Page last updated: 2024-11-06

fluoromisonidazole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Fluoromisonidazole, a nitroimidazole derivative, is a hypoxia marker used in PET imaging to visualize regions of low oxygen levels in tissues. Its synthesis involves fluorination of misonidazole, a known radiosensitizer. Fluoromisonidazole accumulates in hypoxic cells due to enzymatic reduction by nitroreductases, leading to the formation of reactive intermediates that bind to cellular macromolecules. The trapping of fluoromisonidazole in hypoxic cells allows for non-invasive imaging of hypoxic regions using PET. Fluoromisonidazole is of significant interest in cancer research as hypoxia is a hallmark of many solid tumors and is associated with resistance to radiotherapy and chemotherapy. The compound's ability to identify hypoxic areas can aid in treatment planning and monitoring. Furthermore, it is being studied as a potential radiosensitizer itself, enhancing the efficacy of radiation therapy in treating cancer.'

Cross-References

ID SourceID
PubMed CID92242
CHEMBL ID2068841
SCHEMBL ID368122
MeSH IDM0099772

Synonyms (39)

Synonym
1-fluoro-3-(2-(hydroxy(oxido)amino)-1h-imidazol-1-yl)-2-propanol
1-fluoro-3-(2-nitroimidazol-1-yl)propan-2-ol
fmiso
alpha-(fluoromethyl)-2-nitroimidazole-1-ethanol
sr 1369
imidazole-1-ethanol, alpha-(fluoromethyl)-2-nitro-
1h-imidazole-1-ethanol, alpha-(fluoromethyl)-2-nitro
ku 2210
1-(2-nitro-1-imidazolyl)-3-fluoro-2-propanol
nsc 292930
brn 0522249
fluoromisonidazole
sr 1367
ro-07-0741
nsc292930
13551-89-8
nsc-292930
1h-imidazole-1-ethanol, .alpha.-(fluoromethyl)-2-nitro-
1-(2-hydroxy-3-fluoropropyl)-2-nitroimidazole
FT-0691079
AKOS006279809
082285vidf ,
unii-082285vidf
misonidazole, fluoro-
CHEMBL2068841
ku-2210
sr-1367
SCHEMBL368122
1-fluoro-3-(2-nitro-1h-imidazol-1-yl)propan-2-ol
1-(2-nitro-1-imidazolyl)-2-hydroxy-3-fluoropropane
1-fluoro-3-(2-nitro-imidazol-1-yl)-propan-2-ol
alpha-fluoromethyl-2-nitroimidazole-1-ethanol
DTXSID30875662
1-(3-f-2-ohpropyl)-2-no2 imidazole
fluoromisonidazole; ku 2210; nsc 292930; ro 07-0741; sr 1367
Q27236348
1h-imidazole-1-ethanol, alpha-(fluoromethyl)-2-nitro (9ci)
EN300-1647764
AKOS040751825

Research Excerpts

Overview

Fluoromisonidazole (18F‑FMISO) is a proven hypoxia imaging probe. It has been proposed as a positron emission tomography (PET) radiotracer.

ExcerptReferenceRelevance
"[¹⁸F]Fluoromisonidazole (¹⁸F-FMISO) is a nitroimidazole derivative that has been proposed as a positron emission tomography (PET) radiotracer to detect hypoxic tissue in vivo. "( Evaluation of hypoxic tissue dynamics with 18F-FMISO PET in a rat model of permanent cerebral ischemia.
Abad, S; Fernández-Soriano, FJ; Figueiras, FP; Gispert, JD; Herance, JR; Jiménez, X; Pareto, D; Planas, AM; Popota, F; Rojas, S; Ruiz, A; Torrent, È, 2011
)
0.88
"18F-fluoromisonidazole (18F‑FMISO) is a proven hypoxia imaging probe."( Evaluation of changes in the tumor microenvironment after sorafenib therapy by sequential histology and 18F-fluoromisonidazole hypoxia imaging in renal cell carcinoma.
Chowdhury, NF; Kuge, Y; Murakami, M; Nishijima, K; Takiguchi, M; Tamaki, N; Yu, W; Zhao, S; Zhao, Y, 2012
)
1.07

