Tracers / [18F]FMISO
[18F]FMISO
Also written as 1H-1-(3-[18F]fluoro-2-hydroxypropyl)-2-nitroimidazole; [18F]Fluoromisonidazole; [18F]FMISO; [F-18]Fluoromisonidazole; [F-18]FMISO; F-18 Fluoromisonidazole; F-18 FMISO
- Radionuclide
- F-18 t½ 109.7 min
- Modality
- PET
- Production route
- Cyclotron liquid target
- Stage
- Clinical research
- Syntheses indexed
- 22
What it is
- Compound class
- Nitroimidazole
- Target / mechanism
- Bioreductive trapping: after cell entry the 2-nitroimidazole nitro group is reduced and, under hypoxia, binds irreversibly to intracellular macromolecules (re-oxidised and washed out under normoxia) PMID 29212283 / DOI 10.18632/oncotarget.21662
- Clinical application
- Tumour hypoxia; radiotherapy planning PMID 29212283 / DOI 10.18632/oncotarget.21662
- Theranostic pair
- —
Regulatory status
- FDA
- No Drugs@FDA / openFDA drug registry — no approved application found; search: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=BasicSearch.process&searchTerm=fluoromisonidazole
- EMA (centralised)
- —
- Other approvals
- —
- Brand names
- —
Clinical use
- Typical injected activity
- —
- Uptake time
- 120-240 min post-injection (commonly ~2 h) PMID 29212283 / DOI 10.18632/oncotarget.21662
Reported in the literature. Not a dosing recommendation.
Published syntheses
| Module | Cassette | Purification | Yield % | RCP % | Precursor / supplier | Source |
|---|---|---|---|---|---|---|
| Manual synthesis | custom manifold | SPE | 78 yes | — | NITTP (1-(2ʹ-nitro-1ʹ-imidazolyl)-2-O-tetrahydropyranyl-3-O-tosyl-propanediol) | 40113734 2025 EJNMMI Radiopharm Chem following modified non-automated protocols similar to those reported in the literature — the overall corrected radiochemical yield (RCY) was estimated to be 78% |
| FASTlab GE HealthCare | vendor cassette | SPE | 49 ± 7% (n = 30) yes | 99.9% | NITTP ABX | 36897480 2023 EJNMMI Radiopharm Chem a FASTlab1 radiosynthesizer (GE HealthCare) was used — The radiochemical yield of [18F]FMISO using original cassettes for FASTlab was 49 ± 7% (n = 30) within 48 min synthesis time. |
| FASTlab GE HealthCare | custom manifold | SPE | 39 ± 11% (n = 19) yes | 99.8% | NITTP ABX | 36897480 2023 EJNMMI Radiopharm Chem a FASTlab1 radiosynthesizer (GE HealthCare) was used — The radiochemical yield of [18F]FMISO obtained with in-house prepared cassettes and 10 mg (23.5 µmol) NITTP precursor was 39 ± 11% (n = 19), which is somewhat lower in comparison with the original cassettes. |
| In-house / custom built in-house | custom manifold | HPLC | 26 ± 7.5 yes | 99 ± 0.50 | 2-nitroimidazole (6) ABX | 34245396 2021 EJNMMI Radiopharm Chem An automated multi-purpose synthesizer developed in-house was used for all the radiosynthetic runs in this study (Supplemental information: Fig. S1, Fukumura et al. 2007). — The radiochemical yield of [18F]FMISO based on the cyclotron-produced [18F]F− at the end of the synthesis (EOS) was 26 ± 7.5 % (n = 8). |
| — | — | — | — | > 95% | 1-(2′-nitro-1′-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulphonylpropanediol | 31278504 2019 EJNMMI Res |
| In-house / custom built Siemens | custom manifold | HPLC | 38% ± 2% yes | ≥99% | NITTP | 22871433 2012 Appl Radiat Isot a fourth generation microfluidic prototype instrument (P-IV instrument) developed at Siemens Molecular Imaging — Radiochemical yields for [18F] FMISO based on starting [18F] activity was 38% ± 2% |
| — | — | — | — | — | — | 41807884 2026 Mol Diagn Ther |
| — | — | SPE | 56% | >99.5% | — | 34613615 2022 J Labelled Comp Radiopharm [18 F]FMISO was synthesized using a TracerLab FX-FDG module — in 56% radiochemical yield |
| — | — | HPLC | — | — | — | 29520821 2018 J Labelled Comp Radiopharm |
| — | — | — | — | >97% | enantiopure epoxides | 25595134 2015 Nucl Med Biol using custom-made automation module |
| — | — | — | — | >97% | enantiopure epoxides | 25595134 2015 Nucl Med Biol using custom-made automation module |
| — | — | SPE | 25.1 ± 5.0% no | — | 1-(2'-nitro-1'-imidazolyl)-2-O-tetra-hydropyranyl-3-O-toluenesulfonyl propanediol (NITTP) | 24339013 2013 J Labelled Comp Radiopharm automatic synthesis using GE TRACERlab MX — Non-decay-corrected radiochemical yields of 25.1 ± 5.0% and 13.3 ± 5.1% (n = 3) were achieved after solid-phase extraction purification using automatic synthesis with GE TRACERlab MX and KHCO3 at concentrations of 14.1 and 33.0 µmol, respectively |
| — | — | SPE | 13.3 ± 5.1% no | — | 1-(2'-nitro-1'-imidazolyl)-2-O-tetra-hydropyranyl-3-O-toluenesulfonyl propanediol (NITTP) | 24339013 2013 J Labelled Comp Radiopharm automatic synthesis using GE TRACERlab MX — Non-decay-corrected radiochemical yields of 25.1 ± 5.0% and 13.3 ± 5.1% (n = 3) were achieved after solid-phase extraction purification using automatic synthesis with GE TRACERlab MX and KHCO3 at concentrations of 14.1 and 33.0 µmol, respectively |
| — | — | — | 80% for protected [18F]FMISO | — | — | 22001413 2012 Appl Radiat Isot The substitutions were carried out in a microfluidic reaction flow cell — 80% for protected [(18)F]FMISO |
| — | — | SPE | 37.49+/-1.68% no | >95% | 1-(2'-nitro-1'-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulphonylpropanediol (NITTP) | 20493720 2010 Appl Radiat Isot using a modified nuclear interface synthesis module — The maximum overall radiochemical yield obtained was 37.49+/-1.68% with 10mg NITTP (n=3, without any decay correction) |
| — | — | — | 30±5% no | >97% | — | 17379530 2007 Appl Radiat Isot using a Scanditronix Anatech RB III robotic system — an uncorrected radiochemical yield of 30+/-5% at end of synthesis (EOS) |
| — | — | HPLC | 58.5±3.5% yes | — | 1-(2'-nitro-1'-imidazolyl)-2-O-tetrahydrofuranyl-3-O-toluenesulfonylpropanediol | 16253816 2005 Nucl Med Biol Fully automated synthesis of [18F]fluoromisonidazole using a conventional [18F]FDG module. — [18F]FMISO was obtained with high end-of-synthesis (EOS) radiochemical yields of 58.5+/-3.5% for 60.0+/-5.2 min with high-performance liquid chromatography (HPLC) purification |
| — | — | HPLC+SPE | 54.5±2.8% yes | — | 1-(2'-nitro-1'-imidazolyl)-2-O-tetrahydrofuranyl-3-O-toluenesulfonylpropanediol | 16253816 2005 Nucl Med Biol Fully automated synthesis of [18F]fluoromisonidazole using a conventional [18F]FDG module. — the EOS radiochemical yields were 54.5+/-2.8% (337+/-25 GBq/micromol) for 70.0+/-3.8 min |
| — | — | SPE | greater than 40% no | greater than 95% | 1-(2'-nitro-1'-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulphonylpropanediol | 15982586 2005 Nucl Med Biol using a modified commercial Tracerlab FX(F-N) synthesis module — The overall radiochemical yield with no decay correction was greater than 40% |
| — | — | — | 55-80% | — | — | 8358398 1993 Appl Radiat Isot One-step radiolabeling and rapid protection group removal provided 55-80% yield in 50 min. — 55-80% yield in 50 min |
| — | — | — | 40% | — | [18F]fluoride | 2738663 1989 J Nucl Med |
| — | — | — | — | 99±1 | — | 27562785 2016 Curr Radiopharm the novel fully automated platform of the BG75 system |
Precursor
- Common precursor
- NITTP (1-(2'-nitro-1'-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulfonylpropanediol) PMID 35697954 / DOI 10.1186/s41181-022-00165-0
- Suppliers seen in the literature
- ABX advanced biochemical compounds (Radeberg, Germany) (precursor NITTP)
- Cited suppliers in indexed syntheses
- ABX
- Typical final purification
- SPE
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Get in touchQuality control Pharmacopoeial monograph
- Ph. Eur. monograph
- 2459
- USP monograph
- not verified — the USP-NF monograph index is subscription-only and no public confirmation was found
How this set was arrived at. Cross-checked against Ph. Eur. general monograph 0125 (base set), EANM validation guideline (PMC7016057) and cGRPP guidance (PMC7881071). Draft X-marks consistent with the base set; tracer-specific analytical tests follow the specific monograph where one exists.
Tests listed by reference only. Monograph texts are copyrighted and are not reproduced here. How these are derived
Setting up quality control?We can help you scope the equipment needed to release [18F]FMISO.
Get in touchNotes
Reference hypoxia tracer since 1986; slow kinetics require late imaging.