Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > Iopamidol

Iopamidol

pharmaceutical raw materials
Iopamidol structure

Iopamidol 

structure
  • CAS No:

    60166-93-0

  • Formula:

    C17H22I3N3O8

  • Chemical Name:

    Iopamidol

  • Synonyms:

    1,3-Benzenedicarboxamide,N1,N3-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo-;1,3-Benzenedicarboxamide,N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-,(S)-;1,3-Benzenedicarboxamide,N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo-;N1,N3-Bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxamide;Iopamidol;B 15000;Solutrast 370;Solutrast;Niopam;Niopam 300;Iopamiro;Iopamidol 300;Isovue;Jopamiron 200;Iopamiron;Isovue 370;Iopamiron 370;Iopamiron 300;Isovue 300;Iopamiro 370;Gastromiro;Oypalomin;Oypalomin 150;1-N,3-N-Bis(1,3-dihydroxypropan-2-yl)-5-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxamide

  • Categories:

    Active Pharmaceutical Ingredients  >  Diagnostic Agents

Description

Iopamidol (B-15000; SQ-13396) is a nonionic, low-osmolar iodinated contrast agent.


Iopamidol is a benzenedicarboxamide compound having N-substituted carbamoyl groups at the 1- and 3-positions, iodo substituents at the 2-, 4- and 6-positions and a (2S)-2-hydroxypropanamido group at the 5-position. It has a role as a radioopaque medium, an environmental contaminant and a xenobiotic. It is a benzenedicarboxamide, an organoiodine compound and a pentol.|Iopamidol is a contrast agent developed by Bracco with nonionic, low-osmolar properties.|Iopamidol is a Radiographic Contrast Agent. The mechanism of action of iopamidol is as a X-Ray Contrast Activity.|Iopamidol is an organic iodine compound and used as a non-ionic water soluble radiographic contrast medium. Iopamidol blocks x-rays as they pass through the body, thereby allowing body structures not containing iodine to be visualized. The degree of opacity produced by iopamidol is directly proportional to the total amount of the iodinated contrast agent in the path of the x-rays. The visualization of body structures is dependent upon the distribution and elimination of iopamidol. (NCI05)|A non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiological procedures.

Iopamidol Basic Attributes

777.09

777.09

262-093-6

JR13W81H44

759636

DTXSID1023158

C47567

White crystalline powder

V - Various

2924299090

Characteristics

188

-2.4

1

2.3±0.1 g/cm3

>3200C (dec)

785.3°C at 760 mmHg

428.8±32.9 °C

1.739

Very soluble in methanol. Practically insoluble in chloroform. Miscible with boiling ethanol

-20°C Freezer

1.33X10-30 mm Hg at 25 deg C (est)

LD50 in mice, rats, rabbits, dogs (g/kg): 44.5, 28.2, 19.6, 34.7 i.v. (Felder); LD50 in mice (mg iodine/kg body wt): 21,800 i.v.; 20,000 i.p.; 1500 intracerebral (Felder, Pitre).

D20 -2.01° (c = 10 in water)

Odorless

Henry's Law constant = 1.14X10-25 atm-cu m/mol at 25 °C (est)

pKa = 10.70 (25 °C)

205.65 Ų [M-H]-

Physical properties of iopamidol in solution with hydrochloric acid and/or sodium hydroxide.

Safety Information

NONH for all modes of transport

SRP: 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.|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.

Many radiopaque contrast agents are incompatible in vitro with some antihistamines and many other drugs; therefore, no other pharmaceuticals should be admixed with contrast agents.

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including iopamidol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

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.

As 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.

Wear 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.

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.|As 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.

