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

Molecular Formula	C11H9I3N2O4
Molecular Weight	613.9136
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8583	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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf	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

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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/013295s070lbl.pdf

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
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
BLD Pharm	BD134814	http://www.bldpharm.com/products/2276-90-6.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
CSNpharm	CSN11211	https://www.csnpharm.com/products/iotalamic-acid.html
eNovation Chemicals	D141442	https://www.enovationchem.com/ProductDetails.asp?ProductID=D141442
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/
iChemical	EBD2456	http://www.ichemical.com/chemicals/cas-2276-90-6
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

PubMed

Title	Date	PubMed
Multidetector computed tomographic angiography in isolated third nerve palsy.	2008-08	18280569
Experimental study of intracranial hematoma detection with flat panel detector C-arm CT.	2008-04	18202240
Coraco- or costoclavicular paraosteoarthropathies in patients with severe central neurological disorders.	2008-03	18300141
Sweet's syndrome-like neutrophilic dermatosis resulting from exposure to a radiocontrast agent.	2008-03	18280347
[Renal radionuclide scintigraphy in the evaluation of radiopaque substances on renal function].	2008-02-16	18274140
Gradient-recalled echo sequences in direct shoulder MR arthrography for evaluating the labrum.	2008-01	17962935
Evaluation of the effects of noniodinized and iodinized ionic contrast media and gadoteric acid in acute necrotizing pancreatitis: experimental study in rabbits.	2007-11	18090230
Duplicated ectopic ureter with vaginal insertion: 3D CT urography with i.v. and percutaneous contrast administration.	2007-11	17954624
Inadvertent intrathecal administration of ionic contrast medium to a dog.	2007-09-29	17899973
Decreased incidence of acute rejection in adolescent kidney transplant recipients using antithymocyte induction and triple immunosuppression.	2007-09-27	17893604
High performance liquid chromatographic measurement of iothalamate in human serum and urine for evaluation of glomerular filtration rate.	2007-09-01	17599846
Iodide mumps after contrast media imaging: a rare adverse effect to iodine.	2007-07	17650837
Impact of creatinine calibration on performance of GFR estimating equations in a pooled individual patient database.	2007-07	17591522
Elevated vascular endothelial growth factor levels are associated with aortopulmonary collateral vessels in patients before and after the Fontan procedure.	2007-06	17540200
MR shoulder arthrography in patients younger than 40 years of age: frequency of rotator cuff tear versus labroligamentous pathology.	2007-06	17504318
Alteration in renal organic anion transporter 1 after ischemia/reperfusion in cadaveric renal allografts.	2007-06	17312013
Injection rate threshold of triple-lumen central venous catheters: an in vitro study.	2007-05	17434071
Efficacy of single-session percutaneous drainage and 50% acetic Acid sclerotherapy for treatment of simple renal cysts.	2007-04-17	17914652
Transcatheter arterial embolization of renal VX-2 carcinoma: ethiodol-ethanol capillary embolization combined with carboplatin.	2007-04-11	17420631
Renal handling of cystatin C.	2007-04	17110405
Endoscopic treatment of completely occluding anastomotic web using incision and ballooning after dye injection.	2007-02	17440859
Preemptive living donor kidney transplantation: do the benefits extend to all recipients?	2007-01-27	17264810
Evidence that postprandial reduction of renal calcium reabsorption mediates hypercalciuria of patients with calcium nephrolithiasis.	2007-01	17210796
Reproducibility of renal function measurements in adult men with diabetic nephropathy: research and clinical implications.	2007	17284896
A novel approach to flexor hallucis longus tenography.	2006-12	17114532
Estimating absolute glomerular filtration rate in children.	2006-12	17013606
Effect on bone induction of using contrast media to reconstitute recombinant human bone morphogenetic protein-2 in an ectopic model in rats.	2006-11	17120893
Drawbacks and prognostic value of formulas estimating renal function in patients with chronic heart failure and systolic dysfunction.	2006-10-10	17015793
Iodinated contrast induced renal vasoconstriction is due in part to the downregulation of renal cortical and medullary nitric oxide synthesis.	2006-08	16890873
Are prediction equations for glomerular filtration rate useful for the long-term monitoring of type 2 diabetic patients?	2006-08	16702203
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.	2006-05	16738930
Renal extraction of cystatin C vs 125I-iothalamate in hypertensive patients.	2006-05	16421151
[Pancreas anulare as an incidental finding in multidetector computer tomography for symptomatic abdominal aortic aneurysm].	2006-04	16612737
Virtual cystoscopy by intravesical instillation of dilute contrast medium: preliminary experience.	2006-03	16469568
Assessing glomerular filtration rate by estimation equations in kidney transplant recipients.	2006-01	16433763
Influence of iothalamate on renal medullary perfusion and oxygenation in the rat.	2005-12	16392607
Simple HPLC-UV method for determination of iohexol, iothalamate, p-aminohippuric acid and n-acetyl-p-aminohippuric acid in human plasma and urine with ERPF, GFR and ERPF/GFR ratio determination using colorimetric analysis.	2005-11-05	16169291
PET/CT with intravenous contrast can be used for PET attenuation correction in cancer patients.	2005-10	15909196
Virtopsy: postmortem minimally invasive angiography using cross section techniques--implementation and preliminary results.	2005-09	16225226
Analysis of iodinated X-ray contrast agents in water samples by ion chromatography and inductively-coupled plasma mass spectrometry.	2005-08-26	16106857
Performance of the Cockcroft-Gault and modification of diet in renal disease equations in estimating GFR in ill hospitalized patients.	2005-08	16112042
Cytotoxic effects of ionic high-osmolar, nonionic monomeric, and nonionic iso-osmolar dimeric iodinated contrast media on renal tubular cells in vitro.	2005-06	15845795
Telebrix Gastro in the management of adhesive small bowel obstruction.	2005-05	15980741
CT voiding cystourethrography using 16-MDCT for the evaluation of female urethral diverticula: initial experience.	2005-05	15855122
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.	2005-04	15716336
Nephropathy in critically Ill patients without preexisting renal disease.	2005	16416679
[Methods for the quantification of left ventricular volumes assessed by radionuclide ventriculography (first part)].	2005	16405228
Sensitivity variation of doped Fricke gel irradiated with monochromatic synchrotron X rays between 33.5 and 80 keV.	2005	15956218
The value of contrast-enhanced helical CT scan with rectal contrast enema in the diagnosis of acute appendicitis.	2004-06-20	15967316
[Recurrent aseptic meningitis (Mollaret meningitis)--spontaneous and drug-induced origin].	1991-12	1774010

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%

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:55 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:55 GMT 2025`
Record UNII	16CHD79MIX
Record Status	`Validated (UNII)`
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Name

Type

Language

IOTALAMIC ACID

Preferred Name

English

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 [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