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27314-97-2 (Tirapazamine)

1

Identification

Tirapazamine Tirapazamine
Name Tirapazamine
Formula C7H6N4O2
MW 178.15
CAS No. 27314-97-2
EINECS
Smiles NC1=[N+]([O-])C2=CC=CC=C2[N+]([O-])=N1
Synonyms SR259075;SR4233;Tirazone;Win59075; 3-aminobenzo[e][1,2,4]triazine 1,4-dioxide
InChI InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
2

Introduction

Tirapazamine(SR259075; Win59075; SR4233) is an experimental anticancer drug that is activated to a toxic radical only at very low levels of oxygen; a phenomenon known as tumor hypoxia. IC50 value: Target: in vitro: Tirapazamine could downregulate HIF-1α expression by decreasing HIF-1α protein synthesis.

Background Information

Tirapazamine is a bioreductive, anti-neoplastic, anti-cancer agent that is selectively toxic to cells under hypoxic conditions. ......by AdooQ BioScience, LLC
Tirapazamine is a?benzotriazine di-N-oxide with potential antineoplastic activity. Tirapazamine is selectively activated by multiple reductases to form free radicals in hypoxic cells, thereby inducing single-and double-strand breaks in DNA, base damage, a ......by BOC Sciences
Trapazamine, also known as SR-4233,DNA-damaging drug potentially for the treatment of cervical carcinoma, head and neck cancer. 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. ......by MedKoo Biosciences, Inc.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:Pink to red Solid EBNumber:EB000015581

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Tirapazamine Sanofi Head and Neck Neoplasms 2004/10/11 2010/2/1 Phase 3 Clinical
Tirapazamine National Cancer Institute (NCI) Limited Stage Small Cell Lung Cancer 2003/8/6 2012/12/1 Phase 2 Clinical
Tirapazamine National Cancer Institute (NCI) Cervical Adenocarcinoma Cervical Adenosquamous Cell Carcinoma Cervical Squamous Cell Carcinoma Cervical Cancer 2005/12/6 2014/6/1 Phase 3 Clinical
Tirapazamine Teclison Ltd. Hepatocellular Carcinoma 2014/6/10 2015/8/1 Phase 1 Clinical
Tirapazamine Sanofi Lung Cancer 2001/6/6 2010/2/1 Phase 3 Clinical
Tirapazamine - Phase 3
7

Safety Data of Tirapazamine

Hazard Symbols : Xi
Risk Statements : 36/37/38
Safety Statements : 26-36
RTECS : DM0671500
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AdooQ BioScience, LLC USA
Apexbio Technology LLC 50mg/USD60(In stock) USA
BOC Sciences
Biochempartner Co., Ltd China
CHEMSCENE, LLC 50mg/USD72();100mg/USD132() USA
Carbosynth Limited 50mg/USD140()
China Jintai Biocompound Company China
Clearsynth Labs Limited 25mg/USD100() India
Linxiang Huanyu Pharmaceutical Co., Ltd. China
MedChemexpress Co., Ltd. 50mg/USD72();100mg/USD132() USA
MedKoo Biosciences, Inc. USA
Santa Cruz Biotechnology, Inc. 100mg/USD278() USA
Shanghai Haoyuan Chemexpress Co., Ltd. 50mg/USD72();100mg/USD132() China
Sigma-Aldrich, Inc. 10mg/USD54() USA
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Related Products

Other Forms of 27314-97-2

Name CAS No Formula MW

Recommended Compounds in Topoisomerase

Name CAS No Formula MW
Pirarubicin (Hydrochloride) 95343-20-7 C32H38ClNO12 664.1
Exatecan (Mesylate) 169869-90-3 C25H26FN3O7S 531.55
Flumequine 42835-25-6 C14H12FNO3 261.25
Nemorubicin 108852-90-0 C32H37NO13 643.64
Amsacrine (hydrochloride) 54301-15-4 C21H20ClN3O3S 429.92
Ellipticine 519-23-3 C17H14N2 246.31
DOXO-EMCH 151038-96-9 C37H42N4O13 750.75
Topotecan (Hydrochloride) 119413-54-6 C23H24ClN3O5 457.91
Topotecan 123948-87-8 C23H23N3O5 421.45
Teniposide 29767-20-2 C32H32O13S 656.65
TAS-103 174634-08-3 C20H19N3O2 333.38
TAS-103 (dihydrochloride) 174634-09-4 C20H21Cl2N3O2 406.31
Pixantrone (dimaleate) 144675-97-8 C21H23N5O6 441.44
Pixantrone 144510-96-3 C17H19N5O2 325.37
Pirarubicin 72496-41-4 C32H37NO12 627.64
SN-38 86639-52-3 C22H20N2O5 392.4
Irinotecan (hydrochloride) 100286-90-6 C33H39ClN4O6 623.14
Exatecan 171335-80-1 C24H22FN3O4 435.45
Etoposide 33419-42-0 C29H32O13 588.56
Epirubicin (hydrochloride) 56390-09-1 C27H30ClNO11 579.98

Recommended Compounds in Same Indication

Name CAS No Formula MW
Tivantinib 905854-02-6 C23H19N3O2 369.42
Oltipraz 64224-21-1 C8H6N2S3 226.34
Brivanib (alaninate) 649735-63-7 C22H24FN5O4 441.46
Resminostat 864814-88-0 C16H19N3O4S 349.4
Sorafenib (Tosylate) 475207-59-1 C28H24ClF3N4O6S 637.03
Lenvatinib 417716-92-8 C21H19ClN4O4 426.85
Cabozantinib 849217-68-1 C28H24FN3O5 501.51
Ispinesib 336113-53-2 C30H33ClN4O2 517.06
LY2109761 700874-71-1 C26H27N5O2 441.52
LY2157299 700874-72-2 C22H19N5O 369.42
Sorafenib 284461-73-0 C21H16ClF3N4O3 464.83
Seocalcitol 134404-52-7 C30H46O3 454.68
Marimastat 154039-60-8 C15H29N3O5 331.4079
TSU-68 252916-29-3 C18H18N2O3 310.35
DMXAA 117570-53-3 C17H14O4 282.2906
Resminostat (hydrochloride) 1187075-34-8 C16H20ClN3O4S 385.87
Satraplatin 129580-63-8 C10H22Cl2N2O4Pt 500.28
Efaproxiral 131179-95-8 C20H23NO4 341.4
INCB28060 1029712-80-8 C23H17FN6O 412.42
Refametinib 923032-37-5 C19H20F3IN2O5S 572.34
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Route of Synthesis

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References

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More Information

Tirapazamine

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