Explore a selection of our essential drug information below, or:
Identification
- Summary
Iobenguane is a radiopharmaceutical agent used for the diagnosis of primary and metastatic pheochromocytoma or neuroblastoma.
- Brand Names
- Azedra
- Generic Name
- Iobenguane
- DrugBank Accession Number
- DB06704
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Iobenguane (DB06704)
- Weight
- Average: 275.0896
Monoisotopic: 274.991940755 - Chemical Formula
- C8H10IN3
- Synonyms
- ((3-iodophenyl)methyl)guanidine
- 3-iodobenzylguanidine
- m-iodobenzylguanidine
- Metaiodobenzylguanidine
- mIBG
Pharmacology
- Indication
Detection of primary and metastatic pheochromocytoma or neuroblastoma
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Metastatic pheochromocytoma •••••••••••• ••••••••• Diagnostic agent Metastatic neuroblastoma •••••••••••• ••••••••• Diagnostic agent Primary neuroblastomas •••••••••••• ••••••••• Diagnostic agent Primary pheochromocytomas •••••••••••• ••••••••• Treatment of Unresectable, locally advanced iobenguane-scan positive paraganglioma •••••••••••• •••••• ••••••••• ••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ASodium-dependent noradrenaline transporter modulatorHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Acebutolol can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. Amitriptyline Amitriptyline can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. Amitriptylinoxide Amitriptylinoxide may decrease effectiveness of Iobenguane as a diagnostic agent. Amoxapine Amoxapine can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. Amphetamine Amphetamine can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Iobenguane I 123 P2TH1XYZ84 76924-93-1 PDWUPXJEEYOOTR-IUAIQHPESA-N Iobenguane I 131 Q461L7AK4R 77679-27-7 PDWUPXJEEYOOTR-JRGAVVOBSA-N Iobenguane sulfate S8I0922465 87862-25-7 XNACDNPGABUBFR-UHFFFAOYSA-N Iobenguane sulfate I 123 Not Available 139755-80-9 Not applicable Iobenguane sulfate I 131 M575VKV19N 149210-33-3 Not applicable - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image AdreView Injection 2 mCi/1mL Intravenous Medi-Physics Inc. 2008-09-19 Not applicable US 
Azedra Injection, solution 15 mCi/1mL Intravenous Progenics Pharmaceuticals, Inc. 2018-07-30 Not applicable US Iobenguane Sulfate I 131 Injection Injection 2.3 mCi/2mL Intravenous Pharmalucence, Inc. 1994-03-25 2009-09-07 US
Categories
- ATC Codes
- V09IX01 — Iobenguane (123i)
- V09IX — Other diagnostic radiopharmaceuticals for tumour detection
- V09I — TUMOUR DETECTION
- V09 — DIAGNOSTIC RADIOPHARMACEUTICALS
- V — VARIOUS
- V09IX — Other diagnostic radiopharmaceuticals for tumour detection
- V09I — TUMOUR DETECTION
- V09 — DIAGNOSTIC RADIOPHARMACEUTICALS
- V — VARIOUS
- Drug Categories
- Amidines
- Benzene Derivatives
- Compounds used in a research, industrial, or household setting
- Diagnostic Radiopharmaceuticals
- Diagnostic Uses of Chemicals
- Enzyme Inhibitors
- Guanidines
- Hydrocarbons, Halogenated
- Hydrocarbons, Iodinated
- Indicators and Reagents
- Iodine (131I) Compounds
- Iodobenzenes
- Laboratory Chemicals
- Narrow Therapeutic Index Drugs
- Radioactive Diagnostic Agent
- Radiopharmaceutical Activity
- Radiopharmaceuticals
- Therapeutic Radiopharmaceuticals
- Tumour Detection
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Carboximidamide / Guanidine / Hydrocarbon derivative / Iodobenzene / Organic 1,3-dipolar compound / Organic nitrogen compound / Organohalogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 35MRW7B4AD
- CAS number
- 80663-95-2
- 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
- N''-[(3-iodophenyl)methyl]guanidine
- SMILES
- NC(N)=NCC1=CC(I)=CC=C1
References
- 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. [Article]
- FDA Approved Drug Products: AdreView (Iobenguane I 123 Injection) for Intravenous Use [Link]
- AZEDRA® (iobenguane I 131) FDA Label [Link]
- External Links
- KEGG Drug
- D04559
- PubChem Compound
- 60860
- PubChem Substance
- 175427085
- ChemSpider
- 54847
- 14448
- ChEBI
- 92769
- ChEMBL
- CHEMBL818
- ZINC
- ZINC000001538318
- PDBe Ligand
- YMN
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Iobenguane
- PDB Entries
- 8xb3
- FDA label
- Download (187 KB)
- MSDS
- Download (93.8 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Approved for Marketing Not Available Neuroblastoma (NB) 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Paragangliomas / Pheochromocytoma 2 somestatus stop reason just information to hide Not Available Available Not Available Childhood Metastatic Pheochromocytoma / Neuroblastoma (NB) 1 somestatus stop reason just information to hide Not Available Available Not Available Neuroblastoma (NB) 1 somestatus stop reason just information to hide Not Available Available Not Available Neuroblastoma (NB) / Pheochromocytoma 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 2 mCi/1mL Injection, solution Intravenous Injection, solution Intravenous 15 mCi/1mL Injection Intravenous 2.3 mCi/2mL Injection, solution Intravenous 9.25 MBQ/ML Injection, solution, concentrate Intravenous 185 MBq/ml Injection, solution, concentrate Intravenous 246.7 MBq/ml Injection, solution, concentrate Intravenous 493.3 MBq/ml Solution Intravenous 0.5 mg Injection, solution Intravenous 74 MBQ/ML Injection, solution Intravenous 111 MBq Injection, solution Intravenous 185 MBq Injection, solution Intravenous 370 MBq Injection, solution Intravenous 120 MBq/ml Injection, solution Intravenous 18.5 MBq/ml Injection, solution Intravenous 37 MBq/ml Injection, solution Intravenous 55.5 MBq/ml - 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-014l-6390000000-640361ed282a3fc2307a Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-016r-0090000000-554220804ab14b9b2bbc Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0560-0390000000-35571ae437eb4fca7133 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-c90e7098ddef9a2639a7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9200000000-a9d24a6275f4727aca60 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-066u-2970000000-92cd7540f2afb4d7be16 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004l-8900000000-bae4573ae2d66771f811 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 145.47713 predictedDeepCCS 1.0 (2019) [M+H]+ 148.50105 predictedDeepCCS 1.0 (2019) [M+Na]+ 157.70303 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- actin binding
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
- Specific Function
- actin binding
- 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. [Article]
Drug created at May 16, 2010 00:19 / Updated at August 26, 2024 19:23