Ioflupane I-123

Identification

Name
Ioflupane I-123
Accession Number
DB08824  (DB09548)
Type
Small Molecule
Groups
Approved
Description

Ioflupane (I-123) is a radiopharmaceutical used to image dopamine neurons and diagnose Parkinsonian syndromes.

Structure
Thumb
Synonyms
  • 123I-FP-CIT
  • 123I-Ioflupane
  • iodine ioflupane (123I)
  • ioflupane ((123)I)
  • ioflupane (123I)
  • Ioflupane I 123
  • ioflupane I(123)
  • ioflupano (123I)
  • ioflupanum (123I)
External IDs
V-09AB03 / V09AB03
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DaTscanInjection, solution2 mCi/mLIntravenousMedi Physics Inc. Dba Ge Healthcare.2011-03-01Not applicableUs
Categories
UNII
3MM99T8R5Q
CAS number
155798-07-5
Weight
Average: 427.291
Monoisotopic: 427.076880092
Chemical Formula
C18H23FINO2
InChI Key
HXWLAJVUJSVENX-HFIFKADTSA-N
InChI
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
IUPAC Name
methyl (1R,2S,3S,5S)-8-(3-fluoropropyl)-3-[4-(¹²³I)iodophenyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
SMILES
[H][C@]12CC[C@]([H])([C@H]([C@H](C1)C1=CC=C([123I])C=C1)C(=O)OC)N2CCCF

Pharmacology

Indication

Ioflupane I-123 is a SPECT (single photon emission computerized tomography) agent used to distinguish between Parkinson’s syndrome tremors and essential tremor.

Associated Conditions
Pharmacodynamics

iodine-123 labeled ioflupanebinds selectively to striatal presynaptic dopamine neurons by binding reversibly to presynaptic dopamine transporters.

Mechanism of action

Iodine-123 labeled ioflupane binds to presynaptic dopamine transporters. When Iodine-123 decays, a gammay ray is emmitted and detected through SPECT.

Absorption

Absorption is 100% because administered I.V.

Volume of distribution

Compared to the entire brain, about 30% of radioactivity is taken up by the striatum.

Protein binding
Not Available
Metabolism
Not Available
Route of elimination

About 60% is excreted in the urine and 14% in the feces after 48 hours.

Half life

Half life is 13.2 hours.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental, Illicit
AlaproclateAlaproclate may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental
AmoxapineAmoxapine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
AmphetamineAmphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit, Investigational
BenzatropineBenzatropine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
BenzphetamineBenzphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit
BupropionBupropion may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
BuspironeBuspirone may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
ChlorphentermineChlorphentermine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Illicit, Withdrawn
CitalopramCitalopram may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
CocaineCocaine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit
DapoxetineDapoxetine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Investigational
DesvenlafaxineDesvenlafaxine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
DexmethylphenidateDexmethylphenidate may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
DextroamphetamineDextroamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit
DiethylpropionDiethylpropion may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit
DuloxetineDuloxetine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
EscitalopramEscitalopram may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
EtoperidoneEtoperidone may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Withdrawn
FentanylFentanyl may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit, Investigational, Vet Approved
FluoxetineFluoxetine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Vet Approved
FluvoxamineFluvoxamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
GepefrineGepefrine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental
HydroxyamphetamineHydroxyamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
IndalpineIndalpine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Investigational, Withdrawn
Iofetamine I-123Iofetamine I-123 may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
LevomilnacipranLevomilnacipran may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
MephedroneMephedrone may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Investigational
MephentermineMephentermine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
MethamphetamineMethamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit
MethoxyphenamineMethoxyphenamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental
MethylphenidateMethylphenidate may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
MidomafetamineMidomafetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental, Illicit, Investigational
MilnacipranMilnacipran may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
MMDAMMDA may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental, Illicit
NefazodoneNefazodone may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Withdrawn
NorepinephrineNorepinephrine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
ParoxetineParoxetine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
PhenterminePhentermine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Illicit
PhenylephrinePhenylephrine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
PseudoephedrinePseudoephedrine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
RitobegronRitobegron may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Investigational
SelegilineSelegiline may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational, Vet Approved
SertralineSertraline may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
VenlafaxineVenlafaxine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
ZimelidineZimelidine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Withdrawn
Food Interactions
  • No known food interactions.

References

General References
  1. Tolosa E, Borght TV, Moreno E: Accuracy of DaTSCAN (123I-Ioflupane) SPECT in diagnosis of patients with clinically uncertain parkinsonism: 2-year follow-up of an open-label study. Mov Disord. 2007 Dec;22(16):2346-51. [PubMed:17914722]
  2. Benamer TS, Patterson J, Grosset DG, Booij J, de Bruin K, van Royen E, Speelman JD, Horstink MH, Sips HJ, Dierckx RA, Versijpt J, Decoo D, Van Der Linden C, Hadley DM, Doder M, Lees AJ, Costa DC, Gacinovic S, Oertel WH, Pogarell O, Hoeffken H, Joseph K, Tatsch K, Schwarz J, Ries V: Accurate differentiation of parkinsonism and essential tremor using visual assessment of [123I]-FP-CIT SPECT imaging: the [123I]-FP-CIT study group. Mov Disord. 2000 May;15(3):503-10. [PubMed:10830416]
  3. Link [Link]
External Links
KEGG Drug
D10014
PubChem Compound
3086674
PubChem Substance
175427106
ChemSpider
2343241
ChEBI
68855
ChEMBL
CHEMBL3989517
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ioflupane_(123I)
ATC Codes
V09AB03 — Iodine ioflupane (123i)
FDA label
Download (655 KB)
MSDS
Download (97.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherAlzheimer's Disease (AD) / Healthy Volunteers / Progressive Supranuclear Palsy (PSP)1
2CompletedBasic SciencePain / Parkinson's Disease (PD)1
2RecruitingDiagnosticParkinson's Disease (PD)1
3CompletedDiagnosticAlzheimer’s / Dementia, Vascular / Diffuse Lewy Body Disease / Non-DLB Dementia1
3CompletedDiagnosticAmyotrophic Lateral Sclerosis (ALS)1
3WithdrawnDiagnosticParkinson's Disease (PD)1
4Enrolling by InvitationDiagnosticDementias / Mild Cognitive Impairment (MCI) / Parkinsonism / REM Sleep Behavior Disorder1
4Unknown StatusNot AvailableMovement Disorders / Parkinson's Disease (PD)1
Not AvailableCompletedNot AvailableParkinson's Disease (PD)1
Not AvailableRecruitingNot AvailableParkinson's Disease (PD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solutionIntravenous2 mCi/mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5310912No1994-05-102013-02-25Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)82-83Not Available
water solubilitySoluble in waterNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00566 mg/mLALOGPS
logP4.24ALOGPS
logP3.7ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.34 m3·mol-1ChemAxon
Polarizability38.75 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9761
Blood Brain Barrier+0.9729
Caco-2 permeable+0.5307
P-glycoprotein substrateNon-substrate0.5154
P-glycoprotein inhibitor IInhibitor0.7921
P-glycoprotein inhibitor IIInhibitor0.6468
Renal organic cation transporterInhibitor0.7311
CYP450 2C9 substrateNon-substrate0.7871
CYP450 2D6 substrateNon-substrate0.6487
CYP450 3A4 substrateSubstrate0.5905
CYP450 1A2 substrateInhibitor0.5832
CYP450 2C9 inhibitorNon-inhibitor0.6451
CYP450 2D6 inhibitorNon-inhibitor0.5706
CYP450 2C19 inhibitorNon-inhibitor0.5324
CYP450 3A4 inhibitorNon-inhibitor0.8127
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5778
Ames testNon AMES toxic0.7173
CarcinogenicityNon-carcinogens0.927
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8764 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7236
hERG inhibition (predictor II)Inhibitor0.6662
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenyltropanes. These are compounds containing a phenyl group linked to a tropane moiety. Tropane is an organonitrogenous [3.2.1] bicyclic organic compound.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Phenyltropanes
Direct Parent
Phenyltropanes
Alternative Parents
Phenylpiperidines / Piperidinecarboxylic acids / Aralkylamines / Iodobenzenes / Aryl iodides / N-alkylpyrrolidines / Methyl esters / Trialkylamines / Amino acids and derivatives / Azacyclic compounds
show 8 more
Substituents
Phenyltropane / Phenylpiperidine / Piperidinecarboxylic acid / Halobenzene / Aralkylamine / Iodobenzene / Aryl halide / Aryl iodide / Monocyclic benzene moiety / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, azabicycloalkane, methyl ester (CHEBI:68855)

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Link [Link]

Drug created on December 27, 2012 14:00 / Updated on July 02, 2018 19:07