Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H9NO2 |
Molecular Weight | 151.1626 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)NC1=CC=C(O)C=C1
InChI
InChIKey=RZVAJINKPMORJF-UHFFFAOYSA-N
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
Molecular Formula | C8H9NO2 |
Molecular Weight | 151.1626 |
Charge | 0 |
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=15662292 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | TYLENOL Approved UseUses 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 Date7.5798721E11 |
|||
Palliative | TYLENOL Approved UseUses 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 Date7.5790077E11 |
|||
Palliative | TYLENOL Approved UseUses 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 Date7.5790077E11 |
|||
Palliative | TYLENOL Approved UseUses 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 Date7.5790077E11 |
|||
Palliative | TYLENOL Approved UseUses 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 Date7.5790077E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/ Page: - |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes [Ki 2300 uM] | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes [Ki 5300 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
major | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
no | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18232020/ Page: - |
yes [Km 1500 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18232020/ Page: - |
yes [Km 1900 uM] | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes [Km 2300 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18232020/ Page: - |
yes [Km 3700 uM] | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes [Km 4000 uM] | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes [Km 5500 uM] | |||
Page: 6.0 |
yes | |||
Page: 6.0 |
yes | |||
Page: 6.0 |
yes | |||
Page: 6.0 |
yes | |||
Page: 6.0 |
yes | |||
Page: 6.0 |
yes | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes | |||
Sources: https://pubs.acs.org/doi/10.1021/tx050317i Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents. | 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 |
|
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 |
|
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 |
|
Economic evaluation alongside n-of-1 trials: getting closer to the margin. | 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 |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10751557
A time- and concentration-dependent decrease in intracellular GSH occurred in freshly isolated type II pneumocytes and alveolar macrophages exposed to subtoxic (= 1 mM) APAP concentrations.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 22:19:20 UTC 2023
by
admin
on
Thu Jul 06 22:19:20 UTC 2023
|
Record UNII |
362O9ITL9D
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
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Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
N02AJ17
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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||
|
CFR |
21 CFR 341.40
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
|
||
|
WHO-VATC |
QN02BE71
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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||
|
NCI_THESAURUS |
C2356
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
7.1
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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||
|
WHO-VATC |
QN02BE01
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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||
|
WHO-ATC |
N02AJ06
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
|
||
|
CFR |
21 CFR 862.3030
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
|
||
|
WHO-ATC |
N02BE71
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
|
||
|
CFR |
21 CFR 310.201
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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||
|
EPA PESTICIDE CODE |
606318
Created by
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||
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WHO-VATC |
QN02BE51
Created by
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|
LOINC |
75071-1
Created by
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WHO-ATC |
N02BE51
Created by
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|
WHO-ATC |
N02BE01
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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|
WHO-ATC |
N02AJ13
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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|
WHO-ESSENTIAL MEDICINES LIST |
2.1
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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LIVERTOX |
NBK548162
Created by
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|
WHO-ATC |
N02AJ01
Created by
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Code System | Code | Type | Description | ||
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1003009
Created by
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PRIMARY | |||
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SUB09611MIG
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PRIMARY | |||
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DTXSID2020006
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PRIMARY | |||
|
362O9ITL9D
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PRIMARY | |||
|
1983
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PRIMARY | |||
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DB00316
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PRIMARY | |||
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PARACETAMOL
Created by
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PRIMARY | |||
|
8055-08-1
Created by
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SUPERSEDED | |||
|
Acetaminophen
Created by
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PRIMARY | |||
|
M1317
Created by
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PRIMARY | Merck Index | ||
|
ACETAMINOPHEN
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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PRIMARY | Description: A white, crystalline powder; odourless. Solubility: Sparingly soluble in water; freely soluble in ethanol (~750 g/l) TS and acetone R; practically insoluble in ether R. Category: Analgesic; antipyretic. Storage: Paracetamol should be kept in a tightly closed container, protected from light. Definition: Paracetamol contains not less than 98.5% and not more than 101.0% of C8H9NO2, calculated with reference to thedried substance. | ||
|
626
Created by
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PRIMARY | |||
|
109028
Created by
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PRIMARY | |||
|
100000090270
Created by
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PRIMARY | |||
|
203-157-5
Created by
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PRIMARY | |||
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362O9ITL9D
Created by
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PRIMARY | |||
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CHEMBL112
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PRIMARY | |||
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52
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PRIMARY | |||
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161
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PRIMARY | RxNorm | ||
|
3001
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PRIMARY | |||
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46195
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PRIMARY | |||
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3991
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PRIMARY | |||
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D000082
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PRIMARY | |||
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103-90-2
Created by
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PRIMARY | |||
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5239
Created by
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PRIMARY | |||
|
C198
Created by
admin on Thu Jul 06 22:19:26 UTC 2023 , Edited by admin on Thu Jul 06 22:19:26 UTC 2023
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PRIMARY |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Enzyme responsible for the bulk of NAPQI formation
MAJOR
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (UV)
USP
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
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PARENT -> METABOLITE ACTIVE |
Percent of dose excreted in urine as metabolite.
AMOUNT ADMINISTERED
URINE
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PARENT -> METABOLITE ACTIVE |
Percent of dose excreted in urine as metabolite 60-80
URINE
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
Major metabolite in infants and young children glucuronide is major metabolite in adults.
MAJOR
URINE
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
MAJOR
URINE
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT |
MINOR
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE ACTIVE -> PARENT |
May be substrate for formation of AM-404
MINOR
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METABOLITE TOXIC -> PARENT |
Metabolite produced hepatic necrosis in man.
AMOUNT EXCRETED
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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IV, LESS THAN 50 Kg |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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RENAL CLEARANCE | PHARMACOKINETIC |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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MAXIMUM TOLERATED DOSE | TOXICITY |
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