# FMISO

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/FMISO
> Markdown URL: https://mediated.wiki/source/FMISO.md
> Source: https://en.wikipedia.org/wiki/FMISO
> Source revision: 1329566437
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

Chemical compound

Pharmaceutical compound

[18F]Fluoromisonidazole Clinical data Other names [18F]FMISO; 1H-1-(3-[18F]fluoro-2-hydroxypropyl)-2-nitroimidazole Identifiers IUPAC name 1-(2-Nitro-imidazolyl)-3-[18F]fluoro-2-propanol CAS Number 104613-87-8 Y ChemSpider 396524 UNII 8MSY49469G CompTox Dashboard (EPA) DTXSID801313634 Chemical and physical data Formula C6H818FN3O Molar mass 188.15 g/mol

**18F-FMISO** or **fluoromisonidazole** is a [radiopharmaceutical](/source/Radiopharmaceutical) used for [PET](/source/Positron_emission_tomography) imaging of [hypoxia](/source/Hypoxia_(medical)). It consists of a 2-[nitroimidazole](/source/Nitroimidazole) molecule labelled with the positron-emitter [fluorine-18](/source/Fluorine-18).[1]

Hypoxia is considered a negative [prognostic marker](/source/Prognosis_marker) for many [solid tumours](/source/Solid_tumours), and therefore an agent to detect and quantify it is highly desirable.[2] FMISO was one of the first such agents, after initial synthesis in the late 1980s.[3][4][5] It remains among the most popular agents for investigation of hypoxia imaging.[6][7][8]

## Mechanism

Mechanism of the accumulation of FMISO in hypoxic tissue [9]

On entering a viable cell, the [nitro group](/source/Nitro_compound) of the FMISO nitroimidazole is [reduced](/source/Reduction_(chemistry)).[10] In non-hypoxic cells, the reduced FMISO molecule can be [oxidised](/source/Oxidised), and therefore [diffuses](/source/Diffuse) out of the cell to circulate freely and ultimately be excreted. In [hypoxic tumour](/source/Tumour_hypoxia) cells however this oxidation cannot take place and the FMISO molecules accumulate. Their location can then be [quantitatively](/source/Quantification_(science)) imaged using [positron emission tomography](/source/Positron_emission_tomography).[9][11]

## Clinical use

Large scale [clinical trials](/source/Clinical_trial) with FMISO have not been carried out, however there is some evidence from small-scale early-stage imaging trials that PET-measured hypoxia (using FMISO, and the alternative radiotracer FAZA) is linked to [overall survival](/source/Overall_survival) and loco-regional control in [head and neck cancer](/source/Head_and_neck_cancer) patients.[12] Similar correlations have been found in other cancers, including [breast cancer](/source/Breast_cancer) and [brain tumours](/source/Brain_tumour).[10][13] Direct impacts on patient care has not yet been conclusively demonstrated however.[11]

The use of hypoxia imaging to guide [radiotherapy](/source/Radiotherapy) treatments is an area of active research.[14] Despite some positive early results further research is required to characterise the [specificity and sensitivity](/source/Specificity_and_sensitivity) of FMISO, and exactly how hypoxia levels should influence [treatment planning](/source/Treatment_planning) decisions. Similarly, hypoxia imaging could be used to screen patients before the prescription of hypoxic guided drugs. It may also be useful as a post-treatment measure of effectiveness for both radiotherapy and [chemotherapy](/source/Chemotherapy).[15][16]

Outside of [oncology](/source/Oncology), there is interest in cardiac hypoxia imaging. FMISO has had limited interest for this purpose, in part due to low target-to-background [contrast](/source/Contrast_(vision)) and long injection to imaging delays (due to slow blood clearance) requiring high injected activities.[17]

