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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

Molecular Formula C11H12I3NO2
Molecular Weight 570.9319
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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 use of oral radiographic contrast agents in the management of hyperthyroidism.
2001 Jun
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
Tissue-specific regulation of type III iodothyronine 5-deiodinase gene expression mediates the effects of prolactin and growth hormone in Xenopus metamorphosis.
2002 Aug
Preparation with iopanoic acid rapidly controls thyrotoxicosis in patients with amiodarone-induced thyrotoxicosis before thyroidectomy.
2002 Dec
Recombinant lysine:N(6)-hydroxylase: effect of cysteine-->alanine replacements on structural integrity and catalytic competence.
2002 Feb 11
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
Light-induced hormone conversion of T4 to T3 regulates photoperiodic response of gonads in birds.
2003 Nov 13
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
[Levothyroxine poisoning: clinical manifestations and therapeutic management].
2004 Jan
Oral contrast-enhanced CT cholangiography--an initial experience.
2004 Jan
Rapid preoperative preparation for severe hyperthyroid Graves' disease.
2004 May
Effect of iopanoic acid on radioiodine therapy of hyperthyroidism: long-term outcome of a randomized controlled trial.
2005 Dec
Liquid chromatography-electrospray ionization mass spectrometry for direct identification and quantification of iophenoxic acid in serum.
2006 Feb 17
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
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
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
Analysis by LC/ESI-MS of iophenoxic acid derivatives and evaluation as markers of oral baits to deliver pharmaceuticals to wildlife.
2010 Jul 15
Identification of iopanoic acid as substrate of type 1 deiodinase by a novel nonradioactive iodide-release assay.
2012 May
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 Thu Jul 06 22:10:07 UTC 2023
Edited
by admin
on Thu Jul 06 22:10:07 UTC 2023
Record UNII
FE9794P71J
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
WHO-ATC V08AC06
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
NCI_THESAURUS C28500
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
Code System Code Type Description
INN
3
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
NSC
41706
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
RXCUI
5967
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
PUBCHEM
3735
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
HSDB
3345
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
FDA UNII
FE9794P71J
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
SMS_ID
100000083105
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IOPANOIC ACID
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 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 Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
RXCUI
637485
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
ALTERNATIVE
ECHA (EC/EINECS)
202-539-9
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
DRUG BANK
DB08946
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
MERCK INDEX
M6371
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY Merck Index
CAS
17879-93-5
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
SUPERSEDED
WIKIPEDIA
Iopanoic acid
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
CAS
96-83-3
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023159
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL867
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
NCI_THESAURUS
C65942
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
DRUG CENTRAL
1465
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
MESH
D007480
Created by admin on Thu Jul 06 22:10:08 UTC 2023 , Edited by admin on Thu Jul 06 22:10:08 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY