IODIXANOL

Details

Stereochemistry	UNKNOWN
Molecular Formula	C35H44I6N6O15
Molecular Weight	1550.1819
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)N(CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I)C2=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C2I

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 71 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020351s045lbl.pdf	Diagnostic		Approved 8429	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 1996

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
Early and late reactions after the use of iopamidol 340, ioxaglate 320, and iodixanol 320 in cardiac catheterization.	2001 Apr	11275937
Is contrast-related vasodilatation after intra-coronary iodixanol and iopromide in vivo endothelium-dependent?	2001 Dec	11888823
The polyphosphate bodies of Chlamydomonas reinhardtii possess a proton-pumping pyrophosphatase and are similar to acidocalcisomes.	2001 Dec 7	11579086
Investigation of binding of 125I-iodixanol to high molecular weight substances after incubation with rat liver homogenates.	2001 Jan	11167344
Effect of radiologic contrast media on cell volume regulation in rabbit proximal renal tubules.	2001 May	11345270
Iodixanol pharmacokinetics in children.	2001 May-Jun	11343148
Ionic or non-ionic contrast media in stent placement.	2001 Nov	11603915
From COURT to HOMBURG: in search of the optimal contrast agent.	2001 Nov	11603912
Full-motion pulse inversion power Doppler contrast echocardiography differentiates stunning from necrosis and predicts recovery of left ventricular function after acute myocardial infarction.	2001 Nov 1	11691513
Lipoprotein lipase and leptin are accumulated in different secretory compartments in rat adipocytes.	2001 Sep 21	11451949
Contrast medium concentration in epithelial mucosal cells after colonic instillation of lodixanol: a semiquantitative study indicating the route of permeation.	2002 Apr	11942652
Comparison of nitric oxide production and motion characteristics after 3-layer percoll and IxaPrep preparation methods of human sperm.	2002 Aug	12192481
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
Iodixanol in paediatric gastrointestinal imaging: safety and efficacy comparison with iohexol.	2002 Feb	11893636
Contrast media--a contradiction?	2002 Jan	11786001
Isolation of purified oocyst walls and sporocysts from Toxoplasma gondii.	2002 Jul-Aug	12188226
Purification of lipid rafts from cultured cells.	2002 Jun 18	12806159
Purification of islets of Langerhans from porcine pancreas.	2002 Jun 18	12806158
Rapid purification of nuclei from animal and plant tissues and cultured cells.	2002 Jun 7	12806139
Comparison in myelography between iodixanol 270 and 320 mgI/ml and iotrolan 300 mgI/ml: a multicentre, randomised, parallel-group, double-blind, phase III trial.	2002 Mar	11870488
Acidocalcisomes are functionally linked to the contractile vacuole of Dictyostelium discoideum.	2002 Mar 8	11748243
[Sonographic imaging of lymphatic vessels compared to other methods].	2002 May	12063422
Preparation of preformed iodixanol gradients.	2002 May 16	12805919
Purification of intact plant protoplasts by flotation at 1g.	2002 May 21	12805924
Purification of peroxisomes using a density barrier in a swinging-bucket rotor.	2002 May 22	12805925
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
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
Separation of bovine plasma lipoproteins by a rapid ultracentrifugation method.	2003 Jan	12531683
Iodinated contrast media interfere with gel barrier formation in plasma and serum separator tubes.	2003 Jul	12816919
A rapid protocol for the prevention of contrast-induced renal dysfunction: the RAPPID study.	2003 Jun 18	12821233
Delayed side effects induced by iodinated contrast media, especially those associated with iodixanol.	2003 Mar	12659083
Oral acetylcysteine does not protect renal function from moderate to high doses of intravenous radiographic contrast.	2003 Mar	12594698
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 [ORANGE BOOK]

Common Name

English

VISIPAQUE

Brand Name

English

Iodixanol [WHO-DD]

Common Name

English

iodixanol [INN]

Common Name

English

IODIXANOL [MI]

Common Name

English

IODIXANOL [VANDF]

Common Name

English

IODIXANOL [USP MONOGRAPH]

Common Name

English

IODIXANOL [USP IMPURITY]

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