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Merck
CN

14131

Iopanoic acid

analytical standard

Synonym(s):

2-(3-Amino-2,4,6-triiodobenzyl)butyric acid, 3-(3-Amino-2,4,6-triiodophenyl)-2-ethylpropanoic acid, Iodopanoic acid

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About This Item

Empirical Formula (Hill Notation):
C11H12I3NO2
CAS Number:
96-83-3
Molecular Weight:
570.93
UNSPSC Code:
41116107
PubChem Substance ID:
329750405
EC Number:
202-539-9
MDL number:
MFCD00038687

Key Documents

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InChI key

OIRFJRBSRORBCM-UHFFFAOYSA-N

InChI

1S/C11H12I3NO2/c1-2-5(11(16)17)3-6-7(12)4-8(13)10(15)9(6)14/h4-5H,2-3,15H2,1H3,(H,16,17)

SMILES string

O=C(O)C(CC)CC1=C(I)C(N)=C(I)C=C1I

grade

analytical standard

assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

mp

150-156 °C

application(s)

clinical

format

neat

storage temp.

2-8°C

Quality Level

100

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General description

Iopanoic acid is an oral cholecystographic agent, which is rich in iodine and is a potent inhibitor of 5′-deiodinase.
This radiographic contrast agent prevents the release of thyroid hormone from the thyroid gland. It also inhibits the conversion of thyroxine to triiodothyronine.

Application

Iopanoic acid may be used as a standard to investigate the presence and regulation of type 3 iodothyronine deiodinase in human cardiomyocytes.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH4449
BCCC6613
BCBV8566

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Type 3 iodothyronine deiodinase is expressed in human induced pluripotent stem cell derived cardiomyocytes.
Nishimura K, et al.
Life Sciences (2018)
Evidence against a major role of L-thyroxine at the pituitary level: studies in rats treated with iopanoic acid (telepaque).
Obregon JM, et al.
Endocrinology, 106(6), 1827-1836 (1980)
Iopanoic acid rapidly controls type I amiodarone-induced thyrotoxicosis prior to thyroidectomy.
Bogazzi F, et al.
Journal of Endocrinological Investigation, 25(2), 176-180 (2002)
Xuehua Piao et al.
The Journal of allergy and clinical immunology, 143(1), 213-228 (2018-03-30)
A delicate balance between cell death and keratinocyte proliferation is crucial for normal skin development. Previous studies have reported that cellular FLICE (FADD-like ICE)-inhibitory protein plays a crucial role in prevention of keratinocytes from TNF-α-dependent apoptosis and blocking of dermatitis.
Janet L Markman et al.
Nature communications, 11(1), 1613-1613 (2020-04-03)
In men, the incidence of melanoma rises rapidly after age 50, and nearly two thirds of melanoma deaths are male. The immune system is known to play a key role in controlling the growth and spread of malignancies, but whether

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