Florbenazine Chemical Properties

Boiling point:

496.0±45.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

pka

14.75±0.40(Predicted)

InChI

InChI=1S/C21H32FNO3/c1-14(2)9-16-13-23-7-5-15-10-21(26-8-4-6-22)20(25-3)11-17(15)18(23)12-19(16)24/h10-11,14,16,18-19,24H,4-9,12-13H2,1-3H3/t16-,18-,19-/m1/s1

InChIKey

GNKGXQHHUUEYQV-BHIYHBOVSA-N

SMILES

C12=CC(OC)=C(OCCCF)C=C1CCN1[C@]2([H])C[C@@H](O)[C@H](CC(C)C)C1

Florbenazine Usage And Synthesis

Description

Florbenazine (AV-133) is a fluorinated VMAT-2 ligand for PET. It is designed to measure dopaminergic degeneration by in vivo assessment of striat VMAT2 density in patients with Parkinson’s disease (PD). Besides differentiating PD from essential tremor and drug-induced parkinsonism, PET imaging of VMAT2 may help in differentiating Dementia with Lewy Bodies (DLB) from Alzheimer’s disease. AV-45 (florbetapir, AmyvidTM) is the first PET ligand to receive US FDA approval to assess neuritic plaque amyloid[1-2].

Uses

Florbenazine (AV-133) is a diagnostic imaging agent targeting the central nervous system monoamine transporter VMAT2, and its F-18 labeled form can be used for PET scanning. The biodistribution of [18F]Florbenazine in mice shows a high striatum/cerebellum ratio (0.48), which can be used for the diagnostic research of neurodegenerative diseases (including dementia with Lewy bodies and Parkinson's disease)[1].

References

[1] Andrew Siderowf. “PET imaging of amyloid with Florbetapir F 18 and PET imaging of dopamine degeneration with 18F-AV-133 (florbenazine) in patients with Alzheimer’s disease and Lewy body disorders.” BMC Neurology 14 (2014): 79.
[2] Harsh V Gupta. “Clinicopathological Correlation: Dopamine and Amyloid PET Imaging with Neuropathology in Three Subjects Clinically Diagnosed with Alzheimer’s Disease or Dementia with Lewy Bodies.” Journal of Alzheimer’s Disease 80 4 (2021): 1603–1612.