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Details

Stereochemistry RACEMIC
Molecular Formula C15H18I3NO3
Molecular Weight 641.0223
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TYROPANIC ACID

SMILES

CCCC(=Nc1c(cc(c(CC(CC)C(=O)O)c1I)I)I)O

InChI

InChIKey=YMOXVLQZFAUUKI-UHFFFAOYSA-N
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)

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

-5.9616E9
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
Cholecystographic agents and sulfobromophthalein inhibit the binding of L-thyroxine to plasma membranes of rat hepatocytes.
1986 Jun
Prolonged treatment of hyperthyroidism with sodium tyropanoate, an oral cholecystographic agent: a re-evaluation of its clinical utility.
1986 Sep
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
TYROPANIC ACID
Common Name English
2-(3-(BUTYRYLAMINO)-2,4,6-TRIIODOBENZYL)BUTANOIC ACID
Systematic Name English
TYROPANOIC ACID
WHO-DD  
Common Name English
BENZENEPROPANOIC ACID, .ALPHA.-ETHYL-2,4,6-TRIIODO-3-((1-OXOBUTYL)AMINO)-
Common Name English
TYROPANOATE
VANDF  
Common Name English
TYROPANOATE [VANDF]
Common Name English
TYROPANOIC ACID [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C390
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
WHO-ATC V08AC09
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
WHO-VATC QV08AC09
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
Code System Code Type Description
WIKIPEDIA
TYROPANOIC ACID
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
DRUG CENTRAL
2785
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
RXCUI
10960
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY RxNorm
CAS
27293-82-9
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
FDA UNII
4F05V145YR
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
PUBCHEM
5611
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
MESH
D014441
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
NCI_THESAURUS
C76638
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
248-389-8
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
EPA CompTox
27293-82-9
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
DRUG BANK
DB09340
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY
EVMPD
SUB05028MIG
Created by admin on Fri Jun 25 23:23:43 UTC 2021 , Edited by admin on Fri Jun 25 23:23:43 UTC 2021
PRIMARY