IODIXANOL

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020351s045lbl.pdf

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

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cardiovascular diseases 70 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020351s045lbl.pdf	Diagnostic		Approved 8043	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020351s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020351s050lbl.pdf	unknown, unknown		IODIXANOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
100% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020351s050lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/1601604	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: https://pubmed.ncbi.nlm.nih.gov/1601604	Sources: https://pubmed.ncbi.nlm.nih.gov/1601604
651.73116089613 mg/mL single, intrathecal Dose: 651.73116089613 mg/mL Route: intrathecal Route: single Dose: 651.73116089613 mg/mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020351s048,020808s028lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020351s048,020808s028lbl.pdf	Other AEs: Death... Other AEs: Death Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020351s048,020808s028lbl.pdf

AEs

AE	Significance	Dose	Population
Death		651.73116089613 mg/mL single, intrathecal Dose: 651.73116089613 mg/mL Route: intrathecal Route: single Dose: 651.73116089613 mg/mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020351s048,020808s028lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020351s048,020808s028lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31705	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31705
ChemicalBook	CB6465056	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6465056
MolPort	MolPort-006-167-751	https://www.molport.com/shop/molecule-link/MolPort-006-167-751
eMolecules	1987230	https://www.emolecules.com/cgi-bin/more?vid=1987230

PubMed

Title	Date	PubMed
Ionic radiocontrast media disrupt intercellular contacts via an extracellular calcium-independent mechanism.	2002	12053122
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	12188302
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	12142653
Multidetector CT: detection of active hemorrhage in patients with blunt abdominal trauma.	2002 Aug	12130447
Characterization of isolated acidocalcisomes from Toxoplasma gondii tachyzoites reveals a novel pool of hydrolyzable polyphosphate.	2002 Dec 13	12379647
Effects of two dimeric iodinated contrast media on renal medullary blood perfusion and oxygenation in dogs.	2002 Jul	12068157
Isolation of purified oocyst walls and sporocysts from Toxoplasma gondii.	2002 Jul-Aug	12188226
Isolation of human platelets (thrombocytes).	2002 Jun 12	12806147
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	12806146
Purification of gastric mucosal ECL cells from a crude elutriation fraction.	2002 Jun 14	12806154
Isolation of rat and human hippocampal neuron fractions in a discontinuous density gradient.	2002 Jun 14	12806152
Isolation of peripheral blood mononuclear cells from macaques on a density barrier.	2002 Jun 15	12806157
Purification of parietal and chief cells from the gastric mucosa.	2002 Jun 15	12806156
Purification of lipid rafts from cultured cells.	2002 Jun 18	12806159
Purification of islets of Langerhans from porcine pancreas.	2002 Jun 18	12806158
Separation of membrane vesicles and cytosol from cultured cells and bacteria in a preformed discontinuous gradient.	2002 Jun 7	12806140
Rapid purification of nuclei from animal and plant tissues and cultured cells.	2002 Jun 7	12806139
OptiPrep density gradient solutions for macromolecules and macromolecular complexes.	2002 Jun 7	12806138
Isolation of a mouse motoneuron-enriched fraction from mouse spinal cord on a density barrier.	2002 Jun 7	12806137
Purification of peroxisomes in a preformed iodixanol gradient in a fixed-angle rotor.	2002 Jun 7	12806135
Purification of peroxisomes in a self-generated gradient.	2002 Jun 7	12806134
[Sonographic imaging of lymphatic vessels compared to other methods].	2002 May	12063422
Formation of self-generated gradients of iodixanol.	2002 May 16	12805920
Preparation of preformed iodixanol gradients.	2002 May 16	12805919
Fractionation of hepatic nonparenchymal cells.	2002 May 16	12805918
Purification of intact plant protoplasts by flotation at 1g.	2002 May 21	12805924
Isolation of human polymorphonuclear leukocytes (granulocytes) from a leukocyte-rich fraction.	2002 May 21	12805923
Fractionation of Golgi, endoplasmic reticulum, and plasma membrane from cultured cells in a preformed continuous iodixanol gradient.	2002 May 22	12805929
Purification of peroxisomes using a density barrier in a swinging-bucket rotor.	2002 May 22	12805925
[Prospects of the use of non-ionic X-ray contrast media during endoscopic retrograde cholangiopancreatography].	2002 Nov-Dec	12722628
Novel tools for production and purification of recombinant adeno-associated viral vectors.	2003	12526168
Comparison between the efficacy of dimeric and monomeric non-ionic contrast media (iodixanol vs iopromide) in urography in patients with macroscopic haematuria.	2003 Apr	12664121
Identification of organelles in bacteria similar to acidocalcisomes of unicellular eukaryotes.	2003 Aug 8	12783865
The ionic contrast medium ioxaglate interferes with thrombin-mediated feedback activation of factor V, factor VIII and platelets.	2003 Feb	12871500
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	12471034
Contrast-agent-induced acute renal dysfunction--is iodixanol the answer?	2003 Feb 6	12571263
Separation of bovine plasma lipoproteins by a rapid ultracentrifugation method.	2003 Jan	12531683
In vivo comparative antithrombotic effects of ioxaglate and iohexol and interaction with the platelet antiaggregant clopidogrel.	2003 Jan	12496519
Practical considerations of recombinant adeno-associated virus-mediated gene transfer for treatment of retinal degenerations.	2003 Jul	12825197
Iodinated contrast media interfere with gel barrier formation in plasma and serum separator tubes.	2003 Jul	12816919
Assessment of organ volume with different techniques using a living liver model.	2003 Jun	12764643
A rapid protocol for the prevention of contrast-induced renal dysfunction: the RAPPID study.	2003 Jun 18	12821233
[Reduced risk of nepropathy with isoosmolar contrast media].	2003 Jun 5	12833744
Delayed hypersensitivity reaction to the non-ionic X-ray contrast medium Visipaque (iodixanol).	2003 Mar	12755737
Delayed side effects induced by iodinated contrast media, especially those associated with iodixanol.	2003 Mar	12659083
Early and late reactions following the use of iopamidol 340, iomeprol 350 and iodixanol 320 in cardiac catheterization.	2003 Mar	12612387
Protection from contrast-induced nephropathy: is the answer in?	2003 Mar	12594699
Nephropathy induced by contrast medium.	2003 May 29	12774814
Nephropathy induced by contrast medium.	2003 May 29	12773659
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	12917397

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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