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Details

Stereochemistry UNKNOWN
Molecular Formula C35H44I6N6O15
Molecular Weight 1550.1833
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IODIXANOL

SMILES

CC(=O)N(CC(CN(C(=O)C)c1c(c(c(c(c1I)C(=NCC(CO)O)O)I)C(=NCC(CO)O)O)I)O)c2c(c(c(c(c2I)C(=NCC(CO)O)O)I)C(=NCC(CO)O)O)I

InChI

InChIKey=NBQNWMBBSKPBAY-UHFFFAOYSA-N
InChI=1S/C35H44I6N6O15/c1-13(52)46(30-26(38)20(32(59)42-3-15(54)9-48)24(36)21(27(30)39)33(60)43-4-16(55)10-49)7-19(58)8-47(14(2)53)31-28(40)22(34(61)44-5-17(56)11-50)25(37)23(29(31)41)35(62)45-6-18(57)12-51/h15-19,48-51,54-58H,3-12H2,1-2H3,(H,42,59)(H,43,60)(H,44,61)(H,45,62)

HIDE SMILES / InChI
Iodixanol (brand name VISIPAQUE) is an iodine-containing nonionic dimeric hydrophilic contrast agent for intravascular (intravenous and intra-arterial) use during coronary angiography. Pharmacodynamics studies indicated that iodixanol had fewer cardiovascular effects, caused less renal damage and were associated with similar or smaller changes to the blood-brain barrier and neurological function when compared with nonionic contrast media. It is known, that the organic iodine compounds attenuate x-rays as they pass through the body, thereby allowing the body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. Thus, after intravascular administration, iodixanol makes opaque those internal structures in its path of flow, allowing their visualization until significant hemodilution and elimination occur.

CNS Activity

Curator's Comment:: In a normal brain with an intact blood-brain barrier, contrast does not diffuse into the extravascular space. In patients with a disrupted blood-brain barrier, contrast agent accumulates in the interstitial space in the region of disruption.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
VISIPAQUE 270

Approved Use

INTRA-ARTERIAL VISIPAQUE Injection (270 mgI/mL) is indicated for intra-arterial digital subtraction angiography. VISIPAQUE Injection (320 mgI/mL) is indicated for angiocardiography (left ventriculography and selective coronary arteriography), peripheral arteriography, visceral arteriography, and cerebral arteriography. INTRAVENOUS For information on the concentrations and doses for the pediatric population see the Precautions–Pediatric Use, Clinical Pharmacology–Special Populations, and Dosage and Administration sections. VISIPAQUE Injection (270 mgI/mL) is indicated for CECT imaging of the head and body, excretory urography, and peripheral venography. VISIPAQUE Injection (320 mgI/mL) is indicated for CECT imaging of the head and body, and excretory urography.

Launch Date

8.2745282E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.1 h
300 mg/kg bw single, intravenous
dose: 300 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IODIXANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
23 h
unknown, unknown
IODIXANOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
300 mg/kg bw single, intravenous
dose: 300 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IODIXANOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2.44399185336049 g/kg single, intravenous
Highest studied dose
Dose: 2.44399185336049 g/kg
Route: intravenous
Route: single
Dose: 2.44399185336049 g/kg
Sources:
healthy, 29 years (range: 21-44 years)
n = 10
Health Status: healthy
Age Group: 29 years (range: 21-44 years)
Sex: M
Population Size: 10
Sources:
651.73116089613 mg/mL single, intrathecal
Dose: 651.73116089613 mg/mL
Route: intrathecal
Route: single
Dose: 651.73116089613 mg/mL
Sources:
unhealthy
Other AEs: Death...
AEs

AEs

AESignificanceDosePopulation
Death
651.73116089613 mg/mL single, intrathecal
Dose: 651.73116089613 mg/mL
Route: intrathecal
Route: single
Dose: 651.73116089613 mg/mL
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Ionic radiocontrast media disrupt intercellular contacts via an extracellular calcium-independent mechanism.
2002
Adding sodium and calcium ions to iodixanol and mannitol: effects on risk of ventricular fibrillation after infusion into the left coronary artery of pigs.
2002 Aug
Endoscopic transnasal approach for the treatment of medial orbital blow-out fracture: a technique for controlling the fractured wall with a balloon catheter and Merocel.
2002 Aug
Multidetector CT: detection of active hemorrhage in patients with blunt abdominal trauma.
2002 Aug
Characterization of isolated acidocalcisomes from Toxoplasma gondii tachyzoites reveals a novel pool of hydrolyzable polyphosphate.
2002 Dec 13
Effects of two dimeric iodinated contrast media on renal medullary blood perfusion and oxygenation in dogs.
2002 Jul
Isolation of purified oocyst walls and sporocysts from Toxoplasma gondii.
2002 Jul-Aug
Isolation of human platelets (thrombocytes).
2002 Jun 12
Separation of membrane vesicles and cytosol from yeast, cultured cells, and bacteria in a small volume self-generated gradient in a fixed-angle rotor.
2002 Jun 12
Purification of gastric mucosal ECL cells from a crude elutriation fraction.
2002 Jun 14
Isolation of rat and human hippocampal neuron fractions in a discontinuous density gradient.
2002 Jun 14
Isolation of peripheral blood mononuclear cells from macaques on a density barrier.
2002 Jun 15
Purification of parietal and chief cells from the gastric mucosa.
2002 Jun 15
Purification of lipid rafts from cultured cells.
2002 Jun 18
Purification of islets of Langerhans from porcine pancreas.
2002 Jun 18
Separation of membrane vesicles and cytosol from cultured cells and bacteria in a preformed discontinuous gradient.
2002 Jun 7
Rapid purification of nuclei from animal and plant tissues and cultured cells.
2002 Jun 7
OptiPrep density gradient solutions for macromolecules and macromolecular complexes.
2002 Jun 7
Isolation of a mouse motoneuron-enriched fraction from mouse spinal cord on a density barrier.
2002 Jun 7
Purification of peroxisomes in a preformed iodixanol gradient in a fixed-angle rotor.
2002 Jun 7
Purification of peroxisomes in a self-generated gradient.
2002 Jun 7
[Sonographic imaging of lymphatic vessels compared to other methods].
2002 May
Formation of self-generated gradients of iodixanol.
2002 May 16
Preparation of preformed iodixanol gradients.
2002 May 16
Fractionation of hepatic nonparenchymal cells.
2002 May 16
Purification of intact plant protoplasts by flotation at 1g.
2002 May 21
Isolation of human polymorphonuclear leukocytes (granulocytes) from a leukocyte-rich fraction.
2002 May 21
Fractionation of Golgi, endoplasmic reticulum, and plasma membrane from cultured cells in a preformed continuous iodixanol gradient.
2002 May 22
Purification of peroxisomes using a density barrier in a swinging-bucket rotor.
2002 May 22
[Prospects of the use of non-ionic X-ray contrast media during endoscopic retrograde cholangiopancreatography].
2002 Nov-Dec
Novel tools for production and purification of recombinant adeno-associated viral vectors.
2003
Comparison between the efficacy of dimeric and monomeric non-ionic contrast media (iodixanol vs iopromide) in urography in patients with macroscopic haematuria.
2003 Apr
Identification of organelles in bacteria similar to acidocalcisomes of unicellular eukaryotes.
2003 Aug 8
The ionic contrast medium ioxaglate interferes with thrombin-mediated feedback activation of factor V, factor VIII and platelets.
2003 Feb
APH-1 interacts with mature and immature forms of presenilins and nicastrin and may play a role in maturation of presenilin.nicastrin complexes.
2003 Feb 28
Contrast-agent-induced acute renal dysfunction--is iodixanol the answer?
2003 Feb 6
Separation of bovine plasma lipoproteins by a rapid ultracentrifugation method.
2003 Jan
In vivo comparative antithrombotic effects of ioxaglate and iohexol and interaction with the platelet antiaggregant clopidogrel.
2003 Jan
Practical considerations of recombinant adeno-associated virus-mediated gene transfer for treatment of retinal degenerations.
2003 Jul
Iodinated contrast media interfere with gel barrier formation in plasma and serum separator tubes.
2003 Jul
Assessment of organ volume with different techniques using a living liver model.
2003 Jun
A rapid protocol for the prevention of contrast-induced renal dysfunction: the RAPPID study.
2003 Jun 18
[Reduced risk of nepropathy with isoosmolar contrast media].
2003 Jun 5
Delayed hypersensitivity reaction to the non-ionic X-ray contrast medium Visipaque (iodixanol).
2003 Mar
Delayed side effects induced by iodinated contrast media, especially those associated with iodixanol.
2003 Mar
Early and late reactions following the use of iopamidol 340, iomeprol 350 and iodixanol 320 in cardiac catheterization.
2003 Mar
Protection from contrast-induced nephropathy: is the answer in?
2003 Mar
Nephropathy induced by contrast medium.
2003 May 29
Nephropathy induced by contrast medium.
2003 May 29
The conversion of apoB100 low density lipoprotein/high density lipoprotein particles to apoB100 very low density lipoproteins in response to oleic acid occurs in the endoplasmic reticulum and not in the Golgi in McA RH7777 cells.
2003 Oct 24
Patents