Toxicity

ExcerptReferenceRelevance
" Our 100% locoregional control rate suggests that intratreatment functional imaging used to selectively de-escalate node(s) to 60 Gy was confirmed safe using our stringent imaging criteria."( Strategy of Using Intratreatment Hypoxia Imaging to Selectively and Safely Guide Radiation Dose De-escalation Concurrent With Chemotherapy for Locoregionally Advanced Human Papillomavirus-Related Oropharyngeal Carcinoma.
Baxi, S; Beattie, B; Boyle, J; Chan, S; Ganly, I; Humm, J; Katabi, N; Lanning, R; Lee, N; Li, D; McBride, S; Mitrani, L; Morris, LG; Pfister, DG; Riaz, N; Schoder, H; Sherman, E; Wong, R; Yarusi, B; Zhang, Z, 2016
)
0.43

Pharmacokinetics

ExcerptReferenceRelevance
"Elimination half-life in blood (mono-exponential fit) reached 81."( Comparative pharmacokinetics, biodistribution, metabolism and hypoxia-dependent uptake of [18F]-EF3 and [18F]-MISO in rodent tumor models.
Cheguillaume, A; De Bast, M; de Groot, T; Gillart, J; Grégoire, V; Haustermans, K; Labar, D; Mahy, P, 2008
)
0.35
"This study used pharmacokinetic analysis of (18)F-labeled fluoromisonidazole ((18)F-FMISO) dynamic PET to assist the identification of regional tumor hypoxia and to investigate the relationship among a potential tumor hypoxia index (K(i)), tumor-to-blood ratio (T/B) in the late-time image, plasma-to-tissue transport rate (k(1)), and local vascular volume fraction (beta) for head and neck cancer patients."( Pharmacokinetic analysis of hypoxia (18)F-fluoromisonidazole dynamic PET in head and neck cancer.
Georgi, JC; Guillem, J; Humm, JL; Lee, NY; Narayanan, M; Schöder, H; Wang, W, 2010
)
0.87

Compound-Compound Interactions

ExcerptReferenceRelevance
"The aim of this study was to define the recommended dose of oxaliplatin when combined with infusional 5-fluorouracil (5-FU) and concurrent pelvic radiotherapy."( Oxaliplatin combined with infusional 5-fluorouracil and concomitant radiotherapy in inoperable and metastatic rectal cancer: a phase I trial.
Hicks, RJ; Leong, T; Lim-Joon, D; Loi, S; Mackay, J; Michael, M; Mitchell, P; Mukesh, B; Ngan, SY; Rischin, D; Zalcberg, J, 2005
)
0.33

Bioavailability

ExcerptReferenceRelevance
"17), whereas [(18)F]FAc has the highest bioavailability (area under concentration of radiotracer vs."( Biodistribution, pharmacokinetics and PET imaging of [(18)F]FMISO, [(18)F]FDG and [(18)F]FAc in a sarcoma- and inflammation-bearing mouse model.
Chang, CH; Chang, CW; Chang, TJ; Chou, TK; Lin, WJ; Liu, RS; Wang, HE; Wang, SJ; Wu, CY, 2009
)
0.35

Dosage Studied

ExcerptRelevanceReference
" In this paper, fluoromisonidazole (FMISO), a tumor PET imaging agent, was chosen to evaluate the dose-response pharmacokinetics by administering various single intravenous doses (0."( Dose-response relationships of FMISO between trace dose and various macro-doses in rat by ultra-performance liquid chromatography with mass spectrometry and radioactivity analysis.
Deng, A; Du, J; Qiao, J; Yin, W; Zhou, X; Zhu, L, 2012
)
0.72
" There was no obvious difference in dosage distributions on original target volume compared with those in conventional radiotherapy."( Dosimetry study of
Dong, M; Guo, S; Han, X; Li, G; Li, H; Lin, Y; Mi, Y; Ruan, Q; Wang, B; Xu, D; Zhang, X, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID6945821-Octanol-phosphate buffer partition coefficient, log P of the compound at pH 7.4 after 30 mins by shake-flask method2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
A fluorous and click approach for screening potential PET probes: Evaluation of potential hypoxia biomarkers.
AID694583Drug metabolism of the compound assessed as reduction rate assessed per unit of enzyme in anoxic conditions in presence of bovine milk xanthine oxidase2012Bioorganic & medicinal chemistry, Jan-01, Volume: 20, Issue:1
A fluorous and click approach for screening potential PET probes: Evaluation of potential hypoxia biomarkers.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (313)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (2.24)18.7374
1990's29 (9.27)18.2507
2000's79 (25.24)29.6817
2010's170 (54.31)24.3611
2020's28 (8.95)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.01

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.01 (24.57)
Research Supply Index5.87 (2.92)
Research Growth Index5.29 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.01)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials32 (10.00%)5.53%
Reviews28 (8.75%)6.00%
Case Studies8 (2.50%)4.05%
Observational2 (0.63%)0.25%
Other250 (78.13%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]