Iobenguane - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Transporters (1)

Transporters (1)Biointeractions (1)

Identification

Name

Iobenguane

Accession Number

DB06704 (DB09497)

Type

Small Molecule

Groups

Approved

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

((3-iodophenyl)methyl)guanidine

3-iodobenzylguanidine

m-iodobenzylguanidine

Metaiodobenzylguanidine

mIBG

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Iobenguane I 123	P2TH1XYZ84	76924-93-1	Not applicable	Details
Iobenguane I 131	Q461L7AK4R	77679-27-7	Not applicable	Details
Iobenguane sulfate	S8I0922465	87862-25-7	XNACDNPGABUBFR-UHFFFAOYSA-N	Details
Iobenguane sulfate I 123	Not Available	139755-80-9	Not applicable	Details
Iobenguane sulfate I 131	M575VKV19N	149210-33-3	Not applicable	Details

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

35MRW7B4AD

CAS number

80663-95-2

Weight

Average: 275.0896
Monoisotopic: 274.991940755

Chemical Formula

C₈H₁₀IN₃

InChI Key

PDWUPXJEEYOOTR-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.

Absorption

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

Volume of distribution

Not Available

Protein binding

Not 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

Clearance

Not 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

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
4-Methoxyamphetamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with 4-Methoxyamphetamine.	Experimental, Illicit
Acebutolol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Acebutolol.	Approved
Acetyldigitoxin	Acetyldigitoxin may decrease the cardiotoxic activities of Iobenguane.	Approved
Agmatine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Agmatine.	Experimental, Investigational
Amineptine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Amineptine.	Illicit, Withdrawn
Amitriptyline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Amitriptyline.	Approved
Amphetamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Amphetamine.	Approved, Illicit
Apomorphine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Apomorphine.	Approved, Investigational
Apraclonidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Apraclonidine.	Approved
Benzphetamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Benzphetamine.	Approved, Illicit
Bethanidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Bethanidine.	Approved
Bevacizumab	Bevacizumab may increase the cardiotoxic activities of Iobenguane.	Approved, Investigational
Brimonidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Brimonidine.	Approved
Bromocriptine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Bromocriptine.	Approved, Investigational
Bucindolol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Bucindolol.	Investigational
Cabazitaxel	The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Iobenguane.	Approved
Celiprolol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Celiprolol.	Approved, Investigational
Chlorphentermine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Chlorphentermine.	Illicit, Withdrawn
Citalopram	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Citalopram.	Approved
Clenbuterol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Clenbuterol.	Approved, Vet Approved
Clomipramine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Clomipramine.	Approved, Vet Approved
Clonidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Clonidine.	Approved
Cocaine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Cocaine.	Approved, Illicit
Cyclobenzaprine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Cyclobenzaprine.	Approved
Cyclophosphamide	Cyclophosphamide may increase the cardiotoxic activities of Iobenguane.	Approved, Investigational
Dapoxetine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dapoxetine.	Investigational
Desipramine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Desipramine.	Approved
Deslanoside	Deslanoside may decrease the cardiotoxic activities of Iobenguane.	Approved
Desvenlafaxine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Desvenlafaxine.	Approved
Dexmedetomidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dexmedetomidine.	Approved, Vet Approved
Digitoxin	Digitoxin may decrease the cardiotoxic activities of Iobenguane.	Approved
Digoxin	Digoxin may decrease the cardiotoxic activities of Iobenguane.	Approved
Dihydroergotamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dihydroergotamine.	Approved
Dipivefrin	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dipivefrin.	Approved
Dobutamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dobutamine.	Approved
Docetaxel	The risk or severity of adverse effects can be increased when Docetaxel is combined with Iobenguane.	Approved, Investigational
Dopamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dopamine.	Approved
Dosulepin	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Dosulepin.	Approved
Doxepin	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Doxepin.	Approved
Droxidopa	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Droxidopa.	Approved, Investigational
Duloxetine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Duloxetine.	Approved
Ephedra	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Ephedra.	Approved, Nutraceutical, Withdrawn
Ephedrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Ephedrine.	Approved
Epinephrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Epinephrine.	Approved, Vet Approved
Ergotamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Ergotamine.	Approved
Escitalopram	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Escitalopram.	Approved, Investigational
Esmirtazapine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Esmirtazapine.	Investigational
Etilefrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Etilefrine.	Withdrawn
Etomidate	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Etomidate.	Approved
Etoperidone	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Etoperidone.	Approved
Fenoterol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Fenoterol.	Approved
Fluoxetine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Fluoxetine.	Approved, Vet Approved
Fluvoxamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Fluvoxamine.	Approved, Investigational
Guanabenz	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Guanabenz.	Approved
Guanfacine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Guanfacine.	Approved, Investigational
Hydroxyamphetamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Hydroxyamphetamine hydrobromide.	Approved
Imipramine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Imipramine.	Approved
Indalpine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Indalpine.	Investigational, Withdrawn
Isoprenaline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Isoprenaline.	Approved
Isoxsuprine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Isoxsuprine.	Approved, Withdrawn
Labetalol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Labetalol.	Approved
Levomilnacipran	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Levomilnacipran.	Approved
Lofexidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Lofexidine.	Approved, Investigational
Mephentermine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Mephentermine.	Approved
Metaraminol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Metaraminol.	Approved, Investigational
Methamphetamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Methamphetamine.	Approved, Illicit
Methoxamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Methoxamine.	Approved
Methyldopa	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Methyldopa.	Approved
Midodrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Midodrine.	Approved
Milnacipran	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Milnacipran.	Approved
Mirtazapine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Mirtazapine.	Approved
Naphazoline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Naphazoline.	Approved
Nefazodone	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Nefazodone.	Approved, Withdrawn
Norepinephrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Norepinephrine.	Approved
Nortriptyline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Nortriptyline.	Approved
Nylidrin	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Nylidrin.	Approved
Oleandrin	Anvirzel may decrease the cardiotoxic activities of Iobenguane.	Experimental
Opipramol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Opipramol.	Investigational
Orciprenaline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Orciprenaline.	Approved
Ouabain	Ouabain may decrease the cardiotoxic activities of Iobenguane.	Approved
Oxymetazoline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Oxymetazoline.	Approved
Paclitaxel	The risk or severity of adverse effects can be increased when Paclitaxel is combined with Iobenguane.	Approved, Vet Approved
Paliperidone	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Paliperidone.	Approved
Paroxetine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Paroxetine.	Approved, Investigational
Pergolide	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Pergolide.	Approved, Vet Approved, Withdrawn
Phenmetrazine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenmetrazine.	Approved, Illicit
Phentermine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Phentermine.	Approved, Illicit
Phenylephrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenylephrine.	Approved
Phenylpropanolamine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Phenylpropanolamine.	Approved, Vet Approved, Withdrawn
Procaterol	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Procaterol.	Approved
Protriptyline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Protriptyline.	Approved
Pseudoephedrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Pseudoephedrine.	Approved
Racepinephrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Racepinephrine.	Approved
Reserpine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Reserpine.	Approved
Risperidone	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Risperidone.	Approved, Investigational
Ritodrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Ritodrine.	Approved
Ropinirole	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Ropinirole.	Approved, Investigational
Sertraline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Sertraline.	Approved
Synephrine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Synephrine.	Experimental
Terbutaline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Terbutaline.	Approved
Tetryzoline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Tetryzoline.	Approved
Tianeptine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Tianeptine.	Approved
Tizanidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Tizanidine.	Approved
Trastuzumab	Trastuzumab may increase the cardiotoxic activities of Iobenguane.	Approved, Investigational
Trimipramine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Trimipramine.	Approved
Tyramine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Tyramine.	Investigational, Nutraceutical
Venlafaxine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Venlafaxine.	Approved
Xylometazoline	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Xylometazoline.	Approved
Zimelidine	The therapeutic efficacy of Iobenguane can be decreased when used in combination with Zimelidine.	Withdrawn

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

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

Resource	Link
KEGG Drug	D04559
PubChem Compound	60860
PubChem Substance	175427085
ChemSpider	54847
ChEBI	92769
ChEMBL	CHEMBL818
RxList	http://www.rxlist.com/adreview-drug.htm
Drugs.com	http://www.drugs.com/mtm/iobenguane-i-123.html
Wikipedia	Iobenguane

ATC Codes

V09IX02 — Iobenguane (131i)

V09IX01 — Iobenguane (123i)

V10XA02 — Iobenguane (131i)

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (187 KB)

MSDS

Download (93.8 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Terminated	Treatment	Congestive Heart Failure (CHF)	1
1, 2	Completed	Treatment	Paraganglioma / Pheochromocytomas	1
1, 2	Unknown Status	Treatment	Neuroblastomas	1
2	Recruiting	Treatment	MIBG Avid Tumors	1
3	Completed	Diagnostic	Congestive Heart Failure (CHF)	2
3	Completed	Treatment	Neoplasm Metastases / Neuroendocrine Tumors	1
4	Completed	Diagnostic	Heart Failure, Unspecified / Ventricular Dysfunction, Left	1
Not Available	Approved for Marketing	Not Available	Neuroblastomas	1
Not Available	Available	Not Available	Childhood Metastatic Pheochromocytoma / Neuroblastomas / Paraganglioma	1
Not Available	Available	Not Available	Neuroblastomas	1
Not Available	Available	Not Available	Paraganglioma / Pheochromocytomas	1
Not Available	Completed	Treatment	Neuroblastomas	1
Not Available	Temporarily Not Available	Not Available	Neuroblastomas / Pheochromocytomas	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Liquid

Experimental Properties

Property	Value	Source
melting point (°C)	0°C	MSDS
boiling point (°C)	100°C	MSDS
water solubility	Soluble	MSDS

Predicted Properties

Property	Value	Source
Water Solubility	0.0878 mg/mL	ALOGPS
logP	1.53	ALOGPS
logP	1.64	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	11.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.32 m³·mol^-1	ChemAxon
Polarizability	21.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9057
Blood Brain Barrier	+	0.9003
Caco-2 permeable	+	0.5774
P-glycoprotein substrate	Non-substrate	0.6467
P-glycoprotein inhibitor I	Non-inhibitor	0.9591
P-glycoprotein inhibitor II	Non-inhibitor	0.8833
Renal organic cation transporter	Inhibitor	0.5244
CYP450 2C9 substrate	Non-substrate	0.8712
CYP450 2D6 substrate	Non-substrate	0.6132
CYP450 3A4 substrate	Non-substrate	0.7951
CYP450 1A2 substrate	Inhibitor	0.9029
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.9069
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9122
Ames test	Non AMES toxic	0.7308
Carcinogenicity	Non-carcinogens	0.9184
Biodegradation	Not ready biodegradable	0.9961
Rat acute toxicity	2.9081 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9369
hERG inhibition (predictor II)	Non-inhibitor	0.9283

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not 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

Aryl iodides / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds / Organoiodides / Hydrocarbon derivatives

Substituents

Iodobenzene / 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Transporters

Details

1. Sodium-dependent noradrenaline transporter

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

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

Structure for DB06704 (Iobenguane)

Transporters

References