Iobenguane sulfate I-123

Identification

Name
Iobenguane sulfate I-123
Accession Number
DB09546
Type
Small Molecule
Groups
Approved, Investigational
Description

Iobenguane sulfate I-123 is a radiopharmaceutical used in gamma-scintigraphy of adrenergically inervated tissues [Label].

Structure
Thumb
Synonyms
  • Iobenguane sulfate I 123
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
i 123 MIBG meta iodobenzylguanidineIobenguane sulfate I-123 (25 mCi/1)Injection, powder, lyophilized, for solutionIntravenousAnazao Health Corporation2012-05-23Not applicableUs
Categories
UNII
23X1185WBO
CAS number
80663-95-2
Weight
Average: 640.26
Monoisotopic: 639.953520274
Chemical Formula
C16H22I2N6O4S
InChI Key
XNACDNPGABUBFR-FKNPGSCZSA-N
InChI
InChI=1S/2C8H10IN3.H2O4S/c2*9-7-3-1-2-6(4-7)5-12-8(10)11;1-5(2,3)4/h2*1-4H,5H2,(H4,10,11,12);(H2,1,2,3,4)/i2*9-4;
IUPAC Name
bis(N-{[3-(¹²³I)iodophenyl]methyl}guanidine); sulfuric acid
SMILES
OS(O)(=O)=O.NC(=N)NCC1=CC([123I])=CC=C1.NC(=N)NCC1=CC([123I])=CC=C1

Pharmacology

Indication

For use in the diagnostic imaging of adrenergically inervated tissues for the purposes of detecting metastatic pheochromocytoma or neuroblastoma [Label]. Also used to assess the sympathetic inervation of the myocardium via determination of the heart to mediastinum ratio of radioactivity in patients with New York Heart Association class II or III heart failure.

Associated Conditions
Pharmacodynamics

Iobenguane I-123 is taken up by and stored in adrenergic nerve terminals allowing for the radiographic imaging of adrenergically inervated organs and tissues [Label].

Mechanism of action

Iobenguane I-123 is transported into adrenergic nerve terminals via the noradrenaline uptake transporter [Label]. It is rapidly cleared from systemic circulation and collected in adrenergically invervated tissues. This allows for gamma-scintigraphic imaging of these tissues and their associated organs for diagnostic purposes.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Metabolized to m-iodohippuric acid and free radioiodide [Label]. The metabolism of iobenguane I-123 and the enzymes involved has not been well studied.

Route of elimination

Primarily eliminated via the urine as the parent compound (70-90%) [Label]. A small amount is eliminated in the urine as m-iodohippuric acid (</10%) and free radioiodide (</6%). Less than 1% is eliminated in the feces. Iobenguane I-123 is initially rapidly cleared from circulation follwed by a slow clearance from other tissues over 4 days. Retention is the longest in highly adrenergically inervated tissues like the adrenal medulla, heart, and salivary glands. Iobenguane I-123 is not cleared by dialysis.

Half life
Not Available
Clearance
Not Available
Toxicity

As a radiopharmaceutical, iobenguane I-123 carries the risk of radiation toxicity if administered in innappropriately large doses or in patients with renal insufficency [Label]. Fequent voiding of the bladder is encouraged to minimize the radiation dose to the bladder.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Iobenguane sulfate I-123 which could result in a higher serum level.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
56840904
PubChem Substance
347827877
ChemSpider
32701571
ChEMBL
CHEMBL3989523
FDA label
Download (302 KB)
MSDS
Download (100 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedDiagnosticCoronary Artery Disease / Heart Failure, Unspecified1
3RecruitingPreventionHeart Failure, Unspecified1
4CompletedDiagnosticHeart Failure, Unspecified / Prophylaxis of cardiomyopathy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous25 mCi/1
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
water solubilitySolubleMSDS
Radioactivity (mCi/mL)2MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.1 mg/mLALOGPS
logP1.42ALOGPS
logP1.69ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)11.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.61 m3·mol-1ChemAxon
Polarizability21.88 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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 iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Iodobenzenes
Alternative Parents
Organic sulfuric acids / Aryl iodides / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds / Organoiodides / Organic oxides / Hydrocarbon derivatives
Substituents
Iodobenzene / Sulfuric acid / Aryl halide / Aryl iodide / Organic sulfuric acid or derivatives / Guanidine / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Organic nitrogen compound
Molecular Framework
Not Available
External Descriptors
Not Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da

Drug created on November 30, 2015 12:10 / Updated on November 02, 2018 07:03