U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
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
A surface-modified chylomicron remnant-like emulsion for percutaneous computed tomography lymphography: synthesis and preliminary imaging findings.
2002 Apr
Preparation with iopanoic acid rapidly controls thyrotoxicosis in patients with amiodarone-induced thyrotoxicosis before thyroidectomy.
2002 Dec
Iopanoic acid rapidly controls type I amiodarone-induced thyrotoxicosis prior to thyroidectomy.
2002 Feb
Are the effects of T3 on resting metabolic rate in euthyroid rats entirely caused by T3 itself?
2002 Feb
Recombinant lysine:N(6)-hydroxylase: effect of cysteine-->alanine replacements on structural integrity and catalytic competence.
2002 Feb 11
Thyroid status, but not insulin status, affects expression of avian uncoupling protein mRNA in chicken.
2003 Apr
Light-induced hormone conversion of T4 to T3 regulates photoperiodic response of gonads in birds.
2003 Nov 13
Is there a place for thyroidectomy in older patients with thyrotoxic storm and cardiorespiratory failure?
2003 Oct
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
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
Rapid preoperative preparation for severe hyperthyroid Graves' disease.
2004 May
Electrospray ionization mass spectrometry as a tool for determination of drug binding sites to human serum albumin by noncovalent interaction.
2005
Suppression of hypothalamic deiodinase type II activity blunts TRH mRNA decline during fasting.
2005 Aug 29
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
Long-lasting systemic bait markers for Eurasian badgers.
2006 Oct
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
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
Structural basis of GC-1 selectivity for thyroid hormone receptor isoforms.
2008 Jan 31
Vaccination of feral pigs (Sus scrofa) using iophenoxic acid as a simulated vaccine.
2008 Jan-Feb
Effects of different treatments for hyperthyroidism on the hypothalamic-pituitary-adrenal axis.
2008 Sep
Autoimmune thyroid diseases in children.
2010 Dec 14
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 [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 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
WHO-ATC V08AC06
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
NCI_THESAURUS C28500
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
Code System Code Type Description
INN
3
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
NSC
41706
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
RXCUI
5967
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
PUBCHEM
3735
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
HSDB
3345
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
FDA UNII
FE9794P71J
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
SMS_ID
100000083105
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
IOPANOIC ACID
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
RXCUI
637485
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
202-539-9
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
DRUG BANK
DB08946
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
MERCK INDEX
m6371
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY Merck Index
CAS
17879-93-5
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
SUPERSEDED
WIKIPEDIA
Iopanoic acid
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
CAS
96-83-3
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID6023159
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL867
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
NCI_THESAURUS
C65942
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
DRUG CENTRAL
1465
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY
MESH
D007480
Created by admin on Sat Dec 16 16:42:39 GMT 2023 , Edited by admin on Sat Dec 16 16:42:39 GMT 2023
PRIMARY