Metrizamide, 甲泛葡胺

Radiopaque contrast agent; diagnostic aid for myelography.

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.

Metrizamide, also known as amipaque or amipak, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Metrizamide exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Metrizamide has been detected in multiple biofluids, such as urine and blood.

Metrizamide is an amino sugar.

A solute for density gradient centrifugation offering higher maximum solution density without the problems of increased viscosity. It is also used as a resorbable, non-ionic contrast medium.

Title: Metrizamide

CAS Registry Number: 31112-62-6

CAS Name: 2-[[3-(Acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoyl]amino]-2-deoxy-D-glucose

Additional Names: 2-[3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzamido]-2-deoxy-D-glucose; 2-[3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzamido]-2-deoxy-D-glucopyranose

Manufacturers' Codes: Win-39103

Trademarks: Amipaque (Winthrop)

Molecular Formula: C18H22I3N3O8

Molecular Weight: 789.10

Percent Composition: C 27.40%, H 2.81%, I 48.25%, N 5.33%, O 16.22%

Literature References: X-ray contrast agent related to metrizoic acid, q.v. Prepn: H. O. Torsten et al., DE 2031724; eidem, US 3701771 (1971, 1972 both to Nyegaard). Metabolism: J. G. Johansen, S. Kolmannskog, Invest. Radiol. 13, 93 (1978). Pharmacology: T. W. Morris et al., ibid. 74; G. F. Dibona, Proc. Soc. Exp. Biol. Med. 157, 453 (1978). Series of articles on clinical use: Ann. Radiol. 22, 195-206 (1979). Toxicity studies: S. Salvesen, Radiology 123, 241 (1977); M. Sovak et al., ibid. 242; P. Aspelin, Invest. Radiol. 11, 309 (1976). Review: L. Hol et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1977) pp 387-412.

Properties: White crystals from isopropyl alcohol, mp 230° (dec), after drying in vacuo at room temp and 70°. [a]D20 +18.0° (c = 10% in 0.1N HCl; equilibrated with respect to mutarotation). Very sol in water (50% w/v) at room temp. LD50 i.v. in mice: 15 g/kg (Torsten); 18.6 g/kg (Salveson); 11.5 g/kg (Sovak); 17.3 g/kg (Aspelin).

Melting point: mp 230° (dec)

Optical Rotation: [a]D20 +18.0° (c = 10% in 0.1N HCl; equilibrated with respect to mutarotation)

Toxicity data: LD50 i.v. in mice: 15 g/kg (Torsten); 18.6 g/kg (Salveson); 11.5 g/kg (Sovak); 17.3 g/kg (Aspelin)

Therap-Cat: Diagnostic aid (radiopaque medium).

Keywords: Diagnostic Aid (Radiopaque Medium).