Misonidazole
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MedKoo CAT#: 100957

CAS#: 13551-87-6

Description: Misonidazole is a radiosensitizer used in radiation therapy to cause normally resistant hypoxic tumor cells to become sensitive to the treatment.

Chemical Structure

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Misonidazole
CAS# 13551-87-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100957
Name: Misonidazole
CAS#: 13551-87-6
Chemical Formula: C7H11N3O4
Exact Mass: 201.08
Molecular Weight: 201.182
Elemental Analysis: C, 41.79; H, 5.51; N, 20.89; O, 31.81

Price and Availability

Size Price Availability Quantity
10mg USD 450 2 Weeks
50mg USD 950 2 Weeks
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Synonym: Misonidazole; NSC 261037; NSC-261037; NSC261037; Ro 7-0582; SR1354; SRI 1354; SRI-1354

IUPAC/Chemical Name: 1-(2-Hydroxy-3-methoxypropyl)-2-nitroimidazole

InChi Key: RWAFIQZGOJPVRM-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H11N3O4/c1-14-4-6(11)2-5-3-8-7(9-5)10(12)13/h3,6,11H,2,4H2,1H3,(H,8,9)

SMILES Code: O=[N+](C1=NC(CC(O)COC)=CN1)[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

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:

Product Data:
Product Data
Instruction:
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Biological target: Misonidazole (Ro 7-0582; SR 1354) is a hypoxic tumor cell radiosensitizer.
In vitro activity: Magnetization curve showed that SPION-MISO-SpHLs (Superparamagnetic Iron Oxide Nanoparticle-Misonidazole-System with pH-sensitive liposomes) retained superparamagnetic properties. SPION-MISO-SpHLs were compared with MISO+SPION+blank liposome in hypoxia and control groups of A549 cells. MISO and SPION concentrations in culture medium showed significant differences between the same concentration groups (P < 0.0001) and at different times (P < 0.0001). SPION-MISO-SpHLs possess pH-dependent release ability and superparamagnetism, and thus provides a system for targeted delivery and tracing under magnetic resonance. Reference: Curr Drug Deliv. 2019;16(3):254-267. https://pubmed.ncbi.nlm.nih.gov/30426901/
In vivo activity: This study presents here a protocol for orthotopic HCC xenograft creation with and without hepatic artery ligation (HAL) to induce tumor hypoxia and the assessment of their tumor metabolism in vivo using [18F]Fluoromisonidazole ([18F]FMISO) and [18F]Fluorodeoxyglucose ([18F]FDG) PET/magnetic resonance (MR) imaging. Tumor hypoxia could be readily visualized using the hypoxia marker [18F]FMISO, and it was found that the [18F]FMISO uptake was higher in HCC mice that underwent HAL than in the non-HAL group, whereas [18F]FDG could not distinguish tumor hypoxia between the two groups. Reference: J Vis Exp. 2022 Aug 31;(186). https://pubmed.ncbi.nlm.nih.gov/36121278/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 15.0 74.56
DMSO 15.0 74.56
Ethanol 5.0 24.85
PBS (pH 7.2) 2.0 9.94

Preparing Stock Solutions

The following data is based on the product molecular weight 201.18 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. Li B, Li B, He D, Feng C, Luo Z, He M. Preparation, Characterization, and In Vitro pH-sensitivity Evaluation of Superparamagnetic Iron Oxide Nanoparticle- Misonidazole pH-sensitive Liposomes. Curr Drug Deliv. 2019;16(3):254-267. doi: 10.2174/1567201816666181114124333. PMID: 30426901. 2. Josephy PD, Palcic B, Skarsgard LD. In vitro metabolism of misonidazole. Br J Cancer. 1981 Apr;43(4):443-50. doi: 10.1038/bjc.1981.65. PMID: 7236487; PMCID: PMC2010618. 3. Tan KV, Yang X, Chan CY, Shi J, Chang HC, Chiu KW, Man K. Non-invasive PET/MR Imaging in an Orthotopic Mouse Model of Hepatocellular Carcinoma. J Vis Exp. 2022 Aug 31;(186). doi: 10.3791/63958. PMID: 36121278. 4. Gertsenshteyn I, Epel B, Ahluwalia A, Kim H, Fan X, Barth E, Zamora M, Markiewicz E, Tsai HM, Sundramoorthy S, Leoni L, Lukens J, Bhuiyan M, Freifelder R, Kucharski A, Giurcanu M, Roman BB, Karczmar G, Kao CM, Halpern H, Chen CT. The optimal 18F-fluoromisonidazole PET threshold to define tumor hypoxia in preclinical squamous cell carcinomas using pO2 electron paramagnetic resonance imaging as reference truth. Eur J Nucl Med Mol Imaging. 2022 Oct;49(12):4014-4024. doi: 10.1007/s00259-022-05889-4. Epub 2022 Jul 6. PMID: 35792927; PMCID: PMC9529789.
In vitro protocol: 1. Li B, Li B, He D, Feng C, Luo Z, He M. Preparation, Characterization, and In Vitro pH-sensitivity Evaluation of Superparamagnetic Iron Oxide Nanoparticle- Misonidazole pH-sensitive Liposomes. Curr Drug Deliv. 2019;16(3):254-267. doi: 10.2174/1567201816666181114124333. PMID: 30426901. 2. Josephy PD, Palcic B, Skarsgard LD. In vitro metabolism of misonidazole. Br J Cancer. 1981 Apr;43(4):443-50. doi: 10.1038/bjc.1981.65. PMID: 7236487; PMCID: PMC2010618.
In vivo protocol: 1. Tan KV, Yang X, Chan CY, Shi J, Chang HC, Chiu KW, Man K. Non-invasive PET/MR Imaging in an Orthotopic Mouse Model of Hepatocellular Carcinoma. J Vis Exp. 2022 Aug 31;(186). doi: 10.3791/63958. PMID: 36121278. 2. Gertsenshteyn I, Epel B, Ahluwalia A, Kim H, Fan X, Barth E, Zamora M, Markiewicz E, Tsai HM, Sundramoorthy S, Leoni L, Lukens J, Bhuiyan M, Freifelder R, Kucharski A, Giurcanu M, Roman BB, Karczmar G, Kao CM, Halpern H, Chen CT. The optimal 18F-fluoromisonidazole PET threshold to define tumor hypoxia in preclinical squamous cell carcinomas using pO2 electron paramagnetic resonance imaging as reference truth. Eur J Nucl Med Mol Imaging. 2022 Oct;49(12):4014-4024. doi: 10.1007/s00259-022-05889-4. Epub 2022 Jul 6. PMID: 35792927; PMCID: PMC9529789.

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1: Jensen-Kondering U, Mavanaki R, Ejaz S, Sawiak SJ, Carpenter TA, Fryer TD, Aigbirhio FI, Williamson DJ, Baron JC. Brain hypoxia mapping in acute stroke: Back-to-back T2' MR versus (18)F-fluoromisonidazole PET in rodents. Int J Stroke. 2017 Jan 1:1747493017706221. doi: 10.1177/1747493017706221. [Epub ahead of print] PubMed PMID: 28523963.

2: Toyonaga T, Yamaguchi S, Hirata K, Kobayashi K, Manabe O, Watanabe S, Terasaka S, Kobayashi H, Hattori N, Shiga T, Kuge Y, Tanaka S, Ito YM, Tamaki N. Hypoxic glucose metabolism in glioblastoma as a potential prognostic factor. Eur J Nucl Med Mol Imaging. 2017 Apr;44(4):611-619. doi: 10.1007/s00259-016-3541-z. Epub 2016 Oct 18. PubMed PMID: 27752745.

