Tirapazamine
Names
[ CAS No. ]:
27314-97-2
[ Name ]:
Tirapazamine
[Synonym ]:
4-hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine
1,2,4-Benzotriazin-3-amine, 1,4-dioxide
3-Amino-1,2,4-benzotriazine 1,4-Dioxide
1,4-Dioxido-1,2,4-benzotriazin-3-ylamine
SR 259075
1,2,4-Benzotriazin-3-amine 1,4-dioxide
4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine SR 259075 SR 4233 Tirazone Win 59075
Tirazone
Tirapazamine
3-Aminobenzo[e][1,2,4]triazine 1,4-dioxide
Biological Activity
[Description]:
[Related Catalog]:
[References]
[Related Small Molecules]
Chemical & Physical Properties
[ Density]:
1.7±0.1 g/cm3
[ Boiling Point ]:
493.6±28.0 °C at 760 mmHg
[ Melting Point ]:
220ºC
[ Molecular Formula ]:
C7H6N4O2
[ Molecular Weight ]:
178.148
[ Flash Point ]:
252.3±24.0 °C
[ Exact Mass ]:
178.049072
[ PSA ]:
89.83000
[ LogP ]:
-0.31
[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C
[ Index of Refraction ]:
1.777
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- DM0671500
- CHEMICAL NAME :
- 1,2,4-Benzotriazine, 3-amino-, 1,4-dioxide
- CAS REGISTRY NUMBER :
- 27314-97-2
- BEILSTEIN REFERENCE NO. :
- 0179322
- LAST UPDATED :
- 199712
- DATA ITEMS CITED :
- 8
- MOLECULAR FORMULA :
- C7-H6-N4-O2
- MOLECULAR WEIGHT :
- 178.17
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 59390 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD - Lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >36 mg/kg
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Endocrine - other changes Blood - changes in bone marrow (not otherwise specified)
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 89 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 101 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 19 mg/kg/2W-C
- TOXIC EFFECTS :
- Related to Chronic Data - death
MUTATION DATA
- TYPE OF TEST :
- Unscheduled DNA synthesis
- TEST SYSTEM :
- Rodent - rat Mammary gland
- DOSE/DURATION :
- 500 umol/L
- REFERENCE :
- CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 11,1407,1990
Safety Information
[ Symbol ]:
GHS07
[ Signal Word ]:
Warning
[ Hazard Statements ]:
H315-H319-H335
[ Precautionary Statements ]:
P261-P305 + P351 + P338
[ Hazard Codes ]:
Xi: Irritant;
[ Risk Phrases ]:
36/37/38
[ Safety Phrases ]:
26-36
[ RIDADR ]:
NONH for all modes of transport
[ RTECS ]:
DM0671500
Synthetic Route
Precursor & DownStream
Precursor
DownStream
Articles
J. Biomed. Mater. Res. B. Appl. Biomater. 103(3) , 618-28, (2015)
Three-dimensional (3-D) tissue engineered constructs provide a platform for examining how the local extracellular matrix contributes to the malignancy of various cancers, including human glioblastoma ...
Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca²⁺ balance protein levels.Oxid. Med. Cell. Longev. 2012 , 890826, (2012)
Doxorubicin (DOX) causes long-term cardiomyopathy that is dependent on oxidative stress and contractility disorders. Tirapazamine (TP), an experimental adjuvant drug, passes the same red-ox transforma...
Exploiting tumour hypoxia and overcoming mutant p53 with tirapazamine.Br. J. Cancer 77 Suppl 4 , 12-4, (1998)
Human solid tumours are composed of a significant proportion of hypoxic cells, i.e. cells with oxygen levels lower than those of normal tissues. Tumour hypoxic cells have been shown to have a negative...