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MedKoo Cat#: 205870 | Name: RRx-001
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Description:

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

RRx-001, also known as ABDNAZ, is a dinitroazetidine derivative with potential radiosensitizing activity. Upon administration, RRx-001 is able to dilate blood vessels, thereby increasing tumor blood flow and thus improving oxygenation to the tumor site. By increasing oxygen levels, these tumor cells may be more susceptible to radiation therapy. Tumor hypoxia is correlated with tumor aggressiveness, metastasis and resistance to radiotherapy.

Chemical Structure

RRx-001
RRx-001
CAS#925206-65-1

Theoretical Analysis

MedKoo Cat#: 205870

Name: RRx-001

CAS#: 925206-65-1

Chemical Formula: C5H6BrN3O5

Exact Mass: 266.9491

Molecular Weight: 268.02

Elemental Analysis: C, 22.41; H, 2.26; Br, 29.81; N, 15.68; O, 29.85

Price and Availability

Size Price Availability Quantity
25mg USD 150.00 2 Weeks
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,450.00 2 Weeks
1g USD 2,650.00 2 Weeks
2g USD 4,650.00 2 Weeks
5g USD 7,250.00 2 Weeks
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Synonym
RRX001; RRX 001; RRx-001; ABDNAZ; nibrozetonum; nibrozetone
IUPAC/Chemical Name
2-bromo-1-(3,3-dinitroazetidin-1-yl)ethanone
InChi Key
JODKFOVZURLVTG-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H6BrN3O5/c6-1-4(10)7-2-5(3-7,8(11)12)9(13)14/h1-3H2
SMILES Code
O=[N+](C1([N+]([O-])=O)CN(C(CBr)=O)C1)[O-]
Appearance
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, DMF, and ethanol
Shelf Life
>2 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
RRx-001 , a derivative of a geminal dinitroazetidine, has demonstrated promise as a novel cancer therapeutic agent in a number of cell lines and tumor models and is proposed to enter a Phase I clinical trial in cancer patients.  RRx-001 is believed to elicit an anticancer effect through nitrogen oxides released from decomposition of conjugates formed in vivo.          
Product Data
Product Data
Instruction
View handling instruction
Biological target:
RRx-001 inhibits growth in a panel of 12 cancer cell lines (IC50s =1.8-6 μM). RRx-001 increases intracellular levels of reactive oxygen species in HT-29 and SCC VII cells in a concentration- and time-dependent manner and induces apoptosis in SCC VII, HL-60, and Daudi cells. RRx-001 reduces tumor growth and enhances radiation-induced tumor growth reduction in an SCC VII murine squamous cell carcinoma model.
In vitro activity:
In cancer cell lines (namely Hep G2, CACO-2, and HT-29), RRx-001 affects glucose and G6PD enzyme activity. In all of the cancer cell lines tested in this study, RRx-001 induced G6PD inhibition in a concentration dependent fashion. Inhibition of G6PD activity associated with a reduction in ribonucleotide synthesis, glutathione reduction and cell proliferation may explain how RRx-001 exerts its anticancer effects. Reference: Discov Med. 2016 Apr;21(116):251-65. https://pubmed.ncbi.nlm.nih.gov/27232511/
In vivo activity:
This study identifies RRx-001 as a new potential therapeutic agent for NLRP3-driven diseases. RRx-001 treatment attenuates the symptoms of lipopolysaccharide-induced systemic inflammation, dextran sulfate sodium-induced colitis, and experimental autoimmune encephalomyelitis in mice. RRx-001 inhibits the activation of NLRP3 inflammasomes but not the AIM2, NLRC4 or Pyrin inflammasomes. RRx-001 covalently binds to cysteine 409 of NLRP3, blocking the NLRP3-NEK7 interaction. Reference: Cell Mol Immunol. 2021 Jun;18(6):1425-1436. https://pubmed.ncbi.nlm.nih.gov/33972740/
Solvent mg/mL mM
Solubility
DMF 30.0 111.93
DMSO 30.0 111.93
Ethanol 2.0 7.46
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 268.02 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Fang J, She J, Lin F, Wu JC, Han R, Sheng R, Wang G, Qin ZH. RRx-001 Exerts Neuroprotection Against LPS-Induced Microglia Activation and Neuroinflammation Through Disturbing the TLR4 Pathway. Front Pharmacol. 2022 Apr 6;13:889383. doi: 10.3389/fphar.2022.889383. PMID: 35462935; PMCID: PMC9020799. 2. Oronsky B, Scicinski J, Reid T, Oronsky A, Carter C, Oronsky N, Cabrales P. RRx-001, a novel clinical-stage chemosensitizer, radiosensitizer, and immunosensitizer, inhibits glucose 6-phosphate dehydrogenase in human tumor cells. Discov Med. 2016 Apr;21(116):251-65. PMID: 27232511. 3. Chen Y, He H, Lin B, Chen Y, Deng X, Jiang W, Zhou R. RRx-001 ameliorates inflammatory diseases by acting as a potent covalent NLRP3 inhibitor. Cell Mol Immunol. 2021 Jun;18(6):1425-1436. doi: 10.1038/s41423-021-00683-y. Epub 2021 May 10. PMID: 33972740; PMCID: PMC8166941. 4. Jani VP, Asaro R, Oronsky B, Cabrales P. RRx-001 Increases Erythrocyte Preferential Adhesion to the Tumor Vasculature. Int J Mol Sci. 2021 Apr 29;22(9):4713. doi: 10.3390/ijms22094713. PMID: 33946824; PMCID: PMC8124275.
In vitro protocol:
1. Fang J, She J, Lin F, Wu JC, Han R, Sheng R, Wang G, Qin ZH. RRx-001 Exerts Neuroprotection Against LPS-Induced Microglia Activation and Neuroinflammation Through Disturbing the TLR4 Pathway. Front Pharmacol. 2022 Apr 6;13:889383. doi: 10.3389/fphar.2022.889383. PMID: 35462935; PMCID: PMC9020799. 2. Oronsky B, Scicinski J, Reid T, Oronsky A, Carter C, Oronsky N, Cabrales P. RRx-001, a novel clinical-stage chemosensitizer, radiosensitizer, and immunosensitizer, inhibits glucose 6-phosphate dehydrogenase in human tumor cells. Discov Med. 2016 Apr;21(116):251-65. PMID: 27232511.
In vivo protocol:
1. Chen Y, He H, Lin B, Chen Y, Deng X, Jiang W, Zhou R. RRx-001 ameliorates inflammatory diseases by acting as a potent covalent NLRP3 inhibitor. Cell Mol Immunol. 2021 Jun;18(6):1425-1436. doi: 10.1038/s41423-021-00683-y. Epub 2021 May 10. PMID: 33972740; PMCID: PMC8166941. 2. Jani VP, Asaro R, Oronsky B, Cabrales P. RRx-001 Increases Erythrocyte Preferential Adhesion to the Tumor Vasculature. Int J Mol Sci. 2021 Apr 29;22(9):4713. doi: 10.3390/ijms22094713. PMID: 33946824; PMCID: PMC8124275.
