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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8NO2.K
Molecular Weight 189.2529
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POTASSIUM 4-ACETAMIDOPHENOLATE

SMILES

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

InChI

InChIKey=ONXCHMFMYVEUTI-UHFFFAOYSA-M
InChI=1S/C8H9NO2.K/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 K
Molecular Weight 39.0983
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
The degradation of paracetamol (4-hydroxyacetanilide) and other substituted acetanilides by a Penicillium species.
1975
Massive hemolysis caused by acetaminophen. Positive determination by direct Coombs test.
1976 Dec 13
An experimental study on the disorders of hepatic hemodynamics and changes of plasma histamine in dogs with fulminant hepatic failure.
1998
Isolated acute renal failure due to paracetamol intoxication in an alcoholic patient.
1999
Paracetamol-induced fulminant hepatic failure in a child after 5 days of therapeutic doses.
1999
Early metabolic acidosis and coma after acetaminophen ingestion.
1999 Apr
Assay to detect inhibitory substances in serum of patients with acute liver failure.
1999 Feb
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
Risk factors for acetaminophen and nimesulide intolerance in patients with NSAID-induced skin disorders.
1999 Jun
Characteristics and risk factors of acetaminophen-induced hepatitis in Taiwan.
1999 Jun
Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells.
1999 May 21
Clinical use of a bioartificial liver in the treatment of acetaminophen-induced fulminant hepatic failure.
1999 Oct
Stimulatory effects of silibinin and silicristin from the milk thistle Silybum marianum on kidney cells.
1999 Sep
[Does TNF-alpha contribute to liver disease physiopathology?].
2000
The potential of acetaminophen as a prodrug in gene-directed enzyme prodrug therapy.
2000 Apr
The hepatic inflammatory response after acetaminophen overdose: role of neutrophils.
2000 Apr
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.
2000 Aug
Acetaminophen produces cataract in DBA2 mice by Ah receptor-independent induction of CYP1A2.
2000 Aug
Cerebral edema with herniation during acetaminophen-induced fulminant hepatic failure.
2000 Jul
Acetaminophen inhibits iNOS gene expression in RAW 264.7 macrophages: differential regulation of NF-kappaB by acetaminophen and salicylates.
2000 Jun 16
Deafness associated with abuse of hydrocodone/acetaminophen.
2000 Jun 27
Transient neurologic symptoms after epidural analgesia in a five-year-old child.
2000 Oct
Short-term treatment with alcohols causes hepatic steatosis and enhances acetaminophen hepatotoxicity in Cyp2e1(-/-) mice.
2000 Oct 15
Transcriptional activation of heme oxygenase-1 and its functional significance in acetaminophen-induced hepatitis and hepatocellular injury in the rat.
2000 Sep
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.
2001
Let the user beware. OTC drugs aren't necessarily 'safe when taken as directed.'.
2001 Feb
Effect of coadministered drugs and ethanol on the binding of therapeutic drugs to human serum in vitro.
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
NSAID impairment of orthodontic tooth movement.
2001 Jan
Single and multiple dose pharmacokinetics of acetaminophen (paracetamol) in polymedicated very old patients with rheumatic pain.
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
Preoperative rectal diclofenac versus paracetamol for tonsillectomy: effects on pain and blood loss.
2001 Jan
Safety of childhood acetaminophen overdose.
2001 Jan
Treatment of acetaminophen ingestion with a superactivated charcoal-cola mixture.
2001 Jan
High sensitivity of Nrf2 knockout mice to acetaminophen hepatotoxicity associated with decreased expression of ARE-regulated drug metabolizing enzymes and antioxidant genes.
2001 Jan
Causes of Alzheimer's disease: paracetamol (acetaminophen) today? Amphetamines tomorrow?
2001 Jan
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.
2001 Jan 10
Nonsteroidal anti-inflammatory drugs: overused or underused in osteoarthritis?
2001 Jan 8
Allergic reactions due to ibuprofen in children.
2001 Jan-Feb
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 18:19:48 UTC 2023
Edited
by admin
on Sat Dec 16 18:19:48 UTC 2023
Record UNII
WVH4R62LA6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POTASSIUM 4-ACETAMIDOPHENOLATE
Common Name English
POTASSIUM 4-(ACETYLAMINO)PHENOLATE
Common Name English
ACETAMIDE, N-(4-HYDROXYPHENYL)-, POTASSIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
WVH4R62LA6
Created by admin on Sat Dec 16 18:19:49 UTC 2023 , Edited by admin on Sat Dec 16 18:19:49 UTC 2023
PRIMARY
PUBCHEM
23690172
Created by admin on Sat Dec 16 18:19:49 UTC 2023 , Edited by admin on Sat Dec 16 18:19:49 UTC 2023
PRIMARY
CAS
35719-43-8
Created by admin on Sat Dec 16 18:19:49 UTC 2023 , Edited by admin on Sat Dec 16 18:19:49 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY