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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=C(I)C(CC(CC)C(O)=O)=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
8429
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
ChemTik
CTK4F9414
Chemieliva Pharmaceutical Co., Ltd
PBCM0460207
Compound Cloud
541384
Compound Cloud
5611
Hangzhou Yuhao Chemical Technology
RT1499
Hangzhou Yuhao Chemical Technology
RT3685
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
THE BioTek
bt-284540
https://www.thebiotek.com/product/inhibitors/bt-284540
THE BioTek
bt-373169
https://www.thebiotek.com/product/others/bt-373169
Tetrahedron
TS84397
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
eMolecules
48885699
eMolecules
50522826
eMolecules
72980805
mcule
MCULE-8347837509
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

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 Fri Dec 15 16:03:36 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:36 GMT 2023
Record UNII
4F05V145YR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TYROPANIC ACID
Common Name English
Tyropanoic acid [WHO-DD]
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
Classification Tree Code System Code
NCI_THESAURUS C390
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
WHO-ATC V08AC09
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
WHO-VATC QV08AC09
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
Code System Code Type Description
WIKIPEDIA
TYROPANOIC ACID
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
DRUG CENTRAL
2785
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
RXCUI
10960
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY RxNorm
CAS
27293-82-9
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
FDA UNII
4F05V145YR
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
PUBCHEM
5611
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
MESH
D014441
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
NCI_THESAURUS
C76638
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
248-389-8
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID5048269
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
SMS_ID
100000084762
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
DRUG BANK
DB09340
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
EVMPD
SUB05028MIG
Created by admin on Fri Dec 15 16:03:36 GMT 2023 , Edited by admin on Fri Dec 15 16:03:36 GMT 2023
PRIMARY
Related Record Type Details
Structure of TYROPANOATE SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TYROPANIC ACID
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