Acetaminophen
From ToxBankWiki
Executive Summary Information
Compound | Acetaminophen (Paracetamol) |
Toxicities | Cytotoxicity |
Mechanisms | Metabolic oxidation to the quinone imine NAPQI metabolite, which traps cellular thiols, both protein and GSH, by formation of covalent adducts. Studies of quinone imine analogues suggest additional depletion of thiols by redox cycling. |
Comments | Acetaminophen is selected based on its chemical mechanism, which is representative of quinones with a high reduction potential. |
Feedback Contact | Gold Compound Working Group (GCWG) |
Acetaminophen | |
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Identifiers | |
Leadscope Id | LS-32 |
CAS | 103-90-2 |
DrugBank | DB00316 |
ChemSpider | 1906 |
UNII | 362O9ITL9D |
ChEBI | 116450 |
Pathway DBs | |
KEGG | D00217 |
Assay DBs | |
PubChem CID | 1983 |
ChEMBL | 112 |
Omics DBs | |
Open TG-Gate | 00001 |
Properties | |
pKa | 9.48 |
ToxCast Accepted | yes |
Toxic Effect | Apoptosis |
ToxBank Accepted | yes |
Approved on | 2011-06-28 |
Target | COX-2c |
Toxicities | Cytotoxicity |
- In Vivo Data
- LIINTOP Data
- PK-ADME Data
- 'Omics and IC50 Data
- Physical Properties
- Recommended Product and Source
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Human Adverse Events
The following data table has been mined from the Adverse Events Reporting System (AERS) of the US FDA. Significant human liver events. The first column ("# Reports") is the number of reports found for the corresponding adverse event reported in the third column ("Adverse Event"). The second column ("Report:Baseline Ratio") is ratio calculated from the number of reports ("# Reports") divided by a calculated expected statistical baseline number of reports.
# Reports | Report:Baseline Ratio | Adverse Event |
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2 | 6.10464 | acute fatty liver of pregnancy |
227 | 9.85492 | acute hepatic failure |
1 | 13.2267 | bile duct cancer non-resectable |
2 | 7.93603 | glycogen storage disease type i |
25 | 3.37416 | hepatorenal failure |
76 | 4.84060 | liver injury |
FDA and Label Information
The following link will display all of the currently approved FDA drug products on the market. The web page will contain a table listing all current products by their respective Tradenames and primary active ingredients. The list is navigable by simply clicking on the product of interest, which will in turn list all of the NDA's and ANDA's associated with that product. From here users can click on a specific NDA or ANDA and see documents that have been submitted for the product that the FDA has made available via their website. The types of documents include approval history, letters, reviews and labels.
FDA Approved Products
This next url will perform a search in the FDA's system for all labels for products that contain Acetaminophen as an active ingredient.
FDA Label Search
Since every unique drug product receives a separate label, we have included a link to another resource for a specific Acetaminophen product (ACETAMINOPHEN liquid - by Goldline Laboratories, Inc.) which displays the drug label information.
Acetaminophen liquid label
PubMed references
The following resource link will perform a PubMed query for the terms "acetaminophen" and "liver toxicity".
Acetaminophen Search
The table listed below contains a summarized listing of toxic effect information leveraged from the 6th European Framework Programme project LIINTOP. For a complete listing of the Gold Compound evaluation criteria please see the Gold Compound Evaluation and Comments immediately following the summary table below.
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Summary Hepatotoxic Effects from the LIINTOP FP6 Program | |||||||||||||||||||||
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References
- ↑ Gomez-Lechon, M.J., O’Connor, E., Castell, J.V., Jover, R., 2002. Sensitive markers used to identify compounds that trigger apoptosis in cultured hepatocytes. Toxicol. Sci. 65, 299–308. doi:10.1093/toxsci/65.2.299
- ↑ Gomez-Lechon, M.J., Ponsoda, X., O’Connor, E., Donato, T., Jover, R., Castell, J.V., 2003. Diclofenac induces apoptosis in hepatocytes. Toxicol. in Vitro 17, 675– 680. doi:10.1016/S0887-2333(03)00105-X
- ↑ Hynes, J., Marroquin, L.D., Ogurtsov, V.I., Christiansen, K.N., Stevens, G.J., Papkovsky, D.B., Will, Y., 2006. Investigation of drug-induced mitochondrial toxicity using fluorescence-based oxygen-sensitive probes. Toxicol. Sci. 92, 186–200. doi:10.1093/toxsci/kfj208
- ↑ Kass, G.E., Macanas-Pirard, P., Lee, P.C., Hinton, R.H., 2003. The role of apoptosis in acetaminophen-induced injury. Ann. NY Acad. Sci. 1010, 557–559. doi:10.1196/annals.1299.103
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Calculated/Predicted Properties
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