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31112-62-6, Metrizamide, CAS:31112-62-6

31112-62-6 , Metrizamide,
CAS:31112-62-6
C18H22I3N3O8 / 789.1
MFCD00010577

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).

CAS Number31112-62-6
Product NameMetrizamide
IUPAC Name3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
Molecular FormulaC18H22I3N3O8
Molecular Weight789.1 g/mol
InChIInChI=1S/C18H22I3N3O8/c1-5(26)22-12-9(19)8(10(20)14(11(12)21)24(3)6(2)27)17(30)23-13-16(29)15(28)7(4-25)32-18(13)31/h7,13,15-16,18,25,28-29,31H,4H2,1-3H3,(H,22,26)(H,23,30)/t7-,13-,15-,16-,18?/m1/s1
InChI KeyBAQCROVBDNBEEB-UBYUBLNFSA-N
SMILESCC(=O)NC1=C(C(=C(C(=C1I)C(=O)NC2C(C(C(OC2O)CO)O)O)I)N(C)C(=O)C)I
SolubilitySoluble in DMSO, not in water
SynonymsAmipak, Amipaque, Metrizamide
Canonical SMILESCC(=O)NC1=C(C(=C(C(=C1I)C(=O)NC(C=O)C(C(C(CO)O)O)O)I)N(C)C(=O)C)I
Isomeric SMILESCC(=O)NC1=C(C(=C(C(=C1I)C(=O)N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O)I)N(C)C(=O)C)I


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