Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H10IN3 |
Molecular Weight | 275.0896 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=N)NCC1=CC=CC(I)=C1
InChI
InChIKey=PDWUPXJEEYOOTR-UHFFFAOYSA-N
InChI=1S/C8H10IN3/c9-7-3-1-2-6(4-7)5-12-8(10)11/h1-4H,5H2,(H4,10,11,12)
DescriptionSources: http://www.drugbank.ca/drugs/DB06704Curator'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
Sources: http://www.drugbank.ca/drugs/DB06704
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
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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[Urinary pheochromocytoma with normal hormone levels]. | 2001 Apr |
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Functional imaging of malignant paragangliomas and carcinoid tumours. | 2001 Apr |
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[Giant cystic pheochromocytoma: a case report]. | 2001 Aug |
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[Value of 123I-MIBG scanning, neuron-specific enolase and serum ferritin in the diagnosis and follow-up of patients with neuroblastoma]. | 2001 Aug |
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[Therapeutic advances of nuclear medicine in oncology]. | 2001 Dec |
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Interictal cardiac autonomic dysfunction in temporal lobe epilepsy demonstrated by [(123)I]metaiodobenzylguanidine-SPECT. | 2001 Dec |
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Does simple estimation of 131I-metaiodobenzylguanidine uptake in patients with neural crest tumours correlate with clinical outcome? | 2001 Feb |
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Cardiac pheochromocytoma. | 2001 Feb |
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Neuroblastoma imaging using a combined CT scanner-scintillation camera and 131I-MIBG. | 2001 Feb |
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Treatment of advanced neuroblastoma: feasibility and therapeutic potential of a novel approach combining 131-I-MIBG and multiple drug chemotherapy. | 2001 Feb |
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Stabilisation of [131I]meta-iodobenzylguanidine at room temperature as organic extract in ethyl acetate/chloroform. | 2001 Feb |
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[Informed consent in the radioisotopic treatment of neuroendocrine tumors]. | 2001 Feb |
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Effects of asynchronous ventricular activation on myocardial adrenergic innervation in patients with permanent dual-chamber pacemakers; an I(123)-metaiodobenzylguanidine cardiac scintigraphic study. | 2001 Feb |
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A transplantable human carcinoid as model for somatostatin receptor-mediated and amine transporter-mediated radionuclide uptake. | 2001 Feb |
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Comparison of somatostatin analog and meta-iodobenzylguanidine radionuclides in the diagnosis and localization of advanced neuroendocrine tumors. | 2001 Feb |
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[(123)I]metaiodobenzylguanidine and [(111)In]octreotide uptake in begnign and malignant pheochromocytomas. | 2001 Feb |
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Recovery of the cardiac adrenergic nervous system after long-term beta-blocker therapy in idiopathic dilated cardiomyopathy: assessment by increase in myocardial 123I-metaiodobenzylguanidine uptake. | 2001 Jan |
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Modulation of ventricular repolarization and R-R interval is altered in patients with globally impaired cardiac 123I-MIBG uptake. | 2001 Jan |
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Anthracycline-induced cardiomyopathy: long-term effects on myocardial cell integrity, cardiac adrenergic innervation and fatty acid uptake. | 2001 Jan |
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Metastatic brainstem pheochromocytoma in a patient with von Hippel-Lindau disease. Case illustration. | 2001 Jan |
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[131I meta-iodobenzylguanidine in combination with hyperbaric oxygen therapy in the treatment of prognostically high-risk forms of neuroblastoma]. | 2001 Jan 19 |
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Iodine-123 MIBG imaging before treatment of heart failure with carvedilol to predict improvement of left ventricular function and exercise capacity. | 2001 Jan-Feb |
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Combined use of chemotherapy and 131I-metaiodobenzylguanidine in the treatment of advanced-stage neuroblastoma. | 2001 Jan-Mar |
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Assessment of cardiac sympathetic nerve integrity with positron emission tomography. | 2001 Jul |
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Effect of essential hypertension on cardiac autonomic function in type 2 diabetic patients. | 2001 Jul |
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Comparison of cardiac sympathetic nervous function with left ventricular function and perfusion in cardiomyopathies by (123)I-MIBG SPECT and (99m)Tc-tetrofosmin electrocardiographically gated SPECT. | 2001 Jul |
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Chromogranin A assay and (131)I-MIBG scintigraphy for diagnosis and follow-up of pheochromocytoma. | 2001 Jul |
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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 Jul 15 |
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Impaired cardiac adrenergic innervation assessed by MIBG imaging as a predictor of treatment response in childhood dilated cardiomyopathy. | 2001 Jun |
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Megatherapy combining I(131) metaiodobenzylguanidine and high-dose chemotherapy with haematopoietic progenitor cell rescue for neuroblastoma. | 2001 Mar |
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Dosimetry from organ to cellular dimensions. | 2001 Mar-Apr |
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Concordance between rest MIBG and exercise tetrofosmin defects: possible use of rest MIBG imaging as a marker of reversible ischaemia. | 2001 May |
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Myocardial imaging with 123I-metaiodobenzylguanidine in essential hypertension and renovascular hypertension. | 2001 May |
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An efficient batch preparation of high specific activity. | 2001 May |
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Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology. | 2001 May 15 |
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Getting to the heart of dementia. | 2001 Nov |
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Pulmonary involvement in Behçet's disease: evaluation of 123 I-MIBG retention. | 2001 Oct |
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Different histopathology accounting for a decrease in myocardial MIBG uptake in PD and MSA. | 2001 Sep 25 |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C28500
Created by
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100000124418
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m6321
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60860
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35MRW7B4AD
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C87757
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DTXSID4048438
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IOBENGUANE
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SUB32630
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DB06704
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14448
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D019797
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80663-95-2
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)