Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Tyropanoic acid
- DrugBank Accession Number
- DB09340
- Background
Tyropanoic acid is a radiocontrast agent used in cholecystography, the X-ray diagnosis of gallstones under the trade names include Bilopaque, Lumopaque, Tyropaque, and Bilopac. The molecule contains three heavy iodine atoms which obstruct X-rays in the same way as the calcium in bones, which results in a visible image 9.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tyropanoic acid (DB09340)
- Weight
- Average: 641.026
Monoisotopic: 640.84208 - Chemical Formula
- C15H18I3NO3
- Synonyms
- Not Available
Pharmacology
- Indication
For use in cholecystography (X-ray diagnosis/imaging of gallstones).
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Tyropanoate sodium, also known as sodium tyropanoate, is a radiocontrast agent used in cholecystography (X-ray imagining and diagnosis of gallstones). This molecule contains three heavy iodine atoms which obstruct X-rays to produce a visible image. After injection, it is rapidly excreted into the bile 8,9,10.
- Mechanism of action
- Not Available
- Absorption
This triiodide is well absorbed by the small intestine and it is excreted in the bile within 2 h after oral administration 9. It has been found to be readily absorbed and show maximal radiographic definition at 10-12 h post ingestion, but this can occur as early as 4-6h 12.
- Volume of distribution
Not Available
- Protein binding
Less than 5 % 11.
- Metabolism
Conjugated with glucuronic acid in the liver 12.
- Route of elimination
Rapidly excreted into the bile and equally excreted in the urine and feces within 100h of ingestion 12.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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LD50 i.v. in mice: 720 mg/kg 6.
Since the introduction of iopanoic acid (Telepaque) in 1951, widespread clinical application has demonstrated that this medium represents an ideal cholecystographic agent.1 Iopanoic acid [β-(3-amino-2, 4, 6-triiodophenyl)-α-ethylpropionic acid] contains 66.68% iodine. Maximum concentration in the gallbladder occurs at from 10 to 12 hours. Iopanoic acid is excreted primarily through the intestinal tract. Its elimination is rapid and complete within 48 hours. Toxic reactions to this agent are rare, and side-effects rarely occur 9.
Although the foregoing oral cholecystographic agents are relatively non-toxic substances, adverse reactions such as minor gastrointestinal disturbances or allergic reactions are occasionally observed. Therefore, it is highly desirable, in order to minimize the occurrence of these undesirable side-effects, to use as low a dose as possible and maintain the blood plasma iodine concentration at the lowest possible level without sacrificing adequate imaging of the gallbladder 11.
A study was done on this agent in basic form and slow-release form 11. The acute oral toxicity in mice of the basic formulation was determined, and a 7-day LD50 value of 5042 (3623-6596) mg/kg in terms of sodium tyropanoate was obtained. This compared to a Ld50 value of 3158 (1302-3900) for commercial sodium tyropanoate capsule mix (uncoated). The sustained release preparation was thus statistically significantly less toxic than the immediate-release material 11.
- 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 Tyropanoate sodium XRJ0P5FAYO 7246-21-1 KTVKGXZZBQCBGD-UHFFFAOYSA-M - International/Other Brands
- Bilopaque / Tyropaque
Categories
- ATC Codes
- V08AC09 — Tyropanoic acid
- 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
- Anilides / N-arylamides / Iodobenzenes / Fatty amides / Aryl iodides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organoiodides show 3 more
- Substituents
- 3-phenylpropanoic-acid / Anilide / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative show 17 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4F05V145YR
- CAS number
- 27293-82-9
- InChI Key
- YMOXVLQZFAUUKI-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H18I3NO3/c1-3-5-12(20)19-14-11(17)7-10(16)9(13(14)18)6-8(4-2)15(21)22/h7-8H,3-6H2,1-2H3,(H,19,20)(H,21,22)
- IUPAC Name
- 2-[(3-butanamido-2,4,6-triiodophenyl)methyl]butanoic acid
- SMILES
- CCCC(=O)NC1=C(I)C=C(I)C(CC(CC)C(O)=O)=C1I
References
- General References
- Cooke WJ, Cooke LM: Biliary and urinary excretion of tyropanoic acid and its Metabolites in the dog. Invest Radiol. 1983 May-Jun;18(3):285-92. [Article]
- Tyropanoic acid [Link]
- Iopanoic Acid [Link]
- Inhibition of Hepatic Binding of Thyroxine by Cholecystographic Agents [Link]
- Tyropanoate sodium [Link]
- Tyropanoate sodium [Link]
- Foreign Compound Metabolism in Mammals [Link]
- Hormone resistance and other metabolic paradoxes [Link]
- ORAL CHOLECYSTOGRAPHY WITH IOPANOIC ACID (TELEPAQUE) [Link]
- CHOLECYSTOGRAPHIC AGENT: A RE-EVALUATION OF ITS CLINICAL UTILITY [Link]
- Diagnostic process using sodium tyropanoate [Link]
- Drug dosing in renal insufficiency [Link]
- External Links
- PubChem Compound
- 5611
- PubChem Substance
- 310265215
- ChemSpider
- 5409
- ChEBI
- 135862
- ChEMBL
- CHEMBL1201261
- Wikipedia
- Tyropanoic_acid
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) >187 https://www.trc-canada.com/product-detail/?T947900 water solubility slightly water soluble https://www.trc-canada.com/product-detail/?T947900 - Predicted Properties
Property Value Source Water Solubility 0.00318 mg/mL ALOGPS logP 4.14 ALOGPS logP 6.21 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 2.52 Chemaxon pKa (Strongest Basic) -3.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.4 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 115.32 m3·mol-1 Chemaxon Polarizability 44.91 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 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]- 195.78334 predictedDeepCCS 1.0 (2019) [M+H]+ 198.53697 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.35152 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Plays an important role in the degradation of dermatan and keratan sulfates
- Specific Function
- Beta-glucuronidase activity
- Gene Name
- GUSB
- Uniprot ID
- P08236
- Uniprot Name
- Beta-glucuronidase
- Molecular Weight
- 74731.46 Da
References
- Foreign Compound Metabolism in Mammals [Link]
Drug created at November 27, 2015 17:04 / Updated at June 02, 2024 21:56