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MedKoo Cat#: 592608 | Name: Fluoromisonidazole

Description:

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

Fluoromisonidazole is used for imaging tumor hypoxia: imaging the microenvironment for personalized cancer therapy. It is a Radiation-Sensitizing Agent.

Chemical Structure

Fluoromisonidazole
Fluoromisonidazole
CAS#13551-89-8

Theoretical Analysis

MedKoo Cat#: 592608

Name: Fluoromisonidazole

CAS#: 13551-89-8

Chemical Formula: C6H8FN3O3

Exact Mass: 189.0550

Molecular Weight: 189.15

Elemental Analysis: C, 38.10; H, 4.26; F, 10.04; N, 22.22; O, 25.38

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Fluoromisonidazole
IUPAC/Chemical Name
1H-Imidazole-1-ethanol, alpha-(fluoromethyl)-2-nitro (9CI)
InChi Key
HIIJZYSUEJYLMX-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H8FN3O3/c7-3-5(11)4-9-2-1-8-6(9)10(12)13/h1-2,5,11H,3-4H2
SMILES Code
OC(Cn1c([N+]([O-])=O)ncc1)CF
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 189.15 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
1: Cui YL, Wang X, Li XF. (18)F-fluoromisonidazole PET reveals spatial and temporal heterogeneity of hypoxia in mouse models of human non-small-cell lung cancer. Future Oncol. 2015;11(20):2841-9. doi: 10.2217/fon.15.205. Epub 2015 Sep 11. PubMed PMID: 26361064. 2: 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. 3: Rajendran JG, Krohn KA. F-18 fluoromisonidazole for imaging tumor hypoxia: imaging the microenvironment for personalized cancer therapy. Semin Nucl Med. 2015 Mar;45(2):151-62. doi: 10.1053/j.semnuclmed.2014.10.006. Review. PubMed PMID: 25704387; PubMed Central PMCID: PMC4339212. 4: Mateo J, Izquierdo-Garcia D, Badimon JJ, Fayad ZA, Fuster V. Noninvasive assessment of hypoxia in rabbit advanced atherosclerosis using ¹⁸F-fluoromisonidazole positron emission tomographic imaging. Circ Cardiovasc Imaging. 2014 Mar;7(2):312-20. doi: 10.1161/CIRCIMAGING.113.001084. Epub 2014 Feb 7. PubMed PMID: 24508668; PubMed Central PMCID: PMC4083834. 5: Bell C, Dowson N, Fay M, Thomas P, Puttick S, Gal Y, Rose S. Hypoxia imaging in gliomas with 18F-fluoromisonidazole PET: toward clinical translation. Semin Nucl Med. 2015 Mar;45(2):136-50. doi: 10.1053/j.semnuclmed.2014.10.001. Review. PubMed PMID: 25704386. 6: Muzi M, Peterson LM, O'Sullivan JN, Fink JR, Rajendran JG, McLaughlin LJ, Muzi JP, Mankoff DA, Krohn KA. 18F-Fluoromisonidazole Quantification of Hypoxia in Human Cancer Patients Using Image-Derived Blood Surrogate Tissue Reference Regions. J Nucl Med. 2015 Aug;56(8):1223-8. doi: 10.2967/jnumed.115.158717. Epub 2015 Jun 25. PubMed PMID: 26112020; PubMed Central PMCID: PMC4526410. 7: Wiedenmann NE, Bucher S, Hentschel M, Mix M, Vach W, Bittner MI, Nestle U, Pfeiffer J, Weber WA, Grosu AL. Serial [18F]-fluoromisonidazole PET during radiochemotherapy for locally advanced head and neck cancer and its correlation with outcome. Radiother Oncol. 2015 Oct;117(1):113-7. doi: 10.1016/j.radonc.2015.09.015. Epub 2015 Sep 29. PubMed PMID: 26432067. 8: Lee GH, Kim JS, Oh SJ, Kang DW, Kim JS, Kwon SU. (18)F-fluoromisonidazole (FMISO) Positron Emission Tomography (PET) Predicts Early Infarct Growth in Patients with Acute Ischemic Stroke. J Neuroimaging. 2015 Jul-Aug;25(4):652-5. doi: 10.1111/jon.12180. Epub 2014 Oct 14. PubMed PMID: 25311732. 9: Cheney MD, Chen YL, Lim R, Winrich BK, Grosu AL, Trofimov AV, Depauw N, Shih HA, Schwab JH, Hornicek FJ, DeLaney TF. [18F]-Fluoromisonidazole positron emission tomography/computed tomography visualization of tumor hypoxia in patients with chordoma of the mobile and sacrococcygeal spine. Int J Radiat Oncol Biol Phys. 2014 Dec 1;90(5):1030-6. doi: 10.1016/j.ijrobp.2014.08.016. PubMed PMID: 25539367; PubMed Central PMCID: PMC4280072. 10: 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. 11: Yoo K. Systematic Review On Efficacy Of The F-18 Fluoromisonidazole Pet Or Pet/Ct. Value Health. 2015 Nov;18(7):A373. doi: 10.1016/j.jval.2015.09.763. Epub 2015 Oct 20. PubMed PMID: 26532109. 12: Kawai N, Lin W, Cao WD, Ogawa D, Miyake K, Haba R, Maeda Y, Yamamoto Y, Nishiyama Y, Tamiya T. Correlation between ¹⁸F-fluoromisonidazole PET and expression of HIF-1α and VEGF in newly diagnosed and recurrent malignant gliomas. Eur J Nucl Med Mol Imaging. 2014 Oct;41(10):1870-8. doi: 10.1007/s00259-014-2776-9. Epub 2014 Apr 30. PubMed PMID: 24781871. 13: Norikane T, Yamamoto Y, Maeda Y, Kudomi N, Matsunaga T, Haba R, Iwasaki A, Hoshikawa H, Nishiyama Y. Correlation of (18)F-fluoromisonidazole PET findings with HIF-1α and p53 expressions in head and neck cancer: comparison with (18)F-FDG PET. Nucl Med Commun. 2014 Jan;35(1):30-5. doi: 10.1097/MNM.0000000000000010. PubMed PMID: 24121312. 14: 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. 15: Yamaguchi S, Hirata K, Toyonaga T, Kobayashi K, Ishi Y, Motegi H, Kobayashi H, Shiga T, Tamaki N, Terasaka S, Houkin K. Change in 18F-Fluoromisonidazole PET Is an Early Predictor of the Prognosis in the Patients with Recurrent High-Grade Glioma Receiving Bevacizumab Treatment. PLoS One. 2016 Dec 9;11(12):e0167917. doi: 10.1371/journal.pone.0167917. eCollection 2016. PubMed PMID: 27936194; PubMed Central PMCID: PMC5148016. 16: Wei Y, Zhao W, Huang Y, Yu Q, Zhu S, Wang S, Zhao S, Hu X, Yu J, Yuan S. A Comparative Study of Noninvasive Hypoxia Imaging with 18F-Fluoroerythronitroimidazole and 18F-Fluoromisonidazole PET/CT in Patients with Lung Cancer. PLoS One. 2016 Jun 20;11(6):e0157606. doi: 10.1371/journal.pone.0157606. eCollection 2016. PubMed PMID: 27322586; PubMed Central PMCID: PMC4913930. 17: Grkovski M, Schwartz J, Rimner A, Schöder H, Carlin SD, Zanzonico PB, Humm JL, Nehmeh SA. Reproducibility of (18)F-fluoromisonidazole intratumour distribution in non-small cell lung cancer. EJNMMI Res. 2016 Dec;6(1):79. Epub 2016 Nov 7. PubMed PMID: 27822900; PubMed Central PMCID: PMC5099292. 18: Pinker K, Andrzejewski P, Baltzer P, Polanec SH, Sturdza A, Georg D, Helbich TH, Karanikas G, Grimm C, Polterauer S, Poetter R, Wadsak W, Mitterhauser M, Georg P. Multiparametric [18F]Fluorodeoxyglucose/ [18F]Fluoromisonidazole Positron Emission Tomography/ Magnetic Resonance Imaging of Locally Advanced Cervical Cancer for the Non-Invasive Detection of Tumor Heterogeneity: A Pilot Study. PLoS One. 2016 May 11;11(5):e0155333. doi: 10.1371/journal.pone.0155333. eCollection 2016. PubMed PMID: 27167829; PubMed Central PMCID: PMC4864307. 19: 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; PubMed Central PMCID: PMC5423153. 20: 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; PubMed Central PMCID: PMC5575834.