Tirapazamine

Modify Date: 2025-08-20 18:02:07

Tirapazamine structure	Common Name	Tirapazamine
	CAS Number	27314-97-2	Molecular Weight	178.148
	Density	1.7±0.1 g/cm3	Boiling Point	493.6±28.0 °C at 760 mmHg
	Molecular Formula	C₇H₆N₄O₂	Melting Point	220ºC
	MSDS	Chinese USA	Flash Point	252.3±24.0 °C
	Symbol	GHS07	Signal Word	Warning

Use of Tirapazamine

Tirapazamine is an anticancer agent that shows selective cytotoxicity for hypoxic cells in solid tumors, thereby inducing single-and double-strand breaks in DNA, base damage, and cell death.

Name	tirapazamine
Synonym	More Synonyms

Description	Tirapazamine is an anticancer agent that shows selective cytotoxicity for hypoxic cells in solid tumors, thereby inducing single-and double-strand breaks in DNA, base damage, and cell death.
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Cancer
References	[1]. Cai TY, et al. Tirapazamine sensitizes hepatocellular carcinoma cells to topoisomerase I inhibitors via cooperative modulation of hypoxia-inducible factor-1α. Mol Cancer Ther. 2014 Mar;13(3):630-42. [2]. Sliwinska J, et al. Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca2? balance protein levels. Oxid Med Cell Longev. 2012;2012:890826.

Description

Tirapazamine is an anticancer agent that shows selective cytotoxicity for hypoxic cells in solid tumors, thereby inducing single-and double-strand breaks in DNA, base damage, and cell death.

Related Catalog

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

References

[1]. Cai TY, et al. Tirapazamine sensitizes hepatocellular carcinoma cells to topoisomerase I inhibitors via cooperative modulation of hypoxia-inducible factor-1α. Mol Cancer Ther. 2014 Mar;13(3):630-42.

[2]. Sliwinska J, et al. Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca2? balance protein levels. Oxid Med Cell Longev. 2012;2012:890826.

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

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

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

1-oxido-1,2,4-b...

CAS#:5424-06-6

~79%

Tirapazamine

CAS#:27314-97-2

Literature: Suzuki, Hitomi; Kawakami, Takehiko Synthesis, 1997 , # 8 p. 855 - 857

N/A

CAS#:20028-79-9

~75%

Tirapazamine

CAS#:27314-97-2

Literature: Gatenyo, Julia; Johnson, Kevin; Rajapakse, Anuruddha; Gates, Kent S.; Rozen, Shlomo Tetrahedron, 2012 , vol. 68, # 43 p. 8942 - 8944

1-oxido-1,2,4-b...

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3-hydroxy-1,2,4...

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Tirapazamine

CAS#:27314-97-2

Literature: Gatenyo, Julia; Johnson, Kevin; Rajapakse, Anuruddha; Gates, Kent S.; Rozen, Shlomo Tetrahedron, 2012 , vol. 68, # 43 p. 8942 - 8944

1,2,4-benzotria...

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~0%

1-oxido-1,2,4-b...

CAS#:5424-06-6

3-amino-1,2,4-b...

CAS#:27238-43-3

Tirapazamine

CAS#:27314-97-2

Detail

Literature: Fuchs; Chowdhury; Barnes; Gates Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 107 - 114

2-Nitroaniline

CAS#:88-74-4

Tirapazamine

CAS#:27314-97-2

Literature: Fuchs; Chowdhury; Barnes; Gates Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 107 - 114

1,2-Dinitrobenzene

CAS#:528-29-0

Tirapazamine

CAS#:27314-97-2

Literature: Suzuki, Hitomi; Kawakami, Takehiko Synthesis, 1997 , # 8 p. 855 - 857

1,2,4-Benzotria...

CAS#:67692-91-5

Tirapazamine

CAS#:27314-97-2

Literature: Robbins; Schofield Journal of the Chemical Society, 1957 , p. 3186,3191

3-hydroxy-1,2,4...

CAS#:27446-08-8

Tirapazamine

CAS#:27314-97-2

Literature: Robbins; Schofield Journal of the Chemical Society, 1957 , p. 3186,3191

1,2,4-benzotria...

CAS#:20028-80-2

Tirapazamine

CAS#:27314-97-2

Literature: Fuchs; Chowdhury; Barnes; Gates Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 107 - 114

Precursor 6
CAS#:5424-06-6 1-oxido-1,2,4-b... CAS#:20028-80-2 1,2,4-benzotria... CAS#:88-74-4 2-Nitroaniline CAS#:528-29-0 1,2-Dinitrobenzene
CAS#:67692-91-5 1,2,4-Benzotria... CAS#:27446-08-8 3-hydroxy-1,2,4...
DownStream 3
CAS#:5424-06-6 1-oxido-1,2,4-b... CAS#:34371-14-7 (4S,5R)-4-Hydro... CAS#:20028-80-2 1,2,4-benzotria...

An innovative three-dimensional gelatin foam culture system for improved study of glioblastoma stem cell behavior.

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...

Name: Cytotoxicity counterscreen for inhibitors of SARS-CoV-2 cell entry
Source: NCGC
Target: N/A
External Id: TRND-SARS-CoV-2-cytotox-48hr

Name: Primary qHTS to identify inhibitors of SARS-CoV-2 cell entry
Source: NCGC
External Id: TRND-SARS-CoV-2-PP

Name: Interexperimental ratio of hypoxic TPZ C10 to hypoxic BTO C10 using murine SCCVII cel...
Source: ChEMBL
Target: SCC-7
External Id: CHEMBL822490

Name: Inhibitory concentration against murine SCCVII cell line under aerobic condition
Source: ChEMBL
Target: SCC-7
External Id: CHEMBL822489

Name: Inhibitory concentration against murine SCCVII cell line under hypoxic condition
Source: ChEMBL
Target: SCC-7
External Id: CHEMBL822488

Name: Partition coefficient (logP)
Source: ChEMBL
Target: N/A
External Id: CHEMBL637351

Name: Inhibitory concentration against human adenocarcinoma HT-29 cell line under hypoxic c...
Source: ChEMBL
Target: HT-29
External Id: CHEMBL823526

Name: Interexperimental ratio of hypoxic TPZ C10 to hypoxic BTO C10 using human adenocarcin...
Source: ChEMBL
Target: HT-29
External Id: CHEMBL823528

Name: Inhibitory concentration against human adenocarcinoma HT-29 cell line under aerobic c...
Source: ChEMBL
Target: HT-29
External Id: CHEMBL823527

Name: Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Cac...
Source: ChEMBL
Target: Severe acute respiratory syndrome coronavirus 2
External Id: CHEMBL4303805

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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

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Tirapazamine

Use of Tirapazamine

Names

Tirapazamine Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Synthetic Route

Precursor & DownStream

Articles36

TirapazamineBioassay

Synonyms

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