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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

Molecular Formula C15H17I3NO3
Molecular Weight 640.0138
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:57:39 UTC 2023
Edited
by admin
on Fri Dec 15 14:57:39 UTC 2023
Record UNII
XRJ0P5FAYO
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
Code System Code Type Description
EVMPD
SUB10573MIG
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023729
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PRIMARY
SMS_ID
100000084042
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
DRUG BANK
DBSALT001341
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
NCI_THESAURUS
C66647
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201261
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
MERCK INDEX
m11288
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY Merck Index
INN
1239
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
FDA UNII
XRJ0P5FAYO
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
PUBCHEM
541384
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
NSC
107434
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
CAS
7246-21-1
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
RXCUI
282508
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
230-653-9
Created by admin on Fri Dec 15 14:57:39 UTC 2023 , Edited by admin on Fri Dec 15 14:57:39 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY