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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H21I6N5O8.C7H17NO5
Molecular Weight 1464.0926
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOXAGLATE MEGLUMINE

SMILES

CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC(=O)C1=C(I)C(C(=O)NCC(=O)NC2=C(I)C(C(=O)NCCO)=C(I)C(C(O)=O)=C2I)=C(I)C(N(C)C(C)=O)=C1I

InChI

InChIKey=HUHDYASLFWQVOL-WZTVWXICSA-N
InChI=1S/C24H21I6N5O8.C7H17NO5/c1-7(37)35(3)20-17(29)10(21(39)31-2)13(25)11(18(20)30)23(41)33-6-8(38)34-19-15(27)9(22(40)32-4-5-36)14(26)12(16(19)28)24(42)43;1-8-2-4(10)6(12)7(13)5(11)3-9/h36H,4-6H2,1-3H3,(H,31,39)(H,32,40)(H,33,41)(H,34,38)(H,42,43);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6999377 | https://www.ncbi.nlm.nih.gov/pubmed/21414657 | https://www.drugs.com/pro/hexabrix.html | https://www.ncbi.nlm.nih.gov/pubmed/2022451 | https://www.ncbi.nlm.nih.gov/pubmed/11271894

Ioxaglate Sodium Meglumine (trade name Hexabrix) is a new low osmolality ionic contrast agent, that used as a diagnostic radiopaque medium. Following intravascular injection, Ioxaglate Sodium Meglumine is rapidly transported through the circulatory system to the kidneys and is excreted unchanged in the urine. The joint spaces as well as the uterus and fallopian tubes may be visualized by the direct injection of the contrast medium into the region to be studied. The usual adult dose for left coronary arteriography is 8 mL (range 2-14 mL) and for right coronary arteriography is 5 mL (range 1-10 mL). The doses may be repeated as necessary Patients may have clinically insignificant ECG changes during the procedure. The following adverse effects have occurred in conjunction with the administration of iodinated intravascular contrast agents for this procedure: hypotension, shock, anginal pain, myocardial infarction, cardiac arrhythmias (bradycardia, ventricular tachycardia, ventricular fibrillation) and cardiac arrest.

CNS Activity

Curator's Comment: Disruption in the BBB, such as occurs in malignant tumors of the brain, allows accumulation of contrast medium within the interstitial tumor tissue; adjacent normal brain tissue does not contain the contrast medium.

Originator

Curator's Comment: Hexabrix® was first marketed in 1979 in France. Guerbet markets Hexabrix® in Japan (1978) and in the USA (1985)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
HEXABRIX

Approved Use

INDICATIONS AND USAGE.

Launch Date

1986
Diagnostic
HEXABRIX

Approved Use

INDICATIONS AND USAGE. HEXABRIX is indicated for use in pediatric angiocardiography, selective coronary arteriography with or without left ventriculography, peripheral arteriography, aortography, selective visceral arteriography, cerebral angiography, intra-arterial digital subtraction angiography, intravenous digital subtraction angiography, peripheral venography (phlebography), excretory urography, contrast enhancement of computed tomographic head imaging and body imaging, arthrography and hysterosalpingography.

Launch Date

1986
Diagnostic
HEXABRIX

Approved Use

INDICATIONS AND USAGE. HEXABRIX is indicated for use in pediatric angiocardiography, selective coronary arteriography with or without left ventriculography, peripheral arteriography, aortography, selective visceral arteriography, cerebral angiography, intra-arterial digital subtraction angiography, intravenous digital subtraction angiography, peripheral venography (phlebography), excretory urography, contrast enhancement of computed tomographic head imaging and body imaging, arthrography and hysterosalpingography.

Launch Date

1986
Diagnostic
Hexabrix

Approved Use

Coronary Angiography

Launch Date

1985
Diagnostic
Hexabrix

Approved Use

Cerebral angiography

Launch Date

1985
Diagnostic
Hexabrix

Approved Use

Peripheral venography (phlebography)

Launch Date

1985
Diagnostic
Hexabrix

Approved Use

arthrography

Launch Date

1985
Diagnostic
Hexabrix

Approved Use

excretory urography

Launch Date

1985
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2100 μg/mL
26.663 g single, intravenous
dose: 26.663 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IOXAGLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
92 min
26.663 g single, intravenous
dose: 26.663 g
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IOXAGLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Other AEs: Chest pain, Nausea...
Other AEs:
Chest pain (grade 1-2, 4.4%)
Nausea (grade 1-2, 6.4%)
Vomiting (grade 1-2, 1.6%)
Allergic skin reaction (grade 1-2, 5.2%)
Bronchospasm (grade 3, 0.8%)
Warmth (grade 1-2, 4.4%)
Bad taste (grade 1-2, 0.4%)
Sources: Page: p.901
194.8 mL single, intravenous (mean)
Recommended
Dose: 194.8 mL
Route: intravenous
Route: single
Dose: 194.8 mL
Sources: Page: p.926
unhealthy, 68.7+/-7.5
n = 135
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 68.7+/-7.5
Sex: M+F
Population Size: 135
Sources: Page: p.926
Other AEs: Nephropathy...
Other AEs:
Nephropathy (17%)
Sources: Page: p.926
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Other AEs: Cyanosis, Bradycardia...
Other AEs:
Cyanosis (grade 3-5)
Bradycardia (grade 3-5)
Acidosis (grade 3-5)
Pulmonary hemorrhage (grade 3-5)
Convulsions (grade 3-5)
Coma (grade 4-5)
Cardiac arrest (grade 4-5)
Sources: Page: p.11
AEs

AEs

AESignificanceDosePopulation
Bad taste grade 1-2, 0.4%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Vomiting grade 1-2, 1.6%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Chest pain grade 1-2, 4.4%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Warmth grade 1-2, 4.4%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Allergic skin reaction grade 1-2, 5.2%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Nausea grade 1-2, 6.4%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Bronchospasm grade 3, 0.8%
101 mL single, intraarterial
Recommended
Dose: 101 mL
Route: intraarterial
Route: single
Dose: 101 mL
Sources: Page: p.901
unhealthy, 59+/-11
n = 250
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 59+/-11
Sex: M+F
Population Size: 250
Sources: Page: p.901
Nephropathy 17%
194.8 mL single, intravenous (mean)
Recommended
Dose: 194.8 mL
Route: intravenous
Route: single
Dose: 194.8 mL
Sources: Page: p.926
unhealthy, 68.7+/-7.5
n = 135
Health Status: unhealthy
Condition: Cardiovascular diseases
Age Group: 68.7+/-7.5
Sex: M+F
Population Size: 135
Sources: Page: p.926
Acidosis grade 3-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Bradycardia grade 3-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Convulsions grade 3-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Cyanosis grade 3-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Pulmonary hemorrhage grade 3-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Cardiac arrest grade 4-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
Coma grade 4-5
250 mL single, intravenous (min)
Overdose
Dose: 250 mL
Route: intravenous
Route: single
Dose: 250 mL
Sources: Page: p.11
unhealthy
Health Status: unhealthy
Condition: Cardiovascular diseases
Sources: Page: p.11
PubMed

