IOTHALAMATE SODIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H8I3N2O4.Na
Molecular Weight	635.8954
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CNC(=O)C1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I

InChI

InChIKey=WCIMWHNSWLLELS-UHFFFAOYSA-M

InChI=1S/C11H9I3N2O4.Na/c1-3(17)16-9-7(13)4(10(18)15-2)6(12)5(8(9)14)11(19)20;/h1-2H3,(H,15,18)(H,16,17)(H,19,20);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/mmx/iothalamate-meglumine-and-iothalamate-sodium.html
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28028385 | https://www.ncbi.nlm.nih.gov/pubmed/26573558 | https://www.ncbi.nlm.nih.gov/pubmed/18650405

Iothalamic Acid is an iodine-containing organic anion used as a radiocontrast agent. It is available as sodium iothalamate (Iothalamate sodium) and meglumine iothalamate (Iothalmate meglumine). It can be administered intravenously or intravesically (into the urinary bladder). Iothalamate is indicated to visualize specific regions of the vascular system and blood flow in these areas to help in the diagnosis and evaluation of neoplasms (known or suspected) or vascular diseases (congenital or acquired) that may cause changes in normal vascular anatomy or physiology. Iothalamate meglumine injection is indicated for use in cerebral angiography, peripheral arteriography or venography, arterial digital subtraction angiography1 , and intravenous digital subtraction angiography. Iothalamate meglumine and iothalamate sodium injection is indicated for use in selective coronary arteriography, selective renal arteriography, and in intravenous digital subtraction angiography. othalamate meglumine and iothalamate sodium injection and iothalamate sodium injection are indicated to visualize the aorta and its major branches. However, the injection of iothalamate meglumine and iothalamate sodium is preferred because it generally causes less severe hemodynamic, neurotoxic, and cardiotoxic effects than the individual injection of iothalamate sodium. Radioactive formulation is also available as sodium iothalamate I-125 Injection (GLOFIL-125). It is indicated for evaluation of glomerular filtration in the diagnosis or monitoring of patients with renal disease.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Kidney failure 10 Sources: https://www.drugs.com/mmx/iothalamate-meglumine-and-iothalamate-sodium.html	Diagnostic		Approved 8429	IOTHALAMATE SODIUM Approved Use Unknown Launch Date 1976

T_1/2

Value	Dose	Co-administered	Analyte	Population
64 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3230149	63 mmol single, intravascular dose: 63 mmol route of administration: Intravascular experiment type: SINGLE co-administered:		IOTHALAMIC ACID serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
90.45% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11403171			IOTHALAMIC ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5	Disc. AE: Thromboembolic event, Myocardial infarction... AEs leading to discontinuation/dose reduction: Thromboembolic event (serious) Myocardial infarction (serious) Stroke (serious) Paralysis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5
200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6	Disc. AE: Convulsions, Skin and subcutaneous conditions NEC... AEs leading to discontinuation/dose reduction: Convulsions Skin and subcutaneous conditions NEC (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6
200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7	Disc. AE: Stevens-Johnson syndrome, Toxic epidermal necrolysis... AEs leading to discontinuation/dose reduction: Stevens-Johnson syndrome (severe) Toxic epidermal necrolysis (severe) Acute generalized exanthematous pustulosis (severe) Drug reaction with eosinophilia and systemic symptoms (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7

AEs

AE	Significance	Dose	Population
Paralysis	Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5
Myocardial infarction	serious Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5
Stroke	serious Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5
Thromboembolic event	serious Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.5
Convulsions	Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6
Skin and subcutaneous conditions NEC	severe Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.6
Acute generalized exanthematous pustulosis	severe Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7
Drug reaction with eosinophilia and systemic symptoms	severe Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7
Stevens-Johnson syndrome	severe Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7
Toxic epidermal necrolysis	severe Disc. AE	200 mL single, intravenous Recommended Dose: 200 mL Route: intravenous Route: single Dose: 200 mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7	unhealthy Health Status: unhealthy Condition: Excretory urography\|cerebral angiography\| peripheral arteriography\|venography\| arthrography \|direct cholangiography \|endoscopic retrograde cholangiopancreatography\|contrast enhancement of computed tomographic brain images\| cranial computerized angiotomography\| intravenous digital subtraction angiography\|arterial digital subtraction angiography Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf Page: p.7

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY542667	https://www.001chemical.com/chem/2276-90-6
AA Blocks	AA006WJX	https://www.aablocks.com/goods/Goods/detail?id=AA006WJX
Alfa Chemistry	AP2276906	https://reagents.alfa-chemistry.com/product/iotalamic-acid-cas-2276-90-6-8198.html
Angel Pharmatech	AG259162	http://www.angelpharmatech.com/2276-90-6.html
Angene	AGN-PC-047KWE	http://www.angenechemical.com/productshow/AGN-PC-047KWE.html
BLD Pharm	BD134814	http://www.bldpharm.com/products/2276-90-6.html
BioChemPartner	BCP13316	http://www.biochempartner.com/2276-90-6-BCP13316
BioSynth	Q-201246	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-201246.html
CSNpharm	CSN11211	https://www.csnpharm.com/products/iotalamic-acid.html
Chem Scene	CS-4575	http://www.chemscene.com/2276-90-6.html
ChemMol	30112842	http://www.chemmol.com/chemmol/30112842.html
ChemMol	49403218	http://www.chemmol.com/chemmol/49403218.html
Chemspace	CSSB00020677865	https://chem-space.com/CSSB00020677865
Clearsynth	CS-T-29567	https://www.clearsynth.com/en/CST29567.html
Clearsynth	CS-T-56766	https://www.clearsynth.com/en/CST56766.html
Finetech	FT-0740526	http://www.finetechnology-ind.com/prod/detail/pub/2276-90-6.html
Glentham Life Sciences	GK9886	http://www.glentham.com/products/product/GK9886/
Lab Network	LN01305237	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01305237
MedChem Express	HY-B1053	https://www.medchemexpress.com/Iotalamic-acid.html
Molcore	MC542667	https://www.molcore.com/product/2276-90-6
MuseChem	I002737	https://www.musechem.com/product/I002737.html
OChem	13550	http://www.ocheminc.com/index.php?act=psearch&pid=276I906
eNovation Chemicals	D141442	https://www.enovationchem.com/ProductDetails.asp?ProductID=D141442
iChemical	EBD2456	http://www.ichemical.com/chemicals/cas-2276-90-6

PubMed

Title	Date	PubMed
[Recurrent aseptic meningitis (Mollaret meningitis)--spontaneous and drug-induced origin].	1991 Dec	1774010
Comparison of unenhanced and contrast-enhanced spiral CT for assessing interval change in patients with colorectal liver metastases.	2001 Aug	11508748
Functional effects of renal artery stent placement on treated and contralateral kidneys.	2002 Aug	12110020
Inadvertent intrathecal use of ionic contrast agent.	2002 Dec	12522612
Effects of intrathecal injection of diatrizoate on dopamine receptors.	2002 Jul	12139101
Glomerular filtration rate in children with solid tumors: normative values and a new method for estimation.	2003 Jun	12746163
Salutary effects of radiopaque contrast media on the survival of random-pattern skin flaps in the rat: an experimental study.	2004	14748032
Using serum creatinine to estimate glomerular filtration rate: accuracy in good health and in chronic kidney disease.	2004 Dec 21	15611490
Summaries for patients. Estimating kidney function in healthy people.	2004 Dec 21	15611485
Decline in native renal function early after bladder-drained pancreas transplantation alone.	2004 Mar 27	15077024
Effect of contrast media on vascular smooth muscle cells.	2004 Oct	15587421
[Methods for the quantification of left ventricular volumes assessed by radionuclide ventriculography (first part)].	2005	16405228
An alternative formula to the Cockcroft-Gault and the modification of diet in renal diseases formulas in predicting GFR in individuals with type 1 diabetes.	2005 Apr	15716336
Performance of the Cockcroft-Gault and modification of diet in renal disease equations in estimating GFR in ill hospitalized patients.	2005 Aug	16112042
Analysis of iodinated X-ray contrast agents in water samples by ion chromatography and inductively-coupled plasma mass spectrometry.	2005 Aug 26	16106857
Influence of iothalamate on renal medullary perfusion and oxygenation in the rat.	2005 Dec	16392607
Simultaneous determination of anions in nanoliter volumes.	2005 Jan	15610262
[Pancreas anulare as an incidental finding in multidetector computer tomography for symptomatic abdominal aortic aneurysm].	2006 Apr	16612737
Are prediction equations for glomerular filtration rate useful for the long-term monitoring of type 2 diabetic patients?	2006 Aug	16702203
A novel approach to flexor hallucis longus tenography.	2006 Dec	17114532
Virtual cystoscopy by intravesical instillation of dilute contrast medium: preliminary experience.	2006 Mar	16469568
Prospective comparison of helical CT of the abdomen and pelvis without and with oral contrast in assessing acute abdominal pain in adult Emergency Department patients.	2006 May	16738930
Drawbacks and prognostic value of formulas estimating renal function in patients with chronic heart failure and systolic dysfunction.	2006 Oct 10	17015793
Preemptive living donor kidney transplantation: do the benefits extend to all recipients?	2007 Jan 27	17264810
[Renal radionuclide scintigraphy in the evaluation of radiopaque substances on renal function].	2007 Jan-Feb	18274140
Iodide mumps after contrast media imaging: a rare adverse effect to iodine.	2007 Jul	17650837
Elevated vascular endothelial growth factor levels are associated with aortopulmonary collateral vessels in patients before and after the Fontan procedure.	2007 Jun	17540200
Evaluation of the effects of noniodinized and iodinized ionic contrast media and gadoteric acid in acute necrotizing pancreatitis: experimental study in rabbits.	2007 Nov	18090230
Duplicated ectopic ureter with vaginal insertion: 3D CT urography with i.v. and percutaneous contrast administration.	2007 Nov	17954624
Efficacy of single-session percutaneous drainage and 50% acetic Acid sclerotherapy for treatment of simple renal cysts.	2007 Nov-Dec	17914652
Decreased incidence of acute rejection in adolescent kidney transplant recipients using antithymocyte induction and triple immunosuppression.	2007 Sep 27	17893604
Inadvertent intrathecal administration of ionic contrast medium to a dog.	2007 Sep-Oct	17899973
Experimental study of intracranial hematoma detection with flat panel detector C-arm CT.	2008 Apr	18202240
Multidetector computed tomographic angiography in isolated third nerve palsy.	2008 Aug	18280569
Gradient-recalled echo sequences in direct shoulder MR arthrography for evaluating the labrum.	2008 Jan	17962935
Coraco- or costoclavicular paraosteoarthropathies in patients with severe central neurological disorders.	2008 Mar	18300141
Sweet's syndrome-like neutrophilic dermatosis resulting from exposure to a radiocontrast agent.	2008 Mar	18280347

