Page last updated: 2024-11-12

2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane

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Description

2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane: used in PET and SPECT imaging of dopamine transporters; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10048368
CHEMBL ID1945778
SCHEMBL ID16589355
MeSH IDM0231850

Synonyms (28)

Synonym
unii-vf232we742
(1r,2s,3s,5s)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo(3,2,1)octane-2-carboxylic acid methyl ester
8-azabicyclo(3.2.1)octane-2-carboxylic acid, 8-(3-fluoropropyl)-3-(4-iodophenyl)-, methyl ester, (1r-(exo,exo))-
i(123)-n-omega-fluoropropyl-2-beta-carbomethoxy-3-beta(4-iodophenyl)nortropane
n-omega-fluoropropyl-2beta-carbomethoxy-3beta-(4-iodophenyl)tropane
2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane
rti-313
(o-methyl-11c)beta-cit-fp
vf232we742 ,
155797-99-2
methyl 8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo(3.2.1)octane-2-carboxylate (1r-(exo,exo))-
i(123)-n-fluoropropyl-2-beta-carbomethoxy-3-(4-iodophenyl)nortropane
beta-cit-fp
fp-cit
rti 313
ioflupane
nma-78
.beta.-cit-fp
CHEMBL1945778
j731.794h ,
(1r,2s,3s,5s)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo(3.2.1)octane-2-carboxylic acid methyl ester
8-azabicyclo(3.2.1)octane-2-carboxylic acid, 8-(3-fluoropropyl)-3-(4-iodophenyl)-, methyl ester, (1r,2s,3s,5s)-
SCHEMBL16589355
Q27895498
methyl (1r,2s,3s,5s)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
methyl (1s,3s,4s,5r)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo[3.2.1]octane-4-carboxylate
8-azabicyclo[3.2.1]octane-2-carboxylic acid,8-(3-fluoropropyl)-3-(4-iodophenyl)-,methyl ester(1r,2s,3s,5s)-
AKOS040747950

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" WT alpha-synuclein reduced the toxic effect of MPP+ by facilitating DAT internalization, while both A30P and A53T alpha-synuclein aggravated the toxic effect of MPP+ by reducing DAT internalization."( Differential effects of overexpression of wild-type and mutant human alpha-synuclein on MPP+-induced neurotoxicity in PC12 cells.
Cheng, YB; Li, K; Liu, CF; Mao, CJ; Qian, JJ; Qin, ZH; Yang, YP, 2008
)
0.35
" DaTscan was safe and well tolerated."( Impact of DaTscan SPECT imaging on clinical management, diagnosis, confidence of diagnosis, quality of life, health resource use and safety in patients with clinically uncertain parkinsonian syndromes: a prospective 1-year follow-up of an open-label contr
Bajaj, N; Buitendyk, M; Grachev, ID; Klutmann, S; Kupsch, AR; Sherwin, P; Tartaglione, A; Tate, A; Weiland, F, 2012
)
0.38
" DaTscan is safe and well tolerated, and is a useful adjunct to differentiate a diagnosis of CUPS."( Impact of DaTscan SPECT imaging on clinical management, diagnosis, confidence of diagnosis, quality of life, health resource use and safety in patients with clinically uncertain parkinsonian syndromes: a prospective 1-year follow-up of an open-label contr
Bajaj, N; Buitendyk, M; Grachev, ID; Klutmann, S; Kupsch, AR; Sherwin, P; Tartaglione, A; Tate, A; Weiland, F, 2012
)
0.38
" None of the participants experienced any serious adverse effects."( Safety and efficacy of recombinant human erythropoietin treatment of non-motor symptoms in Parkinson's disease.
Ahn, JY; Cho, JW; Jang, W; Kim, HT; Kim, JS; Oh, E; Oh, KW; Park, J; Shin, KJ; Youn, J, 2014
)
0.4
" Percentages of subjects with adverse events by category were as follows: all (22%), considered at least possibly related to DaTscan by the investigator (4%), any severe (3%), headache (4%), nausea (2%), dizziness (2%), nasopharyngitis (1%), and injection site hematoma (1%)."( Safety analysis of 10 clinical trials and for 13 years after first approval of ioflupane 123I injection (DaTscan).
Bajaj, N; Chen, C; Grachev, ID; Grosset, DG; Kupsch, A; O'Brien, JT; Oertel, WH; Seibyl, J; Sherwin, P; Tatsch, K; Tolosa, E; Walker, Z, 2014
)
0.4

