Iopamidol
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MedKoo CAT#: 328714

CAS#: 60166-93-0

Description: Iopamidol, also known as Gastromiro and SQ-13396, is a non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiological procedures.


Chemical Structure

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Iopamidol
CAS# 60166-93-0

Theoretical Analysis

MedKoo Cat#: 328714
Name: Iopamidol
CAS#: 60166-93-0
Chemical Formula: C17H22I3N3O8
Exact Mass: 776.85
Molecular Weight: 777.089
Elemental Analysis: C, 26.28; H, 2.85; I, 48.99; N, 5.41; O, 16.47

Price and Availability

Size Price Availability Quantity
5g USD 250 2 Weeks
25g USD 650 2 Weeks
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Synonym: Iopamidol; Gastromiro; SQ-13396; SQ 13396; SQ13396; Isovue; Niopam

IUPAC/Chemical Name: (S)-N1,N3-bis(1,3-dihydroxypropan-2-yl)-5-(2-hydroxypropanamido)-2,4,6-triiodoisophthalamide

InChi Key: XQZXYNRDCRIARQ-LURJTMIESA-N

InChi Code: InChI=1S/C17H22I3N3O8/c1-6(28)15(29)23-14-12(19)9(16(30)21-7(2-24)3-25)11(18)10(13(14)20)17(31)22-8(4-26)5-27/h6-8,24-28H,2-5H2,1H3,(H,21,30)(H,22,31)(H,23,29)/t6-/m0/s1

SMILES Code: O=C(NC(CO)CO)C1=C(I)C(NC([C@@H](O)C)=O)=C(I)C(C(NC(CO)CO)=O)=C1I

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: Iopamidol is a nonionic, X-Ray iodinated contrast agent (CA) for a wide variety of diagnostic applications. Iopamidol contains amide and hydroxyl functionalities that can be exploited for the generation of the chemical exchange saturation transfer (CEST) contrast.
In vitro activity: The body of data collected so far on the phantom containing iopamidol clearly indicates that this molecule can act as either a T2- or a CEST-MRI contrast agent. On this basis, it is of interest to ascertain the minimum concentration of iopamidol required to detect a contrast in the two imaging modalities. Reference: Magn Reson Med. 2005 Apr;53(4):830-4. https://pubmed.ncbi.nlm.nih.gov/15799043/
In vivo activity: Upon injection of Iopamidol into healthy mice, it has been possible to acquire pH maps of kidney regions. Furthermore, it has been also shown that the proposed method is able to report about pH-changes induced in control mice fed with acidified or basified water for a period of a week before image acquisition. Reference: Magn Reson Med. 2011 Jan;65(1):202-11. https://pubmed.ncbi.nlm.nih.gov/20949634/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 75.0 96.51
Water 100.0 128.69

Preparing Stock Solutions

The following data is based on the product molecular weight 777.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Aime S, Calabi L, Biondi L, De Miranda M, Ghelli S, Paleari L, Rebaudengo C, Terreno E. Iopamidol: Exploring the potential use of a well-established x-ray contrast agent for MRI. Magn Reson Med. 2005 Apr;53(4):830-4. doi: 10.1002/mrm.20441. PMID: 15799043. 2. Longo DL, Dastrù W, Digilio G, Keupp J, Langereis S, Lanzardo S, Prestigio S, Steinbach O, Terreno E, Uggeri F, Aime S. Iopamidol as a responsive MRI-chemical exchange saturation transfer contrast agent for pH mapping of kidneys: In vivo studies in mice at 7 T. Magn Reson Med. 2011 Jan;65(1):202-11. doi: 10.1002/mrm.22608. PMID: 20949634. 3. Rovai D, Ghelardini G, Lombardi M, Trivella MG, Nevola E, Taddei L, Michelassi C, Distante A, DeMaria AN, L'Abbate A. Myocardial washout of sonicated iopamidol reflects coronary blood flow in the absence of autoregulation. J Am Coll Cardiol. 1992 Nov 15;20(6):1417-24. doi: 10.1016/0735-1097(92)90257-n. PMID: 1430693.
In vitro protocol: 1. Aime S, Calabi L, Biondi L, De Miranda M, Ghelli S, Paleari L, Rebaudengo C, Terreno E. Iopamidol: Exploring the potential use of a well-established x-ray contrast agent for MRI. Magn Reson Med. 2005 Apr;53(4):830-4. doi: 10.1002/mrm.20441. PMID: 15799043.
In vivo protocol: 1. Longo DL, Dastrù W, Digilio G, Keupp J, Langereis S, Lanzardo S, Prestigio S, Steinbach O, Terreno E, Uggeri F, Aime S. Iopamidol as a responsive MRI-chemical exchange saturation transfer contrast agent for pH mapping of kidneys: In vivo studies in mice at 7 T. Magn Reson Med. 2011 Jan;65(1):202-11. doi: 10.1002/mrm.22608. PMID: 20949634. 2. Rovai D, Ghelardini G, Lombardi M, Trivella MG, Nevola E, Taddei L, Michelassi C, Distante A, DeMaria AN, L'Abbate A. Myocardial washout of sonicated iopamidol reflects coronary blood flow in the absence of autoregulation. J Am Coll Cardiol. 1992 Nov 15;20(6):1417-24. doi: 10.1016/0735-1097(92)90257-n. PMID: 1430693.

