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| | Metrizamide Basic information |
| Product Name: | Metrizamide | | Synonyms: | 2-((3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoyl)amino)-2-deox;2-(3-acetamido-2,4,6-triiodo-5-(n-methylacetamido)benzamido)-2-deoxy-d-gluco;2-(3-acetamido-5-n-methyl-acetamido-2,4,6-triiodobenzamido)-2-deoxy-d-glucos;3-acetylamino-5-n-methyl-acetylamino-2,4,6-triiodobenzoylglucosamine;amipaque;d-glucose,2-((3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoyl)ami;d-glucose,2-(3-acetamido-2,4,6-triiodo-5-(n-methylacetamido)benzamido)-2-deoxy;no)-2-deoxy- | | CAS: | 31112-62-6 | | MF: | C18H22I3N3O8 | | MW: | 789.1 | | EINECS: | 250-475-5 | | Product Categories: | Active Pharmaceutical Ingredients | | Mol File: | 31112-62-6.mol |  |
| | Metrizamide Chemical Properties |
| Melting point | 222-224°C | | alpha | D20 +18.0° (c = 10% in 0.1N HCl; equilibrated with respect to mutarotation) | | Boiling point | 927.4±65.0 °C(Predicted) | | density | 2.0128 (estimate) | | storage temp. | −20°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 10.39±0.46(Predicted) | | color | White to Off-White | | Merck | 13,6176 | | CAS DataBase Reference | 31112-62-6(CAS DataBase Reference) |
| Safety Statements | 22-24/25 | | RTECS | LZ6650000 | | Toxicity | LD50 i.v. in mice: 15 g/kg (Torsten); 18.6 g/kg (Salveson); 11.5 g/kg (Sovak); 17.3 g/kg (Aspelin) |
| | Metrizamide Usage And Synthesis |
| Description | Metrizamide is a non-ionic contrast agent. In vivo, metrizamide (0.1 ml/kg of a 370 mg I/ml solution) does not induce EEG abnormalities, indicating minimal neurotoxicity in rabbits. It has also been used as a solute in gradient centrifugation applications. | | Chemical Properties | white fine crystalline powder | | Originator | Amipaque,Winthrop laboratories | | Uses | Contrasting product | | Uses | Metrizamide is a X-ray contrast agent related to Metrizoic Acid (M338935). Metrizamide is used as an diagnostic aid (radiopaque medium). | | Uses | Metrizamide is a X-ray contrast agent related to Metrizoic Acid (M338935). Metrizamide is used as a diagnostic aid (radiopaque medium). | | Definition | A
SUGAR that has a six-membered ring form
(five carbon atoms and one oxygen atom). | | Definition | pyranose: A sugar having a sixmemberedring containing five carbonatoms and one oxygen atom. | | Manufacturing Process | 1 mole 3-(acetyl-methyl-amino)-2,4,6-triiodo-5-methylamino-benzoic acid was
suspended in thionyl chloride and reacted by stirring at 70°C for 16 hours.
Excess thionyl chloride was distilled off in vacuum, the residue dissolved in
chloroform, cooled in the ice bath, washed with iced water (3x100 ml),
saturated sodium bicarbonate solution (3 x 100 ml), 2 N sodium carbonate
solution (2 x 100 ml) and finally with water (3 x 100 ml). After drying with
CaCl2 the chloroform distilled off and residue dried in vacuum. Yield of 3-
acetylamino-5-(acetyl-methyl-amino)-2,4,6-triiodo-benzoyl chloride: 66%;
MP: 238°-240°C (the re-crystallization from tetrahydrofuran).
It (0.02 mole) was dissolved in dioxan (120 ml). To the solution was added
(25 ml) and NaHCO3 (0.0022 mol). Glucosamine (0.022 mol) was added in
portions and reaction mixture left by stirring at room temperature for 24
hours. The solution was evaporated to dryness in vacuum, the residue
dissolved in water (500 ml), filtered clear and run through an Amberlite IR120 H+ ion exchange column. The effluent was evaporated to dryness in
vacuum resulting in a white crystalline residue. The crude 3-acetylamino-5-Nmethyl-acetylamino-2,4,6-triiodobenzoyl glucosamine was crystallised from
isopropanol (charcoal-treated when in solution), dissolved in water and
charcoal-treated at 100°C for 20 min. The water was distilled off in vacuum
and the white residue dried in vacuum at 70°C. MP: 190°-195°C. | | Brand name | Amipaque (GE Healthcare). | | Therapeutic Function | Diagnostic aid |
| | Metrizamide Preparation Products And Raw materials |
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