14131

Supelco

Iopanoic acid

analytical standard

Synonym(s):
3-(3-Amino-2,4,6-triiodophenyl)-2-ethylpropanoic acid, Iodopanoic acid, 2-(3-Amino-2,4,6-triiodobenzyl)butyric acid
Empirical Formula (Hill Notation):
C11H12I3NO2
CAS Number:
Molecular Weight:
570.93
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

grade

analytical standard

assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

application(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

150-156 °C

Featured Industry

Clinical

format

neat

storage temp.

2-8°C

SMILES string

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

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)

InChI key

OIRFJRBSRORBCM-UHFFFAOYSA-N

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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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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)
Type 3 iodothyronine deiodinase is expressed in human induced pluripotent stem cell derived cardiomyocytes.
Nishimura K, et al.
Life Sciences (2018)
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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