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Details

Stereochemistry ACHIRAL
Molecular Formula 2C8H10IN3.H2O4S
Molecular Weight 648.258
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOBENGUANE SULFATE

SMILES

OS(O)(=O)=O.NC(=N)NCC1=CC=CC(I)=C1.NC(=N)NCC2=CC=CC(I)=C2

InChI

InChIKey=XNACDNPGABUBFR-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://jnm.snmjournals.org/content/early/2014/03/12/jnumed.113.124057.full.pdf https://en.wikipedia.org/wiki/Iobenguane

Iobenguane, mainly use as a radiopharmaceutical, used in a scintigraphy method called MIBG scan. 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. It localizes to adrenergic tissue and thus can be used to identify the location of tumors such as pheochromocytomas and neuroblastomas. With I-131 it can also be used to eradicate tumor cells that take up and metabolize norepinephrine. The radioactive iodine component is responsible for its imaging properties. Iobenguane and guanethidine are substrates for the norepinephrine transporter (NET) and accumulate by the uptake mechanism into presynaptic nerve endings. Unlike norepinephrine, these drugs are protonated under physiologic conditions; therefore, they do not cross the blood–brain barrier and in vivo uptake is limited primarily to systemic neuronal tissue. The accumulation of iobenguane in myocardial tissue is also dictated by the high fraction of aortic blood flow that enters the coronary arteries. This physiology constitutes an ideal molecular targeting mechanism for diagnosis of various cardiac diseases, including heart failure, heart transplant rejection, ischemic heart disease, dysautonomia, and drug-induced cardiotoxicity, as well as cardiac neuropathy related to diabetes mellitus and Parkinson disease

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
IOBENGUANE SULFATE I 131

Launch Date

1994
PubMed

PubMed

TitleDatePubMed
I-123 metaiodobenzylguanidine myocardial scintigraphy in a patient with Brugada syndrome.
2001-12
Diffuse bone marrow infiltration of a neuroblastoma mimicking the findings of a bone marrow scan on I-123 MIBG scintigraphy.
2001-12
Prognostic significance of cardiac (123)I metaiodobenzylguanidine imaging for mortality and morbidity in patients with chronic heart failure: a prospective study.
2001-12
[Therapeutic advances of nuclear medicine in oncology].
2001-12
Interictal cardiac autonomic dysfunction in temporal lobe epilepsy demonstrated by [(123)I]metaiodobenzylguanidine-SPECT.
2001-12
Olfactory neuroblastoma visualized by Technetium-99m-ECD SPECT.
2001-11-29
Comparative left ventricular functional and neurohumoral effects of chronic treatment with carvedilol versus metoprolol in patients with dilated cardiomyopathy.
2001-11
Analysis of sympathetic nerve activity in end-stage cardiomyopathy patients receiving left ventricular support.
2001-11
Correlation of tumor and whole-body dosimetry with tumor response and toxicity in refractory neuroblastoma treated with (131)I-MIBG.
2001-11
The pathophysiology of cardiac syndrome X--a tale of paradigm shifts.
2001-11
A clinical role for [(123)I]MIBG myocardial scintigraphy in the distinction between dementia of the Alzheimer's-type and dementia with Lewy bodies.
2001-11
Getting to the heart of dementia.
2001-11
Paraganglioma seen with FDG dual-head gamma camera coincidence imaging after false-negative results of I-123 MIBG imaging.
2001-11
Severe oral mucositis after therapeutic administration of [131I]MIBG in a child with neuroblastoma.
2001-10
Does a "false-negative" MIBG scan predict a better outcome in neuroblastoma patients?
2001-10
Pulmonary involvement in Behçet's disease: evaluation of 123 I-MIBG retention.
2001-10
Different histopathology accounting for a decrease in myocardial MIBG uptake in PD and MSA.
2001-09-25
Biological evaluation of ring- and side-chain-substituted m-iodobenzylguanidine analogues.
2001-09-20
Synthesis of ring- and side-chain-substituted m-iodobenzylguanidine analogues.
2001-09-20
Two years' experience using no-carrier-added meta-[123I]iodobenzylguanidine in clinical studies.
2001-09
Total and partial cardiac sympathetic denervation after surgical repair of ascending aortic aneurysm.
2001-09
Cold preservation-warm reoxygenation increases hepatocyte steady-state Ca(2+) and response to Ca(2+)-mobilizing agonist.
2001-09
Studying the neuronal side of the synaptic cleft. A tool for investigating the paradox of sympathetic nervous system and heart failure in dilated cardiomyopathy.
2001-09
Metoprolol-induced changes in myocardial (123)I-metaiodobenzylguanidine uptake in Parkinson's disease.
2001-08-14
[Giant cystic pheochromocytoma: a case report].
2001-08
Detection of denervated but viable myocardium in cardiac sarcoidosis with I-123 MIBG and Tl-201 SPECT imaging.
2001-08
Discordant iodine-123 metaiodobenzylguanidine uptake area reflects recovery time dispersion in acute myocardial infarction.
2001-08
Alternating myocardial sympathetic neural function of athlete's heart in professional cycle racers examined with iodine-123-MIBG myocardial scintigraphy.
2001-08
Ultrasonic tissue characterization can predict beta-blocker efficacy in dilated cardiomyopathy.
2001-08
A "pheo" lurks: novel approaches for locating occult pheochromocytoma.
2001-08
Does a "false negative" MIBG scan predict a better outcome in neuroblastoma patients?
2001-08
False positive MIBG scan due to accessory spleen.
2001-08
Autonomic insufficiency as a factor contributing to dialysis-induced hypotension.
2001-08
[Value of 123I-MIBG scanning, neuron-specific enolase and serum ferritin in the diagnosis and follow-up of patients with neuroblastoma].
2001-08
Extending positron emission tomography scan utility to high-risk neuroblastoma: fluorine-18 fluorodeoxyglucose positron emission tomography as sole imaging modality in follow-up of patients.
2001-07-15
Absence of Crabtree effect in human melanoma cells adapted to growth at low pH: reversal by respiratory inhibitors.
2001-07-15
Low cardiac 123I-MIBG uptake in late-onset familial amyloid polyneuropathy type I (TTR Met30).
2001-07
Assessment of cardiac sympathetic nerve integrity with positron emission tomography.
2001-07
Two years' experience using no-carrier-added meta-[123I]iodobenzylguanidine in clinical studies.
2001-07
Regional alterations of myocardial norepinephrine transporter density in streptozotocin-induced diabetic rats: implications for heterogeneous cardiac accumulation of MIBG in diabetes.
2001-07
Treatment of metastatic carcinoid tumours, phaeochromocytoma, paraganglioma and medullary carcinoma of the thyroid with (131)I-meta-iodobenzylguanidine [(131)I-mIBG].
2001-07
Effect of essential hypertension on cardiac autonomic function in type 2 diabetic patients.
2001-07
Enhancement of hyperglycemia-induced acidification of human melanoma xenografts with inhibitors of respiration and ion transport.
2001-07
Completely inverse images in dual-isotope SPECT with Tl-201 and I-123 MIBG in a patient with myocarditis.
2001-06
[Clinical evaluation of "Takotsubo" cardiomyopathy with 123I-MIBG myocardial scintigraphy: a case report].
2001-05
Thallium-201 scintigraphy of neuroblastoma: different results for primary tumors and skeletal lesions.
2001-04
OPEC/OJEC for stage 4 neuroblastoma in children over 1 year of age.
2001-01
Evaluation of catecholamine metabolites, mIBG scan, and bone marrow cytology as response markers in stage 4 neuroblastoma.
2001-01
Management of malignant phaeochromocytoma: a retrospective review of the use of MIBG and chemotherapy in the West Midlands.
2001
New imaging techniques for cardiovascular autonomic neuropathy: a window on the heart.
2001

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
IOBENGUANE SULFATE
Common Name English
M-IDOBENZYL GUANIDINE SULFATE [VANDF]
Preferred Name English
3-IODOBENZYL-GUANIDINE SULFATE
Systematic Name English
META-IODOBENZYLGUANIDINE SULFATE
Systematic Name English
3-IODOBENZYL-GUANIDINE SULPHATE
Systematic Name English
M-IODOBENZYL GUANIDINE SULFATE
Systematic Name English
IOBENGUANE SULPHATE
Common Name English
M-IODOBENZYL GUANIDINE SULPHATE
Systematic Name English
GUANIDINE, N-((3-IODOPHENYL)METHYL)-, SULFATE (2:1)
Systematic Name English
Code System Code Type Description
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11957572
Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
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DRUG BANK
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Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
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Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
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Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
NON-SPECIFIC STOICHIOMETRY
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Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
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Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
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Created by admin on Mon Mar 31 17:52:09 GMT 2025 , Edited by admin on Mon Mar 31 17:52:09 GMT 2025
PRIMARY