Tracer library / [18F]FAZA

Structure of fluoroazomycinarabinoside (unlabelled parent compound, from PubChem) — Unlabelled parent compoundPubChem CID 10083297

[18F]FAZA

Also written as [18F]FAZA; [18F]fluoroazomycinarabinoside; [F-18]FAZA; [F-18]fluoroazomycinarabinoside; F-18 FAZA; FAZA

Radionuclide: F-18 t½ 109.77 min
Modality: PET
Production route: —
Stage: —
Syntheses indexed: 3

Tumour hypoxia

What it is

Compound class: Radiolabelled 2-nitroimidazole (azomycin arabinoside derivative)
Target / mechanism: Hypoxic cells — bioreductive (nitroreductase-mediated) trapping under low oxygen tension PMID 15632040
Clinical application: Tumour-hypoxia PET imaging (head and neck, lung, prostate, rectal cancers) PMID 24152663
Theranostic pair: —

Published syntheses

Module	Cassette	Purification	Yield %	RCP %	Precursor / supplier	Source
TRACERlab FX FN GE HealthCare	custom manifold	HPLC	4.8% not corrected	—	FAZA precursor Prof. Friedrich Hammerschmidt (Universität Wien, Austria) and Prof. Hans-Jürgen Machulla, Steinbeis Transfer Center Radiopharmacy, Germany	21769163 2011 J Labelled Comp Radiopharm the Tracerlab synthesis module was used in the original "out-of-the-box" configuration illustrated in Figure 3 - Typical yield of [18F]FAZA prepared using this method is 4.8% (non-decay corrected, n = 25).
Nuclear Interface Nuclear Interface (legacy)	—	SPE	21.98±1.40% not corrected	>95%	1-(2,3-di-O-acetyl-5-O-tosyl-alpha-D-arabino…1-(2,3-di-O-acetyl-5-O-tosyl-alpha-D-arabinofuranosyl)-2-nitroimidazole	20478712 2010 Appl Radiat Isot [(18)F]FAZA was prepared via a one-pot, two-step synthesis using a nuclear interface nucleophilic synthesis module. - The overall radiochemical yield obtained was 21.98+/-1.40% (n=5, without decay correction)
In-house / custom built Laboratory	—	—	52.4±5.3% decay-corrected	—	2.5mg (5.2 μmol) of the precursor	21420304 2011 Appl Radiat Isot a modified NIRS original synthesis system for clinical use - a high radiochemical yield of 52.4±5.3% (decay-corrected, n=8)

Precursor

Common precursor: FAZA precursor PMID 21769163 (DOI 10.1002/jlcr.1865)
Suppliers seen in the literature: academic (Univ. Wien / Steinbeis Transfer Center Radiopharmacy)
Cited suppliers in indexed syntheses: Prof. Friedrich Hammerschmidt (Universität Wien, Austria) and Prof. Hans-Jürgen Machulla
Typical final purification: HPLC (semi-preparative)

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Quality control Preliminary - inferred from compound class

Ph. Eur. monograph: not verified No Ph. Eur. check is recorded for this entry.
USP monograph: not verified No USP check is recorded for this entry.

AppearancepHRCP HPLCRCP TLCHPLC UVResidual solvents (GC)Radionuclidic (HPGe)Half-lifeActivityEndotoxins (LAL)SterilityFilter integrity

How this set was arrived at. base set per Ph. Eur. general monograph 0125 (rule); organic solvent confirmed in synthesis data (PMID 21769163) -> GC residual solvents; conventional nucleophilic 18F-fluorination assumed from isotope/compound class, no synthesis data confirming K222 use -> Kryptofix test (preliminary)

Tests listed by reference only. Monograph texts are copyrighted and are not reproduced here. How these are derived

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Notes

Added from reverse module search (stage 6); 7 article(s) with F-18.