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 path of flow of the contrast agent, permitting radiographic visualization of the internal structures until significant hemodilution occurs.

Available as the FDA-approved product Ultravist, iopromide is used in radiographic studies such as 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 aortography.

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 indicated for use as an X-ray contrast agent in the following procedures: Intra-arterial digital subtraction angiography (IA-DSA) (150 mg I/mL) Cerebral arteriography and peripheral arteriography (300 mg I/mL) Coronary arteriography and left ventriculography, visceral angiography and aortography (370 mg I/mL) Peripheral venography (240 mg I/mL) Excretory urography (300 mg I/mL) Contrast computed tomography (CT) imaging of head and body (300 mg I/mL and 370 mg I/mL)

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

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 path of flow of the contrast agent, permitting radiographic visualization of the internal structures until significant hemodilution occurs.

Absorption

Following administration, the degree of contrast enhancement is directly related to the iodine content in the administered dose; peak iodine plasma levels occur immediately following rapid intravenous injection. Iodine plasma levels fall rapidly within 5 to 10 minutes, which can be accounted for by the dilution in the vascular and extravascular fluid compartments. Contrast enhancement appears to be greatest immediately after bolus injections (15 seconds to 120 seconds). Thus, greatest enhancement may be detected by a series of consecutive two-to-three second scans performed within 30 to 90 seconds after injection (that is, dynamic computed tomographic imaging). Injection may be visualized in the renal parenchyma within 30–60 seconds following rapid intravenous injection. Opacification of the calyces and pelves in patients with normal renal function becomes apparent within 1–3 minutes, with optimum contrast occurring within 5–15 minutes.

Volume of distribution

16 L

Protein binding

Plasma protein binding of iopromide is 1%.

Metabolism

Iopromide is not metabolized.

Route of elimination

The amounts excreted unchanged in urine represent 97% of the dose in young 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.

Half-life

After intravenous administration to healthy young volunteers, plasma iopromide concentration time profile shows an initial distribution phase with a half-life of 0.24 hour; a main elimination phase with a half-life of 2 hours; and a terminal elimination phase with a half-life of 6.2 hours.

Clearance

The mean total and renal clearances are 107 mL/min and 104 mL/min, respectively.

Adverse Effects
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Toxicity

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.

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.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Iopromide which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Iopromide which could result in a higher serum level.
AcrivastineIopromide may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Iopromide which could result in a higher serum level.
Adefovir dipivoxilAdefovir dipivoxil may decrease the excretion rate of Iopromide which could result in a higher serum level.
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Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
UltravistInjection370 mg/1mLIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2009-12-30Not applicableUS flag
UltravistInjection311.7 mg/1mLIntra-arterialBerlex2006-07-182006-09-01US flag
UltravistInjection370 mg/1mLIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2022-06-08Not applicableUS flag
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
Ultravist 240Solution50 %IntravascularBayer1994-12-312019-04-16Canada flag
Ultravist 300Solution62 %IntravascularBayer1994-12-31Not applicableCanada flag
Ultravist 370Solution77 %IntravascularBayer1994-12-31Not applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
UltravistIopromide (300 mg/1mL)InjectionIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2022-06-08Not applicableUS flag
UltravistIopromide (370 mg/1mL)InjectionIntra-arterial; IntravenousBayer HealthCare Pharmaceuticals Inc.2022-06-08Not applicableUS 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
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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
Not Available
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
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticCoronary Artery Disease (CAD)1
4CompletedPreventionAcute Myocardial Infarction (AMI) / Prophylaxis of Contrast-induced nephropathy1
4CompletedPreventionRenal Failure, Chronic Renal Failure1
4CompletedTreatmentCoronary Angiography (CAG) / Renal Insufficiency,Chronic1
4Unknown StatusPreventionRenal Failure, Chronic Renal Failure1
4WithdrawnDiagnosticCoronary Artery Disease (CAD) / Diabetes Mellitus / Renal Impairment1
4WithdrawnOtherHypothyroidism1
3CompletedDiagnosticComputerized tomography / Imaging procedure1
Not AvailableActive Not RecruitingNot AvailableAdenocarcinomas of the Pancreas / Neuroendocrine Carcinomas of Pancreas1
Not AvailableCompletedNot AvailableAbdominal CT1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solution
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 %
SolutionIntravascular
InjectionIntra-arterial; Intracavitary; Intravascular; Intravenous623.40 mg
InjectionIntravascular
InjectionIntravenous
Solution370 mg/1ml
SolutionIntravascular77 %
SolutionIntravenous76.886 g
InjectionIntra-arterial; Intracavitary; Intravascular; Intravenous768.86 mg
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Drug created at October 01, 2015 22:05 / Updated at August 12, 2022 17:06