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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

Molecular Formula C7H17NO5
Molecular Weight 195.2136
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C24H21I6N5O8
Molecular Weight 1268.8791
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
A comparison of the efficacy and safety of ioxaglate and iobitridol in renal angioplasty.
2000 Mar-Apr
Effects of radiographic contrast media on pulmonary vascular resistance of normoxic and chronically hypoxic pulmonary hypertensive rats.
2001 Dec
Morphologic degeneration of human microvascular endothelial cells induced by iodinated contrast media.
2001 Feb
Iomeprol: current and future profile of a radiocontrast agent.
2001 Feb
Serum pancreastatin levels predict response to hepatic artery chemoembolization and somatostatin analogue therapy in metastatic neuroendocrine tumors.
2001 Jan 12
Comparison of effects of ioxaglate versus iomeprol on histamine and tryptase release in patients with ischemic cardiomyopathy.
2001 Jul 15
Contrast medium-induced pulmonary vascular hyperpermeability is aggravated in a rat climacterium model.
2001 Mar
Acute and subacute stent occlusion; risk-reduction by ionic contrast media.
2001 Mar
Delayed adverse reaction to sodium ioxaglic acid-meglumine.
2001 Mar-Apr
Comparative effects of ionic and nonionic iodinated low-osmolar contrast media on platelet function with the PFA-100 (platelet function analyzer).
2001 May
Allergic reactions at repeat femoral angiography with ioxaglate.
2001 Nov
The increased histamine release in ischaemic heart disease patients undergoing coronaroangiography is not mediated by specific IgE.
2002
Contrast media--why the confusion?
2002 Jan
Contrast media increase vascular endothelial permeability by inhibiting nitric-oxide production.
2002 Jan
Iodinated contrast medium-induced potassium release: the effect of mixing ratios.
2002 Jul-Aug
Do clinically relevant circulating concentrations of radiographic contrast agents inhibit platelet-dependent arterial thrombosis?
2002 Mar 1
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
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
Similarity and difference in the acute lung injury induced by a radiographic contrast medium and an anticancer agent paclitaxel in rats.
2004 Aug 30
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
Embolic effects of superabsorbent polymer microspheres in rabbit renal model: comparison with tris-acryl gelatin microspheres and polyvinyl alcohol.
2004 Nov-Dec
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
N-acetylcysteine does not prevent contrast induced nephropathy after cardiac catheterisation with an ionic low osmolality contrast medium: a multicentre clinical trial.
2005 Jun
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
The prevention of anaphylactoid reactions to iodinated radiological contrast media: a systematic review.
2006 Apr 27
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:22:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:25 GMT 2023
Record UNII
75JR975T11
Record Status Validated (UNII)
Record Version
  • Download
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
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