IOTHALAMIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H9I3N2O4
Molecular Weight	613.9136
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=O)C1=C(I)C(C(O)=O)=C(I)C(NC(C)=O)=C1I

InChI

InChIKey=UXIGWFXRQKWHHA-UHFFFAOYSA-N

InChI=1S/C11H9I3N2O4/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)

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 2.05718405E11

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
Comparison of unenhanced and contrast-enhanced spiral CT for assessing interval change in patients with colorectal liver metastases.	2001 Aug	11508748
Ionic and non-ionic contrast agent-mediated endothelial injury. Quantitative analysis of cell proliferation during endothelial repair.	2001 Jul	11442469
Iothalamate measured by capillary electrophoresis is a suitable alternative to radiolabeled inulin in renal micropuncture.	2002 Sep	12164892
N-acetylcysteine ameliorates renal microcirculation: studies in rats.	2003 Feb	12631128
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
CT and MR imaging of nitinol stents with radiopaque distal markers.	2004 Jun	15178723
Sensitivity variation of doped Fricke gel irradiated with monochromatic synchrotron X rays between 33.5 and 80 keV.	2005	15956218
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
Analysis of iodinated X-ray contrast agents in water samples by ion chromatography and inductively-coupled plasma mass spectrometry.	2005 Aug 26	16106857
Simultaneous determination of anions in nanoliter volumes.	2005 Jan	15610262
Telebrix Gastro in the management of adhesive small bowel obstruction.	2005 May	15980741
Iodinated contrast induced renal vasoconstriction is due in part to the downregulation of renal cortical and medullary nitric oxide synthesis.	2006 Aug	16890873
Virtual cystoscopy by intravesical instillation of dilute contrast medium: preliminary experience.	2006 Mar	16469568
Effect on bone induction of using contrast media to reconstitute recombinant human bone morphogenetic protein-2 in an ectopic model in rats.	2006 Nov	17120893
Renal handling of cystatin C.	2007 Apr	17110405
Elevated vascular endothelial growth factor levels are associated with aortopulmonary collateral vessels in patients before and after the Fontan procedure.	2007 Jun	17540200
Injection rate threshold of triple-lumen central venous catheters: an in vitro study.	2007 May	17434071
Multidetector computed tomographic angiography in isolated third nerve palsy.	2008 Aug	18280569
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

IOTHALAMIC ACID

Official Name

English

IOTALAMIC ACID [MART.]

Common Name

English

iotalamic acid [INN]

Common Name

English

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

Common Name

English

MI-216

Code

English

IOTHALAMATE [VANDF]

Common Name

English

IOTALAMIC ACID

Official Name

English

IOTALAMIC ACID [EP IMPURITY]

Common Name

English

IOTHALAMATE

Common Name

English

NSC-759891

Code

English

IOTHALAMIC ACID [USAN]

Common Name

English

IOTHALAMIC ACID [MI]

Common Name

English

IOTHALAMIC ACID [USP MONOGRAPH]

Common Name

English

IOTHALAMIC ACID [USP-RS]

Common Name

English

IOTALAMIC ACID [JAN]

Common Name

English

5-Acetamido-2,4,6-triiodo-N-methylisophthalamic acid

Systematic Name

English

Iotalamic acid [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

V08AA04