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meta-Iodobenzylguanidine

meta-Iodobenzylguanidine structure

CAS No:
80663-95-2
Formula:
C8H10IN3
Chemical Name:
meta-Iodobenzylguanidine
Synonyms:
Guanidine,N-[(3-iodophenyl)methyl]-;Guanidine,[(3-iodophenyl)methyl]-;N-[(3-Iodophenyl)methyl]guanidine;meta-Iodobenzylguanidine;m-Iodobenzylguanidine;(3-Iodobenzyl)guanidine;1810731-85-1
Categories:
Chemical Reagents > Organic Reagents

Description

Colourless to off-white solid

2-[(3-iodophenyl)methyl]guanidine is an organoiodine compound.|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.|Iobenguane is a synthetic, aralkylguanidine analogue of the adrenergic neurotransmitter norepinephrine (NE) and adrenergic neuron blocking agent with potential diagnostic imaging or antineoplastic activity when radiolabeled. Iobenguane, also known as metaiodobenzylguanidine (MIBG), is taken up and accumulates in the granules of adrenal medullary chromaffin cells and in the pre-synaptic granules of adrenergic neurons in a manner almost identical with that of NE. In radiolabeled forms, iobenguane may be used to image or eradicate neuroendocrine tissues and tumor cells.|A guanidine analog with specific affinity for tissues of the sympathetic nervous system and related tumors. The radiolabeled forms are used as antineoplastic agents and radioactive imaging agents. (Merck Index, 12th ed) MIBG serves as a neuron-blocking agent which has a strong affinity for, and retention in, the adrenal medulla and also inhibits ADP-ribosyltransferase.

meta-Iodobenzylguanidine Basic Attributes

Molecular Weight：

324.13

Exact Mass：

275.09

UNII：

35MRW7B4AD

DSSTox ID：

DTXSID4048438

NCI Thesaurus Code：

C87757

HScode：

29252900

Characteristics

PSA：

206.78000

XLogP3：

5.35840

Density：

1.85g/cm3

Melting Point：

0°C

Boiling Point：

382.1ºC at 760mmHg

Flash Point：

184.9ºC

Water Solubility：

Soluble

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

Toxicity

Toxicity Summary：

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.

Drug Information

Drug Indication：

Detection of primary and metastatic pheochromocytoma or neuroblastoma|FDA Label

Pharmacology：

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.

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Compounds that are used in medicine as sources of radiation for radiotherapy and for diagnostic purposes. They have numerous uses in research and industry. (Martindale, The Extra Pharmacopoeia, 30th ed, p1161) (See all compounds classified as Radiopharmaceuticals.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Absorption：

Iobenguane rapidly clears from the blood and is highly retained in adrenergic tissues.|Renally excreted unchanged (70%-90%) via glomerular filtration; Fecal (<1%)

Metabolism/Metabolites：

Less than 10% of the dose is metabolized into m-iodohippuric acid (MIHA). However the mechanism in which this metabolite is produced is unknown.

Biological Half-Life：

Physical half life = 13.2 hours

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.

MeSH Entry Terms：

(3-Iodo-(131I)benzyl)guanidine

Computed Properties

Molecular Weight:275.09
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:274.99194
Monoisotopic Mass:274.99194
Topological Polar Surface Area:64.4
Heavy Atom Count:12
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes