TYROPANOATE SODIUM

US Previously Marketed

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20641974 | http://www.tabletwise.com/us/bilopaque-capsule

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

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cholelithiasis 14 Sources: https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=013731 http://www.tabletwise.com/us/bilopaque-capsule	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	Beta-glucuronidase 2

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
Beta-glucuronidase 2	substrate 3367 Sources: https://go.drugbank.com/drugs/DB09340	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Effects of cholecystographic agents and sulfobromophthalein on binding of thyroid hormones to serum proteins.	1983 Jul	6853679
Cholecystographic agents and sulfobromophthalein inhibit the binding of L-thyroxine to plasma membranes of rat hepatocytes.	1986 Jun	3698921
Prolonged treatment of hyperthyroidism with sodium tyropanoate, an oral cholecystographic agent: a re-evaluation of its clinical utility.	1986 Sep	3791669
Sodium-2-[(3-butanoylamino-2,4,6-triiodo-phenyl)methyl]butanoate.	2004	20641974

Patents

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

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 GMT 2023` Edited by `admin` on `Fri Dec 15 14:57:39 GMT 2023`
Record UNII	XRJ0P5FAYO
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TYROPANOATE SODIUM

Official Name

English

WIN-8851-2

Code

English

SODIUM TYROPANOATE

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