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HCID 3739Erstellt: 1. November 2026

Adipiodon

adipiodon · bilignost · ADIPIODONE · biligrafin · cholospect · transbilix · Iodipamide · cholografin

https://huagongshe.com/de/chemical/3739

Molekülstruktur von Adipiodon

Identifikatoren & physikalische Daten

CAS No.606-17-7
SummenformelC20H14I6N2O6
Durchschnittliche Molmasse1.139,8 g/mol
Monoisotopische Masse1.139,512 g/mol
SMILESO=C(CCCCC(=O)Nc1c(I)cc(I)c(C(=O)O)c1I)Nc1c(I)cc(I)c(C(=O)O)c1I
InChIKeyFFINMCNLQNTKLU-UHFFFAOYSA-N
PubChem CID3739
ChEMBLCHEMBL1165268
ChEBICHEBI:31176
EC No.210-105-5
DTXSIDDTXSID6023153
Lokaler NameAdipiodon

Chemische & physikalische Eigenschaften

XLogP5,5
Polarare Oberfläche (TPSA)133
H-Brücken-Donoren4
H-Brücken-Akzeptoren6
Frei drehbare Bindungen9
Schwere Atome34
Formalladung0
Komplexität714
pHpH of saturated solution is 3.5-5.9
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
GeruchNearly odorless
Color/FormCrystalsWhite, crystalline powder
LöslichkeitIn water, 4.036X10-4 mg/L at 20 °CInsoluble in waterSolubility at 20 °C: methanol 0.8%ethanol 0.3%acetone 0.2%ether 0.1%Very slightly soluble in chloroform3.06e-03 g/LDMSO (Slightly), Methanol (Very Slightly)0.46g/L(20 ºC)
Human DrugsBreast FeedingLactationMilk, HumanContrast MediaDiagnostic Agents
Schmelzpunkt306-308306-308 °C307 °C306-308°C (dec.)
BrechungsindexIndex of refraction = 1.3294 at 21.5 °C/D (c = 0.445 in methanol)nD21.5 1.3294 (c = 0.445 in methanol)
Physical DescriptionSolid
Stability/Shelf LifeIn the event that crystallization occurs, the solution may be clarified by placing the vial in hot water and shaking gently for several minutes or until the solids redissolve. If cloudiness persists, discard the preparation. Allow the solution to cool to body temperature before administering.
Collision Cross Section237.94 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Siedepunkt908.6±65.0 °C(Predicted)
Dichte2.5848 (estimate)
LagerbedingungenRoom Temperature
pKa (Säurekonstante)pKa 3.5(H2O) (Uncertain)
AggregatzustandSolid
FarbeWhite
Merck5022
Hauptanwendungenpharmaceutical (small molecule)
InChIKeyFFINMCNLQNTKLU-UHFFFAOYSA-N
SMILESOC(=O)c1c(I)cc(I)c(NC(=O)CCCCC(=O)Nc2c(I)cc(I)c(C(O)=O)c2I)c1I
EPA chemische InformationenBenzoic acid, 3,3'-[(1,6-dioxo-1,6-hexanediyl)diimino]bis[2,4,6-triiodo- (606-17-7)

Sicherheit & Vorschriften

GHS-EinstufungWarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including iodipamide meglumine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Iodipamide meglumine/
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Hazardous Reactivities and IncompatibilitiesDiphenhydramine hydrochloride (Benadryl) and meglumine iodipamide (Cholografin) were mixed in varying proportions and found to consistently form a dense amorphous precipitate.
BrandbekämpfungsverfahrenAs with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.
LagerbedingungenProtect from lightstore at 20-25 °C (68-77 °F)avoid excessive heat.Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.
ReinigungsverfahrenWear approved respiratory protection, chemically compatible gloves, and protective clothing. Wipe up spillage or collect spillage using a high-efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

Anwendungen & Verwendung

Verwenden

Diagnostic aid (radiopaque medium-cholecystographic).

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Preventive MeasuresAs a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Clean equipment and work surfaces with suitable detergent or solvent after use. After removing gloves, wash hands and other exposed skin thoroughly.As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
Personal Protective Equipment (PPE)Respiratory Protection: Where respirators are deemed necessary to reduce or control occupational exposures, use NIOSH-approved respiratory protection and have an effective respirator program in place. Gloves: Chemically compatible. For handling solutions, ensure that the glove material is protective against the solvent being used. Use handling practices that minimize direct hand contact. Employees who are sensitive to natural rubber (latex) should use nitrile or other synthetic nonlatex gloves. Use of powdered latex gloves should be avoided due to the risk of latex allergy. Eye Protection: Safety glasses with sideshields are recommended. Face shields or goggles may be required if splash potential exists or if corrosive materials are present. Approved eye protection (e.g., bearing the ANSI Z87 or CSA stamp) is preferred. Maintain eyewash facilities in the work area. Protective clothing: For handling of laboratory scale quantities, a cloth lab coat is recommended. Where significant quantities are handled, work clothing may be necessary to prevent take-home contamination.Airborne exposure should be controlled primarily by engineering controls such as general dilution ventilation, local exhaust ventilation, or process enclosure. Local exhaust ventilation is generally preferred to general exhaust because it can control the contaminant at its source, preventing dispersion into the work area. An industrial hygiene survey involving air monitoring may be used to determine the effectiveness of engineering controls. Effectiveness of engineering controls intended for use with highly potent materials should be assessed by use of nontoxic surrogate materials. Local exhaust ventilation such as a laboratory fume hood or other vented enclosure is recommended, particularly for grinding, crushing, weighing, or other dust-generating procedures.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+4(SRC), determined from a structure estimation method(2), indicates that iodipamide is expected to be immobile in soil(SRC). However, the estimated pKa of iodipamide is 1.44(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Iodipamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-24 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Iodinated X-ray contrast agents are considered nondegradable by microorganisms(6).AQUATIC FATE: Iodipamide is not expected to adsorb to suspended solids and sediment based upon anionic nature of this compound. The estimated pKa of iodipamide is 1.44(1), indicating that this compound will exist primarily as an anion in the aqueous environment and anions do not volatilize from water. According to a classification scheme(2), an estimated BCF of 10(SRC), from an estimated log Kow of 5.16(3) and a regression-derived equation(4), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Iodinated X-ray contrast agents are considered nondegradable by microorganisms(5).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), iodipamide, which has an estimated vapor pressure of 1.1X10-24 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase iodipamide may be removed from the air by wet or dry deposition(SRC). Iodipamide does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of iodipamide can be estimated to be 1.4X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that iodipamide is expected to be immobile in soil. The estimated pKa of iodipamide is 1.13(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Serious adverse reactions have been reported due to the inadvertent intrathecal administration of iodinated contrast media that are not indicated for intrathecal use. These serious adverse reactions include: death, convulsions, cerebral hemorrhage, coma, paralysis, arachnoiditis, acute renal failure, cardiac arrest, seizures, rhabdomyolysis, hyperthermia, and brain edema. Special attention must be given to insure that this drug product is not inadvertently administered intrathecally./CASE REPORTS/ A 73 year old patient with a chronic cholangitis developed protracted anaphylactic shock after intravenous injection of methylglucamine iodipamide. The post-mortem examinations showed no evidence for septicemia. Although endotoxin-shock cannot be completely excluded, the most likely cause of death was an allergic reaction./CASE REPORTS/ There have been only two reports of severe hepatotoxic reaction caused by meglumine iodipamide. Lately we experienced such a reaction in an 66-year old female with chronic intrahepatic cholestasis. After drip infusion cholangiography was performed by infusing 40 ml. of 50% meglumine iodipamide (Biligrafin) intravenously, the patient developed nausea and abdominal pain. Her serum transaminase rose to more than 2,000 K-A units on the third day and gradually returned to normal by the 18th day. The macrophage migration inhibition test of her blood was positive for meglumine iodipamide. Accordingly some delayed type of hypersensitivity in the above reaction could be considered. When a larger amount than a recommended dose of meglumine iodipamide is infused in cholangiography, a severe hepatotoxic reaction might be induced, especially in icteric cases./CASE REPORTS/ Linear densities which were thought to represent meglumine iodipamide were seen in the renal papillary tubules of three patients for respectively four, six and nine days following intravenous cholangiography (IVC). All three patients were children with hepato-biliary disease. Two patients had biliary roundworm infestation, and one patient had hepatic dysfunction and intestinal ascariasis with possible biliary involvement. Haematuria and renal enlargement were seen in one patient, but the cholangiogram was not conclusively implicated as a cause. This renal tubular "sludging" of biliary contrast medium is recorded because of its potential nephrotoxic significance. The possible causes are discussed./CASE REPORTS/ Two cases of meglumine iodipamide (Cholografin) hepatotoxicity were confirmed by liver biopsy. The hepatic lesion was centrilobular in location and resolved within a short period of time. Nausea and vomiting commonly reported after intravenous cholangiography may be clinical manifestations of this entity.
Artificial Pollution SourcesIodipamide's production and use as a diagnostic contrast(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationPURE CULTURE: Iodinated X-ray contrast agents are considered nondegradable by microorganisms(1,2). However when incubated with 1 mM iodipamide at 30 °C for 32 days, the fungus Trametes versicolor has been shown to partially diiodinate C-14 ring-labeled iodipamide but the iodide release was a very small amount of that calculated for complete deiodination(1).
Environmental BioconcentrationAn estimated BCF of 10 was calculated in fish for iodipamide(SRC), using an estimated log Kow of 5.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/SoilThe estimated pKa of iodipamide is 1.44(1), indicating that this compound will primarily exist as an anion in the aqueous environment and anions do not volatilize from water or moist soil surfaces. Iodipamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-24 mm Hg(SRC), determined from a fragment constant method(2).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ...The present study was designed to assess the hepatotoxic potential of this drug in rats. Iodipamide administered intraperitoneally or intravenously caused a characteristic type of necrosis which began in the midzonal area and spread to the centrilobular region. Only rats weighing 400 g or more developed necrosis when the dose administered was 2 mmol/kg. Rats weighing 200 g failed to develop liver necrosis even when given 3 mmol/kg. Selenium deficiency and pretreatment with 3-methylcholanthrene protected against liver necrosis due to iodipamide. Phenobarbital pretreatment provided little or no protection. Kidney tubular necrosis was also observed but occurred in young rats and in selenium-deficient rats which developed no liver necrosis. These results indicate that iodipamide is a hepatotoxin in rats. There are a number of factors, age being the most striking, that modify its hepatotoxicity.
Populations at Special RiskFDA Pregnancy Risk Category: D /POSITIVE EVIDENCE OF RISK. Studies in humans, or investigational or post-marketing data, have demonstrated fetal risk. Nevertheless, potential benefits from the use of the drug may outweigh the potential risk. For example, the drug may be acceptable if needed in a life-threatening situation or serious disease for which safer drugs cannot be used or are ineffective./Administration of radiopaque materials to patients known or suspected to have pheochromocytoma should be performed with extreme caution. ...... It is also contraindicated in patients with concomitant severe impairment of renal and liver function.Contrast media have been shown to promote the phenomenon of sickling in individuals who are homozygous for sickle cell disease when the material is injected intravenously or intra-arterially.
Environmental Abiotic DegradationIodated diagnostic contrast agents such as iodipamide are very persistent in aquatic environments(1). Iodipamide is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Iodipamide does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
Probable Routes of Human ExposureOccupational exposure to iodipamide may occur through dermal contact with this compound at workplaces where iodipamide is produced or used. Use data indicate that limited general population exposure to iodipamide will be via administration of pharmaceutical products containing iodipamide. (SRC)
Environmental Water ConcentrationsWhile data specific to iodipamide were not located(SRC, 2012), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2).
Wassergefährdungsklasse (WGK)3
Zollcode2924296000
RTECS-Nr.DG0949500
ToxizitätLD50 in mice, rats (mg/kg): 2380 ±290, 4430 ±310 i.v. (Rosenberg)
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten606-17-7(Hazardous Substances Data)