Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H21FINO2 |
Molecular Weight | 429.2677 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1C3=CC=C(F)C=C3)N2C\C=C\I
InChI
InChIKey=GTQLIPQFXVKRKJ-UNSMHXHVSA-N
InChI=1S/C18H21FINO2/c1-23-18(22)17-15(12-3-5-13(19)6-4-12)11-14-7-8-16(17)21(14)10-2-9-20/h2-6,9,14-17H,7-8,10-11H2,1H3/b9-2+/t14-,15+,16+,17-/m0/s1
Alseres Pharmaceuticals is developing an 123I-labelled imaging agent, Altropane®, as a diagnostic aid in Parkinson's disease and other movement disorders. Altropane is a molecular-imaging agent that specifically binds to the dopamine transporter (DAT) protein found on the surface of dopamine-producing neurons, making it visible during SPECT imaging. Since most forms of Parkinsonian Syndromes result in a decreased number of dopamine-producing cells, it would be expected that these patients also have fewer DATs than do patients without PS. Thus, it is believed that altropane used in conjunction with SPECT imaging could be a useful test to distinguish Parkinsonian Syndrome tremors from non-Parkinsonian tremor: non-Parkinsonian patients would have more altropane-binding visible in the SPECT image, while Parkinsonian patients would have less. The E isomer of (123)I-2beta-carbomethoxy-3beta-(4-fluorophenyl)-N-(1-iodoprop-1-en-3-yl)nortropane (Altropane(R)) shows high affinity (IC(50) = 6.62 +/- 0.78 nmol) and selectivity (DA/5-HT = 25) for DAT sites in the striatum. Altropane is presently in Phase III clinical development for the diagnosis of Parkinson's disease.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Altropane, a SPECT or PET imaging probe for dopamine neurons: III. Human dopamine transporter in postmortem normal and Parkinson's diseased brain. | 1998 Jun |
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[(11)C, (127)I] Altropane: a highly selective ligand for PET imaging of dopamine transporter sites. | 2001 Mar 15 |
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Is altropane SPECT more sensitive to fluoroDOPA PET for detecting early Parkinson's disease? | 2001 Nov-Dec |
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Cerebellar vermis involvement in cocaine-related behaviors. | 2006 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00724906
Parkinsonian Syndromes: 8.0 mCi (±1.0 mCi) are administered intravenously to each subject.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9593102
In homogenates of human brain putamen, [125I]altropane bound with high affinity (KD: 4.96 +/- 0.38 nM, n = 4) and site density (BMAX: 212 +/- 41.1 pmol/g original wet tissue weight) well within the density range reported previously for the dopamine transporter in this brain region. In postmortem Parkinson's diseased brain, bound [125I]altropane (1 nM) was markedly reduced (89%, 99% in putamen, depending on measures of nonspecific binding) compared with normal aged-matched controls (normal putamen: 49.2 +/- 8.1 pmol/g; Parkinson's diseased putamen: 0.48 +/- 0.33 pmol/g; n = 4).
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ALTROPANE
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ACTIVE MOIETY