Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H8N4O5 |
| Molecular Weight | 252.1836 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O
InChI
InChIKey=WOCXQMCIOTUMJV-UHFFFAOYSA-N
InChI=1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14)
Tretazicar is a dinitrobenzamide prodrug that is converted in the presence of the enzyme NQO2 and co-substrate caricotamide (EP-0152R) into a potent cytotoxic bifunctional alkylating agent. Tretazicar is a product that belongs to a family of products used in the treatment of cancer because of its capacity to kill cells. The enzyme that activates tretazicar is present in leishmania cells where the product can be transformed and be active. Tretazicar kills infected cells by binding to the genetic material (DNA) of the cells and creating bonds that disrupt the genetic material and its function, finally resulting in the death of the infected cell. On 4 February 2008, orphan designation EU/3/08/529 was granted by the European Commission to Morvus Technology Limited, United Kingdom, for tretazicar for the treatment of visceral leishmaniasis. On 4 February 2008, orphan designation EU/3/08/529 was granted by the European Commission to Morvus Technology Limited, United Kingdom, for tretazicar for the treatment of visceral leishmaniasis. Tretazicar had been in phase II clinical trial for the treatment of liver cancer. However, this development was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Quinone oxidoreductase-2-mediated prodrug cancer therapy. | 2010-07-14 |
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| Transgenic mice expressing nitroreductase gene under the control of the podocin promoter: a new murine model of inductible glomerular injury. | 2010-03 |
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| Bystander or no bystander for gene directed enzyme prodrug therapy. | 2009-11-10 |
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| Antivector and tumor immune responses following adenovirus-directed enzyme prodrug therapy for the treatment of prostate cancer. | 2009-11 |
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| A mammalianized synthetic nitroreductase gene for high-level expression. | 2009-08-27 |
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| Steady-state and stopped-flow kinetic studies of three Escherichia coli NfsB mutants with enhanced activity for the prodrug CB1954. | 2009-08-18 |
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| A phase I/II clinical trial in localized prostate cancer of an adenovirus expressing nitroreductase with CB1954 [correction of CB1984]. | 2009-07 |
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| E. coli NfsA: an alternative nitroreductase for prodrug activation gene therapy in combination with CB1954. | 2009-06-16 |
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| Antitumor activity of a selectively replication competent herpes simplex virus (HSV) with enzyme prodrug therapy. | 2009-06 |
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| A new in vitro model for stem cell differentiation and interaction. | 2009-03 |
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| E. coli nitroreductase/CB1954 gene-directed enzyme prodrug therapy: role of arylamine N-acetlytransferase 2. | 2008-11 |
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| The NprA nitroreductase required for 2,4-dinitrophenol reduction in Rhodobacter capsulatus is a dihydropteridine reductase. | 2008-11 |
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| Optimized clostridium-directed enzyme prodrug therapy improves the antitumor activity of the novel DNA cross-linking agent PR-104. | 2008-10-01 |
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| Metabolic activation of the antitumor drug 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB1954) by NO synthases. | 2008-04 |
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| Escherichia coli nitroreductase plus CB1954 enhances the effect of radiotherapy in vitro and in vivo. | 2008-03 |
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| SALMON: solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy. | 2008-01-10 |
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| Combining gene and immunotherapy for prostate cancer. | 2008 |
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| The nitroreductase prodrug SN 28343 enhances the potency of systemically administered armed oncolytic adenovirus ONYX-411(NTR). | 2007-12 |
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| Hepatic nitroreduction, toxicity and toxicokinetics of the anti-tumour prodrug CB 1954 in mouse and rat. | 2007-10-30 |
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| Validation of nitroreductase, a prodrug-activating enzyme, mediated cell death in embryonic zebrafish (Danio rerio). | 2007-06 |
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| Ablation of central nervous system progenitor cells in transgenic rats using bacterial nitroreductase system. | 2007-05-01 |
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| Kinetic and structural characterisation of Escherichia coli nitroreductase mutants showing improved efficacy for the prodrug substrate CB1954. | 2007-04-27 |
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| Direct positive selection for improved nitroreductase variants using SOS triggering of bacteriophage lambda lytic cycle. | 2007-04 |
