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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:52 UTC
HMDB IDHMDB0015581
Secondary Accession Numbers
  • HMDB15581
Metabolite Identification
Common NameIodipamide
DescriptionIodipamide, also known as adipiodon or bilignost, belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Iodipamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Organic iodine compounds block x-rays as they pass through the body, thereby allowing body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. Ionic radiocontrast agents like iodipamide are cytotoxic to renal cells. The contrast medium is finally eliminated in the feces without passing through the enterohepatic circulation, except for approximately 10 percent of the intravenously administered dose which is excreted through the kidneys. Iodipamide is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography. Following intravenous administration of Iodipamide Meglumine, iodipamide is carried to the liver where it is rapidly secreted. The biliary ducts are readily visualized within about 25 minutes after administration, except in patients with impaired liver function. The degree of opacity produced by these iodinated organic compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. Iodipamide's primary excretion through the hepato-biliary system and concentration in bile allows visualization of the gallbladder and biliary ducts.
Structure
Data?1582753312
Synonyms
ValueSource
3,3'-(Adipoyldiimino)bis(2,4,6-triiodobenzoic acid)ChEBI
AdipiodonChEBI
AdipiodonaChEBI
AdipiodonumChEBI
BilignostChEBI
BilignostumChEBI
BiligrafinChEBI
BiligrafineChEBI
BilipolinumChEBI
CholografinChEBI
CholospectChEBI
EndocistobilChEBI
EndographinChEBI
TransbilixChEBI
AdipiodoneKegg
3,3'-(Adipoyldiimino)bis(2,4,6-triiodobenzoate)Generator
3,3'-[(1,6-Dioxohexane-1,6-diyl)diimino]bis(2,4,6-triiodobenzoic acid)HMDB
IDBHMDB
Iodipamic acidHMDB
Chemical FormulaC20H14I6N2O6
Average Molecular Weight1139.7618
Monoisotopic Molecular Weight1139.51199671
IUPAC Name3-{5-[(3-carboxy-2,4,6-triiodophenyl)carbamoyl]pentanamido}-2,4,6-triiodobenzoic acid
Traditional Nameiodipamide
CAS Registry Number606-17-7
SMILES
OC(=O)C1=C(I)C(NC(=O)CCCCC(=O)NC2=C(I)C=C(I)C(C(O)=O)=C2I)=C(I)C=C1I
InChI Identifier
InChI=1S/C20H14I6N2O6/c21-7-5-9(23)17(15(25)13(7)19(31)32)27-11(29)3-1-2-4-12(30)28-18-10(24)6-8(22)14(16(18)26)20(33)34/h5-6H,1-4H2,(H,27,29)(H,28,30)(H,31,32)(H,33,34)
InChI KeyFFINMCNLQNTKLU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylaminobenzoic acid and derivatives
Alternative Parents
Substituents
  • Acylaminobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 2-halobenzoic acid
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzoic acid
  • Anilide
  • 1-carboxy-2-haloaromatic compound
  • Benzoyl
  • N-arylamide
  • Halobenzene
  • Iodobenzene
  • Dicarboxylic acid or derivatives
  • Aryl iodide
  • Aryl halide
  • Fatty acyl
  • Fatty amide
  • Vinylogous halide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organoiodide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point307 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0031 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP3.42ALOGPS
logP8.25ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.8 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity183.98 m³·mol⁻¹ChemAxon
Polarizability69.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900020000-b5a5aa037fa7d817df43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00tg-1800093000-021cd14ecd426c78058aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-6000190000-ab797bf6191c4bfd4c3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-9700010000-f76a1115bde515a53e50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p9-3900082000-899be96e35a30d50367aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1000190000-4b000454347cb3aa66afSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04711 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04711 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04711
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3608
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAdipiodone
METLIN IDNot Available
PubChem Compound3739
PDB IDIDB
ChEBI ID31176
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lin SK, Moss AA, Riegelman S: Iodipamide kinetics: capacity-limited biliary excretion with simultaneous pseudo-first-order renal excretion. J Pharm Sci. 1977 Dec;66(12):1670-4. [PubMed:925927 ]