ChemicalBook > CAS DataBase List > 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

Product Name: 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE
CAS No.: 27314-97-2
Chemical Name: 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE
Synonyms: TPZ;TIRAPAZAMINE;CS-2810;SR-4233;Tirazone;SR 259075;Tirazamin;NSC130181;NSC 130181;NSC-130181
CBNumber: CB5442522
Molecular Formula: C7H6N4O2
Formula Weight: 178.15
MOL File: 27314-97-2.mol

Less

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Property

Melting point:: 220°C dec.
Boiling point:: 493.6±28.0 °C(Predicted)
Density: 1.68±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMSO: soluble10mg/mL, clear
form: powder
pka: 1.51±0.30(Predicted)
color: orange to dark orange-red
InChI: InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
InChIKey: ORYDPOVDJJZGHQ-UHFFFAOYSA-N
SMILES: [N+]1([O-])C2=CC=CC=C2[N+]([O-])=C(N)N=1

Less

Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
RTECS: DM0671500
HS Code: 2933.99.7500

Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Less

N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0552
Product name: Tirapazamine
Purity: ≥98% (HPLC)
Packaging: 10mg
Price: $78.3
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML0552
Product name: Tirapazamine
Purity: ≥98% (HPLC)
Packaging: 50mg
Price: $160
Updated: 2025/07/31

TCI Chemical

Product number: T3823
Product name: Tirapazamine
Packaging: 50MG
Price: $188
Updated: 2025/07/31

TCI Chemical

Product number: T3823
Product name: Tirapazamine
Packaging: 250MG
Price: $688
Updated: 2025/07/31

Cayman Chemical

Product number: 25981
Product name: Tirapazamine
Purity: ≥98%
Packaging: 10mg
Price: $62
Updated: 2024/03/01

Less

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Chemical Properties,Usage,Production

Description

Tirapazamine is a hypoxia-activated anticancer agent. It is converted to an oxidizing radical under hypoxic conditions and can induce single- and double-strand breaks in DNA, formation of trapped topoisomerase I- and II-DNA complexes, and other chromosomal aberrations, leading to cytotoxicity. Tirapazamine induces hypoxia-enhanced cytotoxicity in DT40 cells (IC₅₀s = 1.02 and 4.34 μM in hypoxic and normoxic conditions, respectively). It also induces cytotoxicity in HT-1080 and A549 cells in a concentration-dependent manner under hypoxic conditions. In vivo, tirapazamine sensitizes tumors to cisplatin in a mouse RIF-1 fibrosarcoma tumor model. Tirapazamine (0.08 mmol/kg) also sensitizes tumors to fractionated irradiation in a FaDu hypopharyngeal squamous cell carcinoma mouse xenograft model.

Chemical Properties

Orange Needles

Uses

A bioreductive anticancer agent. Selectively toxic to cells under hypoxic conditions. An antineoplastic

Uses

Tirapazamine has been used to evaluate its cytotoxic effect on U-251 MG (glioblastoma cell line) cell viability.

Definition

ChEBI: A member of the class of benzotriazines that is 1,2,4-benzotriazine carrying an amino substituent at position 3 and two oxido substituents at positions 1 and 4.

Biochem/physiol Actions

Under hypoxic conditions, tirapazamine is a potent cytotoxic agent that induces 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.

References

[1] BROWN J. SR 4233 (Tirapazamine): a new anticancer drug exploiting hypoxia in solid tumours[J]. British Journal of Cancer, 1993, 67 6: 1163-1170. DOI: 10.1038/bjc.1993.220
[2] SRINI B REDDY Stephen K W. Tirapazamine: a novel agent targeting hypoxic tumor cells.[J]. Expert opinion on investigational drugs, 2009, 18 1: 77-87. DOI: 10.1517/13543780802567250
[3] TAKAHITO MORIWAKI. Cytotoxicity of Tirapazamine (3-Amino-1,2,4-benzotriazine-1,4-dioxide)-Induced DNA Damage in Chicken DT40 Cells[J]. Chemical Research in Toxicology, 2016, 30 2: 699-704. DOI: 10.1021/acs.chemrestox.6b00417
[4] M J DORIE J M B. Tumor-specific, schedule-dependent interaction between tirapazamine (SR 4233) and cisplatin.[J]. Cancer research, 1993, 53 19: 4633-4636.
[5] A EL SAID. Comparison of the effectiveness of tirapazamine and carbogen with nicotinamide in enhancing the response of a human tumor xenograft to fractionated irradiation.[J]. Radiation oncology investigations, 1999, 7 3: 163-169. DOI: 10.1002/(sici)1520-6823(1999)7:3<163::aid-roi5>3.0.co;2-m

