Iodipamide

Identification

Name
Iodipamide
Accession Number
DB04711
Type
Small Molecule
Groups
Approved
Description

Iodipamide is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.

Structure
Thumb
Synonyms
  • 3,3'-(adipoyldiimino)bis(2,4,6-triiodobenzoic acid)
  • Adipiodona
  • Adipiodone
  • Adipiodonum
Product Ingredients
IngredientUNIICASInChI Key
Iodipamide meglumineX064O0Y1A43521-84-4DGIAUNUPXILTJW-VRWDCWMNSA-N
Iodipamide sodium3J6WZA9PXS2618-26-0SIZXNBZGPPPFHM-UHFFFAOYSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cholografin Meglumine InjLiquid52 %IntravenousSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1960-12-311997-08-14Canada
Cholografin Meglumine Inj. - Liq IVLiquid52 %IntravenousBracco Imaging S.P.A.1998-07-31Not applicableCanada
International/Other Brands
Biligrafin (Schering)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
SinografinIodipamide meglumine (26.9 %) + Diatrizoate meglumine (52.7 %)LiquidIntrauterineSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1966-12-311997-08-14Canada
SinografinIodipamide meglumine (268 mg/mL) + Diatrizoate meglumine (527 mg/mL)Injection, solutionIntrauterineBracco Diagnostics, Inc1958-12-02Not applicableUs
Sinografin - Liq IuIodipamide meglumine (26.9 %) + Diatrizoate meglumine (52.7 %)LiquidIntrauterineBracco Imaging S.P.A.1998-01-08Not applicableCanada
Categories
UNII
TKQ858A3VW
CAS number
606-17-7
Weight
Average: 1139.7618
Monoisotopic: 1139.51199671
Chemical Formula
C20H14I6N2O6
InChI Key
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

Pharmacology

Indication

Iodipamide is used as a contrast agent for cholecystography and intravenous cholangiography.

Structured Indications
Not Available
Pharmacodynamics

Following 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 action

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. 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.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Ionic 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AldesleukinThe risk of a hypersensitivity reaction to Iodipamide is increased when it is combined with Aldesleukin.Approved
MetforminThe risk or severity of adverse effects can be increased when Iodipamide is combined with Metformin.Approved
Food Interactions
Not 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
Human Metabolome Database
HMDB15581
KEGG Drug
D01774
PubChem Compound
3739
PubChem Substance
46507320
ChemSpider
3608
ChEBI
31176
ChEMBL
CHEMBL1165268
Therapeutic Targets Database
DAP001226
PharmGKB
PA164745532
HET
IDB
ATC Codes
V08AC04 — Adipiodone
AHFS Codes
  • 36:68.00 — Roentgenography
PDB Entries
2bxn
MSDS
Download (16.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous52 %
Injection, solutionIntrauterine
LiquidIntrauterine
Prices
Unit descriptionCostUnit
Cholografin meglumine 52%4.72USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)306-308U.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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylaminobenzoic acid and derivatives
Alternative Parents
2-halobenzoic acids / 4-halobenzoic acids / Halobenzoic acids / Anilides / Benzoic acids / 1-carboxy-2-haloaromatic compounds / N-arylamides / Benzoyl derivatives / Iodobenzenes / Aryl iodides
show 9 more
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
show 25 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not 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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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]

Drug created on September 11, 2007 11:49 / Updated on November 19, 2017 20:34