tirapazamine
Small moleculeexperimental
Tirapazamine is an experimental anticancer drug that is activated to a toxic radical only at very low levels of oxygen (hypoxia). Such levels are common in human solid tumors, a phenomenon known as tumor hypoxia. Thus, tirapazamine is activated to its toxic form preferentially in the hypoxic areas of solid tumors. Cells in these regions are resistant to killing by radiotherapy and most anticancer drugs. Thus the combination of tirapazamine with conventional anticancer treatments is particularly effective. As of 2006, tirapazamine is undergoing phase III testing in patients with head and neck cancer and gynecological cancer, and similar trials are being undertaken for other solid tumor types. — Wikipedia
Clinical trial activity
18 trials · 18 clinical orgs · 0 marketing orgs
Phase 1
6
Phase 2
12
Phase 3
5
Phase 4
0
Earliest trial started Jun 1, 1996 (NCT00002774)
Timeline
Indications
Studied for
- Carcinoma, Hepatocellular · Phase 2
- Colorectal Neoplasms · Phase 2
- Hamartoma · Phase 2
- Head and Neck Neoplasms · Phase 3
- Intestinal Neoplasms · Phase 1
- Lung Neoplasms · Phase 3
- Neoplasms · Phase 1
- Neuroendocrine Tumors · Phase 1
- Ovarian Neoplasms · Phase 2
- Rhabdomyosarcoma · Phase 2
- Small Cell Lung Carcinoma · Phase 2
- Squamous Cell Carcinoma of Head and Neck · Phase 3
- Stomach Neoplasms · Phase 2
- Uterine Cervical Neoplasms · Phase 3
Mechanism of action
- DNADISRUPTING AGENT
DNA disrupting agent
- Unspecified targetUnclear
unclear
Chemistry & pharmacology
Loading structure…
SMILES
Nc1n[n+]([O-])c2ccccc2[n+]1[O-]- Mol. weight
- 178.15 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaTirapazamine ↗
- ChEMBLCHEMBL50882 ↗
Also known as
- 1,2,4-benzotriazin-3-amine, 1,4-dioxide
- 1,2,4-benzotriazin-3-amine, 1,4-dioxide
- 1,2,4-benzotriazin-3-amine, 1,4-dioxide
- 3-amino-1,2,4-benzothiadi- azine 1,1-dioxide
- 3-amino-1,2,4-benzotriazine 1,4-dioxide
- 3-amino-1,2,4-benzotriazine 1,4-dioxide
- 3-amino-1,2,4-benzotriazine-1,4-dioxide
- nsc 130181
- sr 4233
- sr-4233
- tirapazamine
- tirapazamine
- tirapazamine
- tirapazamine
- tirapazamine
- tirazone
- win 59075
- win-59075
- win-59075
- win-59075
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT03145558 | Phase 2 | Oct 1, 2017 | Teclison Ltd., University of California, Irvine |
| NCT03259867 | Phase 2 | Jul 1, 2017 | Teclison Ltd., University of California, Irvine |
| NCT02174549 | Phase 1 | Sep 1, 2014 | National Taiwan University, Teclison Ltd. |
| NCT00262821 | Phase 3 | Feb 1, 2006 | Canadian Cancer Trials Group, Gynecologic Oncology Group, National Cancer Institute (NCI) |
| NCT00174837 | Phase 3 | Apr 1, 2005 | Groupe Oncologie Radiotherapie Tete et Cou, Sanofi |
| NCT00098995 | Phase 1 | Dec 1, 2004 | National Cancer Institute (NCI), Peter MacCallum Cancer Centre |
| NCT00066742 | Phase 2 | Sep 1, 2003 | National Cancer Institute (NCI), Southwest Oncology Group |
| NCT00094081 | Phase 3 | Oct 1, 2002 | Sanofi |
| NCT00033410 | Phase 1 | Mar 1, 2002 | National Cancer Institute (NCI), University of California, Berkeley, University of California, Davis |
| NCT00025363 | Phase 2 | Nov 1, 2001 | National Cancer Institute (NCI) |
| NCT00020696 | Phase 2 | Jun 1, 2001 | Gynecologic Oncology Group, National Cancer Institute (NCI), University of Toronto |
| NCT00006484 | Phase 3 | Nov 1, 2000 | National Cancer Institute (NCI), Southwest Oncology Group, University of Kansas |
| NCT00006487 | Phase 1 | Oct 1, 2000 | National Cancer Institute (NCI), Southwest Oncology Group, Stanford University |
| NCT00017459 | Phase 3 | Jul 1, 2000 | Sanofi |
| NCT00005078 | Phase 1 | Mar 1, 2000 | City of Hope National Medical Center, National Cancer Institute (NCI) |
| NCT00003288 | Phase 1 | Aug 1, 1998 | National Cancer Institute (NCI), The University of Texas, Dallas |
| NCT00003369 | Phase 2 | Aug 1, 1998 | National Cancer Institute (NCI), Southwest Oncology Group, University of New Mexico |
| NCT00002774 | Phase 2 | Jun 1, 1996 | National Cancer Institute (NCI), Stanford University |
Showing 18 of 18 trials
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Organizations
Research & Development (18)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| National Cancer Institute (NCI) | Government | 12 | 4 | 3 | 1996 |
| Southwest Oncology Group | Academic/Hospital | 4 | 3 | 3 | 1998 |
| Sanofi | For profit | 3 | 3 | 1 | 2000 |
| Teclison Ltd. | For profit | 3 | 3 | 2 | 2014 |
| Gynecologic Oncology Group | Academic/Hospital | 2 | 1 | 2 | 2001 |
| Stanford University | Academic/Hospital | 2 | 1 | 2 | 1996 |
| University of California, Irvine | Academic/Hospital | 2 | 0 | 1 | 2017 |
| Canadian Cancer Trials Group | Academic/Hospital | 1 | 0 | 1 | 2006 |
| City of Hope National Medical Center | Academic/Hospital | 1 | 1 | 1 | 2000 |
| Groupe Oncologie Radiotherapie Tete et Cou | Academic/Hospital | 1 | 0 | 1 | 2005 |
| National Taiwan University | Academic/Hospital | 1 | 0 | 1 | 2014 |
| Peter MacCallum Cancer Centre | Academic/Hospital | 1 | 1 | 1 | 2004 |
| The University of Texas, Dallas | Academic/Hospital | 1 | 0 | 1 | 1998 |
| University of California, Berkeley | Academic/Hospital | 1 | 1 | 1 | 2002 |
| University of California, Davis | Academic/Hospital | 1 | 0 | 1 | 2002 |
| University of Kansas | Academic/Hospital | 1 | 0 | 1 | 2000 |
| University of New Mexico | Academic/Hospital | 1 | 0 | 1 | 1998 |
| University of Toronto | Academic/Hospital | 1 | 0 | 1 | 2001 |
18 organizations
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