Flubatine

Flubatine
Identifiers
	IUPAC name (1R,5S,6S)-6-(6-(18F)fluoranylpyridin-3-yl)-8-azabicyclo[3.2.1]octane;
CAS Number	1012885-77-6;
PubChem CID	71724875;
ChemSpider	129434972;
UNII	CN2ULA1988;
Chemical and physical data
3D model (JSmol)	Interactive image;
	SMILES C1C[C@@H]2C[C@H]([C@H](C1)N2)C3=CN=C(C=C3)[18F];
	InChI InChI=1S/C12H15FN2/c13-12-5-4-8(7-14-12)10-6-9-2-1-3-11(10)15-9/h4-5,7,9-11,15H,1-3,6H2/t9-,10+,11+/m1/s1/i13-1; Key:FDFUKZJWVPEZEH-MEPPPMTQSA-N;

Flubatine ([18F]-norchloro-fluoro-homoepibatidine) is a fluorine-18 (¹⁸F) labeled radiotracer and radioligand for positron emission tomography (PET) imaging, developed as a high-affinity ligand for brain nicotinic acetylcholine receptors (nAChRs) of the α4β2 subtype.^[2]^[3] It is used to image cholinergic deficits in disorders such as Alzheimer’s disease and Parkinson’s disease.^[4] Both (+)- and (−)- enantiomer bind specifically to α4β2 nAChRs.^[5]

References

^ ^a ^b "(-)-(18F)Flubatine". PubChem. U.S. National Library of Medicine. Retrieved May 12, 2025.
^ Fischer S, Hiller A, Deuther-Conrad W, Wenzel B, Patt M, Cumming P, et al. (2014-01-15). "Synthesis and biological evaluation of both enantiomers of [(18)F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors". Bioorganic & Medicinal Chemistry. 22 (2): 804–812. doi:10.1016/j.bmc.2013.12.011. ISSN 1464-3391. PMID 24369841.
^ Tiepolt S, Becker GA, Wilke S, Cecchin D, Rullmann M, Meyer PM, et al. (2020). "(+)-[18F]Flubatine as a novel α4β2 nicotinic acetylcholine receptor PET ligand—results of the first-in-human brain imaging application in patients with β-amyloid PET-confirmed Alzheimer's disease and healthy controls". Eur. J. Nucl. Med. Mol. Imaging. 48 (3): 731–746. doi:10.1007/s00259-020-05029-w. PMC 8036219. PMID 32935187.
^ Esterlis I, Gallezot JD, Bois F, Zheng MQ, Nabulsi N, Lin SF, et al. (2016-11-01). "Imaging of cerebral α4β2* nicotinic acetylcholine receptors with (-)-[(18)F]Flubatine PET: Implementation of bolus plus constant infusion and sensitivity to acetylcholine in human brain". NeuroImage. 141: 71–80. doi:10.1016/j.neuroimage.2016.07.026. ISSN 1095-9572. PMC 5026941. PMID 27426839.
^ Steffen F, René S, Winnie DC, Alexander H, Solveig T, Marianne P, et al. (February 2018). "Exploring the Metabolism of (+)-[18F]Flubatine In Vitro and In Vivo: LC-MS/MS Aided Identification of Radiometabolites in a Clinical PET Study †". Molecules. 23 (2). doi:10.3390/molecule (inactive 12 May 2025). ISSN 1420-3049. Archived from the original on 2025-05-09.{{cite journal}}: CS1 maint: DOI inactive as of May 2025 (link)

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[pubchem-1] "(-)-(18F)Flubatine". PubChem. U.S. National Library of Medicine. Retrieved May 12, 2025.

[2] Fischer S, Hiller A, Deuther-Conrad W, Wenzel B, Patt M, Cumming P, et al. (2014-01-15). "Synthesis and biological evaluation of both enantiomers of [(18)F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors". Bioorganic & Medicinal Chemistry. 22 (2): 804–812. doi:10.1016/j.bmc.2013.12.011. ISSN 1464-3391. PMID 24369841.

[3] Tiepolt S, Becker GA, Wilke S, Cecchin D, Rullmann M, Meyer PM, et al. (2020). "(+)-[18F]Flubatine as a novel α4β2 nicotinic acetylcholine receptor PET ligand—results of the first-in-human brain imaging application in patients with β-amyloid PET-confirmed Alzheimer's disease and healthy controls". Eur. J. Nucl. Med. Mol. Imaging. 48 (3): 731–746. doi:10.1007/s00259-020-05029-w. PMC 8036219. PMID 32935187.

[4] Esterlis I, Gallezot JD, Bois F, Zheng MQ, Nabulsi N, Lin SF, et al. (2016-11-01). "Imaging of cerebral α4β2* nicotinic acetylcholine receptors with (-)-[(18)F]Flubatine PET: Implementation of bolus plus constant infusion and sensitivity to acetylcholine in human brain". NeuroImage. 141: 71–80. doi:10.1016/j.neuroimage.2016.07.026. ISSN 1095-9572. PMC 5026941. PMID 27426839.

[5] Steffen F, René S, Winnie DC, Alexander H, Solveig T, Marianne P, et al. (February 2018). "Exploring the Metabolism of (+)-[18F]Flubatine In Vitro and In Vivo: LC-MS/MS Aided Identification of Radiometabolites in a Clinical PET Study †". Molecules. 23 (2). doi:10.3390/molecule (inactive 12 May 2025). ISSN 1420-3049. Archived from the original on 2025-05-09.{{cite journal}}: CS1 maint: DOI inactive as of May 2025 (link)

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