Identification
NameIobenguane
Accession NumberDB06704  (DB09497)
TypeSmall Molecule
GroupsApproved
Description

Synthetic guanethidine derivative that locates phaeochromocytomas and neuroblastomas. The radioisotope used can either be iodine-123 for imaging or iodine-131 for destruction of tissues that metabolize noradrenaline. Iodine 123 is a cyclotron-produced radionuclide that decays to Te 123 by electron capture. Images are produced by a I123 MIBG scintigraphy. FDA approved on September 19, 2008.

Structure
Thumb
Synonyms
((3-iodophenyl)methyl)guanidine
3-iodobenzylguanidine
m-iodobenzylguanidine
Metaiodobenzylguanidine
mIBG
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Iobenguane I 123P2TH1XYZ84 76924-93-1Not applicableDetails
Iobenguane I 131Q461L7AK4R 77679-27-7Not applicableDetails
Iobenguane sulfateS8I0922465 87862-25-7XNACDNPGABUBFR-UHFFFAOYSA-NDetails
Iobenguane sulfate I 123Not Available139755-80-9Not applicableDetails
Iobenguane sulfate I 131M575VKV19N 149210-33-3Not applicableDetails
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
Categories
UNII35MRW7B4AD
CAS number80663-95-2
WeightAverage: 275.0896
Monoisotopic: 274.991940755
Chemical FormulaC8H10IN3
InChI KeyPDWUPXJEEYOOTR-UHFFFAOYSA-N
InChI
InChI=1S/C8H10IN3/c9-7-3-1-2-6(4-7)5-12-8(10)11/h1-4H,5H2,(H4,10,11,12)
IUPAC Name
2-[(3-iodophenyl)methyl]guanidine
SMILES
NC(N)=NCC1=CC(I)=CC=C1
Pharmacology
Indication

Detection of primary and metastatic pheochromocytoma or neuroblastoma

Structured Indications Not Available
Pharmacodynamics

AdreView is a diagnostic radiopharmaceutical which contains a small quantity of iobenguane that is not expected to produce a pharmacodynamic effect. Patients with renal insufficiency may experience increased radiation exposure and impaired imaging results.

Mechanism of action

Structure of iobenguane is similar to noradrenaline so it can be taken up by adrenergic tissue in the adrenal medulla, liver, heart, and spleen. Once taken up by noradrenaline transporters in the adrenergic nerve terminals, it is stored in the presynaptic storage vesicles. The radioactive iodine component is responsible for its imaging properties.

Related Articles
Absorption

Iobenguane rapidly clears from the blood and is highly retained in adrenergic tissues.

Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Less than 10% of the dose is metabolized into m-iodohippuric acid (MIHA). However the mechanism in which this metabolite is produced is unknown.

Route of elimination

Renally excreted unchanged (70%-90%) via glomerular filtration; Fecal (<1%)

