Iopodic acid
Identification
- Summary
Iopodic acid is an iodine containing cholecystography agent.
- Generic Name
- Iopodic acid
- DrugBank Accession Number
- DB09333
- Background
Iopodic acid, also known by the name of ipodate, is classified as a cholecystographic agent formed by a weak organic acid that contains a tri-iodinated benzene ring with iodine at positions 2, 4 and 6.1 Due to its particular structure, it presents a high degree of lipid solubility and a radiopaque property. It was developed and filed to the FDA by the company BRACCO. This drug was approved on March 15, 1962 but it is nowadays discontinued from the FDA and Health Canada. On September 22, 1981, ipodate was submitted again by the company Schering AG but it is currently under an inactive status.7
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
- Weight
- Average: 597.961
Monoisotopic: 597.81111 - Chemical Formula
- C12H13I3N2O2
- Synonyms
- Ipodate
Pharmacology
- Indication
Iopodic acid is available as a cholecystographic agent. This denomination indicates the iopodic acid is a radiopaque substance that can be used to visualize the gallbladder and biliary channels in abdominal X-ray.8,4 An abdominal X-ray uses a minimal amount of ionizing radiation to produce pictures of the inside of the abdominal cavity. It is commonly used to evaluate the stomach, liver, intestines, and spleen.9
Iopodic acid has also been indicated for the treatment of hyperthyroidism such as Graves disease.2,3 Hyperthyroidism refers to any condition where there is too much thyroid hormone produced in the body (overactive thyroid). When the overactivity involves the entire thyroid gland, it is known as Grave's disease.10
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
The thyroid effects of iopodic acid are related to the blocking of the more potent form of the thyroid hormone. It also blocks thyroid hormone release and it can interfere with its synthesis in some patients. The effects of iopopdic acid on some diseases, such as Graves disease, have been shown not to be as effective and to present a relapse after discontinuation.2,3 The effects of iopodic acid on thyroid has been proven to produce an inactivation of approximately 80% of the type II deiodinase in pituitary and cerebral cortex.4
- Mechanism of action
For cholecystography, iopodic acid blocks the X-rays as they pass through the body which allows delineating the body structures that do not contain this compound.6
The use of iopodic acid in hyperthyroidism is related to the inhibition of 5'-monodeiodinase type I and II; this will later impair the extrathyroidal conversion of thyroxine (T4) to triiodothyronine (T3).2,3
Target Actions Organism AThyroxine 5-deiodinase antagonistHumans - Absorption
The lipophilicity of ipodate is sufficient for passage through the gastrointestinal mucosa.1 After ingestion, iopodic acid is promptly absorbed by passive diffusion in the small intestinal mucosa. The presence of bile salts in the duodenum is essential for its diffusion through the intestine wall and a high-fat diet is important in order to increase the absorption effectivity. The maximum effect is showed to be attained 5 hours after the initial dosage and the effect were retained for more than 60 hours.4
- Volume of distribution
Not Available
- Protein binding
The absence of a substituent at position 5 allows the compound to bind to serum albumin.1 This is the reason why immediately after absorption, iopanoic acid enters the bloodstream it binds to albumin and it is transported to the liver.4
- Metabolism
The absence of a substituent at position 5 facilitates for preferential hepatocyte uptake. Once taken in the liver, the metabolism is mainly performed by glucuronide conjugation in the same pathway as bilirubin.1
- Route of elimination
The metabolism products of ipodate are readily excreted into the bile, follow the bile flow to fill up the gallbladder and then excreted by the biliary system in the feces.1 This mode of excretion accounts for 65% of the eliminated dose whereas the kidneys are responsible for the remaining 35% of the elimination.4
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Iopodic acid is cathegorized as one of the top 10 linked to skin reactions.5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Ipodate calcium 50S7W5M9ZZ 1151-11-7 HVZGHKKROPCBDE-UHFFFAOYSA-L Ipodate sodium F316LLW9WW 1221-56-3 ZFHZUGUCWJVEQC-UHFFFAOYSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oragrafin Sodium 0.5gm Capsule 500 mg / cap Oral Bracco Imaging S.P.A. 1969-12-31 1999-07-30 Canada
Categories
- ATC Codes
