0.008Pa at 25℃
refractive index
1.581 · 1.5810 (rough estimate)
Flash point
11 °C · 11 °C

Safety & regulation

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
AE4200000
ridadr
UN 3077 9/PG III
hs_code
29242930

Chemistry & industry

Applications · 9 items

DescriptionAcetaminophen differs from the nonsteroidal anti-inflammatory agents described in that it is devoid of anti-inflammatory and antirheumatic properties. It was recently shown that acetaminophen, like aspirin, inhibits cyclooxygenase action in the brain and is even stronger than aspirin. On the other hand, the mechanism of analgesic action of acetaminophen is not fully clear, since it acts poorly on peripheral cyclooxygenase.

DescriptionAcetaminophen is an analgesic and antipyretic compound. Unlike many NSAIDs, which inhibit both COX-1 and COX-2, early studies suggested that acetaminophen is a poor inhibitor of both isoforms. However, it does inhibit COX-2 by 83% and COX-1 by 56% in human blood ex vivo, albeit at a high 1,000 mg dose, with IC50 values of 25.8 and 113.7 μM, respectively. Acetaminophen is enzymatically and non-enzymatically converted to several reactive metabolites that contribute to adverse or indirect effects, including liver injury. At toxic doses, the acetaminophen metabolite N-acetyl-4-benzoquinone imine (NAPQI; ) depletes glutathione reserves in the liver, leading to an accumulation of NAPQI and subsequent hepatocyte necrosis. Acetaminophen decreases glutathione levels and reduces glutathione peroxidase activity in mice when administered at a dose of 250 mg/kg and induces ferroptotic cell death in primary mouse hepatocytes, an effect that can be blocked by the ferroptosis inhibitor ferrostatin-1 . Acetaminophen has analgesic and antipyretic properties in animal models.

HistoryAcetaminophen was first discovered by H. N. Morse in 1878. Although many studies on its use as an analgesic were performed, it wasn’t until 1950 that it was marketed under the name Triagesic. Today, its most common trade names are Tylenol and Panadol, but a large percentage of its sales are as a generic drug. It is the most commonly used medication for pain and fever in both the United States and Europe. It is on the World Health Organization's List of Essential Medicines.

UsesAnalgesic; antipyretic

Usesantiinfectant

Usesdispersing agent in liquid scintillation counting

Usesmanufacture of azo dyes, photographic chemicals.

UsesAcetaminophen is widely used as an analgesic and fever-reducing agent. Acetaminophen is designed for moderate analgesia. It is also effective like aspirin and is used in analgesia for headaches (from weak to moderate pain), myalgia, arthralgia, chronic pain, for oncological and post-operational pain, etc.

General DescriptionOdorless white crystalline solid. Bitter taste. pH (saturated aqueous solution) about 6.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北常奥药业有限公司027-87058617 13419515565
Additional notes · 1 item

DefinitionChEBI: Paracetamol is a member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group. It has a role as a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor, a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic, an environmental contaminant, a human blood serum metabolite, a hepatotoxic agent, a ferroptosis inducer and a geroprotector. It is a member of phenols and a member of acetamides. It is functionally related to a 4-aminophenol.

Related reactions

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