Patents

Sample Use Guides

In Vivo Use Guide

For carotid angiography—Percutaneous or via catheter, 5 to 12 mL of a solution containing the equivalent of 282 mg of iodine per mL, repeated as needed. For vertebral angiography— Percutaneous or via catheter, 4 to 10 mL of a solution containing the equivalent of 282 mg of iodine per mL, repeated as needed. For retrograde brachial cerebral angiography— Percutaneous, 35 to 50 mL of a solution containing the equivalent of 282 mg of iodine per mL as a single dose, administered rapidly into the brachial artery.

Route of Administration: Intravascular

In Vitro Use Guide

Since the kidneys were perfused at constant flow, changes in renal perfusion pressure were directly proportional to changes in renal vascular resistance (RVR). The basal renal perfusion pressure was constant throughout each experiment varying between 60 and 80mmHg in different preparations. Each kidney was equilibrated for a 30- minute period prior to the addition of sodium iothalamate via a syringe pump linked to the perfusion line. Recovery to baseline was obtained between individual infusions in any one preparation. The contrast media solution in the syringe pump is termed the infusate, while the solution perfusing the kidney is termed the renal perfusate. Concentration response experiments were performed in each preparation. A 70% solution of sodium iothalamate (Conray 420) was infused into the perfusate line for 10-minute periods at predetermined rates to produce a range of iothalamate concentrations in the renal perfusate varying from 0.07% to 4.2%

Name

Type

Language

IOTHALAMATE SODIUM

Common Name

English

SODIUM IOTALAMATE [JAN]

Common Name

English

IOTHALAMIC ACID SODIUM SALT

Common Name

English

SODIUM IOTALAMATE [MART.]

Common Name

English

Monosodium 5-acetamido-2,4,6-triiodo-N-methylisophthalamate

Systematic Name

English

Iotalamate sodium [WHO-DD]

Common Name

English

IOTHALAMIC ACID SODIUM SALT [MI]

Common Name

English

IOTHALAMATE SODIUM [VANDF]

Common Name

English

ANGIO-CONRAY

Brand Name

English

SODIUM IOTHALAMATE

Common Name

English

VASCORAY COMPONENT IOTHALAMATE SODIUM

Common Name

English

BENZOIC ACID, 3-(ACETYLAMINO)-2,4,6-TRIIODO-5-((METHYLAMINO)CARBONYL)-, MONOSODIUM SALT

Common Name

English

IOTALAMATE SODIUM

Common Name

English

IOTHALAMATE SODIUM [ORANGE BOOK]

Common Name

English

IOTHALAMATE SODIUM [USP IMPURITY]

Common Name

English

IOTHALAMATE SODIUM COMPONENT OF VASCORAY

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28500