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Identification
NameIodipamide
Accession NumberDB04711
TypeSmall Molecule
GroupsApproved
DescriptionIodipamide is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography. [PubChem]
Structure
Thumb
Synonyms
Adipiodona
Adipiodone
Adipiodonum
Iodipamide
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BiligrafinSchering
Brand mixtures
NameLabellerIngredients
SinografinBRACCO DIAGNOSTICS INC
Salts
Name/CASStructureProperties
Iodipamide meglumine
ThumbNot applicableDBSALT001312
Iodipamide sodium
ThumbNot applicableDBSALT001407
Categories
UNIITKQ858A3VW
CAS number606-17-7
WeightAverage: 1139.7618
Monoisotopic: 1139.51199671
Chemical FormulaC20H14I6N2O6
InChI KeyInChIKey=FFINMCNLQNTKLU-UHFFFAOYSA-N
InChI
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)
IUPAC Name
3-{5-[(3-carboxy-2,4,6-triiodophenyl)carbamoyl]pentanamido}-2,4,6-triiodobenzoic acid
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • N-arylamide
  • Halobenzoic acid
  • 4-halobenzoic acid
  • 2-halobenzoic acid
  • Halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Iodobenzene
  • Halobenzene
  • Fatty acyl
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Aryl iodide
  • Aryl halide
  • Vinylogous halide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIodipamide is used as a contrast agent for cholecystography and intravenous cholangiography.
PharmacodynamicsFollowing intravenous administration of Cholografin Meglumine, iodipamide is carried to the liver where it is rapidly secreted. The contrast medium appears in the bile within 10 to 15 minutes after injection, thus permitting visualization of the hepatic and common bile ducts, even in cholecystectomized patients. The biliary ducts are readily visualized within about 25 minutes after administration, except in patients with impaired liver function. The gallbladder begins to fill within an hour after injection; maximum filling is reached after two to two and one-half hours. 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.
Mechanism of actionOrganic 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. 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityIonic radiocontrast agents like iodipamide are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress. Acute IV LD50 is 5000 mg/kg in rat, 3195 mg/kg in mouse, and 1200 mg/kg in dog.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.907
Blood Brain Barrier+0.9516
Caco-2 permeable-0.6235
P-glycoprotein substrateNon-substrate0.5953
P-glycoprotein inhibitor INon-inhibitor0.7827
P-glycoprotein inhibitor IINon-inhibitor0.9661
Renal organic cation transporterNon-inhibitor0.9106
CYP450 2C9 substrateNon-substrate0.76
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateNon-substrate0.5803
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9337
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7712
Ames testNon AMES toxic0.8867
CarcinogenicityNon-carcinogens0.8904
BiodegradationNot ready biodegradable0.9789
Rat acute toxicity2.1403 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9819
hERG inhibition (predictor II)Non-inhibitor0.8177
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintrauterine
Prices
Unit descriptionCostUnit
Cholografin meglumine 52%4.72USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point306-308U.S. Patent 2,776,241.
water solubility460 mg/L (at 20 °C)BEILSTEIN
Predicted Properties
PropertyValueSource
Water Solubility0.00306 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity183.98 m3·mol-1ChemAxon
Polarizability69.71 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
References
Synthesis Reference

U.S. Patent 2,776,241.

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 ]
External Links
ATC CodesV08AC04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (16.8 KB)
Interactions
Drug Interactions
Drug
AldesleukinThe risk of a hypersensitivity reaction to Iodipamide is increased when it is combined with Aldesleukin.
MetforminThe risk or severity of adverse effects can be increased when Iodipamide is combined with Metformin.
Food InteractionsNot Available

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Yamasaki K, Maruyama T, Kragh-Hansen U, Otagiri M: Characterization of site I on human serum albumin: concept about the structure of a drug binding site. Biochim Biophys Acta. 1996 Jul 18;1295(2):147-57. [PubMed:8695640 ]
  2. Zhang Q, Huang Y, Zhao R, Liu G, Chen Y: Determining binding sites of drugs on human serum albumin using FIA-QCM. Biosens Bioelectron. 2008 Sep 15;24(1):48-54. doi: 10.1016/j.bios.2008.03.009. Epub 2008 Mar 21. [PubMed:18436441 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. 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 ]
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Drug created on September 11, 2007 11:49 / Updated on August 17, 2016 12:24