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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
iodine ioflupane (123I)
ioflupane ((123)I)
ioflupane (123I)
Ioflupane I 123
ioflupane I(123)
ioflupano (123I)
ioflupanum (123I)
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DatscanInjection, solution74 MBq/mlIntravenousGe Healthcare Limited2000-07-27Not applicableEu
DatscanInjection, solution74 MBq/mlIntravenousGe Healthcare Limited2000-07-27Not applicableEu
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: 427.291
Monoisotopic: 427.076880092
Chemical FormulaC18H23FINO2
InChI KeyHXWLAJVUJSVENX-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
SMILES
[H][C@]12CC[C@]([H])([[email protected]]([[email protected]](C1)C1=CC=C([123I])C=C1)C(=O)OC)N2CCCF
Pharmacology
IndicationIoflupane I-123 is a SPECT (single photon emission computerized tomography) agent used to distinguish between Parkinson’s syndrome tremors and essential tremor.
Structured Indications Not Available
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
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
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Experimental, Illicit
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine 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
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
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
DexmethylphenidateDexmethylphenidate may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
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.Approved
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
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide 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
LevomilnacipranLevomilnacipran may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
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
MethylphenidateMethylphenidate may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved, Investigational
MilnacipranMilnacipran may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.Approved
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
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 CodesV09AB03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (655 KB)
MSDSDownload (97.7 KB)
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 forms
FormRouteStrength
Injection, solutionIntravenous74 MBq/ml
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
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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

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 November 02, 2016 13:23