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Details

Stereochemistry RACEMIC
Molecular Formula C11H12I3NO2
Molecular Weight 570.9323
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOPANOIC ACID

SMILES

CCC(Cc1c(cc(c(c1I)N)I)I)C(=O)O

InChI

InChIKey=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)

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

-5.8268162E11
Diagnostic
TELEPAQUE

Approved Use

Unknown

Launch Date

-5.8268162E11
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
The activity of antioxidant enzymes and the content of uncoupling protein-1 in the brown adipose tissue of hypothyroid rats: comparison with effects of iopanoic acid.
2001
A test of the hypothesis that T3 is the "seasonality" thyroid hormone in American tree sparrows (Spizella arborea): intracerebroventricular infusion of iopanoic acid, an inhibitor of T3 synthesis and degradation.
2001 Mar
Are the effects of T3 on resting metabolic rate in euthyroid rats entirely caused by T3 itself?
2002 Feb
Acute decrease in circulating T3 levels enhances, but does not normalise, the GH response to GHRP-6 plus GHRH in thyrotoxicosis.
2003 Aug
Convective distribution of macromolecules in the primate brain demonstrated using computerized tomography and magnetic resonance imaging.
2003 Mar
Treatment of type II amiodarone-induced thyrotoxicosis by either iopanoic acid or glucocorticoids: a prospective, randomized study.
2003 May
Inhibition of drug binding to human serum albumin by cholecystographic agents.
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
Oral contrast-enhanced CT cholangiography--an initial experience.
2004 Jan
Thyroid (dys)function in heart failure: is it a potential target for medical treatment?
2005
Effects of tetraiodothyronine and triiodothyronine on hamster cheek pouch microcirculation.
2005 Apr
Effect of iopanoic acid on radioiodine therapy of hyperthyroidism: long-term outcome of a randomized controlled trial.
2005 Dec
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
Vaccination of feral pigs (Sus scrofa) using iophenoxic acid as a simulated vaccine.
2008 Jan-Feb
Amiodarone-induced thyrotoxicosis. A review.
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
IOPANOIC ACID
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
COLEPAX
Common Name English
IOPANOIC ACID [WHO-DD]
Common Name English
IOPANOIC ACID [JAN]
Common Name English
JOPAGNOST
Common Name English
IOPANOIC ACID [INN]
Common Name English
3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODOBENZENEPROPANOIC ACID
Systematic Name English
IOPANOATE
Common Name English
COPANOIC
Common Name English
CISTOBIL
Common Name English
IOPANOIC ACID [HSDB]
Common Name English
IOPANOIC ACID [EP MONOGRAPH]
Common Name English
IOPANOIC ACID [VANDF]
Common Name English
IOPANOIC ACID [MART.]
Common Name English
.ALPHA.-ETHYL-.BETA.-(3-AMINO-2,4,6-TRIIODOPHENYL)PROPIONIC ACID
Systematic Name English
IOPANOIC ACID [EP]
Common Name English
ACIDUM IOPANOICUM [WHO-IP LATIN]
Common Name English
CHOLADINE
Brand Name English
IOPANOIC ACID [WHO-IP]
Common Name English
NSC-41706
Code English
IOPAGNOST
Common Name English
HYDROCINNAMIC ACID, 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODO-
Common Name English
IOPANOIC ACID [USP]
Common Name English
CHOLEVID
Common Name English
IOPANOIC ACID [ORANGE BOOK]
Common Name English
2-(3-AMINO-2,4,6-TRIIODOBENZYL)BUTYRIC ACID
Systematic Name English
TELEPAQUE
Brand Name English
IOPANOIC ACID [MI]
Common Name English
(PM)-3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODOHYDROCINNAMIC ACID
Common Name English
BILIJODON
Common Name English
BENZENEPROPANOIC ACID, 3-AMINO-.ALPHA.-ETHYL-2,4,6-TRIIODO-, (+/-)-
Common Name English
Classification Tree Code System Code
WHO-VATC QV08AC06
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
WHO-ATC V08AC06
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
NCI_THESAURUS C28500
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
Code System Code Type Description
INN
3
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
RXCUI
5967
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
PUBCHEM
3735
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
HSDB
3345
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
FDA UNII
FE9794P71J
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IOPANOIC ACID
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY Description: A light yellowish white powder; odour, faint, characteristic. Solubility: Practically insoluble in water; soluble in ethanol (~750 g/l) TS, and acetone R; dissolves in solutions of alkali hydroxides. Category: Radiocontrast medium. Storage: Iopanoic acid should be kept in a tightly closed container, protected from light. Iopanoic acid is gradually affected by light. Requirements: Iopanoic acid contains not less than 97.0% and not more than the equivalent of 101.0% of C11H12I3NO2, calculated with reference to the dried substance.
EVMPD
SUB08240MIG
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
RXCUI
637485
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
ALTERNATIVE
ECHA (EC/EINECS)
202-539-9
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
DRUG BANK
DB08946
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
MERCK INDEX
M6371
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY Merck Index
CAS
17879-93-5
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
SUPERSEDED
CAS
96-83-3
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
EPA CompTox
96-83-3
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL867
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
NCI_THESAURUS
C65942
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
DRUG CENTRAL
1465
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY
MESH
D007480
Created by admin on Fri Jun 25 21:17:01 UTC 2021 , Edited by admin on Fri Jun 25 21:17:01 UTC 2021
PRIMARY