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Details

Stereochemistry RACEMIC
Molecular Formula C15H18I3NO3
Molecular Weight 641.0217
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TYROPANIC ACID

SMILES

CCCC(=O)NC1=C(I)C(CC(CC)C(O)=O)=C(I)C=C1I

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
Molecular Formula C15H18I3NO3
Molecular Weight 641.0217
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Benisek, G.J.|Gunn, J.A.
2
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

1969
24
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Approved
8583
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Beta-glucuronidase
2
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
Beta-glucuronidase
2
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
AAA Chemistry
AR-1D6774
ABI Chem
AC1L1KQH
ABI Chem
AC1Q4PCM
Alfa Chemistry
220815
Alfa Chemistry
ACM7246211
BLD Pharm
BD01249505
http://www.bldpharm.com/products/27293-82-9.html
BOC Sciences
27293-82-9
Chemieliva Pharmaceutical Co., Ltd
PBCM0460207
ChemTik
CTK4F9414
Compound Cloud
541384
Compound Cloud
5611
eMolecules
48885699
eMolecules
50522826
eMolecules
72980805
Hangzhou Yuhao Chemical Technology
RT1499
Hangzhou Yuhao Chemical Technology
RT3685
mcule
MCULE-8347837509
MuseChem
I009914
https://www.musechem.com/product/I009914.html
NCI Plated 2007
107434
NovoSeek
5611
Smolecule
S546108
http://www.smolecule.com/products/s546108
Smolecule
S601116
https://www.smolecule.com/products/s601116
Tetrahedron
TS84397
THE BioTek
bt-284540
https://www.thebiotek.com/product/inhibitors/bt-284540
THE BioTek
bt-373169
https://www.thebiotek.com/product/others/bt-373169
Toronto Research Chemicals
I810003
Toronto Research Chemicals
T899900
Toronto Research Chemicals
T947900
Yuhao Chemical
RT3685
http://www.chemyuhao.com/27293-82-9.html
ZINC
ZINC000003831594
http://zinc15.docking.org/substances/ZINC000003831594
ZINC
ZINC000003831595
http://zinc15.docking.org/substances/ZINC000003831595
PubMed

PubMed

TitleDatePubMed
Prolonged treatment of hyperthyroidism with sodium tyropanoate, an oral cholecystographic agent: a re-evaluation of its clinical utility.
1986-09
Cholecystographic agents and sulfobromophthalein inhibit the binding of L-thyroxine to plasma membranes of rat hepatocytes.
1986-06
Effects of cholecystographic agents and sulfobromophthalein on binding of thyroid hormones to serum proteins.
1983-07
Patents

Patents

US6576636
7
US8232265
3
US8802596
3

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:17:47 GMT 2025
Edited
by admin
on Mon Mar 31 18:17:47 GMT 2025
Record UNII
4F05V145YR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TYROPANOIC ACID
WHO-DD  
Preferred Name English
TYROPANIC ACID
Common Name English
Tyropanoic acid [WHO-DD]
Common Name English
2-(3-(BUTYRYLAMINO)-2,4,6-TRIIODOBENZYL)BUTANOIC ACID
Systematic 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
Classification Tree Code System Code
NCI_THESAURUS C390
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
WHO-ATC V08AC09
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
WHO-VATC QV08AC09
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
Code System Code Type Description
WIKIPEDIA
TYROPANOIC ACID
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
DRUG CENTRAL
2785
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
RXCUI
10960
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY RxNorm
CAS
27293-82-9
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
FDA UNII
4F05V145YR
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
PUBCHEM
5611
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
MESH
D014441
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
NCI_THESAURUS
C76638
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
248-389-8
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID5048269
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
SMS_ID
100000084762
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
DRUG BANK
DB09340
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
EVMPD
SUB05028MIG
Created by admin on Mon Mar 31 18:17:47 GMT 2025 , Edited by admin on Mon Mar 31 18:17:47 GMT 2025
PRIMARY
Related Record Type Details
Structure of TYROPANOATE SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TYROPANIC ACID
ACTIVE MOIETY
NIH
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