Iopamidol was detected at a concentration of approximately 4000 ng/L in an industrial waste water of the Netherlands in 2002. Total riverine discharge was estimated at 8.841 tons/yr in 2002(1). The compound was present at concentrations of 4.2, 11.1, 4, not detected, 4.2, 2.8, 0.6, and 1 ug/L in individual German municipal sewage treatment plants monitored from 1997 to 1998. The plants were associated with a city, 300,000 population equivalents, with 12 hospitals; 3 plants without hospitals, 20,000-40,000 population equivalents; 3 plants without hospitals, rural with >12,000 population equivalents; and one rural plant associated with a hospital. The median concentration reported in 25 German sewage treatment plants monitored from 1997-1998 was 0.66 ug/L; max of 15 ug/L, with 20 samples above the detection limit of 0.050 ug/L. The influent concentration reported for a plant close to Franfurt/Main was 5.3 ug/L and effluent 4.7 ug/L, indicating the compound is not removed by conventional treatment(2). Iopamidol was detected at a concentration of 2.1 ug/L in effluent from a conventional German waste water treatment plant serving a population equivalent of 285,000, sampled in December, 2009(3).

Toxicity

To determine if depression of creatinine clearance after administration of contrast medium may be prevented with theophylline. A nonionic, low-osmolality contrast medium (iopamidol) or an ionic, high-osmolality contrast medium (sodium diatrizoate) was administered to 93 patients. Before the examination, these patients were given theophylline or a placebo orally. There were also 30 patients who received an adenosine-uptake inhibitor (dipyridamole). Creatinine clearance and urinary adenosine levels were measured before and after angiography. Creatinine clearance decreased 18% +/- 4 in the placebo-iopamidol group but did not decrease in the theophylline group; urinary adenosine increased 67% +/- 7. Creatinine clearance decreased 42% +/- 5 in the placebo-sodium diatrizoate group and decreased 24% +/- 3 in the theophylline group; urinary adenosine increased 119% +/- 8. In the dipyridamole group in which iopamidol was given, urinary adenosine increased 96% +/- 7 and creatinine clearance decreased 37% +/- 5. Intrarenal adenosine can be implicated in the pathogenesis of hypertonic contrast medium nephrotoxicity.|Complete thrombotic occlusion of the arterial blood flow in the upper extremity was produced after mixture of Isovue 370 (iopamidol) and papaverine hydrochloride during routine angiography. Bolus and then continuous infusion of urokinase failed to dissolve the thrombus. The patient required a surgical thrombectomy and recovered uneventfully. This case report demonstrates that caution should be exercised when Isovue 370 and papaverine are used in angiography.|Intrathecal administration of corticosteroids with iopamidol is contraindicated.[US Natl Inst Health; DailyMed. Current Medication Information for ISOVUE-M (iopamidol) injection, solution|In vitro studies with animal blood showed that many radiopaque contrast agents, including iopamidol, produced a slight depression of plasma coagulation factors including prothrombin time, partial thromboplastin time, and fibrinogen, as well as a slight tendency to cause platelet and/or red blood cell aggregation. Transitory changes may occur in red cell and leucocyte counts, serum calcium, serum creatinine, serum glutamic oxaloacetic transaminase (SGOT), and uric acid in urine; transient albuminuria may occur.|Renal toxicity has been reported in a few patients with liver dysfunction who were given oral cholecystographic agents followed by intravascular contrast agents. Administration of intravascular agents should therefore be postponed in any patient with a known or suspected hepatic or biliary disorder who has recently received a cholecystographic contrast agent.

LD50 Rat intraarterial 13,268 mg/kg|LD50 Rat intravenous 22,044 mg/kg|LD50 Mouse intracerebral 3 g/kg|LD50 Mouse intravenous 33 g/kg|For more Non-Human Toxicity Values (Complete) data for Iopamidol (8 total), please visit the HSDB record page.

Caution must be exercised in patients with severely impaired renal function, those with combined renal and hepatic disease, or anuria, particularly when larger doses are administered.|Radiopaque diagnostic contrast agents are potentially hazardous in patients with multiple myeloma or other paraproteinemia, particularly in those with therapeutically resistant anuria. Myeloma occurs most commonly in persons over age 40. Although neither the contrast agent nor dehydration has been proved separately to be the cause of anuria in myelomatous patients, it has been speculated that the combination of both may be causative. The risk in myelomatous patients is not a contraindication; however, special precautions are required.|Safety and effectiveness in children has been established in pediatric angiocardiography, computed tomography (head and body) and excretory urography. Pediatric patients at higher risk of experiencing adverse events during contrast medium administration may include those having asthma, a sensitivity to medication and/or allergens, cyanotic heart disease, congestive heart failure, a serum creatinine greater than 1.5 mg/dL or those less than 12 months of age.|Renal toxicity has been reported in a few patients with liver dysfunction who were given oral cholecystographic agents followed by intravascular contrast agents. Administration of intravascular agents should therefore be postponed in any patient with a known or suspected hepatic or biliary disorder who has recently received a cholecystographic contrast agent.|Contrast media may promote sickling in individuals who are homozygous for sickle cell disease when injected intravenously or intraarterially.

Iopamidol's production and use as a diagnostic contrast agent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that iopamidol is expected to have very high mobility in soil(SRC). Volatilization of iopamidol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-25 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Iopamidol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-30 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Iopamidol exhibited low biotransformation efficiency in a conventional waster water treatment plant(5), indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that iopamidol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-25 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -2.42(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Iopamidol exhibited low biotransformation efficiency in a conventional waster water treatment plant(7), indicating that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), iopamidol, which has an estimated vapor pressure of 1.3X10-30 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 iopamidol may be removed from the air by wet or dry deposition(SRC). Iopamidol contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Iopamidol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Iopamidol contains chromophores that absorb at wavelengths >290 nm(1) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for iopamidol(SRC), using a log Kow of -2.42(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).

The Koc of iopamidol is estimated as 10(SRC), using a log Kow of -2.42(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that iopamidol is expected to have very high mobility in soil.

The Henry's Law constant for iopamidol is estimated as 1.1X10-25 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that iopamidol is expected to be essentially nonvolatile from water surfaces(2). Iopamidol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-30 mm Hg(SRC), determined from a fragment constant method(3).

GROUNDWATER: Iopamidol was detected at 5 of 5 groundwater sites collected from Hessian Reid, Germany. The median concentration in 17 samples was 0.16 ug/L; max of 2.4 ug/L, with 13 samples above the detection limit of 0.010 ug/L(1). The compound was detected at a concentration of 0.60 ug/L in groundwater samples from three riverbank wells close to the Rhine River at Urmitz, Germany, sampled on November 18, 2009(2).|DRINKING WATER: It has been suggested that in all countries with an advanced medical care system, x-ray contrast media can be expected to be present in sewage effluent which, therefore, leads to potential contamination of receiving waters(1). Iopamidol was detected at a concentrations ranging from 6.5 to 272 ng/L in finished drinking water samples from four drinking water treatment plants in Germany(2).|SURFACE WATER: Iopamidol concentrations in surface water of the Netherlands between 1996 and 2005 ranged from approximately 10 to 300 ng/L with an outlier at 500 ng/L(1). The median concentration reported in 25 German rivers and creeks monitored from 1997-1998 was 0.49 ug/L; max of 2.8 ug/L, with 24 samples above the detection limit of 0.010 ug/L(2). The compound was reported at median concentrations of 210 upstream of a sewage treatment plant at Ulm/Boefingen and 210 ng/L downstream at Leipheim (maximum of 470 and 520 ug/L, respectively) both located on the River Danube in South Germany, sampling conducted in 2004(3). The compound was detected at a concentration of 0.30 ug/L in groundwater samples from the Rhine River at Koblenz, Germany sampled on November 18, 2009(4).

Occupational exposure to iopamidol may occur through dermal contact with this compound at workplaces where iopamidol is produced or used. Monitoring data indicate that the general population may be exposed to iopamidol via ingestion of drinking water. (SRC)

Drug Information

FDA Label

/EXPERIMENTAL THER:/ Meconium obstruction of prematurity (MO) often occurs in extremely low-birth weight (ELBW) infants, and its treatment is quite a challenge for neonatologists. /Investigators/ attempted to establish a method of primary treatment for MO of prematurity in ELBW infants. An iopamidol enema with 50 cm H2O static pressure was performed as the primary treatment. This procedure is safe and effective and /was recommended/ as the first treatment for MO in ELBW infants. The procedure was performed 50 times in 23 infants and no complications occurred. Out of 23 patients, 20 (88%) improved, but the other 3 did not. In the failure group, the procedure was performed on a significantly later date and the mortality rate was higher (12.5 vs. 67%). This procedure is safe and effective. /The authors/ recommend this as the first treatment for MO in ELBW infants.|/EXPERIMENTAL THER:/ ... Ninety mice used in this study were divided into three groups: lipiodol, iopamidol, and normal saline. The test compounds were given by submucosal injection to the gastric wall of anesthetized mice. The specimens were subjected to histopathological examination. The mean grades of acute inflammatory response after iopamidol and lipiodol injection were significantly higher than control group. However, there was no significant difference between iopamidol and lipiodol injection. The mean grade of chronic inflammatory response and fibrosis showed no differences between groups. The presence or absence of fibrinoid necrosis and mesothelial hyperplasia showed no statistical differences at each time point between groups. The foam cell, which is similar to human signet ring cell carcinoma, were not identified in normal saline and iopamidol group, but were detected by postoperative day 7 in lipiodol group. /It was concluded/ that iopamidol and lipiodol when used as a contrast media of CT lymphography is an available material for preoperative sentinel node navigation surgery for gastric cancer with an acceptable incidence of pathological alterations in a mouse model. /The/ results are potentially useful to clinical (human) application.|Hematomas and intraparenchymal bleeders seldom demonstrate any contrast enhancement. However, in cases of intraparenchymal clot, for which there is no obvious clinical explanation, contrast media administration may be helpful in ruling out the possibility of associated arteriovenous malformation. /Included in US product label/|Arteriovenous malformations and aneurysms will show contrast enhancement. For these vascular lesions, the enhancement is probably dependent on the iodine content of the circulating blood pool. /Included in US product label/|For more Therapeutic Uses (Complete) data for Iopamidol (9 total), please visit the HSDB record page.

Focal and generalized motor seizures have been reported after intrathecal use of water-soluble contrast agents including iopamidol. In several of those cases reported with iopamidol, higher than recommended doses were employed. Therefore avoid: deviations from recommended neuroradiologic procedure or patient management; use in patients with a history of epilepsy unless medically justified; overdosage; intracranial entry of a bolus or premature diffusion of a high concentration of the medium; failure to maintain elevation of the head during the procedure, on the stretcher, and in bed; excessive and particularly active patient movement or straining.[US Natl Inst Health; DailyMed. Current Medication Information for ISOVUE-M (iopamidol) injection, solution|FDA Pregnancy risk category B: NO EVIDENCE OF RISK IN HUMANS. Adequate, well controlled studies in pregnant women have not shown increased risk of fetal abnormalities despite adverse findings in animals, or, in the absents of adequate human studies, animal studies show no fetal risk. The chance of fetal harm is remote but remains a possibility.|Use of medications that may lower the seizure threshold (phenothiazine derivatives, including those used for their antihistaminic properties; tricyclic antidepressants; MAO inhibitors; CNS stimulants; analeptics; antipsychotic agents) should be carefully evaluated. While the contributory role of such medications has not been established, some physicians have discontinued these agents at least 48 hours before and for at least 24 hours following intrathecal use.[US Natl Inst Health; DailyMed. Current Medication Information for ISOVUE-M (iopamidol) injection, solution|Direct intracisternal or ventricular administration for standard radiography (without computerized tomographic enhancement) is not recommended. Inadvertent intracranial entry of a large or concentrated bolus of the contrast medium, which increases the risk of neurotoxicity, can be prevented by careful patient management. Also, effort should be directed to avoid rapid dispersion of the medium causing inadvertent rise to intracranial levels (e.g., by active patient movement). If such intracranial entry of the medium occurs, prophylactic anticonvulsant treatment with diazepam or barbiturates orally for 24 to 48 hours should be considered.[US Natl Inst Health; DailyMed. Current Medication Information for ISOVUE-M (iopamidol) injection, solution|For more Drug Warnings (Complete) data for Iopamidol (37 total), please visit the HSDB record page.

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

Radiographic contrast media (CM) induce renal vasoconstriction and may initiate induced nephropathy. Endothelin (ET), a vasoconstrictor, and nitric oxide (NO), a vasodilator, which are synthesized in the kidney by the vascular endothelium as well as by tubular epithelial and glomerular mesangial cells, are key modulators of renal circulation after CM administration. Intravascular CM, in addition, induces pronounced diuresis and natriuresis. The aim of the present study was to evaluate and compare changes in endogenous vasoactive mediators and contrast-induced natriuresis after CM administration. Diagnostic angiographic procedures were performed in 14 patients (9 males and 5 females) using the non-ionic CM Iopamidol. Before and immediately after angiography, venous blood and urine samples were obtained. The urinary excretion of ET-1 and nitrates/nitrites (NOx), and the fractional excretion of sodium (FENa) were measured and analyzed. The urinary excretion of both ET-1 and NOx increased significantly (p < 0.05) after angiography, and urinary ET-1 and NOx excretion was correlated with an increase in FENa (p < 0.05). Exposure to CM in humans is associated with an increase in urinary ET and NOx. The excretion of sodium following CM administration is associated with an increase in urinary ET and NOx. ET and NO might be important in the renal change in humans after CM administration.|No iodinated compound other than Iopamidol was found in the urine of subjects who received intrathecal injection of 10 mL of Iopamiro "300". The compound was neither metabolized nor altered in its optical configuration and urinary iodide content was always in the normal range. Between 72 and 85% of injected Iopamidol was excreted within 72 h of injection.|It is not known whether this drug is excreted in human milk.|The pharmacokinetics of iopamidol in both normal and abnormal tissue have been shown to be variable. Contrast enhancement appears to be greatest soon after administration of the contrast medium, and following intraarterial rather than intravenous administration. ...|For more Absorption, Distribution and Excretion (Complete) data for Iopamidol (8 total), please visit the HSDB record page.

No significant metabolism, deiodination, or biotransformation occurs.

The pharmacokinetics of iopamidol 370 (Iopamiro), a non-ionic water soluble organic iodine compound, were studied in adults with different degrees of chronic renal failure and in healthy volunteers. After 50 mL were administered i.v., plasma and urine levels were determined. The main pharmacokinetic parameters were calculated on the basis of bi-compartmental open model. There were significant differences from healthy volunteers in half-life beta, which increased with the degree of renal failure as the clearance values decreased. Half-life beta was equal to 1.67 h in healthy volunteers, 4.24 h in patients with mild renal failure and 10.03 h in patients with severe renal failure. The clearance decreased as follows: 0.11 (L/h kg) in healthy volunteers, 0.06 (L/h kg) in patients with mild renal failure and 0.02 (L/h kg) in patients with severe renal failure. No significant differences were found in distribution volume values nor in half-life alpha.|The pharmacokinetics of intravenously administered iopamidol in normal subjects conform to an open two-compartment model with first order elimination (a rapid alpha phase for drug distribution and a slow beta phase for drug elimination). The elimination serum or plasma half-life is approximately two hours; the half-life is not dose dependent.

To test the hypothesis that iodinated contrast media may induce an elevation in serum potassium level, /contrast media was administered to rabbits and tested in-vitro according to four protocols./ Protocol A: After intravenous infusion of contrast media into six rabbits, alterations of potassium ion concentrations were measured. Protocol B: Fresh rabbit blood was mixed in vitro with contrast media, and the fluctuations in potassium were monitored over a 30-minute period. Protocol C: Similar to protocol B, except that blood from humans with no reaction to contrast media was used. For protocol A, blood potassium levels increased above baseline levels. The elevations were statistically significant (P < .05). For protocol B, diatrizoate and ioxaglate caused a gradual increase in blood potassium levels, but iopamidol did not. In protocol C, all three contrast media caused statistically significant elevation in potassium levels. The release of potassium was statistically significant at 5 minutes (P < .05 for diatrizoate and ioxaglate, and P < .01 for iopamidol). The mean release rates (+/- standard deviation) by means of linear regression analysis were 0.0190 mmol/min +/- 0.0112 with diatrizoate, 0.0159 mmol/min +/- 0.0057 with iopamidol, and 0.0088 mmol/min +/- 0.0033 with ioxaglate. Iodinated contrast media increase blood potassium levels causing release of potassium into intravascular spaces. This potassium release may play some role in contrast medium-induced adverse reactions.|The synthesis of prostaglandins and other metabolic products of arachidonic acid (AA) was investigated in isolated perfused lungs of hamsters during the infusion of various concentrations of meglumine diatrizoate and iopamidol. Forty nmol of (14)C-AA was infused into the pulmonary circulation with radiographic contrast media (RCM), and prostaglandins, thromboxanes, and metabolites of lipoxygenases were analyzed from the nonrecirculating perfusion effluent. Arachidonate infusion increased the perfusion pressure. This pressor response was decreased by iopamidol ... The amount of radioactivity was decreased in the perfusion effluent and increased in lung lipids by iopamidol. ... Almost all arachidonate metabolites were decreased significantly by iopamidol when compared with hypertonic saline ...

Treatment of an overdose of an injectable radiopaque contrast medium is directed toward the support of all vital functions, and prompt institution of symptomatic therapy.[US Natl Inst Health; DailyMed. Current Medication Information for ISOVUE-M (iopamidol) injection, solution|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/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, 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.|/SIGNS AND SYMPTOMS/ ... /Investigators/ report a patient in whom infiltrated erythema of the face and generalized maculopapular rashes occurred on 2 occasions, within 1 day, following the use of the X-ray contrast medium Solutrast (iopamidol) for coronary angiography. ... /There was/ a concomitant cross-reactivity to the contrast media iopromid and iomeprol. ...|/CASE REPORTS/ ... /Investigators/ report a case of permanent sensorineural deafness after abdominal aortic angiography with iopamidol in a woman with end-stage renal disease on hemodialysis therapy ...|/CASE REPORTS/ Iopamidol, a water-soluble contrast agent, has been rarely associated with seizures. /Investigators/ describe a case of generalized tonic-clonic seizure after cervical myelography with iopamidol in a previously healthy young man. In patients presenting with seizures, a history of recent myelography should be considered as an etiology. Iopamidol myelography may be associated with a risk of seizures. Clinicians need to be aware of this complication and inform their patients about such risk.|For more Human Toxicity Excerpts (Complete) data for Iopamidol (21 total), please visit the HSDB record page.

B 15,000

Iopamidol Use and Manufacturing

Methods of Manufacturing

680 g of S-(-)-5-((2-acetyloxy)-1-oxopropyl)amino)-2, 4, 6-triiodo-1, 3-benzendicarboxylic acid dichloride (prepared as described in WO 96/37460) are dissolved in 1360 g of dimethylacetamide at room temperature and after cooling at 15°C [Solution A ]. 181 g of 2-ammino-1, 3-propanediol purified with the method described in the previous are dissolved in 1360 g of dimethylacetamide and added to the solution A in one hour at 8-15°C whilst stirring. The reaction is completed after ten hours at room temperature. The reaction mixture is concentrated at 100°C at 10 mbar until 98percent of the solvent is distilled. 1700 g of water are added to the residue and the solution is purified using the method described in WO 97/30735.Yield on dry Iopamidol: 94percent Contents of by-products determined with HPLC method (according to the method described in USP XXIII-NF, 1996, V°suppl.) = 0.11percent The by-product N-[2-hydroxy-1-(hydroxymethyl)ethyl]-- N'-(2, 3-dihydroxypropyl)-5-(2-hydroxy-1-oxopropyl)-2, 4, 6-triiodo-1, 3-benzenedicarboxamide, coming from isoserinol, is under the detection limit. No presence of other by-products derived from 3-amino-1, 2-propanediol are detected (see as ref. Pharmeuropa, 6, 343-345, 19949.

Uses

Iopamidol, also known as iodoisopeptidol, iodopentaol, iopermitol, iopira, iodopydo, and iodomethasone, is a non-ionic water-soluble contrast agent, which is used for imaging diagnostics. Its chemical structure is The amide compound of triiodoisophthalic acid derivative has low toxicity to blood vessel wall and neurotoxicity, good local and systemic tolerance, low osmotic pressure, low viscosity, good contrast, stable injection, and very little deiodination in the body. It is suitable for Myelography and use in patients with high risk factors for contrast agent reaction. After intravascular injection of iopamidol, it is mainly excreted through the kidneys.

ISOVUE 200 (iopamidol) injection, solution ISOVUE 250 (iopamidol) injection, solution ISOVUE 300 (iopamidol) injection, solution ISOVUE 370 (iopamidol) injection, solution

Analyte: Iopamidol; matrix: blood, urine; procedure: high performance liquid chromatography with ultraviolet detection at 242 nm|Analyte: Iopamidol; matrix: blood, tissue; procedure: high performance liquid chromatography with ultraviolet detection at 254 nm; limit of detection: 640 ng/mL|Analyte: Iopamidol; matrix: solutions; procedure: capillary electrophoresis with ultraviolet detection at 214 nm|Analyte: Iopamidol; matrix: solutions; procedure: capillary electrophoresis with ultraviolet detection at 245 nm|Analyte: Iopamidol; matrix: blood; procedure: capillary electrophoresis with ultraviolet detection at 254 nm; limit of detection: 5 ug/mL

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:777.1
XLogP3:-2.4
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:10
Exact Mass:776.8541
Monoisotopic Mass:776.8541
Topological Polar Surface Area:188
Heavy Atom Count:31
Complexity:583
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a non-ionic water-soluble contrast agent with low toxicity to blood vessel walls and nerves, good local and systemic tolerance, low osmotic pressure, stable injection, and little deiodination in the body. It is suitable for myelography and patients with high risk factors for contrast agent reaction.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • BRACCO IMAGING SPA

    France France
    Active
  • Bracco Imaging Medical Technologies (Shanghai) Co., Ltd.

    China China
    Active
  • Zhejiang Hichi Pharmaceutical Corporation Limited

    China China
    Active

Recommended Suppliers of Iopamidol

  • China CN

    4 YRS

    Business licensed Certified factory
    Manufactory Supplier of Chemical Pesticides,Food Additives,Agrochemicals,Active Pharm Ingredients,Flavors and Fragrances,Chemical Catalyst,Chemical Materials,Chem&Pharm Intermediates,Organic Intermediates,Feed Additive
    CAS No.: 60166-93-0
    Grade: Industrial Grade
    Content: 99.0%
    Inquiry
  • China CN

    5 YRS

    Business licensed
    Trader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives
    CAS No.: 60166-93-0
    Content: 99.00%
    Inquiry

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.