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Details

Stereochemistry ACHIRAL
Molecular Formula C8H8NO2.Na
Molecular Weight 173.1447
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYACETANILIDE SODIUM

SMILES

CC(=Nc1ccc(cc1)O)[O-].[Na+]

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 C8H8NO2
Molecular Weight 150.1549
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Administering granulocyte colony-stimulating factor to acute liver failure patients corrects neutrophil defects.
2000 Dec
Tissue distribution and interindividual variation in human UDP-glucuronosyltransferase activity: relationship between UGT1A1 promoter genotype and variability in a liver bank.
2000 Nov
Establishment of a human hepatoma cell line, HLE/2E1, suitable for detection of p450 2E1-related cytotoxicity.
2000 Oct
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
Pharmacokinetics of acetaminophen from rapidly disintegrating compressed tablet prepared using microcrystalline cellulose (PH-M-06) and spherical sugar granules.
2001 Feb
Preparation of rapidly disintegrating tablet using new types of microcrystalline cellulose (PH-M series) and low substituted-hydroxypropylcellulose or spherical sugar granules by direct compression method.
2001 Feb
Effect of coadministered drugs and ethanol on the binding of therapeutic drugs to human serum in vitro.
2001 Feb
Urine drug screens in overdose patients do not contribute to immediate clinical management.
2001 Feb
A novel pH-sensitive membrane from chitosan--TEOS IPN; preparation and its drug permeation characteristics.
2001 Feb
Management of drug-induced liver disease.
2001 Feb
Postoperative analgesia at home after ambulatory hand surgery: a controlled comparison of tramadol, metamizol, and paracetamol.
2001 Feb
Stroke severity determines body temperature in acute stroke.
2001 Feb
Thermodynamic analysis of compact formation; compaction, unloading, and ejection. II. Mechanical energy (work) and thermal energy (heat) determinations of compact unloading and ejection.
2001 Feb 1
Protective effect of stiripentol on acetaminophen-induced hepatotoxicity in rat.
2001 Feb 1
Pragmatic randomised controlled trial of two prescribing strategies for childhood acute otitis media.
2001 Feb 10
Clinical trial of an air-circulating cooling blanket for fever control in critically ill neurologic patients.
2001 Feb 13
Hemolytic anemia after acetaminophen overdose in patient with glucose-6-phosphate dehydrogenase deficiency.
2001 Feb 15
[About paracetamol again].
2001 Feb 18
The role of acetaminophen in the management of patients with osteoarthritis.
2001 Feb 19
ABC of diseases of liver, pancreas, and biliary system. Other causes of parenchymal liver disease.
2001 Feb 3
Paracetamol (acetaminophen)-induced toxicity: molecular and biochemical mechanisms, analogues and protective approaches.
2001 Jan
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
NSAID impairment of orthodontic tooth movement.
2001 Jan
Separation of cold medicine ingredients by capillary electrophoresis.
2001 Jan
Single and multiple dose pharmacokinetics of acetaminophen (paracetamol) in polymedicated very old patients with rheumatic pain.
2001 Jan
Misoprostol therapeutics revisited.
2001 Jan
Successful use of propranolol in migraine associated with electroconvulsive therapy.
2001 Jan
Risk factors in the development of adverse reactions to N-acetylcysteine in patients with paracetamol poisoning.
2001 Jan
The dark side of a 'detoxification' mechanism.
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
Preoperative rectal diclofenac versus paracetamol for tonsillectomy: effects on pain and blood loss.
2001 Jan
Treatment with paracetamol in infants.
2001 Jan
Gastric emptying in diabetic gastroparetic dogs: ffects of SK-951,a novel prokinetic agent.
2001 Jan
Safety of childhood acetaminophen overdose.
2001 Jan
Treatment of acetaminophen ingestion with a superactivated charcoal-cola mixture.
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
Prevention of acetaminophen-induced liver toxicity by 2(R,S)-n-propylthiazolidine-4(R)-carboxylic acid in mice.
2001 Jan 15
Unexpected and pronounced antinociceptive synergy between spinal acetaminophen (paracetamol) and phentolamine.
2001 Jan 26
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 Fri Jun 25 20:48:27 UTC 2021
Edited
by admin
on Fri Jun 25 20:48:27 UTC 2021
Record UNII
V9E6HW6ZAG
Record Status Validated (UNII)
Record Version
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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 Fri Jun 25 20:48:27 UTC 2021 , Edited by admin on Fri Jun 25 20:48:27 UTC 2021
PRIMARY
CAS
16958-94-4
Created by admin on Fri Jun 25 20:48:27 UTC 2021 , Edited by admin on Fri Jun 25 20:48:27 UTC 2021
PRIMARY
PUBCHEM
23667500
Created by admin on Fri Jun 25 20:48:27 UTC 2021 , Edited by admin on Fri Jun 25 20:48:27 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY