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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
Structure of IOBENGUANE

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)

HIDE SMILES / InChI

Molecular Formula C8H10IN3
Molecular Weight 275.0896
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Management of malignant phaeochromocytoma: a retrospective review of the use of MIBG and chemotherapy in the West Midlands.
2001
The role of nuclear medicine in the evaluation of pancreatic disease.
2001 Apr
Patient dosimetry after 131I-MIBG therapy for neuroblastoma and carcinoid tumours.
2001 Apr
Extensive myocardial stunning showing transient regression of prolonged T wave inversion and prolonged sympathetic denervation.
2001 Apr
Evaluation of beta-blocker therapy in patients with dilated cardiomyopathy--Clinical meaning of iodine 123-metaiodobenzylguanidine myocardial single-photon emission computed tomography.
2001 Apr
Discordant iodine-123 metaiodobenzylguanidine uptake area reflects recovery time dispersion in acute myocardial infarction.
2001 Aug
Does a "false negative" MIBG scan predict a better outcome in neuroblastoma patients?
2001 Aug
Diffuse bone marrow infiltration of a neuroblastoma mimicking the findings of a bone marrow scan on I-123 MIBG scintigraphy.
2001 Dec
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
OPEC/OJEC for stage 4 neuroblastoma in children over 1 year of age.
2001 Jan
Effect of essential hypertension on cardiac autonomic function in type 2 diabetic patients.
2001 Jul
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
The diagnostic role of radionuclide imaging in evaluation of patients with nonhypersecreting adrenal masses.
2001 Jun
Impaired cardiac adrenergic innervation assessed by MIBG imaging as a predictor of treatment response in childhood dilated cardiomyopathy.
2001 Jun
Inhibition of mono-ADP-ribosyltransferase activity during the execution phase of apoptosis prevents apoptotic body formation.
2001 Mar 1
A gene therapy/targeted radiotherapy strategy for radiation cell kill by.
2001 Mar-Apr
Serious arrhythmias in patients with apical hypertrophic cardiomyopathy.
2001 May
Comparative left ventricular functional and neurohumoral effects of chronic treatment with carvedilol versus metoprolol in patients with dilated cardiomyopathy.
2001 Nov
Getting to the heart of dementia.
2001 Nov
Total and partial cardiac sympathetic denervation after surgical repair of ascending aortic aneurysm.
2001 Sep
Olfactory neuroblastoma visualized by Technetium-99m-ECD SPECT.
2001 Sep-Oct

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:12 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:12 GMT 2023
Record UNII
35MRW7B4AD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IOBENGUANE
MI   VANDF  
Common Name English
MIBG
Common Name English
((3-IODOPHENYL)METHYL)GUANIDINE
Systematic Name English
M-IODOBENZYLGUANIDINE
Systematic Name English
IOBENGUANE [VANDF]
Common Name English
IOBENGUANE [MI]
Common Name English
IOBENGUANE (127-I)
Common Name English
3-IODOBENZYLGUANIDINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C28500
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
Code System Code Type Description
SMS_ID
100000124418
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
PRIMARY
MERCK INDEX
m6321
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
PRIMARY Merck Index
PUBCHEM
60860
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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FDA UNII
35MRW7B4AD
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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NCI_THESAURUS
C87757
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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EPA CompTox
DTXSID4048438
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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WIKIPEDIA
IOBENGUANE
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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EVMPD
SUB32630
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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DRUG BANK
DB06704
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
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RXCUI
14448
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
PRIMARY RxNorm
MESH
D019797
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
PRIMARY
CAS
80663-95-2
Created by admin on Fri Dec 15 16:02:12 GMT 2023 , Edited by admin on Fri Dec 15 16:02:12 GMT 2023
PRIMARY
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