NAV

Ioflupane I-123

Identification

Summary

Ioflupane I-123 is a radiopharmaceutical used in single photon emission computed tomography (SPECT) brain imaging to help diagnose patients with suspected Parkinsonian syndromes.

Brand Names
Datscan
Generic Name
Ioflupane I-123
DrugBank Accession Number
DB08824
Background

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

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 427.291
Monoisotopic: 427.076880092
Chemical Formula
C18H23FINO2
Synonyms
  • 123I-FP-CIT
  • 123I-Ioflupane
  • Iodine ioflupane (123I)
  • Ioflupane ((123)I)
  • Ioflupane (123I)
  • Ioflupane I 123
  • Ioflupane I(123)
  • Ioflupano (123I)
  • Ioflupanum (123I)
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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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentParkinsonian syndromes••••••••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAbacavir may decrease the excretion rate of Ioflupane I-123 which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ioflupane I-123 which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ioflupane I-123 which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Ioflupane I-123 which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Ioflupane I-123 which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
  • Take with or without food.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CelsunaxInjection, solution74 MBq/mlIntravenousPinax Pharma Gmb H2021-10-26Not applicableEU flag
CelsunaxInjection, solution74 MBq/mlIntravenousPinax Pharma Gmb H2021-10-26Not applicableEU flag
DatscanInjection, solution74 MBq/mlIntravenousGe Healthcare B.V.2016-09-08Not applicableEU flag
DaTscanInjection, solution2 mCi/1mLIntravenousMedi-Physics Inc. dba GE Healthcare.2011-03-01Not applicableUS flag
DatscanInjection, solution74 MBq/mlIntravenousGe Healthcare B.V.2016-09-08Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ioflupane I 123Injection, solution2 mCi/1mLIntravenousCurium US LLC2022-03-31Not applicableUS flag

Categories

ATC Codes
V09AB03 — Iodine ioflupane (123i)
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl halide / Aryl iodide / Azacycle / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, azabicycloalkane, methyl ester (CHEBI:68855)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
3MM99T8R5Q
CAS number
155798-07-5
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

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. [Article]
  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. [Article]
  3. Link [Link]
KEGG Drug
D10014
PubChem Compound
3086674
PubChem Substance
175427106
ChemSpider
2343241
RxNav
1426874
ChEBI
68855
ChEMBL
CHEMBL3989517
ZINC
ZINC000100091991
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Ioflupane_(123I)
FDA label
Download (655 KB)
MSDS
Download (97.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Enrolling by InvitationDiagnosticDementia / Mild Cognitive Impairment (MCI) / Parkinsonism / Rapid Eye Movement Sleep Behavior Disorder1
3CompletedDiagnosticAlzheimer’s / Dementia With Lewy Body Disease / Non-DLB Dementia / Vascular Dementia (VaD)1
3CompletedDiagnosticAmyotrophic Lateral Sclerosis (ALS)1
3CompletedDiagnosticEssential Tremor / Multiple System Atrophy (MSA) / Parkinson's Disease (PD) / Parkinsonian Syndromes / Progressive Supranuclear Palsy (PSP)1
3WithdrawnDiagnosticParkinson's Disease (PD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solution
Injection, solutionIntravenous
Injection, solutionIntravenous2 mCi/1mL
Injection74 MBq/mL
Injection, solutionIntravenous74 MBq/mL
Injection, solutionParenteral74 MBq/ml
Injection, solution74 MBQ/ML
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5310912No1994-05-102013-02-25US flag

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/MSsplash10-001i-0000900000-38191d83bea9ed2f09ca
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-1c41656bb516f289e853
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0108900000-4955d285e5c0ddd845b0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0002900000-f90b2d7debbdb9c81325
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-5dc5b1fff481213dd1ac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w30-0359800000-eb1ae6ee4215bfa51bde
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-185.5334
predicted
DeepCCS 1.0 (2019)
[M+H]+187.92894
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.84149
predicted
DeepCCS 1.0 (2019)

Transporters

Details1. Sodium-dependent dopamine transporter
Kind
Protein
Organism
Humans
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 at December 27, 2012 21:00 / Updated at June 12, 2020 17:42