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Identification
NameIoflupane I-123
Accession NumberDB08824  (DB09548)
TypeSmall Molecule
GroupsApproved
DescriptionIoflupane (I-123) is a radiopharmaceutical used to image dopamine neurons and diagnose Parkinsonian syndromes.
Structure
Thumb
Synonyms
123I-FP-CIT
123I-Ioflupane
Datscan
Ioflupane
ioflupane ((123)I)
ioflupane (123I)
ioflupane I(123)
ioflupano (123I)
ioflupanum (123I)
methyl (1R,2S,3S,5S)-8-(3-fluoropropyl)-3-[4-((123)I)iodophenyl]-8-azabicyclo[3.2.1]octane-2-carboxylate
Methyl 8-(3-fluoropropyl)-3β-(p-iodo-I(sup 123)-phenyl)-1αH, 5αH-nortropane-2β-carboxylate.
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII3MM99T8R5Q
CAS number155798-07-5
WeightAverage: 431.2836
Monoisotopic: 431.07575061
Chemical FormulaC18H23FINO2
InChI KeyInChIKey=HXWLAJVUJSVENX-MYBQVCMBSA-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+/m1/s1
IUPAC Name
methyl (2S,3S)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
SMILES
COC(=O)[C@@H]1C2CCC(C[C@@H]1C1=CC=C(I)C=C1)N2CCCF
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassPhenyltropanes
Direct ParentPhenyltropanes
Alternative Parents
Substituents
  • Phenyltropane
  • Phenylpiperidine
  • Piperidinecarboxylic acid
  • Aralkylamine
  • Iodobenzene
  • Halobenzene
  • Benzenoid
  • N-alkylpyrrolidine
  • Piperidine
  • Monocyclic benzene moiety
  • Aryl iodide
  • Aryl halide
  • Methyl ester
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIoflupane I-123 is a SPECT (single photon emission computerized tomography) agent used to distinguish between Parkinson’s syndrome tremors and essential tremor.
Pharmacodynamicsiodine-123 labeled ioflupanebinds selectively to striatal presynaptic dopamine neurons by binding reversibly to presynaptic dopamine transporters.
Mechanism of actionIodine-123 labeled ioflupane binds to presynaptic dopamine transporters. When Iodine-123 decays, a gammay ray is emmitted and detected through SPECT.
Related Articles
AbsorptionAbsorption 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 bindingNot Available
MetabolismNot Available
Route of eliminationAbout 60% is excreted in the urine and 14% in the feces after 48 hours.
Half lifeHalf life is 13.2 hours.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5310912 No1994-05-102013-02-25Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point82-83Not 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
Polarizability38.79 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (655 KB)
MSDSDownload (97.7 KB)
Interactions
Drug Interactions
Drug
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
AmoxapineAmoxapine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
AmphetamineAmphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
BenzatropineBenzatropine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
BenzphetamineBenzphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
BupropionBupropion may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
BuspironeBuspirone may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
ChlorphentermineChlorphentermine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
CitalopramCitalopram may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
ClomipramineClomipramine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
CocaineCocaine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
DapoxetineDapoxetine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
DesvenlafaxineDesvenlafaxine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
DexmethylphenidateDexmethylphenidate may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
DextroamphetamineDextroamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
DuloxetineDuloxetine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
EscitalopramEscitalopram may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
EtoperidoneEtoperidone may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
FenfluramineFenfluramine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
FentanylFentanyl may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
FluoxetineFluoxetine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
FluvoxamineFluvoxamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
IndalpineIndalpine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
LevomilnacipranLevomilnacipran may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
LisdexamfetamineLisdexamfetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
Lu AA21004Lu AA21004 may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
MephentermineMephentermine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
MethamphetamineMethamphetamine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
MethylphenidateMethylphenidate may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
MilnacipranMilnacipran may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
NorepinephrineNorepinephrine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
OlanzapineOlanzapine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
ParoxetineParoxetine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
PhenterminePhentermine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
PhenylephrinePhenylephrine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
SelegilineSelegiline may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
SertralineSertraline may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
TrazodoneTrazodone may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
VenlafaxineVenlafaxine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
VilazodoneVilazodone may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
VortioxetineVortioxetine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
ZimelidineZimelidine may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
Food Interactions
  • No known food interactions.

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
Molecular Weight:
68494.255 Da
References
  1. Link [Link]
Comments
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Drug created on December 27, 2012 14:00 / Updated on August 30, 2016 12:05