## References

1. **[^](#cite_ref-1)** Rajendran JG, Mankoff DA, O'Sullivan F, Peterson LM, Schwartz DL, Conrad EU, et al. (April 2004). ["Hypoxia and glucose metabolism in malignant tumors: evaluation by \[18F\]fluoromisonidazole and \[18F\]fluorodeoxyglucose positron emission tomography imaging"](https://doi.org/10.1158%2F1078-0432.ccr-0688-3). *Clinical Cancer Research*. **10** (7): 2245–2252. [doi](/source/Doi_(identifier)):[10.1158/1078-0432.ccr-0688-3](https://doi.org/10.1158%2F1078-0432.ccr-0688-3). [PMID](/source/PMID_(identifier)) [15073099](https://pubmed.ncbi.nlm.nih.gov/15073099).

1. **[^](#cite_ref-2)** Zschaeck S, Steinbach J, Troost EG (2016). ["FMISO as a Biomarker for Clinical Radiation Oncology"](https://link.springer.com/chapter/10.1007%2F978-3-662-49651-0_10). In Baumann M, Krause M, Cordes N (eds.). *Molecular radio-oncology*. Recent Results in Cancer Research. Vol. 198. Berlin: Springer. pp. 189–201. [doi](/source/Doi_(identifier)):[10.1007/978-3-662-49651-0](https://doi.org/10.1007%2F978-3-662-49651-0). [ISBN](/source/ISBN_(identifier)) [978-3-662-49649-7](https://en.wikipedia.org/wiki/Special:BookSources/978-3-662-49649-7).

1. **[^](#cite_ref-3)** Wadsak W, Mitterhauser M (March 2010). "Basics and principles of radiopharmaceuticals for PET/CT". *European Journal of Radiology*. **73** (3): 461–469. [doi](/source/Doi_(identifier)):[10.1016/j.ejrad.2009.12.022](https://doi.org/10.1016%2Fj.ejrad.2009.12.022). [PMID](/source/PMID_(identifier)) [20181453](https://pubmed.ncbi.nlm.nih.gov/20181453).

1. **[^](#cite_ref-4)** Jerabek PA, Patrick TB, Kilbourn MR, Dischino DD, Welch MJ (1986). "Synthesis and biodistribution of 18F-labeled fluoronitroimidazoles: potential in vivo markers of hypoxic tissue". *International Journal of Radiation Applications and Instrumentation, Part A*. **37** (7): 599–605. [doi](/source/Doi_(identifier)):[10.1016/0883-2889(86)90079-1](https://doi.org/10.1016%2F0883-2889%2886%2990079-1). [PMID](/source/PMID_(identifier)) [3021662](https://pubmed.ncbi.nlm.nih.gov/3021662).

1. **[^](#cite_ref-5)** Grunbaum Z, Freauff SJ, Krohn KA, Wilbur DS, Magee S, Rasey JS (January 1987). "Synthesis and characterization of congeners of misonidazole for imaging hypoxia". *Journal of Nuclear Medicine*. **28** (1): 68–75. [PMID](/source/PMID_(identifier)) [3794812](https://pubmed.ncbi.nlm.nih.gov/3794812).

1. **[^](#cite_ref-6)** Tamaki N, Hirata K (August 2016). "Tumor hypoxia: a new PET imaging biomarker in clinical oncology". *International Journal of Clinical Oncology*. **21** (4): 619–625. [doi](/source/Doi_(identifier)):[10.1007/s10147-015-0920-6](https://doi.org/10.1007%2Fs10147-015-0920-6). [PMID](/source/PMID_(identifier)) [26577447](https://pubmed.ncbi.nlm.nih.gov/26577447). [S2CID](/source/S2CID_(identifier)) [30098261](https://api.semanticscholar.org/CorpusID:30098261).

1. **[^](#cite_ref-7)** Fleming IN, Manavaki R, Blower PJ, West C, Williams KJ, Harris AL, et al. (January 2015). ["Imaging tumour hypoxia with positron emission tomography"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4453462). *British Journal of Cancer*. **112** (2): 238–250. [doi](/source/Doi_(identifier)):[10.1038/bjc.2014.610](https://doi.org/10.1038%2Fbjc.2014.610). [PMC](/source/PMC_(identifier)) [4453462](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4453462). [PMID](/source/PMID_(identifier)) [25514380](https://pubmed.ncbi.nlm.nih.gov/25514380).

