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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23FINO2
Molecular Weight 427.2847
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOFLUPANE I-123

SMILES

COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1C3=CC=C([123I])C=C3)N2CCCF

InChI

InChIKey=HXWLAJVUJSVENX-HFIFKADTSA-N
InChI=1S/C18H23FINO2/c1-23-18(22)17-15(12-3-5-13(20)6-4-12)11-14-7-8-16(17)21(14)10-2-9-19/h3-6,14-17H,2,7-11H2,1H3/t14-,15+,16+,17-/m0/s1/i20-4

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://us.datscan.com/ | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000266/WC500035350.pdf | http://jnm.snmjournals.org/content/early/2014/06/19/jnumed.114.138032.full.pdf

Ioflupane I-123 (trade name DaTscan) is a radioiodinated cocaine analogue synthesized from a key starting material Sn FP-CT via oxidative iododestannylation with sodium (123I)-iodide. Ioflupane I-123 binds reversibly with high affinity to the dopamine transporter (DaT) protein, a marker for presynaptic terminals in dopaminergic nigrostriatal neurons. It has been developed as a dopamine transporter imaging agent for single photon emission computed tomography (SPECT) which is claimed to be sensitive enough to differentiate changes in the nigrostriatal dopaminergic system in patients with Parkinsonism and healthy controls. DaTSCAN is unable to discriminate between Parkinson's Disease, Multiple System Atrophy and Progressive Supranuclear Palsy. DaTscan is an adjunct to other diagnostic evaluations. Headache, nausea, vertigo, dry mouth, or dizziness of mild to moderate severity as well as hypersensitivity reactions and injection-site pain have been reported. The DaTscan injection may contain up to 6% of free iodide (iodine 123 or I-123). To decrease thyroid accumulation of I-123, the thyroid gland has to be blocked at least one hour before administration of DaTscan because of the long-term risk for thyroid neoplasia. DaTscan was first approved in the European Union (EU) on July 27, 2000. It is also approved in Israel, Switzerland and in the United States (a total of 33 countries).

CNS Activity

Curator's Comment: In the in vitro studies the specific binding of the FP-CT on the dopamine transporters, in particular in the striatum was demonstrated. In both humans and monkeys FP-CIT acid, the main metabolite of the FP-CIT, is a polar compound unable to cross the blood-brain barrier.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
0.62 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
DaTscan

Approved Use

DaTscan is a radiopharmaceutical indicated for striatal dopamine transporter visualization using single photon emission computed tomography (SPECT) brain imaging to assist in the evaluation of adult patients with suspected Parkinsonian syndromes (PS)

Launch Date

1.29496318E12
PubMed

PubMed

TitleDatePubMed
123I-Ioflupane/SPECT binding to striatal dopamine transporter (DAT) uptake in patients with Parkinson's disease, multiple system atrophy, and progressive supranuclear palsy.
2003 Oct
Clinical utility of dopamine transporter single photon emission CT (DaT-SPECT) with (123I) ioflupane in diagnosis of parkinsonian syndromes.
2013 Nov
Patents

Sample Use Guides

The recommended DaTscan dose is 111 to 185 MBq (3 to 5 mCi).
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Name Type Language
IOFLUPANE I-123
DASH   ORANGE BOOK   VANDF  
Common Name English
IOFLUPANE I 123 [USAN]
Common Name English
IOFLUPANE I 123 [MI]
Common Name English
V09AB03
Code English
IOFLUPANE I-123 [ORANGE BOOK]
Common Name English
IOFLUPANE (123I)
INN   WHO-DD  
INN  
Official Name English
IOFLUPANE (123L)
EMA EPAR  
Common Name English
(123I)FP-CIT
Common Name English
V-09AB03
Code English
IOFLUPANE (SUP 123)I
EMA EPAR  
Common Name English
ioflupane (¹²³I) [INN]
Common Name English
IOFLUPANE (123L) [EMA EPAR]
Common Name English
DATSCAN
Brand Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 8-(3-FLUOROPROPYL)-3-(4-(IODO-(SUP 123)I)PHENYL)-, METHYL ESTER, (1R,2S,3S,5S)-
Common Name English
METHYL 8-(3-FLUOROPROPYL)-3.BETA.-(P-IODO-(SUP 123)I-PHENYL)-1.ALPHA.H,5.ALPHA.H-NORTROPANE-2.BETA.-CARBOXYLATE
Common Name English
IOFLUPANE I-123 [VANDF]
Common Name English
IOFLUPANE I 123
MI   USAN  
USAN  
Official Name English
IOFLUPANE (SUP 123)I [EMA EPAR]
Common Name English
FP-CIT I-123
Common Name English
IOFLUPANE, I-123
Common Name English
Ioflupane (123I) [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000177914
Created by admin on Fri Dec 15 15:37:29 UTC 2023 , Edited by admin on Fri Dec 15 15:37:29 UTC 2023
NCI_THESAURUS C1446
Created by admin on Fri Dec 15 15:37:29 UTC 2023 , Edited by admin on Fri Dec 15 15:37:29 UTC 2023
EMA ASSESSMENT REPORTS DATSCAN (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Dec 15 15:37:29 UTC 2023 , Edited by admin on Fri Dec 15 15:37:29 UTC 2023
EMA ASSESSMENT REPORTS DATSCAN (AUTHORIZED: ALZHEIMER DISEASE)
Created by admin on Fri Dec 15 15:37:29 UTC 2023 , Edited by admin on Fri Dec 15 15:37:29 UTC 2023
EMA ASSESSMENT REPORTS DATSCAN (AUTHORIZED: LEWY BODY DISEASE)
Created by admin on Fri Dec 15 15:37:29 UTC 2023 , Edited by admin on Fri Dec 15 15:37:29 UTC 2023
WHO-VATC QV09AB03
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EMA ASSESSMENT REPORTS DATSCAN (AUTHORIZED: TOMOGRAPHY, EMISSION-COMPUTED, SINGLE PHOTON)
Created by admin on Fri Dec 15 15:37:29 UTC 2023 , Edited by admin on Fri Dec 15 15:37:29 UTC 2023
WHO-ATC V09AB03
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Code System Code Type Description
WIKIPEDIA
IOFLUPANE (123I)
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CHEBI
68855
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CAS
155798-07-5
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INN
7500
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USAN
WW-152
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SMS_ID
100000089027
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LACTMED
Ioflupane I 123
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EPA CompTox
DTXSID90935291
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ChEMBL
CHEMBL2110569
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DRUG BANK
DB08824
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FDA UNII
3MM99T8R5Q
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NCI_THESAURUS
C80644
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EVMPD
SUB08221MIG
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PUBCHEM
3086674
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MERCK INDEX
m6363
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DAILYMED
3MM99T8R5Q
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DRUG CENTRAL
4230
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RXCUI
1426874
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PRIMARY RxNorm