Ioxilan

Identification

Name
Ioxilan
Accession Number
DB09135
Type
Small Molecule
Groups
Approved
Description

Ioxilan is a tri-iodinated diagnostic contrast agent. Intravascular injection results in opacification of vessels in the path of flow of the contrast medium, permitting radiographic visualization of the internal structures of the human body until significant hemodilution occurs.

Structure
Thumb
Synonyms
  • Ioxilane
  • Ioxilanum
  • N-(2,3-dihydroxypropyl)-N’-(2- hydroxyethyl)-5-[N-(2,3-dihydroxypropyl) acetamido]-2,4,6-triiodoisophthal-amide
External IDs
CCRIS 6727 / CID3743 / LS-29720 / MOLI00098
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OxilanInjection, solution300 mg/1mLIntravascularGuerbet2002-03-182017-10-31Us
OxilanInjection, solution350 mg/1mLIntravascularGuerbet2002-03-182017-10-31Us
International/Other Brands
oxilan
Categories
UNII
A4YJ7J11TG
CAS number
107793-72-6
Weight
Average: 791.116
Monoisotopic: 790.86975
Chemical Formula
C18H24I3N3O8
InChI Key
UUMLTINZBQPNGF-UHFFFAOYSA-N
InChI
InChI=1S/C18H24I3N3O8/c1-8(28)24(5-10(30)7-27)16-14(20)11(17(31)22-2-3-25)13(19)12(15(16)21)18(32)23-4-9(29)6-26/h9-10,25-27,29-30H,2-7H2,1H3,(H,22,31)(H,23,32)
IUPAC Name
N1-(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-N3-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
SMILES
CC(=O)N(CC(O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCCO)=C1I

Pharmacology

Indication

When administered intra-arterially, Ioxilan is indicated for the following diagnostic tests: cerebral arteriography (300 mgI/mL), coronary arteriography and left ventriculography (350 mgI/mL), visceral angiography(350 mgI/mL), aortography(350 mgI/mL), and peripheral arteriography(350 mgI/mL). When administered intravenously, Ioxilan is indicated for excretory urography and contrast enhanced computed tomographic (CECT) imaging of the head and body (300 and 350 mgI/mL).

Pharmacodynamics

As with other iodinated contrast agents the degree of contrast enhancement is directly related to the iodine content in the administered dose.

Mechanism of action

Intravascular injection results in opacification of vessels in the path of flow of the contrast medium, permitting radiographic visualization of the internal structures of the human body until significant hemodilution occurs.

Absorption

Peak iodine plasma levels occur immediately following rapid intravenous injection. Iodine plasma levels fall rapidly within 5 to 10 minutes. This can be accounted for by the dilution in the vascular and extravascular fluid compartments.

Volume of distribution

Ioxilan is distributed mainly in the blood as suggested by the apparent volume of distribution (central compartment), 7.2 ± 1.0 L in women and 10.0 ± 2.4 L in men

Protein binding

Binding of ioxilan to plasma protein is negligible.

Metabolism

There is no evidence for metabolism.

Route of elimination

The average amount of ioxilan excreted unchanged in urine at 24 hours represents 93.7% of the dose in young healthy subjects (21-27 years) after intravenous administration. This finding suggests that, compared to the renal excretion, biliary and/or gastrointestinal excretion are not important.

Half life

An initial fast distribution phase with a half-life of 13.1 ± 4.2 minutes (women) or 23.5 ± 15.3 minutes (men) was followed by an elimination phase with a half-life of 102.0 ± 16.9 minutes (women) and 137 ± 35.4 minutes (men).

Clearance

The total clearance values were 95.4 ± 11.1 mL·min-1 and 101.0 ± 14.7 mL·min-1 and the renal clearance values were 89.4 ± 13.3 mL·min-1 and 94.9 ± 16.6 mL·min-1 for women and men, respectively.

Toxicity

Renal toxicity has been reported in a few patients with liver dysfunction who were given an oral cholecystographic agent followed by intravascular contrast agents. Administration of any intravascular contrast agent should therefore be postponed in any patient with a known or suspected hepatic or biliary disorder who has recently received a cholecystographic contrast agent.

Other drugs should not be admixed with this product.

Pregnancy Category B

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

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Ioxilan which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Ioxilan which could result in a higher serum level.
AcrivastineIoxilan may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Ioxilan which could result in a higher serum level.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D02161
PubChem Compound
3743
PubChem Substance
310265050
ChemSpider
3612
ChEBI
135884
ChEMBL
CHEMBL1201075
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ioxilan
ATC Codes
V08AB12 — Ioxilan
FDA label
Download (3.16 MB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solutionIntravascular300 mg/1mL
Injection, solutionIntravascular350 mg/1mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.559 mg/mLALOGPS
logP-2.5ALOGPS
logP-1.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.74ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area179.66 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142.88 m3·mol-1ChemAxon
Polarizability57.05 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 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

Taxonomy

Description
This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylaminobenzoic acid and derivatives
Alternative Parents
O-haloacetanilides / P-haloacetanilides / 2-halobenzoic acids and derivatives / 4-halobenzoic acids and derivatives / Benzamides / Benzoyl derivatives / N-acylethanolamines / Iodobenzenes / Aryl iodides / Tertiary carboxylic acid amides
show 10 more
Substituents
Acylaminobenzoic acid or derivatives / O-haloacetanilide / P-haloacetanilide / Haloacetanilide / Acetanilide / 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Benzamide / Anilide
show 27 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on September 29, 2015 16:16 / Updated on November 02, 2018 06:58