U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H18N2O5
Molecular Weight 294.3031
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIDOFENIN

SMILES

CC1=CC=CC(C)=C1NC(=O)CN(CC(O)=O)CC(O)=O

InChI

InChIKey=DJQJFMSHHYAZJD-UHFFFAOYSA-N
InChI=1S/C14H18N2O5/c1-9-4-3-5-10(2)14(9)15-11(17)6-16(7-12(18)19)8-13(20)21/h3-5H,6-8H2,1-2H3,(H,15,17)(H,18,19)(H,20,21)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.pharmacopeia.cn/v29240/usp29nf24s0_m80670.html | https://www.ncbi.nlm.nih.gov/pubmed/3181685 | https://www.ncbi.nlm.nih.gov/pubmed/6825355

Lidofenin is ligand for a coordination complex consisting of the radioisotope technetium-99m. Technetium Lidofenin is a nontoxic radiopharmaceutical that is used in radionuclide imaging for the clinical evaluation of hepatobiliary disorders in humans. Technetium lidofenin is indicated as a hepatobiliary imaging agent for the evaluation of hepatobiliary tract patency to differentiate jaundice resulting from hepatocellular causes from jaundice resulting from partial or complete biliary obstruction; to differentiate extrahepatic biliary atresia from neonatal hepatitis; to detect cystic duct obstruction associated with acute cholecystitis nd to detect bile leaks. Also, technetium Tc 99m lidofenin may be useful to detect intrahepatic cholestasis and to distinguish it from other hepatobiliary diseases, which involve hepatocyte damage. Following intravenous administration, technetium Tc 99m–labeled IDA derivatives, such as lidofenin, become bound to plasma proteins (mainly albumin). In the liver, in the space of Disse, technetium Tc 99m lidofenin becomes dissociated from the proteins and enters the hepatocyte by a mechanism similar to that of serum bilirubin. Technetium Tc 99m lidofenin traverses through the hepatocyte unmetabolized and enters the bile canaliculi. Flow beyond the canaliculi is influenced to a large extent by the tone of the sphincter of Oddi and the patency of the bile ducts. Clear visualization of the gallbladder and intestines, usually within 15 to 30 minutes of administration, demonstrates hepatobiliary tract patency.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
TECHNESCAN HIDA

Approved Use

Unknown

Launch Date

1986
Diagnostic
TECHNESCAN HIDA

Approved Use

Unknown

Launch Date

1986
Primary
TECHNESCAN HIDA

Approved Use

Unknown

Launch Date

1986
PubMed

PubMed

TitleDatePubMed
Dynamic 99Tcm-HIDA SPET: non-invasive measuring of intrahepatic bile flow. Description of the method and a study in primary sclerosing cholangitis.
2001 Feb
Diagnostic accuracy of 99Tcm-HIDA with cholecystokinin and gallbladder ejection fraction in acalculous gallbladder disease.
2001 Jun
Comparison of fatty meal and intravenous cholecystokinin infusion for gallbladder ejection fraction.
2002 Dec
Ultrasound is not a useful screening tool for acute acalculous cholecystitis in critically ill trauma patients.
2002 Jan
Role of hepatobiliary scintigraphy in the evaluation and management of post-cholecystectomy pain due to biliary dyskinesia.
2002 Jan
Scintigraphy of the small intestine: a simplified standard for study of transit with reference to normal values.
2002 Jul
Outcome of endoscopic sphincterotomy in post cholecystectomy patients with sphincter of Oddi dysfunction as predicted by manometry and quantitative choledochoscintigraphy.
2002 May
Gallbladder function before and after fundoplication.
2002 Nov-Dec
Duodenal intubation and test for bile - a reliable method to rule out biliary atresia.
2002 Sep
[Hepatobiliogastroscintigraphy in assessment of the hepatobiliary system in primary cancer of the liver].
2003
Image of the month.
2004 Jan
Measurement of parenchymal function and bile duct flow in primary sclerosing cholangitis using dynamic 99mTc-HIDA SPECT.
2006 Apr
A comparison of cholecystectomy and observation in children with biliary dyskinesia.
2006 Nov
Impact of bedside right upper quadrant ultrasonography on radiology imaging.
2006 Oct
Duodenogastric reflux after choledochoduodenostomy: evaluation by technetium-99m scintigraphy.
2007 Apr-May
Bile reflux in the esophagus demonstrated by HIDA scintigraphy.
2007 Mar
Detection of a suspected bronchobiliary fistula by hepatobiliary scintigraphy.
2008 Aug
Biloma: a delayed complication of blunt hepatic injury.
2008 Jan
Meta-analysis of cholecystectomy in symptomatic patients with positive hepatobiliary iminodiacetic acid scan results without gallstones.
2009 Feb
A comprehensive overview of radioguided surgery using gamma detection probe technology.
2009 Jan 27
Interesting image. Imaging postoperative bile leaks and assessing integrity of biliary-enteric anastomoses with fusion HIDA SPECT/CT scintigraphy.
2010 Nov
Endoscopic management of a spontaneous gallbladder perforation and bile leak.
2010 Oct
Patents

Patents

Sample Use Guides

Intravenous, 185 megabecquerels (5 millicuries). Dosage is usually adjusted depending on bilirubin levels. A period of 24 hours should elapse before a second dose is administered.
Route of Administration: Intravenous
In Vitro Use Guide
Stock solutions (200 mkM) of bilirubin, BSP, and bile acids were prepared in 0.1% bovine serum albumin. All subsequent dilutions of these ligands were made in SFM containing 0.1% bovine serum albumin. Initial uptake of 99mTc-Disofenin was quantitated under control conditions, or in the presence of 1.5-50 mkM bilirubin, BSP, taurocholate, cholate, deoxycholate, chenodeoxycholate, or glycocholate at 37°C. Initial uptake of the other 99mTc IDAs (Lidofenin) was quantitated in the'presence or absence of 20 pM BSP, bilirubin, or bile acids in 0.1 % bovine serum albumin.
Name Type Language
LIDOFENIN
II   INN   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
Lidofenin [WHO-DD]
Common Name English
HEPATO-SCAN
Brand Name English
LIDOFENIN [USAN]
Common Name English
HID-A
Code English
LIDOFENIN [MI]
Common Name English
N-(2,6-DIMETHYLACETANILIDE) IMINODIACETIC ACID
Systematic Name English
GLYCINE, N-(CARBOXYMETHYL)-N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-
Systematic Name English
HIDA
Code English
lidofenin [INN]
Common Name English
LIDOFENIN [II]
Common Name English
[[(2,6-Xylylcarbamoyl)methyl]imino]diacetic acid
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1937
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
Code System Code Type Description
MERCK INDEX
m6806
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY Merck Index
INN
4455
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-636-4
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL1400608
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID2046389
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
EVMPD
SUB08508MIG
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
NCI_THESAURUS
C66012
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
DRUG CENTRAL
3322
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
CAS
59160-29-1
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
PUBCHEM
42963
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
FDA UNII
EK22QV7701
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
MESH
C049470
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY
EVMPD
SUB121637
Created by admin on Fri Dec 15 16:11:20 GMT 2023 , Edited by admin on Fri Dec 15 16:11:20 GMT 2023
PRIMARY