3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide

• ChemBase ID: 1358
• Molecular Formular: C18H22I3N3O8
• Molecular Mass: 789.09599
• Monoisotopic Mass: 788.85410868
• SMILES: Ic1c(C(=O)N[C@@H]2[C@@H](O)[C@H](O)[C@H](OC2O)CO)c(I)c(NC(=O)C)c(I)c1N(C)C(=O)C
• Canonical SMILES: OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)c1c(I)c(NC(=O)C)c(c(c1I)N(C(=O)C)C)I
• InChI: 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
• InChIKey: BAQCROVBDNBEEB-UBYUBLNFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
• IUPAC Traditional name: amipak; metrizamide
• Brand Name: Amipaque
• Synonyms: Metrizamide; 2-[3-Acetamido-5-(N-methylacetamido)-2,4,6-triiodobenzamido]-2-deoxy-D-glucose; Metrizamide, mixture of anomers; Metrizamide

Database IDs

• CAS Number: 31112-62-6
• EC Number: 250-475-5
• MDL Number: MFCD00010577
• Beilstein Number: 6758226
• PubChem SID: 160964818; 46506223
• PubChem CID: 443944

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.444519
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.24008025
• LogD (pH = 7.4): -0.24011765
• Log P: -0.24007973
• Molar Refractivity: 140.6246 cm^3
• Polarizability: 54.876026 Å^3
• Polar Surface Area: 168.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.2
• LOG S: -3.09
• Solubility (Water): 6.35e-01 g/l

PROPERTIES

Physical Property

• Solubility: 500 mg/mL at 25 oC [MERCK INDEX (1996)]
• Apperance: crystalline
• Melting Point: 222-224 °C (dec.)(lit.)
• Hydrophobicity(logP): -1.89 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: LZ6650000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 95-97%
• Type: Grade II
• Empirical Formula (Hill Notation): C18H22I3N3O8
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

DrugBank - DB01578

• Drug Groups: approved
• Description: Metrizamide is 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.
• Indication: Metrizamide is used for lumbar, thoracic, cervical, and total columnar myelography to determine the presence of abnormalities in the spinal column, spinal canal, and central nervous system (CNS) as well as for cisternography by direct injection using standard radiologic techniques to visualize the basal cistern of the brain. For computerized tomography (CT) of the intracranial subarachnoid spaces and for ventriculography by direct injection using standard radiologic techniques to visualize the cerebral ventricles. Also used in pediatric angiocardiography to visualize lesions or malformations of the heart and obstructions or anomalies of the major thoracic vessels. Also used in adult peripheral arteriography to visualize specific regions of the vascular system and blood flow in such areas to help in the diagnosis and evaluation of neoplasms (known or suspected) or vascular diseases (congenital or acquired) that may cause changes in normal vascular anatomy or physiology. Metrizamide is also indicated in adults for intravenous digital arteriography of head and neck.
• Pharmacology: Metrizamide is a radiocontrast agent used to improve the contrast of internal body structures using different imaging techniques such as computed tomography scans (CT) or radiography (X-ray imaging).
• Toxicity: Non-ionic radiocontrast agents like metrizamide are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress.
• Affected Organisms: Humans and other mammals
• Absorption: Absorption from gastrointestinal tract is negligible following oral or rectal administration.
• References: Azuma H, Nomura S, Ikoma Y, Yokoyama M, Oshino N: A possible mechanism for the neural adverse reactions caused by metrizamide. Fortschr Geb Rontgenstrahlen Nuklearmed Erganzungsbd. 1989;128:134-42. [Pubmed] ; Ekholm SE, Reece K, Coleman JR, Kido DK, Fischer HW: Metrizamide--a potential in vivo inhibitor of glucose metabolism. Radiology. 1983 Apr;147(1):119-21. [Pubmed]

REFERENCES

• Azuma H, Nomura S, Ikoma Y, Yokoyama M, Oshino N: A possible mechanism for the neural adverse reactions caused by metrizamide. Fortschr Geb Rontgenstrahlen Nuklearmed Erganzungsbd. 1989;128:134-42. Pubmed
• Ekholm SE, Reece K, Coleman JR, Kido DK, Fischer HW: Metrizamide--a potential in vivo inhibitor of glucose metabolism. Radiology. 1983 Apr;147(1):119-21. Pubmed