Iodixanol

Iodixanol is an iodine-containing non-ionic radiocontrast agent.[1] It is sold under the trade name Visipaque; it is also sold as a density gradient medium under the name OptiPrep.[2] Visipaque is commonly used as a contrast agent during coronary angiography. It is the only iso-osmolar contrast agent, with an osmolality of 290 mOsm/kg H2O, the same as blood. It is sold in 2 main concentrations 270 mgI/ml and 320 mgI/ml - hence the name Visipaque 270 or 320. It is sold in single dose units and a large 500 ml plastic bottle for multi-dose dispensing.

Iodixanol
Clinical data
Other names5-[acetyl-[3-[acetyl-[3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodo-phenyl]amino]-2-hydroxy-propyl]amino]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-benzene-1,3-dicarboxamide
AHFS/Drugs.comMultum Consumer Information
ATC code
Pharmacokinetic data
Protein bindingNegligible
MetabolismExcreted unchanged
Elimination half-life2.1 hours
ExcretionRenal
Identifiers
IUPAC name
  • 5-{N-[3-(N-{3,5-bis[(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodophenyl}acetamido)-2-hydroxypropyl]acetamido}-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.124.306
Chemical and physical data
FormulaC35H44I6N6O15
Molar mass1550.191 g·mol−1
3D model (JSmol)
SMILES
  • Ic1c(C(=O)NCC(O)CO)c(I)c(C(=O)NCC(O)CO)c(I)c1N(C(=O)C)CC(O)CN(C(=O)C)c2c(I)c(c(I)c(c2I)C(=O)NCC(O)CO)C(=O)NCC(O)CO
InChI
  • InChI=1S/C35H44I6N6O15/c1-13(52)46(30-26(38)20(32(59)42-3-15(54)9-48)24(36)21(27(30)39)33(60)43-4-16(55)10-49)7-19(58)8-47(14(2)53)31-28(40)22(34(61)44-5-17(56)11-50)25(37)23(29(31)41)35(62)45-6-18(57)12-51/h15-19,48-51,54-58H,3-12H2,1-2H3,(H,42,59)(H,43,60)(H,44,61)(H,45,62) Y
  • Key:NBQNWMBBSKPBAY-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

It was originally made by Nycomed, which then merged with Amersham which finally was bought by Jeff Immelt to become GE Healthcare. The majority of Visipaque is made in Cork, Ireland, with additional plants in Shanghai, China and Oslo, Norway. All Iodixanol bulk powder is made in Norway by GE Healthcare.

A very similar product also manufactured by GE Healthcare is Omnipaque (Iohexol as the main drug substance).

Iodixanol is also the active ingredient in a number of 'cushion' products used during the centrifugation of stallion semen. It is layered underneath the extended stallion semen allowing for a higher g force to be used with less sperm damage and better recovery rates. Post centrifugation the supernatant above and the cushion below is removed, leaving a concentrated sperm pellet in the conical tube.[3]

References
  1. Spencer CM, Goa KL (December 1996). "Iodixanol. A review of its pharmacodynamic and pharmacokinetic properties and diagnostic use as an x-ray contrast medium". Drugs. 52 (6): 899–927. doi:10.2165/00003495-199652060-00013. PMID 8957160.
  2. OptiPrep™: The ideal density gradient medium, Axis-Shield Density Gradient Media. Accessed on line Nov. 19, 2015.
  3. Waite JA, Love CC, Brinsko SP, Teague SR, Salazar JL, Mancill SS, Varner DD (September 2008). "Factors impacting equine sperm recovery rate and quality following cushioned centrifugation". Theriogenology. 70 (4): 704–14. doi:10.1016/j.theriogenology.2008.04.047. PMID 18573520.
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