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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
Recombinant lysine:N(6)-hydroxylase: effect of cysteine-->alanine replacements on structural integrity and catalytic competence.
2002 Feb 11
Effect of iodine or iopanoic acid on thyroid Ca2+/NADPH-dependent H2O2-generating activity and thyroperoxidase in toxic diffuse goiters.
2002 Sep
Thyroid status, but not insulin status, affects expression of avian uncoupling protein mRNA in chicken.
2003 Apr
Acute decrease in circulating T3 levels enhances, but does not normalise, the GH response to GHRP-6 plus GHRH in thyrotoxicosis.
2003 Aug
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
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
Oral contrast-enhanced CT cholangiography--an initial experience.
2004 Jan
Electrospray ionization mass spectrometry as a tool for determination of drug binding sites to human serum albumin by noncovalent interaction.
2005
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
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
Effects of different treatments for hyperthyroidism on the hypothalamic-pituitary-adrenal axis.
2008 Sep
Implication of type 3 deiodinase induction in zebrafish fin regeneration.
2010 Aug 1
Analysis by LC/ESI-MS of iophenoxic acid derivatives and evaluation as markers of oral baits to deliver pharmaceuticals to wildlife.
2010 Jul 15
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-?-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 Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
WHO-ATC V08AC06
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
NCI_THESAURUS C28500
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
Code System Code Type Description
INN
3
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
NSC
41706
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
RXCUI
5967
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
PUBCHEM
3735
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
HSDB
3345
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
FDA UNII
FE9794P71J
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IOPANOIC ACID
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
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 Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
RXCUI
637485
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
ALTERNATIVE
ECHA (EC/EINECS)
202-539-9
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
DRUG BANK
DB08946
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
MERCK INDEX
M6371
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY Merck Index
CAS
17879-93-5
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
SUPERSEDED
WIKIPEDIA
Iopanoic acid
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
CAS
96-83-3
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
EPA CompTox
DTXSID6023159
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
ChEMBL
CHEMBL867
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
NCI_THESAURUS
C65942
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
DRUG CENTRAL
1465
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY
MESH
D007480
Created by admin on Sun Dec 18 19:03:20 UTC 2022 , Edited by admin on Sun Dec 18 19:03:20 UTC 2022
PRIMARY