Half life

Physical half life = 13.2 hours

ClearanceNot Available
Toxicity

Oral mouse: LD50 = 300 mg/kg; Oral, rabbit: LD50 = 3200 mg/kg; Oral, rat: LD50=980 mg/kg. The most common adverse reactions, dizziness, rash, pruritis, flushing, headache, and injection site hemorrhage occurred in < 1.3% of patients.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
4-MethoxyamphetamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with 4-Methoxyamphetamine.Experimental, Illicit
AcebutololThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Acebutolol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Iobenguane.Approved
AgmatineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Agmatine.Experimental, Investigational
AmineptineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Amineptine.Illicit, Withdrawn
AmitriptylineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Amitriptyline.Approved
AmphetamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Amphetamine.Approved, Illicit
ApomorphineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Apomorphine.Approved, Investigational
ApraclonidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Apraclonidine.Approved
BenzphetamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Benzphetamine.Approved, Illicit
BethanidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Bethanidine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Iobenguane.Approved, Investigational
BrimonidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Brimonidine.Approved
BromocriptineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Bromocriptine.Approved, Investigational
BucindololThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Bucindolol.Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Iobenguane.Approved
CeliprololThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Celiprolol.Approved, Investigational
ChlorphentermineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Chlorphentermine.Illicit, Withdrawn
CitalopramThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Citalopram.Approved
ClenbuterolThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Clenbuterol.Approved, Vet Approved
ClomipramineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Clomipramine.Approved, Vet Approved
ClonidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Clonidine.Approved
CocaineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Cocaine.Approved, Illicit
CyclobenzaprineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Cyclobenzaprine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Iobenguane.Approved, Investigational
DapoxetineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dapoxetine.Investigational
DesipramineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Iobenguane.Approved
DesvenlafaxineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Desvenlafaxine.Approved
DexmedetomidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dexmedetomidine.Approved, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Iobenguane.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Iobenguane.Approved
DihydroergotamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dihydroergotamine.Approved
DipivefrinThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dipivefrin.Approved
DobutamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dobutamine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Iobenguane.Approved, Investigational
DopamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dopamine.Approved
DosulepinThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Dosulepin.Approved
DoxepinThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Doxepin.Approved
DroxidopaThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Droxidopa.Approved, Investigational
DuloxetineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Duloxetine.Approved
EphedraThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ephedra.Approved, Nutraceutical, Withdrawn
EphedrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ephedrine.Approved
EpinephrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Epinephrine.Approved, Vet Approved
ErgotamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ergotamine.Approved
EscitalopramThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Escitalopram.Approved, Investigational
EsmirtazapineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Esmirtazapine.Investigational
EtilefrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Etilefrine.Withdrawn
EtomidateThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Etomidate.Approved
EtoperidoneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Etoperidone.Approved
FenoterolThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Fenoterol.Approved
FluoxetineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Fluoxetine.Approved, Vet Approved
FluvoxamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Fluvoxamine.Approved, Investigational
GuanabenzThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Guanabenz.Approved
GuanfacineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Guanfacine.Approved, Investigational
HydroxyamphetamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Hydroxyamphetamine hydrobromide.Approved
ImipramineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Imipramine.Approved
IndalpineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Indalpine.Investigational, Withdrawn
IsoprenalineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Isoprenaline.Approved
IsoxsuprineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Isoxsuprine.Approved, Withdrawn
LabetalolThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Labetalol.Approved
LevomilnacipranThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Levomilnacipran.Approved
LofexidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Lofexidine.Approved, Investigational
MephentermineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Mephentermine.Approved
MetaraminolThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Metaraminol.Approved, Investigational
MethamphetamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Methamphetamine.Approved, Illicit
MethoxamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Methoxamine.Approved
MethyldopaThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Methyldopa.Approved
MidodrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Midodrine.Approved
MilnacipranThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Milnacipran.Approved
MirtazapineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Mirtazapine.Approved
NaphazolineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Naphazoline.Approved
NefazodoneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Nefazodone.Approved, Withdrawn
NorepinephrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Norepinephrine.Approved
NortriptylineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Nortriptyline.Approved
NylidrinThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Nylidrin.Approved
OleandrinAnvirzel may decrease the cardiotoxic activities of Iobenguane.Experimental
OpipramolThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Opipramol.Investigational
OrciprenalineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Orciprenaline.Approved
OuabainOuabain may decrease the cardiotoxic activities of Iobenguane.Approved
OxymetazolineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Oxymetazoline.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Iobenguane.Approved, Vet Approved
PaliperidoneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Paliperidone.Approved
ParoxetineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Paroxetine.Approved, Investigational
PergolideThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Pergolide.Approved, Vet Approved, Withdrawn
PhenmetrazineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenmetrazine.Approved, Illicit
PhentermineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Phentermine.Approved, Illicit
PhenylephrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenylephrine.Approved
PhenylpropanolamineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
ProcaterolThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Procaterol.Approved
ProtriptylineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Protriptyline.Approved
PseudoephedrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Pseudoephedrine.Approved
RacepinephrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Racepinephrine.Approved
ReserpineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Reserpine.Approved
RisperidoneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Risperidone.Approved, Investigational
RitodrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ritodrine.Approved
RopiniroleThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Ropinirole.Approved, Investigational
SertralineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Sertraline.Approved
SynephrineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Synephrine.Experimental
TerbutalineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Terbutaline.Approved
TetryzolineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Tetryzoline.Approved
TianeptineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Tianeptine.Approved
TizanidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Tizanidine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Iobenguane.Approved, Investigational
TrimipramineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Trimipramine.Approved
TyramineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Tyramine.Investigational, Nutraceutical
VenlafaxineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Venlafaxine.Approved
XylometazolineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Xylometazoline.Approved
ZimelidineThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Zimelidine.Withdrawn
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Wafelman AR, Hoefnagel CA, Maes RA, Beijnen JH: Radioiodinated metaiodobenzylguanidine: a review of its biodistribution and pharmacokinetics, drug interactions, cytotoxicity and dosimetry. Eur J Nucl Med. 1994 Jun;21(6):545-59. [PubMed:8082671 ]
External Links
ATC CodesV09IX02 — Iobenguane (131i)V09IX01 — Iobenguane (123i)V10XA02 — Iobenguane (131i)
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (187 KB)
MSDSDownload (93.8 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentCongestive Heart Failure (CHF)1
1, 2CompletedTreatmentParaganglioma / Pheochromocytomas1
1, 2Unknown StatusTreatmentNeuroblastomas1
2RecruitingTreatmentMIBG Avid Tumors1
3CompletedDiagnosticCongestive Heart Failure (CHF)2
3CompletedTreatmentNeoplasm Metastases / Neuroendocrine Tumors1
4CompletedDiagnosticHeart Failure, Unspecified / Ventricular Dysfunction, Left1
Not AvailableApproved for MarketingNot AvailableNeuroblastomas1
Not AvailableAvailableNot AvailableChildhood Metastatic Pheochromocytoma / Neuroblastomas / Paraganglioma1
Not AvailableAvailableNot AvailableNeuroblastomas1
Not AvailableAvailableNot AvailableParaganglioma / Pheochromocytomas1
Not AvailableCompletedTreatmentNeuroblastomas1
Not AvailableTemporarily Not AvailableNot AvailableNeuroblastomas / Pheochromocytomas1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point (°C)0°C MSDS
boiling point (°C)100°C MSDS
water solubilitySoluble MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0878 mg/mLALOGPS
logP1.53ALOGPS
logP1.64ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)11.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.4 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.32 m3·mol-1ChemAxon
Polarizability21.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9057
Blood Brain Barrier+0.9003
Caco-2 permeable+0.5774
P-glycoprotein substrateNon-substrate0.6467
P-glycoprotein inhibitor INon-inhibitor0.9591
P-glycoprotein inhibitor IINon-inhibitor0.8833
Renal organic cation transporterInhibitor0.5244
CYP450 2C9 substrateNon-substrate0.8712
CYP450 2D6 substrateNon-substrate0.6132
CYP450 3A4 substrateNon-substrate0.7951
CYP450 1A2 substrateInhibitor0.9029
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9069
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9122
Ames testNon AMES toxic0.7308
CarcinogenicityNon-carcinogens0.9184
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.9081 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9369
hERG inhibition (predictor II)Non-inhibitor0.9283
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentIodobenzenes
Alternative ParentsAryl iodides / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds / Organoiodides / Hydrocarbon derivatives
SubstituentsIodobenzene / Aryl iodide / Aryl halide / Guanidine / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
yes
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
References
  1. Gerson MC, Wagoner LE, McGuire N, Liggett SB: Activity of the uptake-1 norepinephrine transporter as measured by I-123 MIBG in heart failure patients with a loss-of-function polymorphism of the presynaptic alpha2C-adrenergic receptor. J Nucl Cardiol. 2003 Nov-Dec;10(6):583-9. [PubMed:14668769 ]
Drug created on May 15, 2010 18:19 / Updated on September 01, 2017 11:30