92339-11-2 Usage
Chemical Properties
White Solid
Originator
OptiPrep,Nycomed Pharma,Norway
Uses
Nonionic, dimeric x-ray contrast medium. Diagnostic aid (radiopaque medium).
Definition
ChEBI: A dimeric, non-ionic, water-soluble, radiographic contrast agent, used particularly in coronary angiography.
Manufacturing Process
Dimethyl 5-nitroisophthalate (215 g) and 1-amino-2,3-propandiol (196 g)were refluxed in methanol (500 ml). After twenty hours the solution was
cooled and stored in a refrigerator overnight. The product 5-nitro-N,N'-
bis(2,3-dihydroxypropyl)-isophthalamide was filtered and washed with
methanol. Yield: 270 g (84%). M.p. 128-132°C.5-Nitro-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide (18.1 g) was suspended
in water (250 ml), conc. hydrochloric acid (4.2 ml) and 10% PdO/charcoal
(0.5 g) were added, and the mixture hydrogenated in a Parr apparatus for one
day. After filtration the filtrate was heated at 80-90°C and 3.88 M NaICl2
(42.5 ml) was added through a dropping funnel over 1 hour. The solution was
heated for 2.5 hours. After cooling to 20°C 5-amino-2,4,6-triiodo-N,N'-
bis(2,3-dihydroxypropyl)-isophthalamide crystallized out.5-Amino-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide (110 g)
was suspended in acetic anhydride (480 ml) and heated to 50°C.
Concentrated sulfuric acid (3 ml) was then added. The starting material was
dissolved after a few minutes, and the reaction mixture was heated at 60°C
for 75 min. After cooling the residue dissolved in methanol (300 ml) with
water (150 ml) the solution was heated to 50°C and the pH adjusted to about
10.5 by 10 N sodium hydroxide. After 4-5 hours the pH didn't decrease, and
the hydrolysis was complete. The reaction mixture was cooled to 20°C and
neutralized by adding hydrochloric acid. After stirring overnight 5-Acetamido-
2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)-isophthalamide was filtered and
washed with water. Yield: 94 g (80%). Melting point 275°C, dec.2-Methoxyethanol (300 ml) and sodium hydroxide (20 g) was added to the
reactor at 50°C, and 5-acetamido-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-
triiodoisophtalamide (304 g) was added after two hours of stirring. All solids
were allowed to dissolve overnight before cooling to 30°C and adjustment to
pH 12 with diluted hydrochloric acid. Epichlorohydrin (11 g) was added to the
solution after further cooling to 15°C, and the reaction was allowed to proceed
for 51 hours. As a result 1,3-bis(acetamido)-N,N'-bis[3,5-bis(2,3-
dihydroxypropylaminocarbonyl)-2,4,6-triiodophenyl]-2-hydroxypropane was
obtained.
Brand name
Visipaque (GE Healthcare).
General Description
Iodixanol is a viscous, isosmolar,nonionic, water-soluble dimer with 49% iodine content.It is formulated as an isotonic solution for intravascular injectionand indicated for excretory urography, angiography,and CT procedures.
Check Digit Verification of cas no
The CAS Registry Mumber 92339-11-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,2,3,3 and 9 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 92339-11:
(7*9)+(6*2)+(5*3)+(4*3)+(3*9)+(2*1)+(1*1)=132
132 % 10 = 2
So 92339-11-2 is a valid CAS Registry Number.
InChI:InChI=1/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)
92339-11-2Relevant articles and documents
An intermediate of iodoxanol and a method for preparing iodixanol thereof
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, (2022/01/06)
The present invention provides a method for preparing iodoxasol intermediates of iodoxaol, the intermediate formula VI of iodkesarol VI: 5,5'-[(2-hydroxy-1,3-propanedioxy)bis (acetylimino)] bis [N,N'-bis(2,3-dihydroxypropyl)-1,3-benzenedicarboxamide], iodized by formula VI to obtain iodoxaol finished products; the present invention provides a new synthetic idea of first forming a dimer and then iodizing, The prepared iodoxaol finished product: the total impurity content ≤ 1.0%, the impurity G content ≤0.5%; the method of the present invention has mild reaction conditions, low damage to the equipment, simple process, green environmental protection and low cost, can ensure the continuous production of high-quality products, has a high application value, suitable for industrial production.
Iodixanol and synthesis method thereof
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Paragraph 0042-0043; 0046; 0051; 0056, (2018/10/11)
The invention belongs to the technical field of macromolecules, and discloses iodixanol and a synthesis method thereof. With a compound 5-acetamido-N, N'-bis(2, 3-dihydroxypropyl)-2, 4, 6-triiodo-isophthalamide as a raw material, an intermediate compound 5-acetamido-N, N'-bis(2, 3-dimethyl-1, 3-dioxolan-4-yl)methyl)-2, 4, 6-triiodo-isophthalamide is produced through addition of acetic acid and concentrated sulfuric acid. In allusion to the defects of the existing methods for preparing the iodixanol, through production of the novel intermediate compound, production of difficultly removed O-alkylated impurities during a reaction is avoided. The invention provides a method for synthesizing the iodixanol, which is more reasonable, higher in yield and higher in purity. By the method, the reaction cost is lower.
DESALINATION OF A COMPOSITION COMPRISING A CONTRAST AGENT
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Page/Page column 12, (2012/07/13)
The invention relates to industrial preparation of contrast agents, and further to an improved process for the purification of contrast agents. In particular, it relates to a process for reducing the salt content of compositions comprising an MR contrast agent or an X-ray contrast agent, such as a non-ionic iodinated monomeric compound or a non-ionic iodinated dimeric compound.
