Identification
- Summary
Iodipamide is a contrast agent used in cholangiography and cholecystography.
- Generic Name
- Iodipamide
- DrugBank Accession Number
- DB04711
- Background
Iodipamide is a water-soluble radiographic contrast media for cholecystography and intravenous cholangiography.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Iodipamide (DB04711)
- Weight
- Average: 1139.7618
Monoisotopic: 1139.51199671 - Chemical Formula
- C20H14I6N2O6
- Synonyms
- 3,3'-(adipoyldiimino)bis(2,4,6-triiodobenzoic acid)
- Adipiodona
- Adipiodone
- Adipiodonum
- Iodipamide
Pharmacology
- Indication
Iodipamide is used as a contrast agent for cholecystography and intravenous cholangiography.
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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
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAldesleukin The risk of a hypersensitivity reaction to Iodipamide is increased when it is combined with Aldesleukin. Metformin The risk or severity of adverse effects can be increased when Iodipamide is combined with Metformin. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Iodipamide meglumine X064O0Y1A4 3521-84-4 DGIAUNUPXILTJW-VRWDCWMNSA-N Iodipamide sodium 3J6WZA9PXS 2618-26-0 SIZXNBZGPPPFHM-UHFFFAOYSA-L - International/Other Brands
- Biligrafin (Schering)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cholografin Meglumine Injection, solution 520 mg/1mL Intravenous Bracco Diagnostics, Inc 1955-07-09 2015-04-01 US 
Cholografin Meglumine Inj Liquid 52 % Intravenous Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc. 1960-12-31 1997-08-14 Canada 
Cholografin Meglumine Inj. - Liq IV Liquid 52 % Intravenous Bracco Imaging S.P.A. 1998-07-31 2018-01-12 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Sinografin Iodipamide meglumine (26.9 %) + Diatrizoate meglumine (52.7 %) Liquid Intrauterine Squibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc. 1966-12-31 1997-08-14 Canada Sinografin Iodipamide meglumine (268 mg/1mL) + Diatrizoate meglumine (527 mg/1mL) Injection, solution Intrauterine Bracco Diagnostics, Inc 1958-12-02 2016-10-31 US Sinografin - Liq Iu Iodipamide meglumine (26.9 %) + Diatrizoate meglumine (52.7 %) Liquid Intrauterine Bracco Imaging S.P.A. 1998-01-08 2018-01-12 Canada
Categories
- ATC Codes
- V08AC04 — Adipiodone
- Drug Categories
- Acids, Carbocyclic
- Benzene Derivatives
- Benzoates
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Iodinated Contrast Agents
- Iodobenzoates
- Radiographic Contrast Agent
- Roentgenography
- Triiodobenzoic Acids
- Watersoluble, Hepatotropic X-Ray Contrast Media
- X-Ray Contrast Activity
- X-Ray Contrast Media, Iodinated
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-carboxy-2-haloaromatic compound / 2-halobenzoic acid / 2-halobenzoic acid or derivatives / 4-halobenzoic acid / 4-halobenzoic acid or derivatives / Acylaminobenzoic acid or derivatives / Anilide / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide show 25 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- TKQ858A3VW
- CAS number
- 606-17-7
- 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
References
- Synthesis Reference
U.S. Patent 2,776,241.
- General References
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015581
- KEGG Drug
- D01774
- PubChem Compound
- 3739
- PubChem Substance
- 46507320
- ChemSpider
- 3608
- 5936
- ChEBI
- 31176
- ChEMBL
- CHEMBL1165268
- Therapeutic Targets Database
- DAP001226
- PharmGKB
- PA164745532
- PDBe Ligand
- IDB
- Wikipedia
- Adipiodone
- PDB Entries
- 2bxn
- MSDS
- Download (16.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bracco Diagnostics Inc.
- Dosage Forms
Form Route Strength Injection, solution Intravenous 520 mg/1mL Liquid Intravenous 52 % Injection, solution Intrauterine Liquid Intrauterine - Prices
Unit description Cost Unit 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
Property Value Source melting point (°C) 306-308 U.S. Patent 2,776,241. water solubility 460 mg/L (at 20 °C) BEILSTEIN - Predicted Properties
Property Value Source Water Solubility 0.00306 mg/mL ALOGPS logP 3.42 ALOGPS logP 8.25 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 2.03 Chemaxon pKa (Strongest Basic) -3.4 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 132.8 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 183.98 m3·mol-1 Chemaxon Polarizability 69.72 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.907 Blood Brain Barrier + 0.9516 Caco-2 permeable - 0.6235 P-glycoprotein substrate Non-substrate 0.5953 P-glycoprotein inhibitor I Non-inhibitor 0.7827 P-glycoprotein inhibitor II Non-inhibitor 0.9661 Renal organic cation transporter Non-inhibitor 0.9106 CYP450 2C9 substrate Non-substrate 0.76 CYP450 2D6 substrate Non-substrate 0.8869 CYP450 3A4 substrate Non-substrate 0.5803 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9337 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7712 Ames test Non AMES toxic 0.8867 Carcinogenicity Non-carcinogens 0.8904 Biodegradation Not ready biodegradable 0.9789 Rat acute toxicity 2.1403 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9819 hERG inhibition (predictor II) Non-inhibitor 0.8177
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 224.7475812 predictedDarkChem Lite v0.1.0 [M-H]- 260.00327 predictedDeepCCS 1.0 (2019) [M+H]+ 225.7234812 predictedDarkChem Lite v0.1.0 [M+H]+ 262.3613 predictedDeepCCS 1.0 (2019) [M+Na]+ 225.3968812 predictedDarkChem Lite v0.1.0 [M+Na]+ 269.1317 predictedDeepCCS 1.0 (2019)
Carriers
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
Drug created at September 11, 2007 17:49 / Updated at April 23, 2024 11:38