PubMed

TitleDatePubMed
[Arteries of the uterine cervix in reproductive age in microangiographic studies].
2002 Dec
[Arteries of the hilum and parenchymal part of the ovary in reproductive age in microangiographic studies].
2002 Dec
[Iodic allergic reaction with vasospasm occluded coronary during coronarography].
2002 Dec
Effects of gentamicin, lipopolysaccharide, and contrast media on immortalized proximal tubular cells.
2002 Nov
Iodinated contrast media induce neutrophil apoptosis through a mitochondrial and caspase mediated pathway.
2002 Nov
Allergies correlated to adverse reactions induced by non-ionic monomeric and ionic dimeric contrast media for contrast enhanced CT examination.
2002 Sep
Differential effects of the iodinated contrast agents Ioxaglate, Iohexol and Iodixanol on thrombus formation and fibrinolysis.
2003
Roles of intracellular Ca2+ and cyclic AMP in mast cell histamine release induced by radiographic contrast media.
2003 Apr
Involvement of proteinase-activated receptor-2 in mast cell tryptase-induced barrier dysfunction in bovine aortic endothelial cells.
2003 Aug
[Absence of nephro-protective effect of acetylcysteine in patients with chronic renal failure investigated by coronary angiography].
2003 Dec
No difference among modern contrast media's effect on neointimal proliferation and restenosis after coronary stenting in pigs.
2003 Dec
Nonionic low-osmolar contrast media have no impact on major adverse cardiac events in patients undergoing coronary stenting with appropriate antiplatelet therapy.
2003 Dec
The ionic contrast medium ioxaglate interferes with thrombin-mediated feedback activation of factor V, factor VIII and platelets.
2003 Feb
In vivo comparative antithrombotic effects of ioxaglate and iohexol and interaction with the platelet antiaggregant clopidogrel.
2003 Jan
Calcium-dependent injury of human microvascular endothelial cells induced by a variety of iodinated radiographic contrast media.
2003 Jun
Delayed side effects induced by iodinated contrast media, especially those associated with iodixanol.
2003 Mar
A potent tryptase inhibitor nafamostat mesilate dramatically suppressed pulmonary dysfunction induced in rats by a radiographic contrast medium.
2003 Mar
Contrast media augmented apoptosis of cultured renal mesangial, tubular, epithelial, endothelial, and hepatic cells.
2003 Mar
Review article: Effects of radiographic contrast media on the lung.
2003 May
Inflammatory markers increase following exposure to radiographic contrast media.
2003 Sep
Glaucoma as a complication of superselective ophthalmic angiography.
2003 Sep
Similarity and difference in the acute lung injury induced by a radiographic contrast medium and an anticancer agent paclitaxel in rats.
2004 Aug 30
Evaluation of the nitric oxide production in rat renal artery smooth muscle cells culture exposed to radiocontrast agents.
2004 Feb
Hepatopulmonary syndrome induced by common bile duct ligation in a rabbit model: correlation between pulmonary vascular dilatation on thin-section CT and angiography and serum nitrite concentration or endothelial nitric oxide synthase (eNOS)1 expression.
2004 Jul-Sep
Prediction of the no-reflow phenomenon with ultrasonic tissue characterization in patients with anterior wall acute myocardial infarction.
2004 Jun 1
Role of osmolality of contrast media in the development of post-ERCP pancreatitis: a metanalysis.
2004 Mar
Embolic effects of superabsorbent polymer microspheres in rabbit renal model: comparison with tris-acryl gelatin microspheres and polyvinyl alcohol.
2004 Nov-Dec
Influence of contrast media (iopromide, ioxaglate, gadolinium-DOTA) on blood viscosity, erythrocyte morphology and platelet function.
2005
Iodinated radiographic contrast media possess antioxidant properties in vitro.
2005 Dec
The effects of carbon dioxide versus ioxaglate in the rat kidney.
2005 Feb
Ultrasound findings of iodide mumps.
2005 Feb
Renal effects of CO2 and iodinated contrast media in patients undergoing renovascular intervention: a prospective, randomized study.
2005 Jan
Contrast-induced nephropathy after percutaneous coronary interventions in relation to chronic kidney disease and hemodynamic variables.
2005 Jan 1
N-acetylcysteine does not prevent contrast induced nephropathy after cardiac catheterisation with an ionic low osmolality contrast medium: a multicentre clinical trial.
2005 Jun
Contrast medium attenuates platelet activation and platelet-leukocyte cross-talk.
2005 May
Usefulness of a new grading system based on coronary flow velocity pattern in predicting outcome in patients with acute myocardial infarction having percutaneous coronary intervention.
2005 Oct 1
Adverse reactions of low osmolar non-ionic and ionic contrast media when used together or separately during percutaneous coronary intervention.
2005 Sep
