Tirapazamine | CAS#27314-97-2 | MedKoo Biosciences

MedKoo Cat#: 202940 | Name: Tirapazamine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Tirapazamine

CAS#27314-97-2

Theoretical Analysis

MedKoo Cat#: 202940

Name: Tirapazamine

CAS#: 27314-97-2

Chemical Formula: C7H6N4O2

Exact Mass: 178.0491

Molecular Weight: 178.15

Elemental Analysis: C, 47.19; H, 3.39; N, 31.45; O, 17.96

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 weeks
250mg	USD 650.00	2 Weeks
500mg	USD 1,050.00	2 Weeks
1g	USD 1,750.00	2 Weeks
2g	USD 2,650.00	2 Weeks
5g	USD 3,950.00	2 Weeks

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Related CAS #

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Synonym

Tirapazamine; Tirazone; SR 4233; SR-4233; SR4233; SR259075; SR-259075; SR 259075; WIN 59075; NSC130181.

IUPAC/Chemical Name

3-aminobenzo[e][1,2,4]triazine 1,4-dioxide

InChi Key

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)

SMILES Code

NC1=[N+]([O-])C2=CC=CC=C2[N+]([O-])=N1

Appearance

Orange to dark orange-red solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#S7G12M05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 178.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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Triggered Cascade- Activation Nanoplatform to Alleviate Hypoxia for Effective Tumor Immunotherapy Guided by NIR-II Imaging. ACS Nano. 2024 Nov 12;18(45):31421-31434. doi: 10.1021/acsnano.4c11334. Epub 2024 Nov 4. PMID: 39494467. 5: Yan Z, Duan Z, Liu S, Zhao Z. Supramolecular PEG-DNA-Ferrocene Nanogels for Synergistically Amplified Chemodynamic Therapy via Cascade Reactions. Biomacromolecules. 2024 Nov 11;25(11):7123-7133. doi: 10.1021/acs.biomac.4c00562. Epub 2024 Oct 14. PMID: 39401173. 6: Zhang X, Bai Z, Cui Z, Liang W, Shi M, Liu Z, Li K, Wang J, Jiao T, Li J. Development of a sequential release nanomaterial for co-delivery of hypoxia- induced tirapazamine and HIF-1α siRNA in cancer therapy. Colloids Surf B Biointerfaces. 2025 Jan;245:114260. doi: 10.1016/j.colsurfb.2024.114260. Epub 2024 Sep 18. PMID: 39305549. 7: Zeng B, Pian L, Liu Y, Wang S, Wang N, Liu C, Wu H, Wan H, Chen L, Huang W, Gao Z, Yin X, Jin M. Preparation and effects of functionalized liposomes targeting breast cancer tumors using chemotherapy, phototherapy, and immunotherapy. J Nanobiotechnology. 2024 Sep 12;22(1):558. doi: 10.1186/s12951-024-02838-1. PMID: 39267061; PMCID: PMC11391708. 8: Gong Y, Zhou T, Aimaiti W, Lin Y, Xu Y, Yang J, Huang Z, Wen H, Jiang H, Wang J. Corrigendum to "Tirapazamine combined with photodynamic therapy improves the efficacy of ABZSO nanoparticles on Echinococcosis granulosus via further enhancing "breaking-then-curing"" [Journal of Photochemistry and Photobiology B: Biology volume 248 (2023) 112798]. J Photochem Photobiol B. 2024 Sep;258:112972. doi: 10.1016/j.jphotobiol.2024.112972. Epub 2024 Aug 1. Erratum for: J Photochem Photobiol B. 2023 Nov;248:112798. doi: 10.1016/j.jphotobiol.2023.112798. PMID: 39089901. 9: Wang Q, Suo Y, Shi R, Wang Y. Studies related to the enhanced the effect of 5-aminolevulinic acid-based photodynamic therapy combined with tirapazamine. Photodiagnosis Photodyn Ther. 2024 Oct;49:104287. doi: 10.1016/j.pdpdt.2024.104287. Epub 2024 Jul 25. PMID: 39059759. 10: Zhang H, Jiang M, Xing W, Zhao R, Li G, Zheng Z. Peptide-IR820 Conjugate: A Promising Strategy for Efficient Vascular Disruption and Hypoxia Induction in Melanoma. ACS Appl Mater Interfaces. 2024 Aug 7;16(31):40641-40652. doi: 10.1021/acsami.4c07503. Epub 2024 Jul 25. PMID: 39051862. 11: Buravchenko GI, Scherbakov AM, Krymov SK, Salnikova DI, Zatonsky GV, Schols D, Vullo D, Supuran CT, Shchekotikhin AE. Synthesis and evaluation of sulfonamide derivatives of quinoxaline 1,4-dioxides as carbonic anhydrase inhibitors. RSC Adv. 2024 Jul 23;14(32):23257-23272. doi: 10.1039/d4ra04548c. PMID: 39045402; PMCID: PMC11265520. 12: Yu N, Zhou J, Xu H, Wang F, Wang X, Tang L, Li J, Wang X, Lu X. Near- infrared photoactivatable three-in-one nanoagents to aggravate hypoxia and enable amplified photo-chemotherapy. Biomater Adv. 2024 Oct;163:213962. doi: 10.1016/j.bioadv.2024.213962. Epub 2024 Jul 19. PMID: 39032435. 13: Liu B, Zheng Q, Shi X, Shen J, Li R, Zhou J. Construction and synergistic anti-tumor study of a tumor microenvironment-based multifunctional nano-drug delivery system. J Photochem Photobiol B. 2024 Sep;258:112977. doi: 10.1016/j.jphotobiol.2024.112977. Epub 2024 Jul 3. PMID: 38991294. 14: Sheng D, Liu T, Qian L, Chen J, Wei Y, Chen H, Chang C. Sonodynamic and sonomechanical effect on cellular stemness and extracellular physicochemical environment to potentiate chemotherapy. J Nanobiotechnology. 2024 Jun 21;22(1):358. doi: 10.1186/s12951-024-02623-0. PMID: 38907270; PMCID: PMC11191306. 15: Zhu L, Ren Y, Dong M, Sun B, Huang J, Chen L, Xia X, Dong X, Zheng C. Ultrasmall Metal TPZ Complexes with Deep Tumor Penetration for Enhancing Radiofrequency Ablation Therapy and Inducing Antitumor Immune Responses. Small. 2024 Oct;20(43):e2311244. doi: 10.1002/smll.202311244. Epub 2024 Jun 19. PMID: 38898764. 16: Hao Y, Zhu W, Li J, Lin R, Huang W, Ain QU, Liu K, Wei N, Cheng D, Wu Y, Lv W. Sustained release hypoxia-activated prodrug-loaded BSA nanoparticles enhance transarterial chemoembolization against hepatocellular carcinoma. J Control Release. 2024 Aug;372:155-167. doi: 10.1016/j.jconrel.2024.06.026. Epub 2024 Jun 18. PMID: 38879131. 17: Yu S, Jiang Y, Li Q, Li M, Su J, Lai S, Gan Z, Ding Z, Yu Q. Nano-sensitizer with self-amplified drug release and hypoxia normalization properties potentiates efficient chemoradiotherapy of pancreatic cancer. Biomaterials. 2024 Oct;310:122634. doi: 10.1016/j.biomaterials.2024.122634. Epub 2024 May 27. PMID: 38823195. 18: Rastogi S, Ansari MN, Saeedan AS, Yadav S, Kumar D, Singh SK, Mukerjee A, Singh M, Kaithwas G. Novel carbamodithioate regulates cellular hypoxia through chemical activation of prolyl hydroxylase-2 for breast cancer chemoprevention. Chem Biol Drug Des. 2024 May;103(5):e14531. doi: 10.1111/cbdd.14531. PMID: 38726798. 19: Li F, Zhu P, Zheng B, Lu Z, Fang C, Fu Y, Li X. A Customized Biohybrid Presenting Cascade Responses to Tumor Microenvironment. Adv Mater. 2024 Jul;36(30):e2404901. doi: 10.1002/adma.202404901. Epub 2024 May 15. PMID: 38723206. 20: Lv J, Xu Y, Liu Y, Sakurai K, Yu H, Tang Z. Co-delivery of Plinabulin and Tirapazamine boosts anti-tumor efficacy by simultaneously destroying tumor blood vessels and killing tumor cells. Biomaterials. 2024 Sep;309:122586. doi: 10.1016/j.biomaterials.2024.122586. Epub 2024 Apr 30. PMID: 38718615.