Identification

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Name
Tyropanoic acid
Accession Number
DB09340
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Tyropanoate sodiumXRJ0P5FAYO7246-21-1KTVKGXZZBQCBGD-UHFFFAOYSA-M
International/Other Brands
Bilopaque / Tyropaque
Categories
UNII
4F05V145YR
CAS number
27293-82-9
Weight
Average: 641.026
Monoisotopic: 640.84208
Chemical Formula
C15H18I3NO3
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

Pharmacology

Indication

For use in cholecystography (X-ray diagnosis/imaging of gallstones).

Pharmacodynamics

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
Toxicity

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.

Affected organisms
Not Available
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

References

General References
  1. 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. [PubMed:6618819]
  2. Tyropanoic acid [Link]
  3. Iopanoic Acid [Link]
  4. Inhibition of Hepatic Binding of Thyroxine by Cholecystographic Agents [Link]
  5. Tyropanoate sodium [Link]
  6. Tyropanoate sodium [Link]
  7. Foreign Compound Metabolism in Mammals [Link]
  8. Hormone resistance and other metabolic paradoxes [Link]
  9. ORAL CHOLECYSTOGRAPHY WITH IOPANOIC ACID (TELEPAQUE) [Link]
  10. CHOLECYSTOGRAPHIC AGENT: A RE-EVALUATION OF ITS CLINICAL UTILITY [Link]
  11. Diagnostic process using sodium tyropanoate [Link]
  12. Drug dosing in renal insufficiency [Link]
External Links
PubChem Compound
5611
PubChem Substance
310265215
ChemSpider
5409
ChEBI
135862
ChEMBL
CHEMBL1201261
Wikipedia
Tyropanoic_acid
ATC Codes
V08AC09 — Tyropanoic acid

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)>187https://www.trc-canada.com/product-detail/?T947900
water solubilityslightly water soluble https://www.trc-canada.com/product-detail/?T947900
Predicted Properties
PropertyValueSource
Water Solubility0.00318 mg/mLALOGPS
logP4.14ALOGPS
logP6.21ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity115.32 m3·mol-1ChemAxon
Polarizability44.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / N-arylamide / Halobenzene / Iodobenzene / Aryl halide / Aryl iodide / Monocyclic benzene moiety / Fatty amide / Fatty acyl
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Receptor binding
Specific Function
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name
GUSB
Uniprot ID
P08236
Uniprot Name
Beta-glucuronidase
Molecular Weight
74731.46 Da
References
  1. Foreign Compound Metabolism in Mammals [Link]

Drug created on November 27, 2015 10:04 / Updated on February 06, 2020 12:59