Identification
- Generic Name
- Metrizamide
- DrugBank Accession Number
- DB01578
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Metrizamide (DB01578)
- Weight
- Average: 789.1
Monoisotopic: 788.8541 - Chemical Formula
- C18H22I3N3O8
- Synonyms
- Metrizamida
- Metrizamide
- Metrizamidum
- External IDs
- WIN 39103
- WIN-39103
Pharmacology
- 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.
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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).
- Mechanism of action
Organic iodine compounds such as metrizamide block x-rays as they pass through the body, thereby allowing body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. After intrathecal administration into the subarachnoid space, diffusion of metrizamide in the CSF allows the visualization of the subarachnoid spaces of the head and spinal canal. After intravascular administration, metrizamide makes opaque those vessels in its path of flow, allowing visualization of the internal structures until significant hemodilution occurs. Metrazamide also has some toxic effects which are thought to be due to its ability to inhibit glucose metabolism.
- Absorption
Absorption from gastrointestinal tract is negligible following oral or rectal administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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- Amipaque
Categories
- ATC Codes
- V08AB01 — Metrizamide
- Drug Categories
- Acids, Carbocyclic
- Benzene Derivatives
- Benzoates
- Carbohydrates
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Glycosides
- Iodobenzoates
- Triiodobenzoic Acids
- Watersoluble, Nephrotropic, Low Osmolar X-Ray Contrast Media
- X-Ray Contrast Media, Iodinated
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Acylaminobenzoic acid and derivatives
- Alternative Parents
- Hexoses / O-haloacetanilides / P-haloacetanilides / 2-halobenzoic acids and derivatives / 4-halobenzoic acids and derivatives / Benzamides / N-acetylarylamines / Benzoyl derivatives / Iodobenzenes / Aminosaccharides show 13 more
- Substituents
- 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Acetamide / Acetanilide / Acylaminobenzoic acid or derivatives / Alcohol / Aldehyde / Amino saccharide / Anilide / Aromatic homomonocyclic compound show 33 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- RHH3W8F1CO
- CAS number
- 31112-62-6
- InChI Key
- DTZMSDADRKLCQE-RFMXWLSYSA-N
- InChI
- InChI=1S/C18H22I3N3O8/c1-6(27)22-14-11(19)10(12(20)15(13(14)21)24(3)7(2)28)18(32)23-8(4-25)16(30)17(31)9(29)5-26/h4,8-9,16-17,26,29-31H,5H2,1-3H3,(H,22,27)(H,23,32)/t8-,9+,16+,17+/m0/s1
- IUPAC Name
- 3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]benzamide
- SMILES
- CN(C(C)=O)C1=C(I)C(C(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)=C(I)C(NC(C)=O)=C1I
References
- General 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. [Article]
- 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. [Article]
- External Links
- PubChem Compound
- 20056604
- PubChem Substance
- 46506223
- ChemSpider
- 16739315
- 6920
- ChEMBL
- CHEMBL1200889
- ZINC
- ZINC000150485244
- PharmGKB
- PA164742936
- Wikipedia
- Metrizamide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 223 dec °C PhysProp water solubility 5E+005 mg/L (at 25 °C) MERCK INDEX (1996) logP -1.89 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.335 mg/mL ALOGPS logP -1.3 ALOGPS logP -0.88 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 11.75 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 176.5 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 142.05 m3·mol-1 Chemaxon Polarizability 55.68 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9938 Blood Brain Barrier - 0.9376 Caco-2 permeable - 0.6755 P-glycoprotein substrate Non-substrate 0.624 P-glycoprotein inhibitor I Non-inhibitor 0.6859 P-glycoprotein inhibitor II Non-inhibitor 0.7024 Renal organic cation transporter Non-inhibitor 0.9491 CYP450 2C9 substrate Non-substrate 0.6989 CYP450 2D6 substrate Non-substrate 0.8594 CYP450 3A4 substrate Substrate 0.5506 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8116 Ames test Non AMES toxic 0.7685 Carcinogenicity Non-carcinogens 0.8852 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.6272 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9949 hERG inhibition (predictor II) Non-inhibitor 0.7864
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 225.21956 predictedDeepCCS 1.0 (2019) [M+H]+ 227.11536 predictedDeepCCS 1.0 (2019) [M+Na]+ 232.89407 predictedDeepCCS 1.0 (2019)
Drug created at August 29, 2007 14:52 / Updated at February 21, 2021 18:51