Iopromide
Identification
- Summary
Iopromide is an X-ray contrast agent used during various types of imaging tests such as angiography and contrast computed tomography (CT) imaging tests.
- Brand Names
- Ultravist
- Generic Name
- Iopromide
- DrugBank Accession Number
- DB09156
- Background
Iopromide is a low osmolar, non-ionic X-ray contrast agent for intravascular administration. It functions as a contrast agent by opacifying blood vessels in the flow path of the contrast agent, permitting radiographic visualization of the internal structures until significant hemodilution occurs.1 Although iopromide can cause several serious adverse effects, including cardiac events, thromboembolism, hypersensitivity reaction, and even death if administered intrathecally inadvertently, it is still deemed to have a favorable safety profile, with only 0.7% of patients in a 2 years study experiencing adverse events.2 Although the mechanism is unclear, women and outpatients tend to have a higher incidence of adverse events compared to other population groups.2
Approved by the FDA in 1995 and Health Canada in 1994 under the brand name ULTRAVIST, iopromide is used in radiological diagnosis, including, but not limited to, intra-arterial digital subtraction angiography (IA-DSA), cerebral and peripheral arteriography, peripheral venography, excretory urography, brain computer tomography (CT), coronary arteriography, left ventriculography, visceral angiography, and orthography.3,6
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 791.1119
Monoisotopic: 790.869745019 - Chemical Formula
- C18H24I3N3O8
- Synonyms
- Iopromida
- Iopromide
- N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino]-N-methylisophthalamide
- External IDs
- ZK 35760
- ZK-35760
- ZK35760
Pharmacology
- Indication
Iopromide, as the product IOVIST, is approved by the FDA for use as an intra-arterial or intravenous X-ray contrast agent.3 For intra-arterial administration, iopromide is indicated for cerebral arteriography, peripheral arteriography, coronary arteriography, left ventriculography, visceral angiography, and aortography in adults and radiographic evaluation of cardiac chambers and related arteries in pediatric patients aged 2 years and older.3 For intravenous administration, iopromide is indicated for excretory urography in adults and pediatric patients aged 2 years and older, contrast Computed Tomography (CT) of the head and body (intrathoracic, intra-abdominal, and retroperitoneal regions) for the evaluation of neoplastic and non-neoplastic lesions in adults and pediatric patients aged 2 years and older, and contrast mammography to visualize known or suspected lesions of the breast in adults, as an adjunct following mammography and/or ultrasound.3
Iopromide is also approved by Health Canada as an intravascular contrasting agent, although the indications differ depending on the dosage. At 300 mg I/mL, iopromide is indicated for computed tomography (CT), excretory urography, pediatric excretory urography, renal arteriography, peripheral arteriography (bifemoral pelvis/leg), cerebral arteriography, phlebography of the extremities, and arthrography.6
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Diagnostic agent Breast lesions •••••••••••• ••••• ••••••••• Diagnostic agent Neoplastic lesion •••••••••••• •••••• ••••••••• ••••••••• Diagnostic agent Non-neoplastic lesion •••••••••••• •••••• ••••••••• ••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
After intravenous injection, opacification of the renal parenchyma begins within 1 minute. Excretion of the contrast agent becomes apparent in 1 to 3 minutes with optimal contrast in the calyces and collecting system occurring between 5 and 15 minutes. In nephropathic conditions, particularly when excretory capacity has been altered, the excretion rate varies unpredictably and opacification may be delayed for several hours after injection.6 the degree of contrast enhancement is related to the iodine concentration in the tissue of interest.3
- Mechanism of action
Iopromide is a nonionic iodinated, water-soluble, radiographic contrast medium that is available in two stable, ready-to-use solutions of different concentrations (i.e., 300 mg I/mL and 370 mg I/mL). Following intravascular injection, iopromide provides radiographic opacification of the vasculature and extracellular space in the path of flow of the agent, allowing diagnostic assessment of the limbs and internal organs until significant dilution occurs.6
- Absorption
Immediately following intravascular injection, iopromide reaches peak plasma concentrations and is then rapidly distributed throughout the extracellular fluid compartment. It displays little tendency to bind to serum or plasma proteins.6 Iodinated contrast agents cross a disrupted blood-brain barrier.3
- Volume of distribution
The total volume of distribution at steady state is about 16 L, suggesting distribution into extracellular space.3
- Protein binding
The plasma protein binding of iopromide is 1%.3
- Metabolism
Iopromide does not undergo significant metabolism, deiodination, or biotransformation.3
- Route of elimination
The amounts excreted unchanged in urine represent 97% of the dose in adult healthy subjects. Only 2% of the dose is recovered in the feces. Similar recoveries in urine and feces are observed in middle-aged and elderly patients. This finding suggests that, compared to the renal route, biliary and/or gastrointestinal excretion is not important for iopromide. During the slower terminal phase, only 3% of the dose is eliminated; 97% of the dose is disposed of during the earlier phases, the largest part of which occurs during the main elimination phase.3
The ratio of the renal clearance of iopromide to the creatinine clearance is 0.82, suggesting that iopromide is mainly excreted by glomerular filtration. Additional tubular reabsorption is possible.3
- Half-life
After intravenous administration to healthy adult subjects, the plasma iopromide concentration-time profile shows an initial distribution phase with a half-life of 0.24 hours; a main elimination phase with a half-life of 2 hours; and a terminal elimination phase with a half-life of 6.2 hours.3
- Clearance
The mean total and renal clearances are 107 mL/min and 104 mL/min, respectively.3
- Adverse Effects
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- Toxicity
There are no data on iopromide use in pregnant women to evaluate for a drug-associated risk of major birth defects, miscarriage, or adverse maternal or fetal outcomes. Iopromide crosses the placenta and reaches fetal tissues in small amounts. In animal reproduction studies, intravenous administration of iopromide to pregnant rats and rabbits during organogenesis at doses up to 0.35 and 0.7 times, respectively, the maximum recommended human dose based on body surface area resulted in no relevant adverse developmental effects.3
The safety and efficacy of iopromide have been established in pediatric patients aged 2 years and older for radiographic evaluation of cardiac chambers and related arteries, excretory urography, and contrast computed tomography of the head and body. The use of iopromide in these age groups for these indications is supported by evidence from adequate and well-controlled studies in adults and additional safety data in pediatric patients aged 2 years and older, including data from published studies.3
Pediatric patients who are at higher risk of experiencing an adverse reaction during and after the administration of any contrast agent include those with asthma, sensitivity to medication and/or allergens, cyanotic and acyanotic heart disease, congestive heart failure, or serum creatinine greater than 1.5 mg/dL.3
Thyroid function tests indicative of thyroid dysfunction, characterized by hypothyroidism or transient thyroid suppression have been reported following iodinated contrast media administration in pediatric patients, including term and preterm neonates; Some patients were treated for hypothyroidism. After exposure to iodinated contrast media, individualize thyroid function monitoring in pediatric patients 0 to 3 years of age based on underlying risk factors, especially in term and preterm neonates.3
The clearance of iopromide decreases with increasing degree of renal impairment and results in delayed opacification of the urinary system. In addition, preexisting renal impairment increases the risk of acute kidney injury. Iopromide can be removed by dialysis.3
Long-term animal studies have not been performed with iopromide to evaluate carcinogenic potential or effects on fertility. Iopromide was not genotoxic in a series of studies including the Ames test, an in vitro human lymphocytes analysis of chromosomal aberrations, an in vivo mouse micronucleus assay, and an in vivo mouse dominant lethal assay.3
The manifestations of overdosage are life-threatening and affect mainly the pulmonary and cardiovascular systems. Treatment of overdosage is directed toward the support of all vital functions, and prompt institution of symptomatic therapy.3
The most common adverse reactions (>1%) are headache, nausea, injection site and infusion site reactions, vasodilatation, vomiting, back pain, urinary urgency, chest pain, pain, dysgeusia, and abnormal vision. Inadvertent intrathecal administration may cause death, convulsions, cerebral hemorrhage, coma, paralysis, arachnoiditis, acute renal failure, cardiac arrest, seizures, rhabdomyolysis, hyperthermia, and brain edema.3
- 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 softwareAbacavir Abacavir may decrease the excretion rate of Iopromide which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Iopromide which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Iopromide which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Iopromide which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Iopromide which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
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.
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ultravist Injection 300 mg/1mL Intra-arterial; Intravenous Bayer HealthCare Pharmaceuticals Inc. 2022-06-08 Not applicable US Ultravist Injection 240 mg/1mL Intra-arterial; Intravenous Bayer HealthCare Pharmaceuticals Inc. 2009-12-30 2021-01-03 US Ultravist Injection 370 mg/1mL Intra-arterial; Intravenous Bayer HealthCare Pharmaceuticals Inc. 2009-12-30 Not applicable US Ultravist Injection 311.7 mg/1mL Intra-arterial Berlex 2006-07-18 2006-09-01 US Ultravist Injection 370 mg/1mL Intra-arterial; Intravenous Bayer HealthCare Pharmaceuticals Inc. 2022-06-08 Not applicable US
Categories
- ATC Codes
- V08AB05 — Iopromide
- Drug Categories
- Benzene Derivatives
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Iodinated Contrast Agents
- Radiographic Contrast Agent
- Roentgenography
- Watersoluble, Nephrotropic, Low Osmolar 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 4-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 4-position of the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- 4-halobenzoic acids and derivatives
- Alternative Parents
- 2-halobenzoic acids and derivatives / Benzamides / Benzoyl derivatives / Iodobenzenes / Aryl iodides / Vinylogous halides / Tertiary carboxylic acid amides / Secondary alcohols / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids show 7 more
- Substituents
- 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Alcohol / Aromatic homomonocyclic compound / Aryl halide / Aryl iodide / Benzamide / Benzoyl / Carboxamide group / Carboximidic acid show 21 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- dicarboxylic acid diamide, organoiodine compound (CHEBI:63578)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 712BAC33MZ
- CAS number
- 73334-07-3
- InChI Key
- DGAIEPBNLOQYER-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H24I3N3O8/c1-24(4-9(28)6-26)18(31)12-13(19)11(17(30)22-3-8(27)5-25)14(20)16(15(12)21)23-10(29)7-32-2/h8-9,25-28H,3-7H2,1-2H3,(H,22,30)(H,23,29)
- IUPAC Name
- N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylbenzene-1,3-dicarboxamide
- SMILES
- COCC(=O)NC1=C(I)C(C(=O)N(C)CC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I
References
- General References
- Gharekhanloo F, Torabian S: Comparison of allergic adverse effects and contrast enhancement between iodixanol and iopromide. Iran J Radiol. 2012 Jun;9(2):63-6. doi: 10.5812/iranjradiol.7696. Epub 2012 Jun 30. [Article]
- Mortele KJ, Oliva MR, Ondategui S, Ros PR, Silverman SG: Universal use of nonionic iodinated contrast medium for CT: evaluation of safety in a large urban teaching hospital. AJR Am J Roentgenol. 2005 Jan;184(1):31-4. doi: 10.2214/ajr.184.1.01840031. [Article]
- FDA Approved Drug Products: ULTRAVIST (iopromide) injection, for intra-arterial or intravenous use [Link]
- NPRA: Ultravist (Iopromide) Intravascular Injection [Link]
- Health Canada Approved Drug Products: Ultravist (Iopromide) Intravascular Injection [Link]
- Health Canada Approved Drug Proucts: ULTRAVIST (Iopromide) injection for intravascular use (March 2022) [Link]
- AIFA approved drug products: Ultravist (Iopromide) injectable solution [Link]
- External Links
- Human Metabolome Database
- HMDB0041910
- KEGG Drug
- D01893
- PubChem Compound
- 3736
- PubChem Substance
- 310265069
- ChemSpider
- 3605
- 27781
- ChEBI
- 63578
- ChEMBL
- CHEMBL1725
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Iopromide
- FDA label
- Download (2.53 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Coronary Artery Disease (CAD) 1 4 Completed Prevention Acute Myocardial Infarction (AMI) / Prophylaxis of Contrast-induced nephropathy 1 4 Completed Prevention Renal Failure, Chronic Renal Failure 1 4 Completed Treatment Coronary Angiography (CAG) / Renal Insufficiency,Chronic 1 4 Unknown Status Prevention Renal Failure, Chronic Renal Failure 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection 300 mg/ImL Injection, solution 370 mgI/mL Injection, solution Intravascular Injection Intra-arterial 311.7 mg/1mL Injection Intra-arterial; Intravenous 240 mg/1mL Injection Intra-arterial; Intravenous 300 mg/1mL Injection Intra-arterial; Intravenous 370 mg/1mL Injection, solution Intravenous 150 mg/mL Injection, solution Intravenous 300 mg/mL Injection, solution Intravenous 370 mg/mL Injection, solution Parenteral 150 MG/ML Injection, solution Parenteral 240 MG/ML Injection, solution Parenteral 300 MG/ML Injection, solution Parenteral 370 MG/ML Solution Intravascular 50 % Injection Intravascular 623 mg/ml Solution 300 mg/1ml Solution Intravascular 62 % Injection Intravascular Injection Intra-arterial; Intracavitary; Intravascular; Intravenous 623.40 mg Solution Intravascular 300 mg/ml Injection Intravascular 769 mg/ml Injection Intravenous Solution 370 mg/1ml Solution Intravascular 77 % Solution Intravenous 76.886 g Injection Intra-arterial; Intracavitary; Intravascular; Intravenous 768.86 mg Solution Intravascular 370 mg/ml Solution Parenteral 623.4 mg Solution, concentrate Intravenous 768.86 mg Injection - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.366 mg/mL ALOGPS logP -1.9 ALOGPS logP -0.44 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 11.09 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 168.66 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 144.82 m3·mol-1 Chemaxon Polarizability 57.56 Å3 Chemaxon Number of Rings 1 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 217.9460697 predictedDarkChem Lite v0.1.0 [M-H]- 225.42287 predictedDeepCCS 1.0 (2019) [M+H]+ 221.3845697 predictedDarkChem Lite v0.1.0 [M+H]+ 227.78087 predictedDeepCCS 1.0 (2019) [M+Na]+ 220.4251697 predictedDarkChem Lite v0.1.0 [M+Na]+ 234.17833 predictedDeepCCS 1.0 (2019)
Drug created at October 01, 2015 22:05 / Updated at March 28, 2024 03:23