The effect of contrast media on the synovial membrane.
2005 Sep
The prevention of anaphylactoid reactions to iodinated radiological contrast media: a systematic review.
2006 Apr 27
A randomized trial of saline hydration to prevent contrast nephropathy in chronic renal failure patients.
2006 Aug
Effects of different contrast media on glutathione peroxidase and superoxide dismutase activities in the heart and kidneys of normal and streptozotocin-induced diabetic rats.
2006 Jul
Cardiac events after low osmolar ionic or isosmolar nonionic contrast media utilization in the current era of coronary angioplasty.
2006 Jun
Renal failure in 57 925 patients undergoing coronary procedures using iso-osmolar or low-osmolar contrast media.
2006 Nov
Renal toxicity evaluation and comparison between visipaque (iodixanol) and hexabrix (ioxaglate) in patients with renal insufficiency undergoing coronary angiography: the RECOVER study: a randomized controlled trial.
2006 Sep 5
Reactive oxygen species independent cytotoxicity induced by radiocontrast agents in tubular cells (LLC-PK1 and MDCK).
2007
Iodixanol vs ioxaglate for preventing contrast nephropathy: who is winner?
2007 Apr
Evaluation and comparison between visipaque (iodixanol) and hexabrix (ioxaglate) in coronary angiography.
2007 Apr 17
Visipaque (iodixanol) and hexabrix (ioxaglate) in renal insufficiency.
2007 Apr 17
Contrast agent enhanced pQCT of articular cartilage.
2007 Feb 21
Effects of iodinated contrast media on endothelium: An in vitro study.
2007 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Hexabrix may be administered by catheter injection into the chambers of the heart or associated large blood vessels. Hexabrix may be injected to visualize the peripheral arterial circulation. Hexabrix may be injected centrally, in either the superior or inferior vena cava or right atrium; or peripherally into an appropriate arm vein. Hexabrix may be injected to visualize the peripheral venous circulation. Venograms are obtained by injection or infusion into an appropriate vein in the upper or lower extremity.
For PEDIATRIC ANGIOCARDIOGRAPHY the usual total dose of Hexabrix per procedure, which includes diagnostic and test doses is about 4 mL/kg. This dosage may be as small as 1.5 mL/kg and should not normally exceed 5 mL/kg. For SELECTIVE CORONARY ARTERIOGRAPHY the usual adult dose for left coronary arteriography is 8 mL (range 2-14 mL) and for right coronary arteriography is 5 mL (range 1-10 mL). For PHLEBOGRAPHY the dose for adults will usually range from 50-100 mL per extremity of full strength (32% iodine) Hexabrix as a single rapid injection.
Route of Administration: Intravascular
In Vitro Use Guide
Bovine patellar cartilage samples were immersed in 21 mM Hexabrix (Ioxaglic Acid) solution for 24 hours to be successfully scanned with a clinical pQCT instrument.
Name Type Language
IOXAGLATE MEGLUMINE
ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
Ioxaglate meglumine [WHO-DD]
Common Name English
MEGLUMINE IOXAGLATE
MART.  
Common Name English
BENZOIC ACID, 3-((((3-(ACETYLMETHYLAMINO)-2,4,6-TRIIODO-5-((METHYLAMINO)CARBONYL)BENZOYL)AMINO)ACETYL)AMINO)-5-(((2-HYDROXYETHYL)AMINO)CARBONYL)-2,4,6-TRIIODO-, COMPOUND WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:1)
Common Name English
IOXAGLATE MEGLUMINE COMPONENT OF HEXABRIX
Common Name English
IOXAGLATE MEGLUMINE [ORANGE BOOK]
Common Name English
MEGLUMINE IOXAGLATE [MART.]
Common Name English
N-(2-HYDROXYETHYL)-2,4,6-TRIIODO-5-(2-(2,4,6-TRIIODO-3-(N-METHYLACETAMIDO)-5-(METHYLCARBAMOYL)BENZAMIDO)ACETAMIDO)ISOPHTHALAMIC ACID, COMPOUND WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:1)
Common Name English
IOXAGLATE MEGLUMINE [VANDF]
Common Name English
MP 302 (MIXT. WITH IOXAGLATE SODIUM)
Code English
IOXAGLATE MEGLUMINE [USAN]
Common Name English
HEXABRIX COMPONENT IOXAGLATE MEGLUMINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28500
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
Code System Code Type Description
EVMPD
SUB02756MIG
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
CAS
59018-13-2
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
RXCUI
66895
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY RxNorm
SMS_ID
100000090621
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
PUBCHEM
20055342
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
FDA UNII
75JR975T11
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
DRUG BANK
DBSALT001301
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID20974491
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
NCI_THESAURUS
C47571
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
261-561-7
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201291
Created by admin on Fri Dec 15 15:22:25 GMT 2023 , Edited by admin on Fri Dec 15 15:22:25 GMT 2023
PRIMARY