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

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

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
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
Clinical review 129: Oral cholecystographic agents and the thyroid.
2001 May
Preparation with iopanoic acid rapidly controls thyrotoxicosis in patients with amiodarone-induced thyrotoxicosis before thyroidectomy.
2002 Dec
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
Use of oral cholecystography agents in the treatment of hyperthyroidism of subacute thyroiditis.
2003 Mar
Light-induced hormone conversion of T4 to T3 regulates photoperiodic response of gonads in birds.
2003 Nov 13
[Levothyroxine poisoning: clinical manifestations and therapeutic management].
2004 Jan
Thyroid (dys)function in heart failure: is it a potential target for medical treatment?
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
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
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
Amiodarone-induced thyrotoxicosis. A review.
2008 Sep
Effects of different treatments for hyperthyroidism on the hypothalamic-pituitary-adrenal axis.
2008 Sep
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
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:42:39 GMT 2023
Edited
by admin
on Sat Dec 16 16:42:39 GMT 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 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
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY