5050. Ioflupane 123I

Nomenclature

CAS number: 155798-07-5
[1R-(exo,exo)]-8-(3-Fluoropropyl)-3-[4-(iodo123I)phenyl]-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester; N-(3-fluoropropyl)-2β-carbomethoxy-3β-(4-123I-iodophenyl)nortropane; methyl 8-(3-fluoropropyl)-3β-(p-iodo-123I-phenyl)-1αH,5αH-nortropane-2β-carboxylate; 123I-FP-CIT; DaTSCAN (GE Healthcare).
C18H23FINO2; mol wt 431.28.
C 50.13%, H 5.38%, F 4.41%, I 29.43%, N 3.25%, O 7.42%.

Description and references

Analog of cocaine, q.v., that binds specifically to the dopamine transporters (DAT) in the membrane of the presynaptic dopaminergic neuron; designed as SPECT imaging agent to determine nigrostriatal neuronal integrity. Prepn: J. L. Neumeyer et al., US 5310912 (1994 to Research Biochemicals); idem et al., J. Med. Chem. 37, 1558 (1994). HPLC determn in biological fluids: K. A. Bergstroem et al., Hum. Psychopharmacol. 11, 483 (1996). Binding study: J. L. Neumeyer et al., J. Med. Chem. 39, 543 (1996). Clinical biodistribution: J. Booij et al., Eur. J. Nucl. Med. 25, 24 (1998). Clinical imaging for tremor differentiation: H. T. S. Benamer et al., Mov. Disord. 15, 503 (2000); for dementia differentiation: D. C. Costa et al., ibid. 18, Suppl. 7, S34 (2003). Functional imaging for dopaminergic deficit: H. T. S. Benamer et al., ibid. 18, 977 (2003). Clinical use in diagnosis of parkinsonism: A. M. Catafau et al., ibid. 19, 1175 (2004). Review of role in dopaminergic imaging: P. M. Kemp, Nucl. Med. Commun. 26, 87-96 (2005).

Chemical structure

Properties

mp 82-83°. [α]D24 12.8°.

Therapeutic Category

Diagnostic aid (radioactive imaging agent).

Keywords

Diagnostic Aid (Radioactive Imaging Agent)