1: Izadi F, Luxford TFM, Sedmidubská B, Arthur-Baidoo E, Kočišek J, Ončák M, Denifl S. Dissociative Electron Attachment Dynamics of a Promising Cancer Drug Indicates Its Radiosensitizing Potential. Angew Chem Int Ed Engl. 2024 Oct 7;63(41):e202407469. doi: 10.1002/anie.202407469. Epub 2024 Sep 6. PMID: 38980970. 2: Gaur V, Tyagi W, Das S, Ganguly S, Bhattacharyya J. CD40 agonist engineered immunosomes modulated tumor microenvironment and showed pro-immunogenic response, reduced toxicity, and tumor free survival in mice bearing glioblastoma. Biomaterials. 2024 Dec;311:122688. doi: 10.1016/j.biomaterials.2024.122688. Epub 2024 Jun 25. PMID: 38943821. 3: Wang D, Deng X, Wang J, Che S, Ma X, Zhang S, Dong Q, Huang C, Chen J, Shi C, Zhang MR, Hu K, Luo L, Xiao Z. Environmentally responsive hydrogel promotes vascular normalization to enhance STING anti-tumor immunity. J Control Release. 2024 Aug;372:403-416. doi: 10.1016/j.jconrel.2024.06.052. Epub 2024 Jun 25. PMID: 38914207. 4: Xie T, Huang C, Wang Y, Zhang H, Guo P, Phann TT, Cheng Y, Lei L, Tao Z, Gao Q, Wei H, Yu CY. An "All-In-One" Immunomodulator-Engineered Clinical Translatable Immunotherapy of Advanced Hepatocellular Carcinoma. Adv Healthc Mater. 2024 Jul;13(19):e2304476. doi: 10.1002/adhm.202304476. Epub 2024 Apr 3. PMID: 38519415. 5: Xie F, Niu Y, Lian L, Wang Y, Zhuang A, Yan G, Ren Y, Chen X, Xiao M, Li X, Xi Z, Zhang G, Qin D, Yang K, Zheng Z, Zhang Q, Xia X, Li P, Gu L, Wu T, Luo C, Lin SH, Li W. Multi-omics joint analysis revealed the metabolic profile of retroperitoneal liposarcoma. Front Med. 2024 Apr;18(2):375-393. doi: 10.1007/s11684-023-1020-z. Epub 2023 Dec 29. PMID: 38157196. 6: Guo Y, Bao Q, Hu P, Shi J. Nanomedicine-based co-delivery of a calcium channel inhibitor and a small molecule targeting CD47 for lung cancer immunotherapy. Nat Commun. 2023 Nov 11;14(1):7306. doi: 10.1038/s41467-023-42972-2. PMID: 37951973; PMCID: PMC10640620. 7: Oronsky B, Cabrales P, Alizadeh B, Caroen S, Stirn M, Williams J, Reid TR. TGF-β: the apex predator of immune checkpoints. Future Oncol. 2023 Sep;19(30):2013-2015. doi: 10.2217/fon-2023-0491. Epub 2023 Jul 28. PMID: 37503560. 8: Oronsky B, Burbano E, Stirn M, Brechlin J, Abrouk N, Caroen S, Coyle A, Williams J, Cabrales P, Reid TR. Data Management 101 for drug developers: A peek behind the curtain. Clin Transl Sci. 2023 Sep;16(9):1497-1509. doi: 10.1111/cts.13582. Epub 2023 Jul 6. PMID: 37382299; PMCID: PMC10499417. 9: Fine H, Reid T, Caroen S, Oronsky B, Abrouk N, Butowski N. A multicenter, phase 1, dose escalation clinical trial (G-FORCE-1) of XRT, RRx-001 and temozolomide followed by temozolomide +/- RRx-001 in newly diagnosed glioblastoma. Front Oncol. 2023 Jun 5;13:1176448. doi: 10.3389/fonc.2023.1176448. PMID: 37342189; PMCID: PMC10277641. 10: Oronsky B, Takahashi L, Gordon R, Cabrales P, Caroen S, Reid T. RRx-001: a chimeric triple action NLRP3 inhibitor, Nrf2 inducer, and nitric oxide superagonist. Front Oncol. 2023 May 29;13:1204143. doi: 10.3389/fonc.2023.1204143. PMID: 37313460; PMCID: PMC10258348. 11: Reid T, Oronsky B, Caroen S, Quinn M, Williams J, Cabrales P, Abrouk N. Phase 1 pilot study of RRx-001 + nivolumab in patients with advanced metastatic cancer (PRIMETIME). Front Immunol. 