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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=C(I)C(N)=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

Molecular Formula C11H11I3NO2
Molecular Weight 569.924
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Health Status: unknown
Age Group: 42 years
Sex: M
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
Health Status: unknown
Age Group: adult
Sex: unknown
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
Health Status: unknown
Age Group: 42 years
Sex: M
Sources:
Gastrointestinal disorders 39 patients
3 g single, oral
Recommended
Dose: 3 g
Route: oral
Route: single
Dose: 3 g
Sources:
unknown, adult
Health Status: unknown
Age Group: adult
Sex: unknown
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells.
2013-06
Identification of iopanoic acid as substrate of type 1 deiodinase by a novel nonradioactive iodide-release assay.
2012-05
Autoimmune thyroid diseases in children.
2010-12-14
Implication of type 3 deiodinase induction in zebrafish fin regeneration.
2010-08-01
Analysis by LC/ESI-MS of iophenoxic acid derivatives and evaluation as markers of oral baits to deliver pharmaceuticals to wildlife.
2010-07-15
Colloid formation by drugs in simulated intestinal fluid.
2010-05-27
Anesthetic considerations in a patient with amiodarone-induced thyrotoxicosis.
2010
A thyroid hormone deiodinase inhibitor can decrease cutaneous cell proliferation in vitro.
2009-02
Competitive inhibition of organic anion transporting polypeptide 1c1-mediated thyroxine transport by the fenamate class of nonsteroidal antiinflammatory drugs.
2009-02
Effects and safety of iopanoic acid in cats administered levothyroxine.
2009-02
Pharmacodynamic effect of iopanoic acid on free T(3) and T(4) levels in amiodarone-induced thyrotoxicosis.
2008-12
Amiodarone-induced thyrotoxicosis. A review.
2008-09
Effects of different treatments for hyperthyroidism on the hypothalamic-pituitary-adrenal axis.
2008-09
Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXalpha.
2008-08-29
Vaccination of feral pigs (Sus scrofa) using iophenoxic acid as a simulated vaccine.
2008-02-15
[Rapid preoperative preparation with iopanoic acid in severe liver toxicity due to methimazole: anesthetic implications].
2008-02
Morphological and biochemical changes in the Harderian gland of hypothyroid rats.
2008-02
Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms.
2008-01-31
A fatal case of recurrent amiodarone-induced thyrotoxicosis after percutaneous tracheotomy: a case report.
2007-11-13
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.
2007-11
An in vivo multiwell-based fluorescent screen for monitoring vertebrate thyroid hormone disruption.
2007-08-15
Hashimoto's thyroiditis and the role of selenium. Current concepts.
2007-02-12
Unliganded thyroid hormone receptor is essential for Xenopus laevis eye development.
2006-10-18
Long-lasting systemic bait markers for Eurasian badgers.
2006-10
Liquid chromatography-electrospray ionization mass spectrometry for direct identification and quantification of iophenoxic acid in serum.
2006-02-17
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.
2006-01
Effect of iopanoic acid on radioiodine therapy of hyperthyroidism: long-term outcome of a randomized controlled trial.
2005-12
Thin-section multiplanar reformats from multidetector-row CT data: utility for assessment of regional tumor extent in non-small cell lung cancer.
2005-10
Suppression of hypothalamic deiodinase type II activity blunts TRH mRNA decline during fasting.
2005-08-29
Percutaneous transcholecystic biliary interventions using gallbladder anchors: feasibility study in the swine.
2005-07-08
Effects of tetraiodothyronine and triiodothyronine on hamster cheek pouch microcirculation.
2005-04
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
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.
2004-08
Rapid preoperative preparation for severe hyperthyroid Graves' disease.
2004-05
Expression of type II iodothyronine deiodinase marks the time that a tissue responds to thyroid hormone-induced metamorphosis in Xenopus laevis.
2004-02-01
Treatment of hyperthyroidism associated with thyrotropin-secreting pituitary adenomas with iopanoic acid.
2004-02
Iopanoic acid in the management of neonatal Graves' disease.
2004-02
[Levothyroxine poisoning: clinical manifestations and therapeutic management].
2004-01
Oral contrast-enhanced CT cholangiography--an initial experience.
2004-01
Rapid preparation of severe uncontrolled thyrotoxicosis due to Graves' disease with Iopanoic acid--a case report.
2004-01
Light-induced hormone conversion of T4 to T3 regulates photoperiodic response of gonads in birds.
2003-11-13
Is there a place for thyroidectomy in older patients with thyrotoxic storm and cardiorespiratory failure?
2003-10
Inhibition of drug binding to human serum albumin by cholecystographic agents.
2003-09
Thyroid hormones interact with glucocorticoids to affect somatotroph abundance in chicken embryonic pituitary cells in vitro.
2003-09
Acute decrease in circulating T3 levels enhances, but does not normalise, the GH response to GHRP-6 plus GHRH in thyrotoxicosis.
2003-08
Perioperative management of the thyrotoxic patient.
2003-06
Treatment of type II amiodarone-induced thyrotoxicosis by either iopanoic acid or glucocorticoids: a prospective, randomized study.
2003-05
Use of oral cholecystography agents in the treatment of hyperthyroidism of subacute thyroiditis.
2003-03
Additive nephrotoxicity from roentgenographic contrast media. Its occurrence in phenazopyridine-induced acute renal failure.
1981-05
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:00:16 GMT 2025
Edited
by admin
on Mon Mar 31 23:00:16 GMT 2025
Record UNII
439WET4G58
Record Status Validated (UNII)
Record Version
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Name Type Language
IOPANOATE SODIUM
WHO-DD  
Common Name English
IOPANOIC ACID SODIUM SALT
MI  
Preferred Name English
SODIUM IOPANOATE, (±)-
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 Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
MERCK INDEX
m6371
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY Merck Index
EVMPD
SUB02750MIG
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
FDA UNII
439WET4G58
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
PUBCHEM
23669441
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
RXCUI
340398
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID20947842
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
SMS_ID
100000086410
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
CAS
138711-85-0
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
SUPERSEDED
CAS
2497-78-1
Created by admin on Mon Mar 31 23:00:16 GMT 2025 , Edited by admin on Mon Mar 31 23:00:16 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE