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MedKoo Cat#: 318261 | Name: Metrizamide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metrizamide is a nonionic radiopaque contrast agent.

Chemical Structure

Metrizamide
Metrizamide
CAS#31112-62-6

Theoretical Analysis

MedKoo Cat#: 318261

Name: Metrizamide

CAS#: 31112-62-6

Chemical Formula: C18H22I3N3O8

Exact Mass: 788.8541

Molecular Weight: 789.10

Elemental Analysis: C, 27.40; H, 2.81; I, 48.25; N, 5.33; O, 16.22

Price and Availability

Size Price Availability Quantity
5g USD 450.00 2 Weeks
10mg USD 800.00 2 weeks
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Related CAS #
No Data
Synonym
Metrizamide, Amipak, Amipaque
IUPAC/Chemical Name
3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
InChi Key
BAQCROVBDNBEEB-UBYUBLNFSA-N
InChi Code
InChI=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
SMILES Code
O=C(N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)C2=C(I)C(N(C(C)=O)C)=C(I)C(NC(C)=O)=C2I
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Metrizamide inhibits human brain hexokinase.
In vitro activity:
The nonionic radiographic contrast material (RCM) metrizamide causes consumption of total complement activity in normal human serum (NHS) in vitro in the absence and to a lesser extent also in the presence of EDTA. The depression of titers of total complement is related to an inactivating effect of metrizamide on component C2. Furthermore, metrizamide induces activation of the alternative pathway as evidenced by the appearance of C3 and factor B cleavage products in NHS, dependent on the presence of divalent cations. Reference: Int Arch Allergy Appl Immunol. 1984;73(4):321-9. https://pubmed.ncbi.nlm.nih.gov/6421748/
In vivo activity:
One hundred fifty mice (18-21 days old), divided into groups, received either 75 microL of metrizamide, using the manufacturer's diluent (190 mg iodine [I]/mL), or saline solution administered to the lungs by injection into the trachea. The incidence of lung tumors was increased (P less than .05) in the lungs of mice receiving metrizamide compared with those receiving saline. Eighteen percent of the lung tumors in the metrizamide-treated mice were lymphomas, a histologic type not found in the saline-treated controls. Reference: Invest Radiol. 1992 Jul;27(7):525-8. https://pubmed.ncbi.nlm.nih.gov/1644552/
Solvent mg/mL mM comments
Solubility
DMSO 50.0 63.36
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 789.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. von Zabern I, Przyklenk H, Nolte R, Vogt W. Effect of metrizamide, a nonionic radiographic contrast agent, on human serum complement. Comparison with ionic contrast media. Int Arch Allergy Appl Immunol. 1984;73(4):321-9. doi: 10.1159/000233492. PMID: 6421748. 2. Pavia CS, Diggs CL, Williams J. The use of metrizamide for isopyknic separation and enrichment of Plasmodium falciparum schizonts from continuous culture. Am J Trop Med Hyg. 1983 Jul;32(4):675-81. doi: 10.4269/ajtmh.1983.32.675. PMID: 6349396. 3. Baker DG, Alford BA, Feldman PS. Lung tumor incidence after intrabronchial administration of the nonionic contrast agent metrizamide. Invest Radiol. 1992 Jul;27(7):525-8. doi: 10.1097/00004424-199207000-00010. PMID: 1644552. 4. Simon JH, Ekholm SE, Morris TW, Isaac L, Tayrien MW. The effect of subarachnoid metrizamide and iohexol on cerebral glucose metabolism in vivo. Acta Radiol Suppl. 1986;369:549-53. PMID: 2980555.
In vitro protocol:
1. von Zabern I, Przyklenk H, Nolte R, Vogt W. Effect of metrizamide, a nonionic radiographic contrast agent, on human serum complement. Comparison with ionic contrast media. Int Arch Allergy Appl Immunol. 1984;73(4):321-9. doi: 10.1159/000233492. PMID: 6421748. 2. Pavia CS, Diggs CL, Williams J. The use of metrizamide for isopyknic separation and enrichment of Plasmodium falciparum schizonts from continuous culture. Am J Trop Med Hyg. 1983 Jul;32(4):675-81. doi: 10.4269/ajtmh.1983.32.675. PMID: 6349396.
In vivo protocol:
1. Baker DG, Alford BA, Feldman PS. Lung tumor incidence after intrabronchial administration of the nonionic contrast agent metrizamide. Invest Radiol. 1992 Jul;27(7):525-8. doi: 10.1097/00004424-199207000-00010. PMID: 1644552. 2. Simon JH, Ekholm SE, Morris TW, Isaac L, Tayrien MW. The effect of subarachnoid metrizamide and iohexol on cerebral glucose metabolism in vivo. Acta Radiol Suppl. 1986;369:549-53. PMID: 2980555.
1: Grobovschek M. [Lumbosacral functional myelography including the dorsolumbar transitional region (medullary cone). Clinical comparative studies--2000 myelographies with metrizamide]. Radiologe. 1984 Aug;24(8):389-98. Review. German. PubMed PMID: 6237384. 2: Hanus PM. Metrizamide: a review with emphasis on drug interactions. Am J Hosp Pharm. 1980 Apr;37(4):510-3. Review. PubMed PMID: 6103672. 3: Salvesen S. Experimental investigations with metrizamide with relevance to the myelographic use. Acta Radiol Suppl. 1977;355:9-13. Review. PubMed PMID: 400909. 4: Almén T. Angiography with metrizamide. Animal experiments and preliminary clinical experiences. Acta Radiol Suppl. 1977;355:419-30. Review. PubMed PMID: 400907. 5: Buchman AS, Klawans HL, Russell EJ. Metrizamide and its neurologic complications. Clin Neuropharmacol. 1987;10(1):1-25. Review. PubMed PMID: 3545458. 6: Winkler SS, Sackett JF. Explanation of metrizamide brain penetration: a review. J Comput Assist Tomogr. 1980 Apr;4(2):191-3. Review. PubMed PMID: 6988475. 7: Birnie GD. Fractionation of chromatin by buoyant density-gradient sedimentation in metrizamide. Methods Cell Biol. 1978;18:23-39. Review. PubMed PMID: 355790. 8: Amundsen P. Metrizamide in cervical myelography. Survey and present state. Acta Radiol Suppl. 1977;355:85-97. Review. PubMed PMID: 400908. 9: Skalpe IO. Adverse effects of water-soluble contrast media in myelography, cisternography and ventriculography. A review with special reference to metrizamide. Acta Radiol Suppl. 1977;355:359-70. Review. PubMed PMID: 400906.