Identification
NameTechnetium Tc-99m mebrofenin
Accession NumberDB09137
TypeSmall Molecule
GroupsApproved
Description

Technetium Tc 99m Mebrofenin is a diagnostic radiopharmaceutical composed of diisopropyl-iminodiacetic acid (DISIDA) attached to a technetium-99m ion. Following intravenous injection, single photon emission computer tomography (SPECT) imaging of the liver or gallbladder is performed using a gamma camera to detect the gamma rays emitted by the technetium-99m as it decays. This is possible as Technetium-99m decays by isomeric transition to technetium-99 through the release of a gamma ray. Liver and gallbladder imaging is enabled through attachment to mebrofenin as this molecule has high hepatic uptake and fast biliary excretion, resulting in improved hepatic imaging. More specifically, mebrofenin is taken up into hepatocytes through the action of OATP1B1 and OATP1B3 transporters.

Currently available within a sterile kit, Tc-99m Mebrofenin is indicated for imaging of the liver and gallbladder.

Structure
Thumb
Synonyms
Bis(2-[[2-(3-bromo-2,4,6-trimethylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetate) technetium
Technetium (99mTc) mebrofenin
Technetium Tc 99m diisopropyl-iminodiacetic acid
Technetium Tc 99m DISIDA
Technetium Tc 99m Mebrofenin
Technetium Tc-99m mebrofenin kit
External IDs Not Available
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CholetecInjection, powder, lyophilized, for solution45 mg/1IntravenousBracco Diagnostics, Inc1987-01-21Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Kit for the Preparation of Technetium Tc 99m MebrofeninInjection, powder, lyophilized, for solution45 mg/10mLIntravenousPharmalucence, Inc.2008-01-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MebrofeninInjection, powder, lyophilized, for solution10 mg/1IntravenousAnazao Health Corporation2012-06-19Not applicableUs
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII7PV0B6ED98
CAS number1415247-71-0
WeightAverage: 486.136
Monoisotopic: 484.953989
Chemical FormulaC15H19BrN2O5Tc
InChI KeyJLJSYHOPCNWUNE-NLQOEHMXSA-N
InChI
InChI=1S/C15H19BrN2O5.Tc/c1-8-4-9(2)15(10(3)14(8)16)17-11(19)5-18(6-12(20)21)7-13(22)23;/h4H,5-7H2,1-3H3,(H,17,19)(H,20,21)(H,22,23);/i;1+2
IUPAC Name
2-({[(3-bromo-2,4,6-trimethylphenyl)carbamoyl]methyl}(carboxymethyl)amino)acetic acid (⁹⁹Tc)technetium
SMILES
[99Tc].[H]OC(=O)C([H])([H])N(C([H])([H])C(=O)O[H])C([H])([H])C(=O)N([H])C1=C(C(Br)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
Pharmacology
Indication

Technetium Tc 99m Mebrofenin is indicated as a hepatobiliary imaging agent.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

Technetium Tc 99m Mebrofenin has no known pharmacologic activity at the recommended doses. It is used as a diagnostic agent as Technetium-99m decays by isomeric transition to technetium-99 through the release of a detectable gamma ray.

Related Articles
Absorption

Visualisation in the liver could be detected by 5 minutes and maximum liver uptake occurred at 11 minutes post-injection. Hepatic duct and gallbladder visualization occurred by 10 to 15 minutes and intestinal activity was visualized by 30 to 60 minutes in subjects with normal hepatobiliary function The mean percent injected dose remaining in the blood at 10 minutes was 17%.

Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of elimination

The mean percent injected dose excreted in the urine during the first 3 hours was 1%.

Half life

Technetium Tc 99m decays by isomeric transition with a physical half-life of 6.02 hours.

Clearance

Following intravenous administration in normal subjects, Technetium Tc 99m Mebrofenin was rapidly cleared from the circulation.

ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
EltrombopagThe serum concentration of Technetium Tc 99m Mebrofenin can be increased when it is combined with Eltrombopag.Approved
TeriflunomideThe serum concentration of Technetium Tc 99m Mebrofenin can be increased when it is combined with Teriflunomide.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Krishnamurthy GT, Turner FE: Pharmacokinetics and clinical application of technetium 99m-labeled hepatobiliary agents. Semin Nucl Med. 1990 Apr;20(2):130-49. [PubMed:2184521 ]
  2. de Graaf W, Hausler S, Heger M, van Ginhoven TM, van Cappellen G, Bennink RJ, Kullak-Ublick GA, Hesselmann R, van Gulik TM, Stieger B: Transporters involved in the hepatic uptake of (99m)Tc-mebrofenin and indocyanine green. J Hepatol. 2011 Apr;54(4):738-45. doi: 10.1016/j.jhep.2010.07.047. Epub 2010 Oct 1. [PubMed:21163547 ]
External Links
ATC CodesV09DA04 — Technetium (99mtc) mebrofenin
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (2.51 MB)
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceNon-Alcoholic Steatohepatitis1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntravenous45 mg/1
Injection, powder, lyophilized, for solutionIntravenous45 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous10 mg/1
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0568 mg/mLALOGPS
logP-0.39ALOGPS
logP0.45ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.81ChemAxon
pKa (Strongest Basic)2.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity89.27 m3·mol-1ChemAxon
Polarizability35 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative ParentsAlpha amino acids / Anilides / N-arylamides / Bromobenzenes / Dicarboxylic acids and derivatives / Aryl bromides / Trialkylamines / Secondary carboxylic acid amides / Amino acids / Carboxylic acids
SubstituentsAlpha-amino acid amide / Alpha-amino acid / Anilide / N-arylamide / Bromobenzene / Halobenzene / Aryl bromide / Aryl halide / Monocyclic benzene moiety / Dicarboxylic acid or derivatives
Molecular FrameworkNot Available
External DescriptorsNot Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Uniprot Name:
Solute carrier organic anion transporter family member 1B1
Molecular Weight:
76447.99 Da
References
  1. de Graaf W, Hausler S, Heger M, van Ginhoven TM, van Cappellen G, Bennink RJ, Kullak-Ublick GA, Hesselmann R, van Gulik TM, Stieger B: Transporters involved in the hepatic uptake of (99m)Tc-mebrofenin and indocyanine green. J Hepatol. 2011 Apr;54(4):738-45. doi: 10.1016/j.jhep.2010.07.047. Epub 2010 Oct 1. [PubMed:21163547 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Uniprot Name:
Solute carrier organic anion transporter family member 1B3
Molecular Weight:
77402.175 Da
References
  1. de Graaf W, Hausler S, Heger M, van Ginhoven TM, van Cappellen G, Bennink RJ, Kullak-Ublick GA, Hesselmann R, van Gulik TM, Stieger B: Transporters involved in the hepatic uptake of (99m)Tc-mebrofenin and indocyanine green. J Hepatol. 2011 Apr;54(4):738-45. doi: 10.1016/j.jhep.2010.07.047. Epub 2010 Oct 1. [PubMed:21163547 ]
Drug created on September 29, 2015 16:59 / Updated on September 01, 2017 12:02