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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIobenguane
Identification
- Name
- Iobenguane
- Accession Number
- DB06704 (DB09497)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- 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
Structure for Iobenguane (DB06704)
- Synonyms
- ((3-iodophenyl)methyl)guanidine
- 3-iodobenzylguanidine
- m-iodobenzylguanidine
- Metaiodobenzylguanidine
- mIBG
- 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 - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 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
- Amidines
- Antineoplastic Agents
- Benzene Derivatives
- Diagnostic Radiopharmaceuticals
- Diagnostic Uses of Chemicals
- Enzyme Inhibitors
- Guanidines
- Hydrocarbons, Halogenated
- Hydrocarbons, Iodinated
- Indicators and Reagents
- Iodine (131I) Compounds
- Iodobenzenes
- Laboratory Chemicals
- Radioactive Diagnostic Agent
- Radiopharmaceutical Activity
- Radiopharmaceuticals
- Therapeutic Radiopharmaceuticals
- Tumour Detection
- 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
- 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 2,5-Dimethoxy-4-ethylamphetamine 2,5-Dimethoxy-4-ethylamphetamine can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. 2,5-Dimethoxy-4-ethylthioamphetamine 2,5-Dimethoxy-4-ethylthioamphetamine can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. 3,4-Methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. 4-Bromo-2,5-dimethoxyamphetamine 4-Bromo-2,5-dimethoxyamphetamine can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. Acebutolol Acebutolol can cause a decrease in the absorption of Iobenguane resulting in a reduced serum concentration and potentially a decrease in efficacy. Alaproclate Alaproclate may decrease effectiveness of Iobenguane as a diagnostic agent. Amineptine Amineptine may decrease effectiveness of Iobenguane as a diagnostic agent. Amitraz The therapeutic efficacy of Iobenguane can be decreased when used in combination with Amitraz. 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. - Food Interactions
- Not Available
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. [PubMed:8082671]
- External Links
- KEGG Drug
- D04559
- PubChem Compound
- 60860
- PubChem Substance
- 175427085
- ChemSpider
- 54847
- ChEBI
- 92769
- ChEMBL
- CHEMBL818
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Iobenguane
- ATC Codes
- V09IX02 — Iobenguane (131i)
- 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
- FDA label
- Download (187 KB)
- MSDS
- Download (93.8 KB)
Clinical Trials
- 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 Completed 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 Neuroblastomas / Pheochromocytomas 1 Not Available Available Not Available Paraganglioma / Pheochromocytomas 1 Not Available Completed Treatment Neuroblastomas 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Injection Intravenous 2 mCi/1mL Injection, solution Intravenous 15 mCi/1mL Injection Intravenous 2.3 mCi/2mL - 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 Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS 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
- 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 November 02, 2018 09:11