Compound-Compound Interactions

ExcerptReferenceRelevance
" In a marmoset model of Parkinson's disease, which was generated by unilateral injections of 6-hydroxydopamine (6-OHDA) into the nigro-striatal projection pathway, complete loss of striatal DAT binding in combination with behavioral deficits was observed."( Visualizing dopamine transporter integrity with iodine-123-FP-CIT SPECT in combination with high resolution MRI in the brain of the common marmoset monkey.
Czéh, B; Fuchs, E; Garea-Rodríguez, E; Heckmann, C; Helms, G; König, J; Meller, B; Meller, J; Schlumbohm, C, 2012
)
0.38
" The present study investigated the utility of [(123)I]-Ioflupane single photon emission computed tomography (SPECT) combined with MIBG myocardial scintigraphy for the diagnosis of PD."( [(123)I]-Ioflupane SPECT in combination with MIBG myocardial scintigraphy in Parkinson's disease: a case series study.
Iikuni, Y; Ito, H; Kang, Y; Morimatsu, A; Murakami, T; Shirata, A; Ugawa, Y; Yamada, A; Yamane, K, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
"All patients improved motor scores at 3 months (-65 +/- 22% 'off', -89 +/- 12% 'on') and most received fewer dopaminergic drugs (-30% dosage in average)."( Dopamine transporter imaging under high-dose transdermal nicotine therapy in Parkinson's disease: an observational study.
Brugières, P; Capacchione, D; Cesaro, P; Itti, E; Itti, L; Maison, P; Malek, Z; Meignan, M; Villafane, G, 2009
)
0.35
" There were no correlations between changes in 123I-FP-CIT uptake ratios with disease duration, changes in medication dosage and motor UPDRS scores."( Chronic motor cortex stimulation in patients with advanced Parkinson's disease and effects on striatal dopaminergic transmission as assessed by 123I-FP-CIT SPECT: a preliminary report.
Bentivoglio, AR; Calcagni, ML; Cioni, B; Cocciolillo, F; Di Giuda, D; Fasano, A; Giordano, A; Piano, C; Soleti, F; Totaro, M, 2012
)
0.38
"The degree of reduction in presynaptic dopaminergic uptake at baseline is associated with higher antiparkinson drug dosage at follow-up, but the wide variation means that the baseline FP-CIT SPECT does not reliably predict drug use in individual cases."( Baseline [(123) I]FP-CIT SPECT (DaTSCAN) severity correlates with medication use at 3 years in Parkinson's disease.
Grosset, DG; Grosset, KA; Hadley, D; Malek, N; Newman, EJ; Nissen, T; Patterson, J, 2014
)
0.4
"Pooling the four studies, 928 participants were enrolled, 849 were dosed and 764 completed their study."( Is ioflupane I123 injection diagnostically effective in patients with movement disorders and dementia? Pooled analysis of four clinical trials.
Grachev, ID; Grosset, DG; McKeith, IG; O'Brien, JT; Oertel, WH; Sherwin, PF; Tatsch, K; Tolosa, E; Walker, Z, 2014
)
0.4
"We recruited 52 newly diagnosed, drug-naïve PD patients, and performed serum UA dosage and [(123) I]FP-CIT-SPECT."( Uric acid relates to dopamine transporter availability in Parkinson's disease.
Amboni, M; Barone, P; Erro, R; Longo, K; Moccia, M; Palladino, R; Pappatà, S; Pellecchia, MT; Picillo, M; Vitale, C, 2015
)
0.42
" Present findings may have implications for escitalopram dosage and side effect profile in younger MDD patients."( Altered serotonin and dopamine transporter availabilities in brain of depressed patients upon treatment with escitalopram: A [123 I]β-CIT SPECT study.
Bartenstein, P; Brendel, M; Cumming, P; Karch, S; Koch, W; la Fougère, C; Pogarell, O; Rominger, A; Tatsch, K; Xiong, G; Zach, C, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent dopamine transporter Homo sapiens (human)Ki0.02820.00021.11158.0280AID644411
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent dopamine transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent dopamine transporter Homo sapiens (human)
lactationSodium-dependent dopamine transporter Homo sapiens (human)
sensory perception of smellSodium-dependent dopamine transporter Homo sapiens (human)
locomotory behaviorSodium-dependent dopamine transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent dopamine transporter Homo sapiens (human)
response to iron ionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine transportSodium-dependent dopamine transporter Homo sapiens (human)
adenohypophysis developmentSodium-dependent dopamine transporter Homo sapiens (human)
response to nicotineSodium-dependent dopamine transporter Homo sapiens (human)