1. **[^](#cite_ref-8)** Kelada OJ, Carlson DJ (April 2014). ["Molecular imaging of tumor hypoxia with positron emission tomography"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5555673). *Radiation Research*. **181** (4): 335–349. [Bibcode](/source/Bibcode_(identifier)):[2014RadR..181..335K](https://ui.adsabs.harvard.edu/abs/2014RadR..181..335K). [doi](/source/Doi_(identifier)):[10.1667/RR13590.1](https://doi.org/10.1667%2FRR13590.1). [PMC](/source/PMC_(identifier)) [5555673](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5555673). [PMID](/source/PMID_(identifier)) [24673257](https://pubmed.ncbi.nlm.nih.gov/24673257).

1. ^ [***a***](#cite_ref-MasakiMechanism15_9-0) [***b***](#cite_ref-MasakiMechanism15_9-1) Masaki Y, Shimizu Y, Yoshioka T, Tanaka Y, Nishijima K, Zhao S, et al. (November 2015). ["The accumulation mechanism of the hypoxia imaging probe "FMISO" by imaging mass spectrometry: possible involvement of low-molecular metabolites"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4652161). *Scientific Reports*. **5** (1) 16802. [Bibcode](/source/Bibcode_(identifier)):[2015NatSR...516802M](https://ui.adsabs.harvard.edu/abs/2015NatSR...516802M). [doi](/source/Doi_(identifier)):[10.1038/srep16802](https://doi.org/10.1038%2Fsrep16802). [PMC](/source/PMC_(identifier)) [4652161](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4652161). [PMID](/source/PMID_(identifier)) [26582591](https://pubmed.ncbi.nlm.nih.gov/26582591).

1. ^ [***a***](#cite_ref-Drake20_10-0) [***b***](#cite_ref-Drake20_10-1) Drake LR, Hillmer AT, Cai Z (January 2020). ["Approaches to PET Imaging of Glioblastoma"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7037643). *Molecules*. **25** (3): 568. [doi](/source/Doi_(identifier)):[10.3390/molecules25030568](https://doi.org/10.3390%2Fmolecules25030568). [PMC](/source/PMC_(identifier)) [7037643](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7037643). [PMID](/source/PMID_(identifier)) [32012954](https://pubmed.ncbi.nlm.nih.gov/32012954).

1. ^ [***a***](#cite_ref-SemNM2020_11-0) [***b***](#cite_ref-SemNM2020_11-1) Sorace AG, Elkassem AA, Galgano SJ, Lapi SE, Larimer BM, Partridge SC, et al. (November 2020). ["Imaging for Response Assessment in Cancer Clinical Trials"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7573201). *Seminars in Nuclear Medicine*. **50** (6): 488–504. [doi](/source/Doi_(identifier)):[10.1053/j.semnuclmed.2020.05.001](https://doi.org/10.1053%2Fj.semnuclmed.2020.05.001). [PMC](/source/PMC_(identifier)) [7573201](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7573201). [PMID](/source/PMID_(identifier)) [33059819](https://pubmed.ncbi.nlm.nih.gov/33059819).

1. **[^](#cite_ref-12)** Zschaeck S, Löck S, Hofheinz F, Zips D, Saksø Mortensen L, Zöphel K, et al. (August 2020). "Individual patient data meta-analysis of FMISO and FAZA hypoxia PET scans from head and neck cancer patients undergoing definitive radio-chemotherapy". *Radiotherapy and Oncology*. **149**: 189–196. [doi](/source/Doi_(identifier)):[10.1016/j.radonc.2020.05.022](https://doi.org/10.1016%2Fj.radonc.2020.05.022). [hdl](/source/Hdl_(identifier)):[2078.1/250290](https://hdl.handle.net/2078.1%2F250290). [PMID](/source/PMID_(identifier)) [32417350](https://pubmed.ncbi.nlm.nih.gov/32417350). [S2CID](/source/S2CID_(identifier)) [218678537](https://api.semanticscholar.org/CorpusID:218678537).