3: Yuan H, Frank JE, Merrill JR, Hillesheim DA, Khachaturian MH, Anzellotti AI. Hypoxia Radiotracer Produced Automatically in Dose-on-Demand Fashion. Curr Radiopharm. 2016;9(2):178. PubMed PMID: 27593257.

4: Bittner MI, Wiedenmann N, Bucher S, Hentschel M, Mix M, Rücker G, Weber WA, Meyer PT, Werner M, Grosu AL, Kayser G. Analysis of relation between hypoxia PET imaging and tissue-based biomarkers during head and neck radiochemotherapy. Acta Oncol. 2016 Nov;55(11):1299-1304. Epub 2016 Sep 3. PubMed PMID: 27593107.

5: Sorace AG, Syed AK, Barnes SL, Quarles CC, Sanchez V, Kang H, Yankeelov TE. Quantitative [(18)F]FMISO PET Imaging Shows Reduction of Hypoxia Following Trastuzumab in a Murine Model of HER2+ Breast Cancer. Mol Imaging Biol. 2017 Feb;19(1):130-137. doi: 10.1007/s11307-016-0994-1. PubMed PMID: 27506906; PubMed Central PMCID: PMC5214951.

6: Wack LJ, Mönnich D, Yaromina A, Zips D, Baumann M, Thorwarth D. Correlation of FMISO simulations with pimonidazole-stained tumor xenografts: A question of O2 consumption? Med Phys. 2016 Jul;43(7):4113. doi: 10.1118/1.4951728. PubMed PMID: 27370131.

7: Vordermark D, Horsman MR. Hypoxia as a Biomarker and for Personalized Radiation Oncology. Recent Results Cancer Res. 2016;198:123-42. doi: 10.1007/978-3-662-49651-0_6. PubMed PMID: 27318684.

8: Okamoto S, Shiga T, Yasuda K, Watanabe S, Hirata K, Nishijima KI, Magota K, Kasai K, Onimaru R, Tuchiya K, Kuge Y, Shirato H, Tamaki N. The reoxygenation of hypoxia and the reduction of glucose metabolism in head and neck cancer by fractionated radiotherapy with intensity-modulated radiation therapy. Eur J Nucl Med Mol Imaging. 2016 Nov;43(12):2147-2154. Epub 2016 Jun 1. PubMed PMID: 27251644.

9: Song C, Hong BJ, Bok S, Lee CJ, Kim YE, Jeon SR, Wu HG, Lee YS, Cheon GJ, Paeng JC, Carlson DJ, Kim HJ, Ahn GO. Real-time Tumor Oxygenation Changes After Single High-dose Radiation Therapy in Orthotopic and Subcutaneous Lung Cancer in Mice: Clinical Implication for Stereotactic Ablative Radiation Therapy Schedule Optimization. Int J Radiat Oncol Biol Phys. 2016 Jul 1;95(3):1022-1031. doi: 10.1016/j.ijrobp.2016.01.064. Epub 2016 Feb 13. PubMed PMID: 27130790.

10: Wang H, Zhang Y, Yu W, Zhao X, Xue Y, Xu H. Radiosensitizing effect of irisquinone on glioma through the downregulation of HIF-1α evaluated by 18F-FDG and 18F-FMISO PET/CT. Nucl Med Commun. 2016 Jul;37(7):705-14. doi: 10.1097/MNM.0000000000000498. PubMed PMID: 26963468.

11: Yu Y, Chan C, Ma T, Liu Y, Gallezot JD, Naganawa M, Kelada OJ, Germino M, Sinusas AJ, Carson RE, Liu C. Event-by-Event Continuous Respiratory Motion Correction for Dynamic PET Imaging. J Nucl Med. 2016 Jul;57(7):1084-90. doi: 10.2967/jnumed.115.167676. Epub 2016 Feb 23. PubMed PMID: 26912437.

12: Muzi M, Krohn KA. Imaging Hypoxia with ¹⁸F-Fluoromisonidazole: Challenges in Moving to a More Complicated Analysis. J Nucl Med. 2016 Apr;57(4):497-8. doi: 10.2967/jnumed.115.171694. Epub 2016 Feb 18. PubMed PMID: 26912434.

13: Toyonaga T, Hirata K, Yamaguchi S, Hatanaka KC, Yuzawa S, Manabe O, Kobayashi K, Watanabe S, Shiga T, Terasaka S, Kobayashi H, Kuge Y, Tamaki N. (18)F-fluoromisonidazole positron emission tomography can predict pathological necrosis of brain tumors. Eur J Nucl Med Mol Imaging. 2016 Jul;43(8):1469-76. doi: 10.1007/s00259-016-3320-x. Epub 2016 Feb 3. PubMed PMID: 26841941.

14: Hernández-Agudo E, Mondejar T, Soto-Montenegro ML, Megías D, Mouron S, Sanchez J, Hidalgo M, Lopez-Casas PP, Mulero F, Desco M, Quintela-Fandino M. Monitoring vascular normalization induced by antiangiogenic treatment with (18)F-fluoromisonidazole-PET. Mol Oncol. 2016 May;10(5):704-18. doi: 10.1016/j.molonc.2015.12.011. Epub 2015 Dec 22. PubMed PMID: 26778791.

15: Yoshimoto M. [Current Status and Prospects on PET Radiopharmaceuticals for Radiotherapy]. Igaku Butsuri. 2015;35(1):10-5. Review. Japanese. PubMed PMID: 26753391.

16: Arteaga-Marrero N, Brekke Rygh C, Mainou-Gomez JF, Adamsen TC, Lutay N, Reed RK, Olsen DR. Radiation treatment monitoring using multimodal functional imaging: PET/CT ((18)F-Fluoromisonidazole & (18)F-Fluorocholine) and DCE-US. J Transl Med. 2015 Dec 18;13:383. doi: 10.1186/s12967-015-0708-5. Erratum in: J Transl Med. 2016;14:59. PubMed PMID: 26682742; PubMed Central PMCID: PMC4683758.

17: Grkovski M, Schwartz J, Gönen M, Schöder H, Lee NY, Carlin SD, Zanzonico PB, Humm JL, Nehmeh SA. Feasibility of 18F-Fluoromisonidazole Kinetic Modeling in Head and Neck Cancer Using Shortened Acquisition Times. J Nucl Med. 2016 Mar;57(3):334-41. doi: 10.2967/jnumed.115.160168. Epub 2015 Nov 25. PubMed PMID: 26609178; PubMed Central PMCID: PMC4977990.

18: Masaki Y, Shimizu Y, Yoshioka T, Tanaka Y, Nishijima K, Zhao S, Higashino K, Sakamoto S, Numata Y, Yamaguchi Y, Tamaki N, Kuge Y. The accumulation mechanism of the hypoxia imaging probe "FMISO" by imaging mass spectrometry: possible involvement of low-molecular metabolites. Sci Rep. 2015 Nov 19;5:16802. doi: 10.1038/srep16802. PubMed PMID: 26582591; PubMed Central PMCID: PMC4652161.

19: Tamaki N, Hirata K. Tumor hypoxia: a new PET imaging biomarker in clinical oncology. Int J Clin Oncol. 2016 Aug;21(4):619-25. doi: 10.1007/s10147-015-0920-6. Epub 2015 Nov 14. Review. PubMed PMID: 26577447.

20: Mönnich D, Welz S, Thorwarth D, Pfannenberg C, Reischl G, Mauz PS, Nikolaou K, la Fougère C, Zips D. Robustness of quantitative hypoxia PET image analysis for predicting local tumor control. Acta Oncol. 2015;54(9):1364-9. doi: 10.3109/0284186X.2015.1071496. PubMed PMID: 26481464.