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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

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
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
Created by admin on Fri Dec 15 14:57:39 GMT 2023 , Edited by admin on Fri Dec 15 14:57:39 GMT 2023
PRIMARY
NSC
107434
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PRIMARY
CAS
7246-21-1
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PRIMARY
RXCUI
282508
Created by admin on Fri Dec 15 14:57:39 GMT 2023 , Edited by admin on Fri Dec 15 14:57:39 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
230-653-9
Created by admin on Fri Dec 15 14:57:39 GMT 2023 , Edited by admin on Fri Dec 15 14:57:39 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of TYROPANIC ACID
SUBSTANCE RECORD
Structure of TYROPANOATE SODIUM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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