2023 Mar 7;14:1104753. doi: 10.3389/fimmu.2023.1104753. PMID: 36960054; PMCID: PMC10028591. 12: Jayabalan N, Oronsky B, Cabrales P, Reid T, Caroen S, Johnson AM, Birch NA, O'Sullivan JD, Gordon R. A Review of RRx-001: A Late-Stage Multi-Indication Inhibitor of NLRP3 Activation and Chronic Inflammation. Drugs. 2023 Apr;83(5):389-402. doi: 10.1007/s40265-023-01838-z. Epub 2023 Mar 15. PMID: 36920652; PMCID: PMC10015535. 13: Niu S, Cheng K, Jia L, Liang J, Mu L, Wang Y, Yang X, Yang C, Zhang Y, Wang C, Huang L, Wang H, Zhang S, Zhang H. Lineage tracing of mutant granulosa cells reveals in vivo protective mechanisms that prevent granulosa cell tumorigenesis. Cell Death Differ. 2023 May;30(5):1235-1246. doi: 10.1038/s41418-023-01132-1. Epub 2023 Feb 23. PMID: 36823373; PMCID: PMC10154338. 14: Gong M, Huang Y, Feng H, Lin J, Huang A, Hu J, Tang Q, Zhu X, Han S, Lu J, Wang J. A nanodrug combining CD47 and sonodynamic therapy efficiently inhibits osteosarcoma deterioration. J Control Release. 2023 Mar;355:68-84. doi: 10.1016/j.jconrel.2023.01.038. Epub 2023 Feb 2. PMID: 36682726. 15: Bonomi M, Blakaj DM, Kabarriti R, Colvett K, Takiar V, Biagioli M, Bar-Ad V, Goyal S, Muzyka B, Niermann K, Abrouk N, Oronsky B, Reid T, Caroen S, Sonis S, Sher DJ. PREVLAR: Phase 2a Randomized Trial to Assess the Safety and Efficacy of RRx-001 in the Attenuation of Oral Mucositis in Patients Receiving Head and Neck Chemoradiotherapy. Int J Radiat Oncol Biol Phys. 2023 Jul 1;116(3):551-559. doi: 10.1016/j.ijrobp.2022.12.031. Epub 2023 Jan 14. PMID: 36646388. 16: Oronsky B, Caroen S, Brinkhaus F, Reid T, Stirn M, Kumar R. Patent and Marketing Exclusivities 101 for Drug Developers. Recent Pat Biotechnol. 2023;17(3):257-270. doi: 10.2174/1872208317666230111105223. PMID: 36635930; PMCID: PMC10242760. 17: Hammond TC, Lee RC, Oronsky B, Reid TR, Caroen S, Juarez TM, Gill J, Heng A, Kesari S. Clinical Course of Two Patients with COVID-19 Respiratory Failure After Administration of the Anticancer Small Molecule, RRx-001. Int Med Case Rep J. 2022 Dec 15;15:735-738. doi: 10.2147/IMCRJ.S389690. PMID: 36545548; PMCID: PMC9762260. 18: Reid TR, Abrouk N, Caroen S, Oronsky B, Stirn M, Larson C, Beale K, Knox SJ, Fisher G. ROCKET: Phase II Randomized, Active-controlled, Multicenter Trial to Assess the Safety and Efficacy of RRx-001 + Irinotecan vs. Single-agent Regorafenib in Third/Fourth Line Colorectal Cancer. Clin Colorectal Cancer. 2023 Mar;22(1):92-99. doi: 10.1016/j.clcc.2022.11.003. Epub 2022 Dec 2. PMID: 36529613. 19: Oronsky B, Caroen S, Abrouk N, Reid TR. RRx-001 and the "Right stuff": Protection and treatment in outer space. Life Sci Space Res (Amst). 2022 Nov;35:69-75. doi: 10.1016/j.lssr.2022.05.001. Epub 2022 May 12. PMID: 36336372. 20: Song W, Yang F, Yang H, Xu Y, Song SJ, Meng Y, Wei ST, Wan T, Zhou Y, Zhou B, Kuang J, Yu T, Qiu WX. Enhanced Immunotherapy Based on Combining the Pro- phagocytosis and Anti-phagocytosis Checkpoint Blockade for Tumor Eradication. J Med Chem. 2022 Nov 10;65(21):14832-14842. doi: 10.1021/acs.jmedchem.2c01351. Epub 2022 Oct 19. PMID: 36260348.

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