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Purity: =99.87%
Trapazamine (also known as TP, SR-4233; SR259075; Win59075; SR4233) is an experimental adjuvant drug and a DNA-damaging agent that has the potential for the treatment of cervical carcinoma, head and neck cancer. Tirapazamine selectively activates HIF-1α to its toxic form in hypoxic areas of solid tumors, which may lead to downregulation of HIF-1α expression through decreased protein synthesis. Trazamine significantly reduced HIF-1α protein accumulation, reduced HIF-1α transcriptional activation, and hindered the phosphorylation of proteins involved in the homologous recombination repair pathway when combined with chemotherapeutic medications like doxorubicin (DOX) and SN-38 (the active metabolite of irinotecan). This ultimately led to the synergism of these two drugs.
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Tirapasamine and topoisomerase I inhibitors together demonstrated synergistic cytotoxicity and significantly reduced the number of cells in several hepatocellular carcinoma cell lines. Increased mitochondrial depolarization and caspase pathway activation correlated with the enhanced apoptosis induced by tirapazamine plus SN-38, the active metabolite of irinotecan. These two drugs work in concert because of the combination treatment, which significantly reduced HIF-1α protein accumulation, reduced HIF-1α transcriptional activation, and hampered the phosphorylation of proteins involved in the homologous recombination repair pathway.
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| Molecular Formula |
C7H6N4O2
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| Molecular Weight |
178.05
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| Exact Mass |
178.05
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| Elemental Analysis |
C, 47.19; H, 3.39; N, 31.45; O, 17.96
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| CAS # |
27314-97-2
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| Appearance |
Orange to dark orange-red solid powder
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| SMILES |
C1=CC=C2C(=C1)[N+](=C(N=[N+]2[O-])N)[O-]
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| InChi Key |
ORYDPOVDJJZGHQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
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| Chemical Name |
1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine
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| Synonyms |
SR 4233; SR-4233; SR4233; SR259075; SR-259075; SR 259075; WIN 59075; WIN-59075; WIN59075; NSC130181; NSC-130181; NSC 130181; Tirazone; TP; Tirapazamine;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (14.03 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 2.08 mg/mL (11.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (11.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10 mg/mL (56.13 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6164 mL | 28.0820 mL | 56.1640 mL | |
| 5 mM | 1.1233 mL | 5.6164 mL | 11.2328 mL | |
| 10 mM | 0.5616 mL | 2.8082 mL | 5.6164 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02174549 | Active Recruiting |
Procedure: Conventional Transarterial Embolization (TAE) Drug: Tirapazamine |
Hepatocellular Carcinoma Neuroendocrine Tumors |
Teclison Ltd. | September 2014 | Phase 1 Phase 2 |
| NCT00003369 | Completed | Drug: tirapazamine Drug: cisplatin |
Cervical Cancer | SWOG Cancer Research Network | August 1998 | Phase 2 |
| NCT00098995 | Completed | Drug: tirapazamine Drug: cisplatin |
Cervical Cancer | Peter MacCallum Cancer Centre, Australia |
December 2004 | Phase 1 |
| NCT00094081 | Completed | Drug: tirapazamine (SR259075) Drug: cisplatin |
Head and Neck Neoplasms | Sanofi | October 2002 | Phase 3 |
| NCT00020696 | Completed | Drug: cisplatin Drug: tirapazamine |
Primary Peritoneal Cavity Cancer Ovarian Cancer |
Gynecologic Oncology Group | June 2001 | Phase 21 |
 DNA oxidative damage (AP/100 kbp) in heart homogenates.
Schematic presentation of one-electron reduction of DOX and TP in hypoxic and normoxic conditions.Oxid Med Cell Longev. 2012; 2012: 890826. |
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(a) Increased eosinophilia of scattered cardiomyocytes (10TP+DOX group; H&E, objective magnification 10x). (b) Positive color reaction detecting necrosis (group 10TP+DOX; Selyes method, objective magnification 20x).Oxid Med Cell Longev. 2012; 2012: 890826. |
Representative Western blot analysis for RyR2 protein in cardiac muscle homogenates (beta-actin is shown as a loading control) and densitometric analysis (mean ± SD) of total RyR2 content expressed as percent changes with respect to the control group, which was established at 100%.Oxid Med Cell Longev. 2012; 2012: 890826. |
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