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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8NO2.Na
Molecular Weight 173.1444
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYACETANILIDE SODIUM

SMILES

[Na+].CC(=O)NC1=CC=C([O-])C=C1

InChI

InChIKey=QOGCGSWEVWTHNX-UHFFFAOYSA-M
InChI=1S/C8H9NO2.Na/c1-6(10)9-7-2-4-8(11)5-3-7;/h2-5,11H,1H3,(H,9,10);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H8NO2
Molecular Weight 150.1546
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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. 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). 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. 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 centers of the hypothalamus resulting in peripheral vasodilation, sweating and hence heat dissipation.

Originator

Curator's Comment: was first synthesized in 1877 at Johns Hopkins University by Harmon Northrop Morse

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
TYLENOL

Approved Use

Uses temporarily relieves minor aches and pains due to: minor pain of arthritis, muscular aches, backache, premenstrual abd menstrual cramps, the common cold, headache, toochache; temporary reduce fever

Launch Date

7.5798721E11
Palliative
TYLENOL

Approved Use

Uses temporarily relieves minor aches and pains due to: minor pain of arthritis, muscular aches, backache, premenstrual abd menstrual cramps, the common cold, headache, toochache; temporary reduce fever

Launch Date

7.5790077E11
Palliative
TYLENOL

Approved Use

Uses temporarily relieves minor aches and pains due to: minor pain of arthritis, muscular aches, backache, premenstrual abd menstrual cramps, the common cold, headache, toochache; temporary reduce fever

Launch Date

7.5790077E11
Palliative
TYLENOL

Approved Use

Uses temporarily relieves minor aches and pains due to: minor pain of arthritis, muscular aches, backache, premenstrual abd menstrual cramps, the common cold, headache, toochache; temporary reduce fever

Launch Date

7.5790077E11
Palliative
TYLENOL

Approved Use

Uses temporarily relieves minor aches and pains due to: minor pain of arthritis, muscular aches, backache, premenstrual abd menstrual cramps, the common cold, headache, toochache; temporary reduce fever

Launch Date

7.5790077E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28 μg/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ACETAMINOPHEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
43 μg × h/mL
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ACETAMINOPHEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.4 h
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ACETAMINOPHEN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes [Ki 2300 uM]
yes [Ki 5300 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
no
no
no
no
no
no
yes [Km 1500 uM]
yes [Km 1900 uM]
yes [Km 2300 uM]
yes [Km 3700 uM]
yes [Km 4000 uM]
yes [Km 5500 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Modifying effects of a mixture of acetaminophen, aspirin, dipyrone and ethenzamide on a multiorgan initiation model and its carcinogenicity in male F344 rats.
1999 Jan 8
Role of CYP1A2 in the toxicity of long-term phenacetin feeding in mice.
1999 Jul
Regular use of analgesics is a risk factor for renal cell carcinoma.
1999 Oct
[Does TNF-alpha contribute to liver disease physiopathology?].
2000
Time to onset of analgesia and analgesic efficacy of effervescent acetaminophen 1000 mg compared to tablet acetaminophen 1000 mg in postoperative dental pain: a single-dose, double-blind, randomized, placebo-controlled study.
2000 Apr
Acetaminophen controlled-release sprinkles versus acetaminophen immediate-release elixir in febrile children.
2000 Apr
[Acetaminophen toxicity in children as a "therapeutic misadventure"].
2000 Apr 16
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.
2000 Aug
Reduction of liver Fas expression by an antisense oligonucleotide protects mice from fulminant hepatitis.
2000 Aug
Hepatocellular response to chemical stress in CD-1 mice: induction of early genes and gamma-glutamylcysteine synthetase.
2000 Aug
Long-chain hydroxydicarboxylic aciduria, carnitine depletion and acetaminophen exposure.
2000 Mar
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
p-Aminophenol-induced liver toxicity: tentative evidence of a role for acetaminophen.
2001
Let the user beware. OTC drugs aren't necessarily 'safe when taken as directed.'.
2001 Feb
Opioids for chronic nonmalignant pain. Attitudes and practices of primary care physicians in the UCSF/Stanford Collaborative Research Network. University of California, San Francisco.
2001 Feb
Management of drug-induced liver disease.
2001 Feb
Hemolytic anemia after acetaminophen overdose in patient with glucose-6-phosphate dehydrogenase deficiency.
2001 Feb 15
[About paracetamol again].
2001 Feb 18
Idiosyncratic acute hepatitis caused by paracetamol in two patients with melanoma treated with high-dose interferon-alpha.
2001 Feb 20
ABC of diseases of liver, pancreas, and biliary system. Other causes of parenchymal liver disease.
2001 Feb 3
Acetaminophen toxicity induced non-oliguric acute tubular necrosis.
2001 Jan
Simultaneous determination of paracetamol and methocarbamol in tablets by ratio spectra derivative spectrophotometry and LC.
2001 Jan
Economic evaluation alongside n-of-1 trials: getting closer to the margin.
2001 Jan
Risk factors in the development of adverse reactions to N-acetylcysteine in patients with paracetamol poisoning.
2001 Jan
A comparison of the effect of nitroparacetamol and paracetamol on liver injury.
2001 Jan
One hundred percent online identity check of pharmaceutical products by near-infrared spectroscopy on the packaging line.
2001 Jan
Treatment of acetaminophen ingestion with a superactivated charcoal-cola mixture.
2001 Jan
Effects of rectally administered paracetamol on infants delivered by vacuum extraction.
2001 Jan
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.
2001 Jan 10
[Dexketoprofen-trometamol and tramadol in acute lumbago].
2001 Jan 11
Pharmacokinetics of oral diclofenac and acetaminophen in children after surgery.
2001 Mar
Experimental and theoretical microdialysis studies of in situ metabolism.
2001 Mar
Pediatric acetaminophen poisoning.
2001 Mar
A comparison of ropivacaine and bupivacaine for cervical plexus block.
2001 Mar
Patents

Sample Use Guides

2 caplets every 8 hours with water; don't take more than 6 caplets in 24 hours
Route of Administration: Oral
A time- and concentration-dependent decrease in intracellular GSH occurred in freshly isolated type II pneumocytes and alveolar macrophages exposed to subtoxic (
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:58:13 UTC 2023
Edited
by admin
on Sat Dec 16 18:58:13 UTC 2023
Record UNII
V9E6HW6ZAG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-HYDROXYACETANILIDE SODIUM
Common Name English
SODIUM P-ACETAMIDOPHENOLATE
Common Name English
4'-HYDROXYACETANILIDE, SODIUM SALT
Common Name English
ACETAMIDE, N-(4-HYDROXYPHENYL)-, SODIUM SALT (1:1)
Systematic Name English
SODIUM 4-ACETYLAMINOPHENOLATE
Common Name English
Code System Code Type Description
FDA UNII
V9E6HW6ZAG
Created by admin on Sat Dec 16 18:58:13 UTC 2023 , Edited by admin on Sat Dec 16 18:58:13 UTC 2023
PRIMARY
CAS
16958-94-4
Created by admin on Sat Dec 16 18:58:13 UTC 2023 , Edited by admin on Sat Dec 16 18:58:13 UTC 2023
PRIMARY
PUBCHEM
23667500
Created by admin on Sat Dec 16 18:58:13 UTC 2023 , Edited by admin on Sat Dec 16 18:58:13 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY