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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Diagnostic agentBreast lesions••••••••••••••••••••••••••
Diagnostic agentNeoplastic lesion•••••••••••••••••• ••••••••••••••••••
Diagnostic agentNon-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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Iopromide which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Iopromide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Iopromide which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Iopromide which could result in a higher serum level.
AcetazolamideAcetazolamide 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

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
UltravistInjection300 mg/1mLIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2009-12-30Not applicableUS flag
UltravistInjection300 mg/1mLIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2022-06-08Not applicableUS flag
UltravistInjection240 mg/1mLIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2009-12-302021-01-03US flag
UltravistInjection370 mg/1mLIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2009-12-30Not applicableUS flag
UltravistInjection311.7 mg/1mLIntra-arterialBerlex2006-07-182006-09-01US flag

Categories

ATC Codes
V08AB05 — Iopromide
Drug Categories
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
  1. 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]
  2. 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]
  3. FDA Approved Drug Products: ULTRAVIST (iopromide) injection, for intra-arterial or intravenous use [Link]
  4. NPRA: Ultravist (Iopromide) Intravascular Injection [Link]
  5. Health Canada Approved Drug Products: Ultravist (Iopromide) Intravascular Injection [Link]
  6. Health Canada Approved Drug Proucts: ULTRAVIST (Iopromide) injection for intravascular use (March 2022) [Link]
  7. AIFA approved drug products: Ultravist (Iopromide) injectable solution [Link]
Human Metabolome Database
HMDB0041910
KEGG Drug
D01893
PubChem Compound
3736
PubChem Substance
310265069
ChemSpider
3605
RxNav
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

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection300 mg/ImL
Injection, solution370 mgI/mL
Injection, solutionIntravascular
InjectionIntra-arterial311.7 mg/1mL
InjectionIntra-arterial; Intravenous240 mg/1mL
InjectionIntra-arterial; Intravenous300 mg/1mL
InjectionIntra-arterial; Intravenous370 mg/1mL
Injection, solutionIntravenous150 mg/mL
Injection, solutionIntravenous300 mg/mL
Injection, solutionIntravenous370 mg/mL
Injection, solutionParenteral150 MG/ML
Injection, solutionParenteral240 MG/ML
Injection, solutionParenteral300 MG/ML
Injection, solutionParenteral370 MG/ML
SolutionIntravascular50 %
InjectionIntravascular623 mg/ml
Solution300 mg/1ml
SolutionIntravascular62 %
InjectionIntravascular
InjectionIntra-arterial; Intracavitary; Intravascular; Intravenous623.40 mg
SolutionIntravascular300 mg/ml
InjectionIntravascular769 mg/ml
InjectionIntravenous
Solution370 mg/1ml
SolutionIntravascular77 %
SolutionIntravenous76.886 g
InjectionIntra-arterial; Intracavitary; Intravascular; Intravenous768.86 mg
SolutionIntravascular370 mg/ml
SolutionParenteral623.4 mg
Solution, concentrateIntravenous768.86 mg
Injection
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.366 mg/mLALOGPS
logP-1.9ALOGPS
logP-0.44Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.09Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area168.66 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity144.82 m3·mol-1Chemaxon
Polarizability57.56 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0aor-3000009800-d4eb7c00f7ef4e3c3ada
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0000141900-d1cdbb1581082c3c638a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-006x-0010081900-484ea8ffab12f96d512e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0019760000-3dc5bf91bdb47815fee9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0059200000-047e7c4128fbfd6816ae
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0397000000-8b00b54a00693ed16a30
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01bd-2972000000-0565b4327c485775e9e7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ftr-5930000000-4a161f4b926d1da7163f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00dl-0000081900-4b5238662a76892280cb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fr-0019760000-c5512d68987f36b4b08e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0069200000-62d759cca8eecea14e65
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014j-0297000000-f4e7a88b722caf35d20d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014m-1892000000-99c1943fa38d86cc5f25
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0000041900-31808f9ea15ef7e148c0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000000900-f3d819502a6cfcc78db8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000b-1000009600-04561f8db7953c957f6f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-5300001900-f77005fdd9d2218c37d1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000009400-6d657755b23cc13bb546
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00yi-0000009800-2e26aa8c5095cf4aec92
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-4100039000-f032b8928ca3076c6e68
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-217.9460697
predicted
DarkChem Lite v0.1.0
[M-H]-225.42287
predicted
DeepCCS 1.0 (2019)
[M+H]+221.3845697
predicted
DarkChem Lite v0.1.0
[M+H]+227.78087
predicted
DeepCCS 1.0 (2019)
[M+Na]+220.4251697
predicted
DarkChem Lite v0.1.0
[M+Na]+234.17833
predicted
DeepCCS 1.0 (2019)

Drug created at October 01, 2015 22:05 / Updated at June 18, 2024 20:06