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1: Rodríguez-Romero V, González-Villalva KI, Reyes JL, Franco-Bourland RE, Guízar-Sahagún G, Castañeda-Hernández G, Cruz-Antonio L. A novel, simple and inexpensive procedure for the simultaneous determination of iopamidol and p-aminohippuric acid for renal function assessment from plasma samples in awake rats. J Pharm Biomed Anal. 2015 Mar 25;107:196-203. doi: 10.1016/j.jpba.2014.12.009. Epub 2015 Jan 3. PubMed PMID: 25594899.

2: Müller-Lutz A, Khalil N, Schmitt B, Jellus V, Pentang G, Oeltzschner G, Antoch G, Lanzman RS, Wittsack HJ. Pilot study of Iopamidol-based quantitative pH imaging on a clinical 3T MR scanner. MAGMA. 2014 Dec;27(6):477-85. doi: 10.1007/s10334-014-0433-8. Epub 2014 Feb 26. PubMed PMID: 24570337.

3: Wendel FM, Lütke Eversloh C, Machek EJ, Duirk SE, Plewa MJ, Richardson SD, Ternes TA. Transformation of iopamidol during chlorination. Environ Sci Technol. 2014 Nov 4;48(21):12689-97. doi: 10.1021/es503609s. Epub 2014 Oct 17. PubMed PMID: 25325766.

4: Weiland FL, Marti-Bonmati L, Lim L, Becker HC. Comparison of patient comfort between iodixanol and iopamidol in contrast-enhanced computed tomography of the abdomen and pelvis: a randomized trial. Acta Radiol. 2014 Jul;55(6):715-24. doi: 10.1177/0284185113505277. Epub 2013 Sep 23. PubMed PMID: 24060817.

5: Sun PZ, Longo DL, Hu W, Xiao G, Wu R. Quantification of iopamidol multi-site chemical exchange properties for ratiometric chemical exchange saturation transfer (CEST) imaging of pH. Phys Med Biol. 2014 Aug 21;59(16):4493-504. doi: 10.1088/0031-9155/59/16/4493. Epub 2014 Jul 23. PubMed PMID: 25054859; PubMed Central PMCID: PMC4139413.

6: Tian FX, Xu B, Lin YL, Hu CY, Zhang TY, Gao NY. Photodegradation kinetics of iopamidol by UV irradiation and enhanced formation of iodinated disinfection by-products in sequential oxidation processes. Water Res. 2014 Jul 1;58:198-208. doi: 10.1016/j.watres.2014.03.069. Epub 2014 Apr 5. PubMed PMID: 24762552.

7: Singh RR, Lester Y, Linden KG, Love NG, Atilla-Gokcumen GE, Aga DS. Application of metabolite profiling tools and time-of-flight mass spectrometry in the identification of transformation products of iopromide and iopamidol during advanced oxidation. Environ Sci Technol. 2015 Mar 3;49(5):2983-90. doi: 10.1021/es505469h. Epub 2015 Feb 17. PubMed PMID: 25651339.

8: Akyıldız Akçay F, Bayata S, Semerci T, Yeşil M, Toklu O, Arıkan E, Yakar Tülüce S, Köseoğlu M, Koçağra Yağız I. The effects of iodixanol and iopamidol on adhesion molecule serum levels in patients with angina pectoris undergoing coronary angiography: a randomized study. Anadolu Kardiyol Derg. 2014 Mar;14(2):156-61. doi: 10.5152/akd.2014.4737. Epub 2014 Jan 14. PubMed PMID: 24449631.

9: Borrelli MP, Setacci F, de Donato G, Galzerano G, Benevento D, Mele M, Rosadini D, Messina G, Setacci C. Patient Discomfort during Carotid Artery Stenting: A Comparison Study between Iodixanol versus Iopamidol. Ann Vasc Surg. 2016 Aug 10. pii: S0890-5096(16)30609-4. doi: 10.1016/j.avsg.2016.04.018. [Epub ahead of print] PubMed PMID: 27521830.

10: Zhao C, Arroyo-Mora LE, DeCaprio AP, Sharma VK, Dionysiou DD, O'Shea KE. Reductive and oxidative degradation of iopamidol, iodinated X-ray contrast media, by Fe(III)-oxalate under UV and visible light treatment. Water Res. 2014 Dec 15;67:144-53. doi: 10.1016/j.watres.2014.09.009. Epub 2014 Sep 18. PubMed PMID: 25269106.