Iopromide

Identification

Name
Iopromide
Accession Number
DB09156
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino]-N-methylisophthalamide
External IDs
ZK 35760 / ZK-35760 / ZK35760
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
UltravistInjection240 mg/1mLIntra-arterial; IntravenousBayer2009-12-30Not applicableUs
UltravistInjection370 mg/1mLIntra-arterialBayer HealthCare Pharmaceuticals Inc.2009-12-30Not applicableUs
UltravistInjection300 mg/1mLIntra-arterialBayer HealthCare Pharmaceuticals Inc.2009-12-30Not applicableUs
Ultravist 240Solution50 %IntravascularBayer1994-12-31Not applicableCanada
Ultravist 300Solution62 %IntravascularBayer1994-12-31Not applicableCanada
Ultravist 370Solution77 %IntravascularBayer1994-12-31Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
UltravistIopromide (311.7 mg/1mL)InjectionIntra-arterialBerlex2006-07-18Not applicableUs
International/Other Brands
Ultravist
Categories
UNII
712BAC33MZ
CAS number
73334-07-3
Weight
Average: 791.1119
Monoisotopic: 790.869745019
Chemical Formula
C18H24I3N3O8
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
N-(2,3-dihydroxypropyl)-3-[(2,3-dihydroxypropyl)(methyl)carbamoyl]-5-[(1-hydroxy-2-methoxyethylidene)amino]-2,4,6-triiodobenzene-1-carboximidic acid
SMILES
COCC(O)=NC1=C(I)C(C(O)=NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I

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)

Associated Conditions
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.

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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Iopromide which could result in a higher serum level.
AcarboseAcarbose 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.
AcetarsolIopromide may decrease the excretion rate of Acetarsol which could result in a higher serum level.
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.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0041910
KEGG Drug
D01893
PubChem Compound
3736
PubChem Substance
310265069
ChemSpider
3605
ChEBI
63578
ChEMBL
CHEMBL1725
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Iopromide
ATC Codes
V08AB05 — Iopromide
AHFS Codes
  • 36:68.00 — Roentgenography
FDA label
Download (2.53 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingDiagnosticCardiovascular Disease (CVD) / Coronary Artery Disease1
4CompletedNot AvailableAbdominal CT1
4CompletedDiagnosticCoronary Artery Disease1
4CompletedPreventionAcute Myocardial Infarction (AMI) / Contrast Induced Nephropathy (CIN)1
4CompletedPreventionChronic Renal Failure (CRF)1
4CompletedTreatmentCoronary Angiography / Renal Insufficiency,Chronic1
4Not Yet RecruitingOtherHypothyroidism1
4TerminatedDiagnosticCoronary Artery Disease / Diabetes Mellitus (DM) / Impaired Renal Function1
4Unknown StatusPreventionChronic Renal Failure (CRF)1
Not AvailableActive Not RecruitingNot AvailableAdenocarcinoma of the Pancreas / Neuroendocrine Carcinoma of Pancreas1
Not AvailableCompletedNot AvailableAngiography / Multidetector Computed Tomography1
Not AvailableCompletedNot AvailableCoronary angiogram1
Not AvailableCompletedNot AvailableDiagnostic Imaging2
Not AvailableNot Yet RecruitingNot AvailableContrast Medium1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InjectionIntra-arterial300 mg/1mL
InjectionIntra-arterial311.7 mg/1mL
InjectionIntra-arterial370 mg/1mL
InjectionIntra-arterial; Intravenous240 mg/1mL
SolutionIntravascular50 %
SolutionIntravascular62 %
SolutionIntravascular77 %
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0915 mg/mLALOGPS
logP-1ALOGPS
logP1.1ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.23ChemAxon
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.64 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity146.1 m3·mol-1ChemAxon
Polarizability57.65 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

Taxonomy

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
4-halobenzoic acid or derivatives / 2-halobenzoic acid or derivatives / Benzamide / Benzoyl / Halobenzene / Iodobenzene / Aryl halide / Aryl iodide / Vinylogous halide / Tertiary carboxylic acid amide
show 21 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dicarboxylic acid diamide, organoiodine compound (CHEBI:63578)

Drug created on October 01, 2015 16:05 / Updated on September 21, 2018 00:17