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| NAD(P)H:quinone oxidoreductase 1 and nrh:quinone oxidoreductase 2 activity and expression in bladder and ovarian cancer and lower NRH:quinone oxidoreductase 2 activity associated with an NQO2 exon 3 single-nucleotide polymorphism. | 2007-03-01 |
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| Gateways to clinical trials. | 2007-03 |
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| Reduction of mitomycin C is catalysed by human recombinant NRH:quinone oxidoreductase 2 using reduced nicotinamide adenine dinucleotide as an electron donating co-factor. | 2006-11-06 |
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| Repeated cycles of Clostridium-directed enzyme prodrug therapy result in sustained antitumour effects in vivo. | 2006-11-06 |
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| Application of a microfluidic reactor for screening cancer prodrug activation using silica-immobilized nitrobenzene nitroreductase. | 2006-09 |
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| Design, synthesis, and biological evaluation of cyclic and acyclic nitrobenzylphosphoramide mustards for E. coli nitroreductase activation. | 2006-07-13 |
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| Hypoxia: targeting the tumour. | 2006-07 |
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| Nitroreductase-based therapy of prostate cancer, enhanced by raising expression of heat shock protein 70, acts through increased anti-tumour immunity. | 2006-03 |
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| Delivery of the bacterial nitroreductase gene into endothelial cells prolongs the survival of tumour-bearing mice by bystander mechanisms. | 2006-02 |
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| New enzyme for reductive cancer chemotherapy, YieF, and its improvement by directed evolution. | 2006-01 |
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| Aerobic 2- and 4-nitroreduction of CB 1954 by human liver. | 2005-12-15 |
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| Binding of the anticancer prodrug CB1954 to the activating enzyme NQO2 revealed by the crystal structure of their complex. | 2005-12-01 |
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| Towards gene therapy in prosthesis loosening: efficient killing of interface cells by gene-directed enzyme prodrug therapy with nitroreductase and the prodrug CB1954. | 2005-11 |
|
| Crystal structure of quinone reductase 2 in complex with cancer prodrug CB1954. | 2005-10-14 |
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| Inhibition of NF-kappaB enhances the cytotoxicity of virus-directed enzyme prodrug therapy and oncolytic adenovirus cancer gene therapy. | 2005-08 |
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| Antitumor immune responses mediated by adenoviral GDEPT using nitroreductase/CB1954 is enhanced by high-level coexpression of heat shock protein 70. | 2005-06 |
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| Nitroreductase: a prodrug-activating enzyme for cancer gene therapy. | 2004-11 |
|
| Enhanced efficacy of Escherichia coli nitroreductase/CB1954 prodrug activation gene therapy using an E1B-55K-deleted oncolytic adenovirus vector. | 2004-07 |
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| Aziridinyldinitrobenzamides: synthesis and structure-activity relationships for activation by E. coli nitroreductase. | 2004-06-03 |
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| Genes in the service of therapeutic index: progress for virus-directed enzyme prodrug therapy. | 2004-05-01 |
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| 2-Amino metabolites are key mediators of CB 1954 and SN 23862 bystander effects in nitroreductase GDEPT. | 2004-03-08 |
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| Enzyme-catalyzed activation of anticancer prodrugs. | 2004-03 |
|
| The gene suicide system Ntr/CB1954 causes ablation of differentiated 3T3L1 adipocytes by apoptosis. | 2004 |
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| Quinone reductase-mediated nitro-reduction: clinical applications. | 2004 |
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| The nitroreductase/CB1954 enzyme-prodrug system. | 2004 |
|
| Methods to improve efficacy in suicide gene therapy approaches: targeting prodrug-activating enzymes carboxypeptidase G2 and nitroreductase to different subcellular compartments. | 2004 |
|
| Clostridia in cancer therapy. | 2003-12 |
| Name | Type | Language | ||
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Official Name | English | ||
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Preferred Name | English | ||
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Systematic Name | English | ||
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Code | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/08/529
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NCI_THESAURUS |
C274
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C100099
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115829
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21919-05-1
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7865D5D01M
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100000175669
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C81554
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8607
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ACTIVE MOIETY
SUBSTANCE RECORD
