Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H10N4O4 |
| Molecular Weight | 238.2001 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CC(N2CC2)=C(NO)C=C1[N+]([O-])=O
InChI
InChIKey=OAALBIMEFVOQBY-UHFFFAOYSA-N
InChI=1S/C9H10N4O4/c10-9(14)5-3-8(12-1-2-12)6(11-15)4-7(5)13(16)17/h3-4,11,15H,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 |
|---|---|---|
| Combined adenovirus-mediated nitroreductase gene delivery and CB1954 treatment: a well-tolerated therapy for established solid tumors. | 2001 Feb |
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| Demonstration of the activation of prodrug CB 1954 using human DT-diaphorase mutant Q104Y-transfected MDA-MB-231 cells and mouse xenograft model. | 2001 Jan 1 |
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| E. coli nitroreductase/CB1954: in vitro studies into a potential system for feline cancer gene therapy. | 2001 May |
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| Telomerase-specific suicide gene therapy vectors expressing bacterial nitroreductase sensitize human cancer cells to the pro-drug CB1954. | 2001 Nov 22 |
|
| Virus-directed, enzyme prodrug therapy with nitroimidazole reductase: a phase I and pharmacokinetic study of its prodrug, CB1954. | 2001 Sep |
|
| Nitroreductase-based GDEPT. | 2002 |
|
| Bacillus amyloliquefaciens orthologue of Bacillus subtilis ywrO encodes a nitroreductase enzyme which activates the prodrug CB 1954. | 2002 Jan |
|
| Hypoxia-inducible regulation of a prodrug-activating enzyme for tumor-specific gene therapy. | 2002 Jan-Feb |
|
| Quantitation of bystander effects in nitroreductase suicide gene therapy using three-dimensional cell cultures. | 2002 Mar 1 |
|
| Inducible ablation of adipocytes in adult transgenic mice expressing the E. coli nitroreductase gene. | 2002 Nov |
|
| Gene therapy trials: a patient pathway. | 2002 Oct 2-8 |
|
| Effect of nitroreduction on the alkylating reactivity and cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the corresponding nitrogen mustard SN 23862: distinct mechanisms of bioreductive activation. | 2003 Apr |
|
| Professor Tom Connors and the development of novel cancer therapies by the Phase I/II Clinical Trials Committee of Cancer Research UK. | 2003 Aug 4 |
|
| Immune enhancement of nitroreductase-induced cytotoxicity: studies using a bicistronic adenovirus vector. | 2003 Mar 10 |
|
| Studies on the nitroreductase prodrug-activating system. Crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form. | 2003 Sep 11 |
|
| 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 |
|
| Methods to improve efficacy in suicide gene therapy approaches: targeting prodrug-activating enzymes carboxypeptidase G2 and nitroreductase to different subcellular compartments. | 2004 |
|
| Aziridinyldinitrobenzamides: synthesis and structure-activity relationships for activation by E. coli nitroreductase. | 2004 Jun 3 |
|
| Enzyme-catalyzed activation of anticancer prodrugs. | 2004 Mar |
|
| Genes in the service of therapeutic index: progress for virus-directed enzyme prodrug therapy. | 2004 May 1 |
|
| Inhibition of NF-kappaB enhances the cytotoxicity of virus-directed enzyme prodrug therapy and oncolytic adenovirus cancer gene therapy. | 2005 Aug |
|
| Binding of the anticancer prodrug CB1954 to the activating enzyme NQO2 revealed by the crystal structure of their complex. | 2005 Dec 1 |
|
| Aerobic 2- and 4-nitroreduction of CB 1954 by human liver. | 2005 Dec 15 |
|
| Towards gene therapy in prosthesis loosening: efficient killing of interface cells by gene-directed enzyme prodrug therapy with nitroreductase and the prodrug CB1954. | 2005 Nov |
|
| Delivery of the bacterial nitroreductase gene into endothelial cells prolongs the survival of tumour-bearing mice by bystander mechanisms. | 2006 Feb |
|
| New enzyme for reductive cancer chemotherapy, YieF, and its improvement by directed evolution. | 2006 Jan |
|
| Design, synthesis, and biological evaluation of cyclic and acyclic nitrobenzylphosphoramide mustards for E. coli nitroreductase activation. | 2006 Jul 13 |
|
| 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 Nov 6 |
|
| Repeated cycles of Clostridium-directed enzyme prodrug therapy result in sustained antitumour effects in vivo. | 2006 Nov 6 |
|
| Application of a microfluidic reactor for screening cancer prodrug activation using silica-immobilized nitrobenzene nitroreductase. | 2006 Sep |
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| Direct positive selection for improved nitroreductase variants using SOS triggering of bacteriophage lambda lytic cycle. | 2007 Apr |
|
| Validation of nitroreductase, a prodrug-activating enzyme, mediated cell death in embryonic zebrafish (Danio rerio). | 2007 Jun |
|
| 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 Mar 1 |
|
| Hepatic nitroreduction, toxicity and toxicokinetics of the anti-tumour prodrug CB 1954 in mouse and rat. | 2007 Oct 30 |
|
| SALMON: solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy. | 2008 Jan 10 |
|
| E. coli nitroreductase/CB1954 gene-directed enzyme prodrug therapy: role of arylamine N-acetlytransferase 2. | 2008 Nov |
|
| A mammalianized synthetic nitroreductase gene for high-level expression. | 2009 Aug 27 |
|
| E. coli NfsA: an alternative nitroreductase for prodrug activation gene therapy in combination with CB1954. | 2009 Jun 16 |
|
| Bystander or no bystander for gene directed enzyme prodrug therapy. | 2009 Nov 10 |
|
| Quinone oxidoreductase-2-mediated prodrug cancer therapy. | 2010 Jul 14 |
|
| Transgenic mice expressing nitroreductase gene under the control of the podocin promoter: a new murine model of inductible glomerular injury. | 2010 Mar |
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YW6FGD83AT
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5487972
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119643-82-2
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DTXSID00152538
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
