Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H21I6N5O8 |
Molecular Weight | 1268.8791 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=TYYBFXNZMFNZJT-UHFFFAOYSA-N
InChI=1S/C24H21I6N5O8/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/h36H,4-6H2,1-3H3,(H,31,39)(H,32,40)(H,33,41)(H,34,38)(H,42,43)
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 |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018905s024lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018905s025lbl.pdfCurator'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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/018905s024lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018905s025lbl.pdf
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
Sources: http://medlibrary.org/lib/rx/meds/hexabrix-1/https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018905s025lbl.pdf
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL204 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12871500 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | HEXABRIX Approved UseINDICATIONS AND USAGE. Launch Date1986 |
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Diagnostic | HEXABRIX Approved UseINDICATIONS 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 Date1986 |
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Diagnostic | HEXABRIX Approved UseINDICATIONS 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 Date1986 |
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Diagnostic | Hexabrix Approved UseCoronary Angiography Launch Date1985 |
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Diagnostic | Hexabrix Approved UseCerebral angiography Launch Date1985 |
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Diagnostic | Hexabrix Approved UsePeripheral venography (phlebography) Launch Date1985 |
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Diagnostic | Hexabrix Approved Usearthrography Launch Date1985 |
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Diagnostic | Hexabrix Approved Useexcretory urography Launch Date1985 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Sources: Page: p.901Nausea (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%) |
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... |
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) Sources: Page: p.11Bradycardia (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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
[Arteries of the uterine cervix in reproductive age in microangiographic studies]. | 2002 Dec |
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[Arteries of the hilum and parenchymal part of the ovary in reproductive age in microangiographic studies]. | 2002 Dec |
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[Iodic allergic reaction with vasospasm occluded coronary during coronarography]. | 2002 Dec |
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Effects of gentamicin, lipopolysaccharide, and contrast media on immortalized proximal tubular cells. | 2002 Nov |
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Iodinated contrast media induce neutrophil apoptosis through a mitochondrial and caspase mediated pathway. | 2002 Nov |
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Allergies correlated to adverse reactions induced by non-ionic monomeric and ionic dimeric contrast media for contrast enhanced CT examination. | 2002 Sep |
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Differential effects of the iodinated contrast agents Ioxaglate, Iohexol and Iodixanol on thrombus formation and fibrinolysis. | 2003 |
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Roles of intracellular Ca2+ and cyclic AMP in mast cell histamine release induced by radiographic contrast media. | 2003 Apr |
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Involvement of proteinase-activated receptor-2 in mast cell tryptase-induced barrier dysfunction in bovine aortic endothelial cells. | 2003 Aug |
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[Absence of nephro-protective effect of acetylcysteine in patients with chronic renal failure investigated by coronary angiography]. | 2003 Dec |
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No difference among modern contrast media's effect on neointimal proliferation and restenosis after coronary stenting in pigs. | 2003 Dec |
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Nonionic low-osmolar contrast media have no impact on major adverse cardiac events in patients undergoing coronary stenting with appropriate antiplatelet therapy. | 2003 Dec |
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The ionic contrast medium ioxaglate interferes with thrombin-mediated feedback activation of factor V, factor VIII and platelets. | 2003 Feb |
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In vivo comparative antithrombotic effects of ioxaglate and iohexol and interaction with the platelet antiaggregant clopidogrel. | 2003 Jan |
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Calcium-dependent injury of human microvascular endothelial cells induced by a variety of iodinated radiographic contrast media. | 2003 Jun |
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Delayed side effects induced by iodinated contrast media, especially those associated with iodixanol. | 2003 Mar |
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A potent tryptase inhibitor nafamostat mesilate dramatically suppressed pulmonary dysfunction induced in rats by a radiographic contrast medium. | 2003 Mar |
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Contrast media augmented apoptosis of cultured renal mesangial, tubular, epithelial, endothelial, and hepatic cells. | 2003 Mar |
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Review article: Effects of radiographic contrast media on the lung. | 2003 May |
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Inflammatory markers increase following exposure to radiographic contrast media. | 2003 Sep |
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Glaucoma as a complication of superselective ophthalmic angiography. | 2003 Sep |
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Similarity and difference in the acute lung injury induced by a radiographic contrast medium and an anticancer agent paclitaxel in rats. | 2004 Aug 30 |
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Evaluation of the nitric oxide production in rat renal artery smooth muscle cells culture exposed to radiocontrast agents. | 2004 Feb |
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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 |
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Prediction of the no-reflow phenomenon with ultrasonic tissue characterization in patients with anterior wall acute myocardial infarction. | 2004 Jun 1 |
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Role of osmolality of contrast media in the development of post-ERCP pancreatitis: a metanalysis. | 2004 Mar |
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Embolic effects of superabsorbent polymer microspheres in rabbit renal model: comparison with tris-acryl gelatin microspheres and polyvinyl alcohol. | 2004 Nov-Dec |
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Influence of contrast media (iopromide, ioxaglate, gadolinium-DOTA) on blood viscosity, erythrocyte morphology and platelet function. | 2005 |
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Iodinated radiographic contrast media possess antioxidant properties in vitro. | 2005 Dec |
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The effects of carbon dioxide versus ioxaglate in the rat kidney. | 2005 Feb |
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Ultrasound findings of iodide mumps. | 2005 Feb |
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Renal effects of CO2 and iodinated contrast media in patients undergoing renovascular intervention: a prospective, randomized study. | 2005 Jan |
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Contrast-induced nephropathy after percutaneous coronary interventions in relation to chronic kidney disease and hemodynamic variables. | 2005 Jan 1 |
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N-acetylcysteine does not prevent contrast induced nephropathy after cardiac catheterisation with an ionic low osmolality contrast medium: a multicentre clinical trial. | 2005 Jun |
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Contrast medium attenuates platelet activation and platelet-leukocyte cross-talk. | 2005 May |
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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 |
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Adverse reactions of low osmolar non-ionic and ionic contrast media when used together or separately during percutaneous coronary intervention. | 2005 Sep |
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The effect of contrast media on the synovial membrane. | 2005 Sep |
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The prevention of anaphylactoid reactions to iodinated radiological contrast media: a systematic review. | 2006 Apr 27 |
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A randomized trial of saline hydration to prevent contrast nephropathy in chronic renal failure patients. | 2006 Aug |
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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 |
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Cardiac events after low osmolar ionic or isosmolar nonionic contrast media utilization in the current era of coronary angioplasty. | 2006 Jun |
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Renal failure in 57 925 patients undergoing coronary procedures using iso-osmolar or low-osmolar contrast media. | 2006 Nov |
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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 |
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Reactive oxygen species independent cytotoxicity induced by radiocontrast agents in tubular cells (LLC-PK1 and MDCK). | 2007 |
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Iodixanol vs ioxaglate for preventing contrast nephropathy: who is winner? | 2007 Apr |
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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 |
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Contrast agent enhanced pQCT of articular cartilage. | 2007 Feb 21 |
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Effects of iodinated contrast media on endothelium: An in vitro study. | 2007 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.drugs.com/pro/hexabrix.html
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19052932
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
Edited
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on
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Record UNII |
Z40X7EI2AF
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Record Status |
Validated (UNII)
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N0000180185
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NCI_THESAURUS |
C28500
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V08AB03
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QV08AB03
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N0000010258
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |