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Details

Stereochemistry RACEMIC
Molecular Formula C11H11I3NO2.Na
Molecular Weight 592.9137
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOPANOATE SODIUM

SMILES

[Na+].CCC(CC1=C(I)C(N)=C(I)C=C1I)C([O-])=O

InChI

InChIKey=LEXZDSSHLHPSQC-UHFFFAOYSA-M
InChI=1S/C11H12I3NO2.Na/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);/q;+1/p-1

HIDE SMILES / InChI
Iopanoic acid is a representative iodinated ionic monomeric contrast medium.

Originator

Curator's Comment: M. Sovak. Radiocontrast Agents. (1984), p. 383. ISBN13: 9783642695179

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
TELEPAQUE

Approved Use

Unknown

Launch Date

1951
Diagnostic
TELEPAQUE

Approved Use

Unknown

Launch Date

1951
Doses

Doses

DosePopulationAdverse events​
75 g single, oral
Overdose
Dose: 75 g
Route: oral
Route: single
Dose: 75 g
Sources:
unknown, 42 years
n = 1
Health Status: unknown
Condition: used for diagnosis
Age Group: 42 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1 patient)
Sources:
3 g single, oral
Recommended
Dose: 3 g
Route: oral
Route: single
Dose: 3 g
Sources:
unknown, adult
n = 48
Health Status: unknown
Condition: used for diagnosis
Age Group: adult
Sex: unknown
Population Size: 48
Sources:
Other AEs: Gastrointestinal disorders...
Other AEs:
Gastrointestinal disorders (39 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 1 patient
Disc. AE
75 g single, oral
Overdose
Dose: 75 g
Route: oral
Route: single
Dose: 75 g
Sources:
unknown, 42 years
n = 1
Health Status: unknown
Condition: used for diagnosis
Age Group: 42 years
Sex: M
Population Size: 1
Sources:
Gastrointestinal disorders 39 patients
3 g single, oral
Recommended
Dose: 3 g
Route: oral
Route: single
Dose: 3 g
Sources:
unknown, adult
n = 48
Health Status: unknown
Condition: used for diagnosis
Age Group: adult
Sex: unknown
Population Size: 48
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Additive nephrotoxicity from roentgenographic contrast media. Its occurrence in phenazopyridine-induced acute renal failure.
1981 May
Effect of iodine or iopanoic acid on thyroid Ca2+/NADPH-dependent H2O2-generating activity and thyroperoxidase in toxic diffuse goiters.
2002 Sep
Acute decrease in circulating T3 levels enhances, but does not normalise, the GH response to GHRP-6 plus GHRH in thyrotoxicosis.
2003 Aug
Perioperative management of the thyrotoxic patient.
2003 Jun
Use of oral cholecystography agents in the treatment of hyperthyroidism of subacute thyroiditis.
2003 Mar
Light-induced hormone conversion of T4 to T3 regulates photoperiodic response of gonads in birds.
2003 Nov 13
Is there a place for thyroidectomy in older patients with thyrotoxic storm and cardiorespiratory failure?
2003 Oct
Inhibition of drug binding to human serum albumin by cholecystographic agents.
2003 Sep
Thyroid hormones interact with glucocorticoids to affect somatotroph abundance in chicken embryonic pituitary cells in vitro.
2003 Sep
Thyroid hormone-dependent seasonality in American tree sparrows (Spizella arborea): effects of GC-1, a thyroid receptor beta-selective agonist, and of iopanoic acid, a deiodinase inhibitor.
2004 Aug
Treatment of hyperthyroidism associated with thyrotropin-secreting pituitary adenomas with iopanoic acid.
2004 Feb
Iopanoic acid in the management of neonatal Graves' disease.
2004 Feb
Expression of type II iodothyronine deiodinase marks the time that a tissue responds to thyroid hormone-induced metamorphosis in Xenopus laevis.
2004 Feb 1
[Levothyroxine poisoning: clinical manifestations and therapeutic management].
2004 Jan
Oral contrast-enhanced CT cholangiography--an initial experience.
2004 Jan
Rapid preparation of severe uncontrolled thyrotoxicosis due to Graves' disease with Iopanoic acid--a case report.
2004 Jan
Rapid preoperative preparation for severe hyperthyroid Graves' disease.
2004 May
Thyroid (dys)function in heart failure: is it a potential target for medical treatment?
2005
Electrospray ionization mass spectrometry as a tool for determination of drug binding sites to human serum albumin by noncovalent interaction.
2005
Effects of tetraiodothyronine and triiodothyronine on hamster cheek pouch microcirculation.
2005 Apr
Suppression of hypothalamic deiodinase type II activity blunts TRH mRNA decline during fasting.
2005 Aug 29
Effect of iopanoic acid on radioiodine therapy of hyperthyroidism: long-term outcome of a randomized controlled trial.
2005 Dec
Percutaneous transcholecystic biliary interventions using gallbladder anchors: feasibility study in the swine.
2005 Jul-Aug
Thin-section multiplanar reformats from multidetector-row CT data: utility for assessment of regional tumor extent in non-small cell lung cancer.
2005 Oct
Liquid chromatography-electrospray ionization mass spectrometry for direct identification and quantification of iophenoxic acid in serum.
2006 Feb 17
Comparison of enhancing effects of different goitrogen treatments in combination with beta-estradiol-3-benzoate for establishing a rat two-stage thyroid carcinogenesis model to detect modifying effects of estrogenic compounds.
2006 Jan
Long-lasting systemic bait markers for Eurasian badgers.
2006 Oct
Unliganded thyroid hormone receptor is essential for Xenopus laevis eye development.
2006 Oct 18
An in vivo multiwell-based fluorescent screen for monitoring vertebrate thyroid hormone disruption.
2007 Aug 15
Hashimoto's thyroiditis and the role of selenium. Current concepts.
2007 Jan-Apr
Combination of minimally invasive thyroid surgery and local anesthesia associated to iopanoic acid for patients with amiodarone-induced thyrotoxicosis and severe cardiac disorders: a pilot study.
2007 Nov
A fatal case of recurrent amiodarone-induced thyrotoxicosis after percutaneous tracheotomy: a case report.
2007 Nov 13
Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXalpha.
2008 Aug 29
Pharmacodynamic effect of iopanoic acid on free T(3) and T(4) levels in amiodarone-induced thyrotoxicosis.
2008 Dec
[Rapid preoperative preparation with iopanoic acid in severe liver toxicity due to methimazole: anesthetic implications].
2008 Feb
Morphological and biochemical changes in the Harderian gland of hypothyroid rats.
2008 Feb
Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms.
2008 Jan 31
Vaccination of feral pigs (Sus scrofa) using iophenoxic acid as a simulated vaccine.
2008 Jan-Feb
Amiodarone-induced thyrotoxicosis. A review.
2008 Sep
Effects of different treatments for hyperthyroidism on the hypothalamic-pituitary-adrenal axis.
2008 Sep
A thyroid hormone deiodinase inhibitor can decrease cutaneous cell proliferation in vitro.
2009 Feb
Competitive inhibition of organic anion transporting polypeptide 1c1-mediated thyroxine transport by the fenamate class of nonsteroidal antiinflammatory drugs.
2009 Feb
Effects and safety of iopanoic acid in cats administered levothyroxine.
2009 Feb
Anesthetic considerations in a patient with amiodarone-induced thyrotoxicosis.
2010
Implication of type 3 deiodinase induction in zebrafish fin regeneration.
2010 Aug 1
Autoimmune thyroid diseases in children.
2010 Dec 14
Analysis by LC/ESI-MS of iophenoxic acid derivatives and evaluation as markers of oral baits to deliver pharmaceuticals to wildlife.
2010 Jul 15
Colloid formation by drugs in simulated intestinal fluid.
2010 May 27
Identification of iopanoic acid as substrate of type 1 deiodinase by a novel nonradioactive iodide-release assay.
2012 May
Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells.
2013 Jun
Patents

Patents

Sample Use Guides

Take 500 mg orally twice a day for the first 3 weeks.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
IOPANOATE SODIUM
WHO-DD  
Common Name English
SODIUM IOPANOATE, (±)-
Common Name English
IOPANOIC ACID SODIUM SALT
MI  
Common Name English
IOPANOIC ACID SODIUM SALT [MI]
Common Name English
HYDROCINNAMIC ACID, 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODO-, MONOSODIUM SALT
Common Name English
SODIUM 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODOBENZENEPROPANOATE
Systematic Name English
BENZENEPROPANOIC ACID, 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODO-, MONOSODIUM SALT
Common Name English
SODIUM IOPANOATE
Common Name English
HYDROCINNAMIC ACID, 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODO-, SODIUM SALT
Common Name English
Iopanoate sodium [WHO-DD]
Common Name English
BENZENEPROPANOIC ACID, 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODO-, SODIUM SALT (1:1)
Systematic Name English
SODIUM 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODOHYDROCINNAMATE
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
219-683-3
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY
MERCK INDEX
m6371
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY Merck Index
EVMPD
SUB02750MIG
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY
FDA UNII
439WET4G58
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY
PUBCHEM
23669441
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY
RXCUI
340398
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID20947842
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY
SMS_ID
100000086410
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY
CAS
138711-85-0
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
SUPERSEDED
CAS
2497-78-1
Created by admin on Sat Dec 16 10:04:20 GMT 2023 , Edited by admin on Sat Dec 16 10:04:20 GMT 2023
PRIMARY