positive regulation of multicellular organism growthSodium-dependent dopamine transporter Homo sapiens (human)
regulation of dopamine metabolic processSodium-dependent dopamine transporter Homo sapiens (human)
response to cocaineSodium-dependent dopamine transporter Homo sapiens (human)
dopamine biosynthetic processSodium-dependent dopamine transporter Homo sapiens (human)
dopamine catabolic processSodium-dependent dopamine transporter Homo sapiens (human)
response to ethanolSodium-dependent dopamine transporter Homo sapiens (human)
cognitionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent dopamine transporter Homo sapiens (human)
response to cAMPSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent dopamine transporter Homo sapiens (human)
prepulse inhibitionSodium-dependent dopamine transporter Homo sapiens (human)
dopamine uptakeSodium-dependent dopamine transporter Homo sapiens (human)
hyaloid vascular plexus regressionSodium-dependent dopamine transporter Homo sapiens (human)
amino acid transportSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine transportSodium-dependent dopamine transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent dopamine transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
protease bindingSodium-dependent dopamine transporter Homo sapiens (human)
signaling receptor bindingSodium-dependent dopamine transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent dopamine transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent dopamine transporter Homo sapiens (human)
protein bindingSodium-dependent dopamine transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent dopamine transporter Homo sapiens (human)
dopamine bindingSodium-dependent dopamine transporter Homo sapiens (human)
amine bindingSodium-dependent dopamine transporter Homo sapiens (human)
protein-containing complex bindingSodium-dependent dopamine transporter Homo sapiens (human)
metal ion bindingSodium-dependent dopamine transporter Homo sapiens (human)
protein phosphatase 2A bindingSodium-dependent dopamine transporter Homo sapiens (human)
heterocyclic compound bindingSodium-dependent dopamine transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent dopamine transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
cytoplasmSodium-dependent dopamine transporter Homo sapiens (human)
plasma membraneSodium-dependent dopamine transporter Homo sapiens (human)
cell surfaceSodium-dependent dopamine transporter Homo sapiens (human)
membraneSodium-dependent dopamine transporter Homo sapiens (human)
axonSodium-dependent dopamine transporter Homo sapiens (human)
neuron projectionSodium-dependent dopamine transporter Homo sapiens (human)
neuronal cell bodySodium-dependent dopamine transporter Homo sapiens (human)
axon terminusSodium-dependent dopamine transporter Homo sapiens (human)
membrane raftSodium-dependent dopamine transporter Homo sapiens (human)
postsynaptic membraneSodium-dependent dopamine transporter Homo sapiens (human)
dopaminergic synapseSodium-dependent dopamine transporter Homo sapiens (human)
flotillin complexSodium-dependent dopamine transporter Homo sapiens (human)
axonSodium-dependent dopamine transporter Homo sapiens (human)
presynaptic membraneSodium-dependent dopamine transporter Homo sapiens (human)
plasma membraneSodium-dependent dopamine transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent dopamine transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID644411Displacement of [3H]WIN35428 from human cloned DAT receptor expressed in human HEK293 cells2012Bioorganic & medicinal chemistry, Feb-15, Volume: 20, Issue:4
QSAR study and synthesis of new phenyltropanes as ligands of the dopamine transporter (DAT).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (810)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's25 (3.09)18.2507
2000's188 (23.21)29.6817
2010's485 (59.88)24.3611
2020's112 (13.83)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.58

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.58 (24.57)
Research Supply Index6.79 (2.92)
Research Growth Index5.38 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials47 (5.56%)5.53%
Reviews31 (3.67%)6.00%
Case Studies129 (15.27%)4.05%
Observational4 (0.47%)0.25%
Other634 (75.03%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]