Tirazamin - 10mM in DMSO , DNA disrupting agent, CAS No.27314-97-2, DNA disrupting agent

CAS: 27314-97-2 Cat. No.: T580542 Molecular Weight: 178.15 EC Number: 636-678-5
AVAILABLE TO ORDER
GRADE & PURITY 10mM in DMSO
Synonyms
TIRAPAZAMINE|27314-97-2|3-Aminobenzo[e][1,2,4]triazine 1,4-dioxide|1,2,4-Benzotriazin-3-amine, 1,4-dioxide|Tirazone|3-Amino-1,2,4-benzotriazine 1,4-dioxide|Win-59075|WIN 59075|SR 4233|SR-4233|CHEBI:78887|SR-259075|NSC-130181|SR259075|1UD32YR59G|SR259075;S
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
Size
Status
Price
Qty
1ml
T580542-1ml
2
$48.90
Enter a quantity for the sizes you want to add.
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Why this grade

10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

🌡

Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

📋

Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

📚

Literature proof

Cited in 5 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

Tirapazamine (Win59075) is a potent cytotoxic agent under hypoxic conditions, can induce apoptosis by inducing breaks in single and double-stranded DNA, as well as chromosomal breaks. The compound sensitizes cells to other ionizing radiation and other cytotoxic agents like cisplatin.

Specifications

Synonyms
TIRAPAZAMINE | 27314-97-2 | 3-Aminobenzo[e][1, 2, 4]triazine 1, 4-dioxide | 1, 2, 4-Benzotriazin-3-amine, 1, 4-dioxide | Tirazone | 3-Amino-1, 2, 4-benzotriazine 1, 4-dioxide | Win-59075 | WIN 59075 | SR 4233 | SR-4233 | CHEBI:78887 | SR-259075 | NSC-130181 | SR259075 | 1UD32YR59G | SR259075;S
Specifications & Purity
10mM in DMSO
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
This product requires cold chain shipping. Ground and other economy services are not available.
Action Type
DISRUPTING AGENT
Mechanism of action
DNA disrupting agent
Product Properties
ALogP-0.3
Names and Identifiers
Pubchem Sid528772061
Canonical SmilesC1=CC=C2C(=C1)[N+](=C(N=[N+]2[O-])N)[O-]
IUPAC Name1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine
InChIKeyORYDPOVDJJZGHQ-UHFFFAOYSA-N
INCHI1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
Isomeric SMILES C1=CC=C2C(=C1)[N+](=C(N=[N+]2[O-])N)[O-]
WGK Germany 3
RTECS DM0671500
Molecular Weight 178.15
Reaxy-Rn 179322
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=179322&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

Download SDS →

✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

Look up COA →

📊 Datasheet

Quick-reference summary of product specifications and applications.

View datasheet →

🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTriazines
SubclassAminotriazines
Intermediate Tree Nodes Not available
Direct ParentAminotriazines
Alternative Parents Benzenoids  1,2,4-triazines  Heteroaromatic compounds  Azacyclic compounds  Primary amines  Organopnictogen compounds  Organic oxides  Hydrocarbon derivatives  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Aminotriazine - 1,2,4-triazine - Benzenoid - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminotriazines. These are organic compounds containing an amino group attached to a triazine ring.
External Descriptors aromatic amine - N-oxide - benzotriazines
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA1 Tclin Carbonic anhydrase I (13240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA12 Tclin Carbonic anhydrase XII (6231 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA9 Tclin Carbonic anhydrase IX (8255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHN (49357 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAKI-1 (44928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COLO 205 (50209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DMS-273 (14108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
M14 (47487 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-468 (9477 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLT-4 (49676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-4 (44535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-5 (45555 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-8 (47708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPMI-8226 (44974 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXF 393 (41971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXF 631 (11415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-295 (48000 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SiHa (2051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-28 (48833 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-5 (47095 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SN12C (47755 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-19 (46794 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-78 (14240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TK-10 (45540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-257 (46019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-62 (47335 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UO-31 (46270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
XF498 (12972 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
786-0 (47912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EKVX (44102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H322M (45589 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-92 (41141 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IGROV-1 (47897 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
H9c2 (3506 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NRK (373 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SCC-7 (114 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
V79 (1637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
SensitivityHeat sensitive
Melt Point(°C)230℃
Molecular Weight178.150 g/mol
XLogP3-0.300
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass178.049 Da
Monoisotopic Mass178.049 Da
Topological Polar Surface Area89.800 Ų
Heavy Atom Count13
Formal Charge0
Complexity191.000
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Documents & Articles
Citations of This Product
References
1. Zhang Xiaoge, Cheng Lili, Lu Yao, Tang Junjie, Lv Qijun, Chen Xiaomei, Chen You, Liu Jie.  (2021)  A MXene-Based Bionic Cascaded-Enzyme Nanoreactor for Tumor Phototherapy/Enzyme Dynamic Therapy and Hypoxia-Activated Chemotherapy.  Nano-Micro Letters,  14  (1): (1-21).  [PMID:34882297] [10.1007/s40820-021-00761-w]
2. Kunpeng Lin, Shaochen Wang, Shuling Yu, Wen Si, Miaojie Yang, Ningning Xu, Yu Liu, Yan Zheng, Shuang Zhao, Jiahua Shi, Jintao Yuan.  (2025)  Porphyrin-based covalent organic framework with NIR absorption: Preparation, hyaluronic acid modification, and cascading a hypoxia-sensitive drug for synergistic therapy of cancer phototherapy/chemotherapy.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40158586] [10.1016/j.ijbiomac.2025.142645]
3. Jialiang Zheng, Zhenhang Lin, Xi Li, Fenglin Miao, Tuerhong Maimaitiming, Yuan Ma, Zhao Wang, Yilai Gao, Zhe Xi, Aobo Zhuang, Ruyi Zhang, Yingxue Cheng, Xiaogang Xia, Yue Wang, Yan Huang, Xu Kong, Fanghong Luo, Huichen Li, Chundong Yu, Wengang Li.  (2025)  Tumor Microenvironment-Responsive Nanodrug for Embolotherapy and Enhanced Chemotherapy.  ACS Applied Materials & Interfaces,      [PMID:40014576] [10.1021/acsami.4c18502]
4. An Jie, Chu Kaile, Li Xirong, Ma Huizhu, Zhou Qin, Niu Chenliang, Gao Jie, Lv Junping, Cao Jianbo, Zhang XinYu, Zhou Haitao, Wang Hongliang, Li Min, Wu Zhifang, Li Sijin.  (2025)  Hypoxia-augmented chemotherapy potentiates imaging-guided combinatorial radionuclide-sonodynamic therapy for pancreatic cancer.  JOURNAL OF NANOBIOTECHNOLOGY,  23  (1): (1-18).  [PMID:40707984] [10.1186/s12951-025-03611-8]
5. Hong Jiang, Qin-Xie Xie, Tianzhao Tian, Qingqing Yang, Peipei Qian, Jia-Yi Liu, Wending Yan, Shengfeng Huang, Cui Shao, Wei Yi, Yifa Chen, Xu-Jia Hong.  (2026)  Oxygen-Adaptive Covalent Organic Framework Nanoarchitectonics with High Photothermal Conversion Efficiency for Quadruple-Modal Tumor Therapy.  Advanced Healthcare Materials,      [PMID:] [10.1002/adhm.202504853]
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