Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H17I3NO3.Na |
Molecular Weight | 663.0036 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCC(=O)NC1=C(I)C=C(I)C(CC(CC)C([O-])=O)=C1I
InChI
InChIKey=KTVKGXZZBQCBGD-UHFFFAOYSA-M
InChI=1S/C15H18I3NO3.Na/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);/q;+1/p-1
Tyropanic acid and its salt sodium tyropanoate are radiocontrast agents used in cholecystography (X-ray diagnosis of gallstones). Tyropanic acid is sold under the trade names 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 to produce a visible image. After injection it is rapidly excreted into the bile.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13867240
Curator's Comment: Tyropanic acid was first synthesized in1962 as a modification of an earlier cholecystographic agent, iopanoic acid, in an effort to decrease its toxicity
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
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0.65 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6618819/ |
0.5 μmol/kg/min other, intravenous dose: 0.5 μmol/kg/min route of administration: Intravenous experiment type: OTHER co-administered: |
TYROPANIC ACID plasma | Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://go.drugbank.com/drugs/DB09340 |
yes |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20641974
Human biochemical studies indicated that after oral ingestion of 4.5 g of tyropanoate sodium, tyropanoate sodium was rapidly absorbed from the intestinal tract and a peak serum iodine level of 330-460 mg/liter could be reached in 1-4 h
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3698921
Curator's Comment: Tyropanic acid inhibits the binding of L-thyroxine to plasma membranes of rat hepatocytes. Specific binding of T4 (Ka, 1.01 X 10(8) M) was confirmed by displacement of labeled T4 by unlabeled hormone (10(-10)-10(-5) M).
At 5-mM concentrations of Tyropanic acid, the Ka for T4 declined to 5.62 X 10(7) M
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NCI_THESAURUS |
C390
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ACTIVE MOIETY
SUBSTANCE RECORD