Sample Use Guides

Intra-arterial digital subtraction angiography (IA-DSA) (270 and 320 mg Iodine/mL). Angiocardiography (left ventriculography and selective coronary arteriography), peripheral arteriography, visceral arteriography, and cerebral arteriography (320 mg Iodine/mL) Intravenous Dosage and Administration: Computed Tomography of the Head or Body (270 mg Iodine/mL and 320 mg Iodine/mL). Excretory Urography (270 mg Iodine/mL and 320 mg Iodine/mL). Peripheral Venography (270 mg Iodine/mL). Coronary Computed Tomography Angiography (CCTA) (320 mg Iodine/mL).
Route of Administration: Other
Contrast media (CM) possess both pro-thrombotic and anticoagulant properties. There were investigated the effect of three classes of CM; Iohexol, Iodixanol and Ioxaglate, on thrombus formation and fibrinolysis in vitro and evaluated the contribution of platelets to this process. Non-anticoagulated blood was mixed with CM or saline (50% or 20% (v/v)) for 1 min then citrated. Thrombus structure was visualized by immunohistochemistry using FITC-fibrinogen antibodies, and propidium iodide to identify nucleated blood cells. Thrombi formed with Iohexol or Iodixanol weighed > OR = 10x more than saline controls (116+/-52 and 230+/-128 mg vs. 11+/-3 mg, respectively; p<0.0005), and were more resistant to thrombolysis as evidenced by the release of FITC over 24 h (19.1+/-8.9 and 31.9+/-17.2 U vs. 65.1+/-19.1 U, respectively; p<0.02).
Name Type Language
IODIXANOL
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-760069
Code English
IODIXANOL [USAN]
Common Name English
1,3-BENZENEDICARBOXAMIDE, 5,5'-((2-HYDROXY-1,3-PROPANEDIYL)BIS(ACETYLIMINO))BIS(N,N'-BIS(2,3-DIHYDROXYPROPYL)-2,4,6-TRIIODO-
Common Name English
IODIXANOL [USP-RS]
Common Name English
IODIXANOL [WHO-DD]
Common Name English
IODIXANOL [USP]
Common Name English
IODIXANOL [ORANGE BOOK]
Common Name English
VISIPAQUE
Brand Name English
IODIXANOL [INN]
Common Name English
IODIXANOL [MI]
Common Name English
IODIXANOL [VANDF]
Common Name English
IODIXANOL [USP MONOGRAPH]
Common Name English
2-5410-3A
Code English
IODIXANOL [EP MONOGRAPH]
Common Name English
IODIXANOL [JAN]
Common Name English
2-541O-3A
Code English
IODIXANOL [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28500
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
WHO-ATC V08AB09
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
WHO-VATC QV08AB09
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
NDF-RT N0000180185
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
NDF-RT N0000010258
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
Code System Code Type Description
DRUG CENTRAL
3302
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
USP_CATALOG
1343517
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY USP-RS
INN
5692
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200507
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
DRUG BANK
DB01249
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
CAS
92339-11-2
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
MERCK INDEX
M6336
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY Merck Index
HSDB
8076
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
WIKIPEDIA
Iodixanol
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
PUBCHEM
3724
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
RXCUI
27729
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY RxNorm
EPA CompTox
92339-11-2
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
NCI_THESAURUS
C65931
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
FDA UNII
HW8W27HTXX
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
LACTMED
Iodixanol
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
MESH
C044834
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY
EVMPD
SUB08213MIG
Created by admin on Fri Jun 25 21:01:47 UTC 2021 , Edited by admin on Fri Jun 25 21:01:47 UTC 2021
PRIMARY