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Preparation Products And Raw materials

Raw materials

Preparation Products

Less

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Suppliers

Canada 1 China 157 Europe 2 Germany 1 India 4 Japan 1 Switzerland 1 United Kingdom 3 United States 18 Global 188

Nanjing LuoDa Chemical Co., Ltd

Tel: 025-66016961 13382082786
Fax: 025-52204547
Country: China
ProdList: 222
Advantage: 55

Wuhan Acumen Bio-Technology Co.,ltd

Tel: 027-027-16602739303 16602739303
Email: 673003916@qq.com
Country: China
ProdList: 2935
Advantage: 58

Wuhan Chuangshuo Chemical Technology Co., Ltd

Tel: 180-62205282 18062205282
Email: turbo_cq@163.com
Country: China
ProdList: 34
Advantage: 58

J & K SCIENTIFIC LTD.

Tel: 18210857532; 18210857532
Fax: 86-10-82849933
Email: jkinfo@jkchemical.com
Country: China
ProdList: 96815
Advantage: 76

3B Pharmachem (Wuhan) International Co.,Ltd.

Tel: 821-50328103-801 18930552037
Fax: 86-21-50328109
Email: 3bsc@sina.com
Country: China
ProdList: 15838
Advantage: 69

Chembest Research Laboratories Limited

Tel: +86-21-20908456
Fax: 021-58180499
Email: sales@BioChemBest.com
Country: China
ProdList: 6003
Advantage: 61

Beijing HwrkChemical Technology Co., Ltd

Tel: 18515581800 18501085097
Fax: 010-89508210
Email: sales.bj@hwrkchemical.com
Country: China
ProdList: 9400
Advantage: 55

NOTA Chemical (Shanghai) Co.,Ltd

Tel: 021-50189163
Fax: 021-51687927
Email: sales@notachem.com
Country: China
ProdList: 205
Advantage: 64

Chemsky（shanghai）International Co.,Ltd.

Tel: 021-50135380
Email: shchemsky@sina.com
Country: China
ProdList: 32321
Advantage: 50

Hunan Hui Bai Shi Biotechnology Co., Ltd.

Tel: 0731-85526065 13308475853
Email: ivy@hnhbsj.com
Country: China
ProdList: 7247
Advantage: 62

Dalian Meilun Biotech Co., Ltd.

Tel: 0411-62910999 13889544652
Email: sales@meilune.com
Country: China
ProdList: 4747
Advantage: 58

China Kouting Group Limited

Tel: +86 (21) 5811-6473 5811-6475
Fax: +86 (21) 6129-4103
Email: sales@koutingchina.com
Country: China
ProdList: 496
Advantage: 60

Haoyuan Chemexpress Co., Ltd.

Tel: 021-58950125
Fax: (86) 21-58955996
Email: info@chemexpress.com
Country: China
ProdList: 7552
Advantage: 61

Shanghai Aladdin Bio-Chem Technology Co.,LTD

Tel: 400-6206333 13167063860
Fax: 021-50323701
Email: anhua.mao@aladdin-e.com
Country: China
ProdList: 25003
Advantage: 65

TargetMol Chemicals Inc.

Tel: 021-021-33632979 15002134094
Fax: 021-33632979
Email: marketing@targetmol.com
Country: China
ProdList: 7782
Advantage: 58

Bide Pharmatech Ltd.