- V08AC08 — Sodium iopodate
- V08AC — Watersoluble, hepatotropic X-ray contrast media
- V08A — X-RAY CONTRAST MEDIA, IODINATED
- V08 — CONTRAST MEDIA
- V — VARIOUS
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Phenylpropanoic acids
- Sub Class
- Not Available
- Direct Parent
- Phenylpropanoic acids
- Alternative Parents
- Iodobenzenes / Aryl iodides / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Formamidines / Carboxylic acids / Carboxamidines / Organopnictogen compounds / Organoiodides / Organic oxides show 2 more
- Substituents
- 3-phenylpropanoic-acid / Amidine / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid amidine / Carboxylic acid derivative show 16 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- F604ZKI910
- CAS number
- 5587-89-3
- InChI Key
- YQNFBOJPTAXAKV-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H13I3N2O2/c1-17(2)6-16-12-9(14)5-8(13)7(11(12)15)3-4-10(18)19/h5-6H,3-4H2,1-2H3,(H,18,19)
- IUPAC Name
- 3-(3-{[(dimethylamino)methylidene]amino}-2,4,6-triiodophenyl)propanoic acid
- SMILES
- CN(C)C=NC1=C(I)C=C(I)C(CCC(O)=O)=C1I
References
- General References
- Cheng KT: Sodium-2-[(3-butanoylamino-2,4,6-triiodo-phenyl)methyl]butanoate . [Article]
- Martino E, Balzano S, Bartalena L, Loviselli A, Sica V, Petrini L, Grasso L, Piga M, Braverman LE: Therapy of Graves' disease with sodium ipodate is associated with a high recurrence rate of hyperthyroidism. J Endocrinol Invest. 1991 Nov;14(10):847-51. doi: 10.1007/BF03347940. [Article]
- Chopra IJ, van Herle AJ, Korenman SG, Viosca S, Younai S: Use of sodium ipodate in management of hyperthyroidism in subacute thyroiditis. J Clin Endocrinol Metab. 1995 Jul;80(7):2178-80. doi: 10.1210/jcem.80.7.7608275. [Article]
- Braga M, Cooper DS: Clinical review 129: Oral cholecystographic agents and the thyroid. J Clin Endocrinol Metab. 2001 May;86(5):1853-60. doi: 10.1210/jcem.86.5.7484. [Article]
- Woo T.M. and Robinson M. (2016). Pharmacotherapeutics for advanced practice nurse prescribers (4th ed.). Davis Company.
- Swanson D., et al. (1990). Pharmaceuticals in medical imaging. McGraw-Hill Professional.
- FDA Submission [Link]
- Up to date [Link]
- Radiologyinfo [Link]
- Endocrinology association [Link]
- External Links
- PubChem Compound
- 5241
- PubChem Substance
- 310265212
- ChemSpider
- 20473670
- 5976
- ChEMBL
- CHEMBL3306201
- MSDS
- Download (36.7 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 500 mg / cap - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 168-169ºC ChemSrc boiling point (°C) 579.8ºC at 760 mmHg ChemSrc water solubility Insoluble Cheng K. (2005). Molecular imaging and contrast agent database. logP 3.73 ChemSrc pKa 4.8 Elks. The dictionary of Drugs. (1990) - Predicted Properties
Property Value Source Water Solubility 0.00819 mg/mL ALOGPS logP 3.59 ALOGPS logP 3.4 Chemaxon logS -4.9 ALOGPS pKa (Strongest Acidic) 1.99 Chemaxon pKa (Strongest Basic) 4.16 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.9 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 104.91 m3·mol-1 Chemaxon Polarizability 40.23 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.13966 predictedDeepCCS 1.0 (2019) [M+H]+ 184.68999 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.65782 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into RT3 (3,3',5'-triiodothyronine) and of T3 (3,5,3'-triiodothyronine) into T2 (3,3'-diiodothyronine). RT3 and T2 are inactive metabolites. May play a role in preventing premature exposure of developing fetal tissues to adult levels of thyroid hormones. Can regulate circulating fetal thyroid hormone concentrations throughout gestation. Essential role for regulation of thyroid hormone inactivation during embryological development.
- Specific Function
- Thyroxine 5'-deiodinase activity
- Gene Name
- DIO3
- Uniprot ID
- P55073
- Uniprot Name
- Thyroxine 5-deiodinase
- Molecular Weight
- 33947.175 Da
References
- Martino E, Balzano S, Bartalena L, Loviselli A, Sica V, Petrini L, Grasso L, Piga M, Braverman LE: Therapy of Graves' disease with sodium ipodate is associated with a high recurrence rate of hyperthyroidism. J Endocrinol Invest. 1991 Nov;14(10):847-51. doi: 10.1007/BF03347940. [Article]
- Chopra IJ, van Herle AJ, Korenman SG, Viosca S, Younai S: Use of sodium ipodate in management of hyperthyroidism in subacute thyroiditis. J Clin Endocrinol Metab. 1995 Jul;80(7):2178-80. doi: 10.1210/jcem.80.7.7608275. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Cheng KT: Sodium-2-[(3-butanoylamino-2,4,6-triiodo-phenyl)methyl]butanoate . [Article]
Drug created at November 24, 2015 19:31 / Updated at February 02, 2024 22:53