1. **[^](#cite_ref-13)** Inubushi M, Tatsumi M, Yamamoto Y, Kato K, Tsujikawa T, Nishii R (November 2018). ["European research trends in nuclear medicine"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6208859). *Annals of Nuclear Medicine*. **32** (9): 579–582. [doi](/source/Doi_(identifier)):[10.1007/s12149-018-1303-7](https://doi.org/10.1007%2Fs12149-018-1303-7). [PMC](/source/PMC_(identifier)) [6208859](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6208859). [PMID](/source/PMID_(identifier)) [30242670](https://pubmed.ncbi.nlm.nih.gov/30242670).

1. **[^](#cite_ref-14)** Lopes S, Ferreira S, Caetano M (June 2021). ["PET/CT in the Evaluation of Hypoxia for Radiotherapy Planning in Head and Neck Tumors: Systematic Literature Review"](https://doi.org/10.2967%2Fjnmt.120.249540). *Journal of Nuclear Medicine Technology*. **49** (2): 107–113. [doi](/source/Doi_(identifier)):[10.2967/jnmt.120.249540](https://doi.org/10.2967%2Fjnmt.120.249540). [hdl](/source/Hdl_(identifier)):[10400.21/13161](https://hdl.handle.net/10400.21%2F13161). [PMID](/source/PMID_(identifier)) [33361182](https://pubmed.ncbi.nlm.nih.gov/33361182).

1. **[^](#cite_ref-15)** Xu Z, Li XF, Zou H, Sun X, Shen B (November 2017). ["18F-Fluoromisonidazole in tumor hypoxia imaging"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5706929). *Oncotarget*. **8** (55): 94969–94979. [doi](/source/Doi_(identifier)):[10.18632/oncotarget.21662](https://doi.org/10.18632%2Foncotarget.21662). [PMC](/source/PMC_(identifier)) [5706929](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5706929). [PMID](/source/PMID_(identifier)) [29212283](https://pubmed.ncbi.nlm.nih.gov/29212283).

1. **[^](#cite_ref-16)** Marcus C, Subramaniam RM (January 2021). "Role of Non-FDG-PET/CT in Head and Neck Cancer". *Seminars in Nuclear Medicine*. **51** (1): 68–78. [doi](/source/Doi_(identifier)):[10.1053/j.semnuclmed.2020.07.008](https://doi.org/10.1053%2Fj.semnuclmed.2020.07.008). [PMID](/source/PMID_(identifier)) [33246541](https://pubmed.ncbi.nlm.nih.gov/33246541). [S2CID](/source/S2CID_(identifier)) [225405293](https://api.semanticscholar.org/CorpusID:225405293).

1. **[^](#cite_ref-17)** Pell VR, Baark F, Mota F, Clark JE, Southworth R (March 2018). ["PET Imaging of Cardiac Hypoxia: Hitting Hypoxia Where It Hurts"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5830463). *Current Cardiovascular Imaging Reports*. **11** (3): 7. [doi](/source/Doi_(identifier)):[10.1007/s12410-018-9447-3](https://doi.org/10.1007%2Fs12410-018-9447-3). [PMC](/source/PMC_(identifier)) [5830463](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5830463). [PMID](/source/PMID_(identifier)) [29515752](https://pubmed.ncbi.nlm.nih.gov/29515752).

## External links

- [18F-Fluoromisonidazole](https://www.ncbi.nlm.nih.gov/books/NBK23099/), Molecular Imaging and Contrast Agent Database (MICAD)

---
Adapted from the Wikipedia article [FMISO](https://en.wikipedia.org/wiki/FMISO) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/FMISO?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.