Tel: 400-164-7117 13681763483
Fax: +86-21-61629029
Email: product02@bidepharm.com
Country: China
ProdList: 39966
Advantage: 60

Finetech Industry Limited

Tel: 027-87465837 19945049750
Fax: 027-8777-2287
Email: sales@finetechnology-ind.com
Country: China
ProdList: 9637
Advantage: 58

Shanghai Macklin Biochemical Co.,Ltd.

Tel: 15221275939
Fax: 021-50706099
Email: shenlinxing@macklin.cn
Country: China
ProdList: 15873
Advantage: 55

Hangzhou J&H Chemical Co., Ltd.

Tel: 0571-87396432
Fax: 0571-87396431
Email: sales@jhechem.com
Country: China
ProdList: 14912
Advantage: 59

AdooQ Bioscience CHINA

Tel: 025-58849295 18951903616;
Fax: 025-68650336
Email: info@adooq.cn
Country: China
ProdList: 2990
Advantage: 60

Credit Asia Chemical Co., Ltd.

Tel: +86 (21) 61124340
Fax: +86 (21) 6129-4103
Country: China
ProdList: 9756
Advantage: 58

Hubei Jusheng Technology Co.,Ltd

Tel: 027-59599241 18871490274
Fax: 027-59599241
Email: 1400878000@qq.com
Country: China
ProdList: 9858
Advantage: 58

LETOPHARM LIMITED

Tel: +86-21-5821 5861
Fax: +86-21-5106 2861
Email: sales@letopharm.com
Country: China
ProdList: 2384
Advantage: 58

Sigma-Aldrich

Tel: 021-61415566 800-8193336
Email: orderCN@merckgroup.com
Country: China
ProdList: 51395
Advantage: 80

Shanghai Lollane Biological Technology Co.,Ltd.

Tel: 021-52996696，15000506266 15000506266
Fax: +86-21-52996696
Country: China
ProdList: 4769
Advantage: 55

AN PharmaTech Co Ltd

Tel: 86(21)68097365
Fax: 86(21)33321566
Email: sales@anpharma.net
Country: China
ProdList: 4891
Advantage: 55

Nanjing Vital Chemical Co., Ltd.

Tel: 025-87193546 18652950785
Fax: 025-87193546
Email: chemweiao@163.com
Country: China
ProdList: 9021
Advantage: 60

Nanjing XiLang Chemical Products Co., Ltd.

Tel: 18936048580
Email: chemxilang@163.com
Country: China
ProdList: 3909
Advantage: 58

Guangzhou QiYun Biotechnology Co., Ltd.

Tel: 020-61288194 61288195
Fax: 020-61288700
Email: 505721671@qq.com
Country: China
ProdList: 3866
Advantage: 58

Shanghai YuanYe Biotechnology Co., Ltd.

Tel: 021-61312847; 18021002903
Fax: QQ:3008007432
Email: 3008007409@qq.com
Country: China
ProdList: 71826
Advantage: 60

Shanghai Chaolan Chemical Technology Center

Tel: 021-QQ：65489617 15618227136
Fax: 21-5161 9052
Email: Sales@ATKchemical.com
Country: China
ProdList: 9125
Advantage: 58

Amadis Chemical Company Limited

Tel: 571-89925085
Fax: 0086-571-89925065
Email: sales@amadischem.com
Country: China
ProdList: 131957
Advantage: 58

Beijing Jin Ming Biotechnology Co., Ltd.

Tel: 010-60605840 18892239720
Fax: 010-60605840
Email: psaitong@jm-bio.com
Country: China
ProdList: 12306
Advantage: 58

Chuzhou KeMail Chemical Technology Co., Ltd

Tel: 0550-5196001 15000891977
Fax: 0550-5196001
Email: wj520wjxby@126.com
Country: China
ProdList: 1944
Advantage: 55

Hefei Hirisun Pharmatech Co., Ltd.

Tel: +86-0551-62678551 +86-15056975894
Fax: 05512678551
Email: sales@hirisunpharm.com
Country: China
ProdList: 176
Advantage: 55

Dezhou LonWel Pharmaceutical Technology Co., Ltd.

