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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
Structure of TYROPANOATE SODIUM

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

HIDE SMILES / InChI
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

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
BILOPAQUE

Approved Use

Oral X-ray cholecystographic agent used to aid the radiographic visualization of the gallbladder for detecting the presence of gallstones in cholelithiasis patients

Launch Date

1969
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.65 nM
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Effects of cholecystographic agents and sulfobromophthalein on binding of thyroid hormones to serum proteins.
1983 Jul
Sodium-2-[(3-butanoylamino-2,4,6-triiodo-phenyl)methyl]butanoate.
2004
Patents

Sample Use Guides

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
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
Name Type Language
TYROPANOATE SODIUM
MI   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
WIN-8851-2
Code English
SODIUM TYROPANOATE
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
sodium tyropanoate [INN]
Common Name English
Sodium 3-butyramido-α-ethyl-2,4,6-triiodohydrocinnamate
Systematic Name English
Sodium tyropanoate [WHO-DD]
Common Name English
BENZENEPROPANOIC ACID, .ALPHA.-ETHYL-2,4,6-TRIIODO-3-((1-OXOBUTYL)AMINO)-, MONOSODIUM SALT
Common Name English
TYROPANOATE SODIUM [ORANGE BOOK]
Common Name English
TYROPANOATE SODIUM [USAN]
Common Name English
TYROPANOATE SODIUM [VANDF]
Common Name English
SODIUM TYROPANOATE [JAN]
Common Name English
NSC-107434
Code English
TYROPANOATE SODIUM [MI]
Common Name English
WIN 8851-2
Code English
BILOPAQUE
Brand Name English
SODIUM TYROPANOATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C390
Created by admin on Fri Dec 15 14:57:39 GMT 2023 , Edited by admin on Fri Dec 15 14:57:39 GMT 2023
Code System Code Type Description
EVMPD
SUB10573MIG
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PRIMARY
EPA CompTox
DTXSID2023729
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PRIMARY
SMS_ID
100000084042
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PRIMARY
DRUG BANK
DBSALT001341
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PRIMARY
NCI_THESAURUS
C66647
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PRIMARY
ChEMBL
CHEMBL1201261
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PRIMARY
MERCK INDEX
m11288
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PRIMARY Merck Index
INN
1239
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PRIMARY
FDA UNII
XRJ0P5FAYO
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PRIMARY
PUBCHEM
541384
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PRIMARY
NSC
107434
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PRIMARY
CAS
7246-21-1
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PRIMARY
RXCUI
282508
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PRIMARY RxNorm
ECHA (EC/EINECS)
230-653-9
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PRIMARY