Chloroquine
From ToxBankWiki
Chloroquine | |
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Identifiers | |
Leadscope Id | LS-141726 |
CAS | 54-05-7 |
DrugBank | APRD00468 |
ChemSpider | 2618 |
UNII | 886U3H6UFF |
Pathway DBs | |
KEGG | D02366 |
Assay DBs | |
PubChem CID | 2719 |
ChEMBL | 76 |
Omics DBs | |
Properties | |
pKa | 7.5 |
ToxCast Accepted | no |
Toxic Effect | Apoptosis |
ToxBank Accepted | no |
Target | homozoin |
Executive Summary
Summary Information
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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[1] [2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] [13] [14] [15] [16] |
Gold Compound Evaluation and Comments
The following table is organized into four main sections and provides a detailed assessment by the Gold Compound Working Group for the use of this compound as a standard hepatotoxin. The table's four sections (collapsed by default but will expand when the "show" link is clicked) contains detailed information for the core set of SEURAT compound acceptance criteria.
Standard to Meet | Compound Assessment | ||||||||||||||||||
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Proprietary Toxicity Literature Report
The toxicity literature report contains proprietary information and references for studies performed on this compound relevant to liver toxicity findings and is restricted for use within the SEURAT program only.
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 "Chloroquine" as an active ingredient.
FDA Label Search
PubMed references
The following resource link will perform a PubMed query for the terms "Chloroquine" and "liver toxicity".
Chloroquine Search
References
- ↑ Feldmann, G., 2006. Liver apoptosis. Gastroenterol. Clin. Biol. 30, 533–545.
- ↑ 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.
- ↑ Gomez-Lechon, M.J., O’Connor, J.E., Lahoz, A., Castell, J.V., Donato, M.T., 2008. Identification of apoptotic drugs: multiparametric evaluation in cultured hepatocytes. Curr. Med. Chem. 15, 2071–2085.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Johannsen, D.L., Ravussin, E., 2009. The role of mitochondria in health and disease. Curr. Opin. Pharmacol. 9, 780–786.
- ↑ Jones, D.P., Lemasters, J.J., Han, D., Boelsterli, U.A., Kaplowitz, N., 2010. Mechanisms of pathogenesis in drug hepatotoxicity putting the stress on mitochondria. Mol. Interv. 10, 98–111.
- ↑ Labbe, G., Pessayre, D., Fromenty, B., 2008. Drug-induced liver injury through mitochondrial dysfunction: mechanisms and detection during preclinical safety studies. Fundam. Clin. Pharmacol. 22, 335–353.
- ↑ Masubuchi, Y., 2006. Metabolic and non-metabolic factors determining troglitazone hepatotoxicity: a review. Drug Metab. Pharmacokinet. 21, 347–356.
- ↑ Criddle, D.N., Gillies, S., Baumgartner-Wilson, H.K., Jaffar, M., Chinje, E.C., Passmore, S., Chvanov, M., Barrow, S., Gerasimenko, O.V., Tepikin, A.V., Sutton, R., Petersen, O.H., 2006. Menadione-induced reactive oxygen species generation via redox cycling promotes apoptosis of murine pancreatic acinar cells. J. Biol. Chem. 281, 40485–40492.
- ↑ Hanley, P.J., Ray, J., Brandt, U., Daut, J., 2002. Halothane, isoflurane and sevoflurane inhibit NADH:ubiquinone oxidoreductase (complex I) of cardiac mitochondria. J. Physiol. 544, 687–693.
- ↑ Moridani, M.Y., Cheon, S.S., Khan, S., O’Brien, P.J., 2003. Metabolic activation of 3- hydroxyanisole by isolated rat hepatocytes. Chem. Biol. Interact. 142, 317–333.
- ↑ Pereira, C.V., Moreira, A.C., Pereira, S.P., Machado, N.G., Carvalho, F.S., Sardao, V.A., Oliveira, P.J., 2009. Investigating drug-induced mitochondrial toxicity: a biosensor to increase drug safety? Curr. Drug Saf. 4, 34–54.
- ↑ Sanz, A., Caro, P., Gomez, J., Barja, G., 2006. Testing the vicious cycle theory of mitochondrial ROS production: effects of H2O2 and cumene hydroperoxide treatment on heart mitochondria. J. Bioenerg. Biomembr. 38, 121–127.
- ↑ Yuan, L., Kaplowitz, N., 2009. Glutathione in liver diseases and hepatotoxicity. Mol. Aspects Med. 30, 29–41.
Calculated/Predicted Properties
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Accepted by ToxBank | no + |
Accepted by ToxCast | no + |
Equivalent URIThis property is a special property in this wiki. | http://bio2rdf.org/drugbank_drugs:APRD00468 +, http://bio2rdf.org/cas:54-05-7 +, http://www.chemspider.com/Chemical-Structure.2618.rdf +, http://bio2rdf.org/pubchem:2719 +, http://bio2rdf.org/dr:D02366 +, and http://rdf.openmolecules.net/?InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21) + |
Has CAS | 54-05-7 + |
Has ChEMBL Id | 76 + |
Has ChemSpider Id | 2618 + |
Has DrugBank Id | APRD00468 + |
Has InChI | InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21) + |
Has InChIKey | WHTVZRBIWZFKQO-UHFFFAOYSA-N + |
Has KEGG Id | D02366 + |
Has Leadscope Id | LS-141726 + |
Has PubChem CID | 2719 + |
Has Smiles | c12c(nccc1N[C@@H](CCCN(CC)CC)C)cc(Cl)cc2 + |
Has category | Hepatotoxic + |
Has image | Chloroquine.png + |
Has pKa | 7.5 + |
Has target | homozoin + |
Has toxic effect | Apoptosis + |