Tel: 13761310616
Fax: QQ: 39324283
Email: 39324283@qq.com
Country: China
ProdList: 1632
Advantage: 58

Shanghai CR Corporation Limited

Tel: 13062833949; 4006653949 4006653949
Fax: QQ: 2136646215
Email: fred.wen@crcorporation.cn
Country: China
ProdList: 9756
Advantage: 58

Amatek Scientific Co. Ltd.

Tel: 0512-56316828
Fax: 0512-56316826
Email: info@amateksci.com
Country: China
ProdList: 28785
Advantage: 58

Shenzhen Regent Biochemical Technology Co., Ltd.

Tel: 0755-85201366 18938635012
Fax: 0755-85201366
Email: sales@regentsciences.com
Country: China
ProdList: 9751
Advantage: 58

Aikon International Limited

Tel: 025-58859352 18068836627
Fax: 02557626880
Email: sales01@aikonchem.com
Country: China
ProdList: 16027
Advantage: 58

Rhawn Reagent

Tel: 400-400-1332688 18019345275
Fax: 400-133-2688
Email: amy@rhawn.cn
Country: China
ProdList: 14948
Advantage: 58

Tianjin heowns Biochemical Technology Co., Ltd.

Tel: 400-6387771-6039 18920764717
Email: sales@heowns.com
Country: China
ProdList: 23771
Advantage: 60

Hubei Xinyuanshun Pharmaceutical Chemical Co., Ltd.

Tel: 027-51831887 15337167856
Fax: 027-51837635 QQ1165326703
Email: hubeixinyuanshun@163.com
Country: China
ProdList: 10295
Advantage: 58

Chengdu Saint - Kay Biotechnology Co., Ltd.

Tel: 028-85157043 15882256948
Email: 676046971@qq.com
Country: China
ProdList: 4181
Advantage: 58

Beijing OKA biological technology co., LTD

Tel: 010-62971590 18548936886
Fax: 010-62340519
Email: 3462612863@qq.com
Country: China
ProdList: 10063
Advantage: 58

Shanghai Moss Medicine Technology Co., Ltd.

Tel: +86-188369842 +86-15618151133
Fax: QQ188369842
Email: 188369842@qq.com
Country: China
ProdList: 1959
Advantage: 58

Shenzhen Polymeri Biochemical Technology Co., Ltd.

Tel: +86-400-002-6226 +86-13028896684;
Email: sales@rrkchem.com
Country: China
ProdList: 57422
Advantage: 58

Taizhou Crene Biotechnology Co. Ltd.

Tel: +86-0576-88813233 +86-13396860566
Email: sales@pharm-intermediates.com
Country: China
ProdList: 1991
Advantage: 58

Aishilun biotechnology (Shanghai) co., LTD

Tel: 021-50676523 18019098996
Email: info@acelybio.com
Country: China
ProdList: 3960
Advantage: 58

CR Corporation Limited

Tel: +8613062833949
Email: fred.wen@crcorporation.cn
Country: China
ProdList: 8645
Advantage: 58

27314-97-2, 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDERelated Search:

Norfloxacin Gemcitabine POLYETHYLENEIMINE 3-Amino-7-chloro-1,2,4-benzotriazine 1,4-dioxide 1,2,4-benzotriazin-3-amine 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE 3-AMINO-1,2,4-BENZOTRIAZINE-1-N-OXIDE 3-AMINO-1,2,4-TRIAZINE

Tirapazamine (Synonyms: SR259075

CS-2810

Tirazazamine

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

SR-4233, Tirapazamine, TPZ

Tirapazamine(SR259075

1,2,4-benzotriazin-3-amine,1,4-dioxide

1,2,4-benzotriazine,3-amino-,1,4-dioxide

SR-4233

TIRAPAZAMINE

SR-4233, Tirapazamine

SR 259075

Tirazone

4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine

TPZ

3-Aminobenzo[e][1,2,4]triazine 1,4-Dioxide

irapazamine

Tirazamin

NSC 130181

NSC130181

NSC-130181

Tirapazamine, 10 mM in DMSO

27314-97-2

Intermediates & Fine Chemicals

Pharmaceuticals

Amines

Heterocycles

WMH

API