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Details

Stereochemistry RACEMIC
Molecular Formula C11H12I3NO2
Molecular Weight 570.9319
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOPANOIC ACID

SMILES

CCC(CC1=C(I)C(N)=C(I)C=C1I)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
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
A surface-modified chylomicron remnant-like emulsion for percutaneous computed tomography lymphography: synthesis and preliminary imaging findings.
2002 Apr
Tissue-specific regulation of type III iodothyronine 5-deiodinase gene expression mediates the effects of prolactin and growth hormone in Xenopus metamorphosis.
2002 Aug
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
Use of oral cholecystography agents in the treatment of hyperthyroidism of subacute thyroiditis.
2003 Mar
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
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
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
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
Amiodarone-induced thyrotoxicosis. A review.
2008 Sep
Effects and safety of iopanoic acid in cats administered levothyroxine.
2009 Feb
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
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 [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 [USP IMPURITY]
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 IMPURITY]
Common Name English
Iopanoic acid [WHO-DD]
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
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-α-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 Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
WHO-ATC V08AC06
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
NCI_THESAURUS C28500
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
Code System Code Type Description
INN
3
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
NSC
41706
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
RXCUI
5967
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
PUBCHEM
3735
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
HSDB
3345
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
FDA UNII
FE9794P71J
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
SMS_ID
100000083105
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IOPANOIC ACID
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
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 Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
RXCUI
637485
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
ALTERNATIVE
ECHA (EC/EINECS)
202-539-9
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
DRUG BANK
DB08946
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
MERCK INDEX
m6371
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY Merck Index
CAS
17879-93-5
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
SUPERSEDED
WIKIPEDIA
Iopanoic acid
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
CAS
96-83-3
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023159
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL867
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
NCI_THESAURUS
C65942
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
DRUG CENTRAL
1465
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY
MESH
D007480
Created by admin on Sat Dec 16 16:42:39 UTC 2023 , Edited by admin on Sat Dec 16 16:42:39 UTC 2023
PRIMARY