131410-48-5

Basic information

• Product Name: Gadodiamide
• Synonyms: gadolinium 2-[bis[2-(carboxylatomethyl-(methylcarbamoylmethyl)amino)ethyl]amino]acetate;GADODIAMIDE;GADODIAMIDE (500 MG);Omniscan;[5，8-Bis(carboxymethyl)-11-[2-(methylamino)-2-oxoethyl]-3-oxo-2，5，8，11-tetraaza-tridecan-13-oato(3-)]gadolinium;Gd-DTPA-BMA;S-041
• CAS NO: 131410-48-5
• Molecular Formula: C₁₆H₂₆N₅O₈*Gd
• Molecular Weight: 573.658
• Mol File: 131410-48-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 769.1 °C at 760 mmHg
• Flash Point: 419 °C
• Appearance: /
• Vapor Pressure: 6.54E-26mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Methanol (Slightly, Heated), Water (Slightly)
• CAS DataBase Reference: Gadodiamide(CAS DataBase Reference)
• NIST Chemistry Reference: Gadodiamide(131410-48-5)
• EPA Substance Registry System: Gadodiamide(131410-48-5)

Safety Data

• Hazardous Substances Data: 131410-48-5(Hazardous Substances Data)

Usage

Uses

Gadodiamide is an apoptosis inducing agent used in chondrocytes. It is primarily used in muscoskeletal diagnosis as a contrast agent.

Definition

ChEBI: A non-ionic gadolinium chelate having a macrocyclic triamine framework. It is used as a paramagnetic contrast agent in magnetic resonance imaging (MRI).

General Description

Gadodiamide is a clear,colorless to slightly yellow, gadolinium-based contrastagent indicated to visualize lesions with abnormal vascularityin the CNS and body. It is a nonionic gadoliniumcomplex administered by intravenous injection with an osmolalityof 2.8 times that of plasma. Gadodiamide decreasesboth the T1 and T2 relaxation times in tissueswhere it is distributed. In clinical MRI, the effect is primarily on the T1 relaxation time resulting in an increase inT1-weighted sequence signal intensity.

InChI:InChI=1/C16H29N5O8.Gd/c1-17-12(22)7-20(10-15(26)27)5-3-19(9-14(24)25)4-6-21(11-16(28)29)8-13(23)18-2;/h3-11H2,1-2H3,(H,17,22)(H,18,23)(H,24,25)(H,26,27)(H,28,29);/q;+3/p-3

Synthetic route

gadolinium(III) chloride (10138-52-0) + H3DTPA-BMA → gadodiamide (131410-48-5)

Conditions	Yield
With NaOH In hydrogenchloride; water soln. of GdCl3 in aq. HCl mixed with aq. soln. of ligand, pH adjusted to6 by NaOH;

gadodiamide (131410-48-5) + triethylenetetramine-N,N,N',N'',N''',N'''-hexaacetic acid (869-52-3) → Gd(triethylenetetraaminehexaacetate)(3-) (129648-61-9, 741237-26-3)

Conditions	Yield
Kinetics; Gd-complex reacted with ligand at 25°C pH 6.5-11;

Upstream product

• 10138-52-0 gadolinium(III) chloride 
• 119895-95-3 H₃DTPA-BMA 

Relevant articles and documents

Kinetics of the exchange reactions between Gd(DTPA)2-, Gd(BOPTA)2-, and Gd(DTPA-BMA) complexes, used as MRI contrast agents, and the triethylenetetraamine-hexaacetate ligand

The kinetics of ligand exchange reactions occurring between the Gd(DTPA), Gd(BOPTA), and Gd(DTPABMA) complexes, used as contrast agents in MRI, and the ligand TTHA, have been studied in the pH range 6.5-11.0 by measuring the water proton relaxation rates at 25 °C in 0.15 M NaCl. The rates of the reactions are directly proportional to the concentration of TTHA, indicating that the reactions take place with the direct attack of the HiTTHA (6-i)- (i = 0, 1, 2 and 3) species on the Gd3+ complexes, through the formation of ternary intermediates. The rates of the exchange reactions of the neutral Gd(DTPA-BMA) increase when the pH is increased from 6.5 to 9, because the less protonated HiTTHA(6-i)- species can more efficiently attack the Gd3+ complex. The rates of the exchange reactions of [Gd(DTPA)]2- and [Gd(BOPTA)]2- also increase from pH 8.5 to 11, but from 6.5 to 8.5 an unexpected decrease was observed in the reaction rates. The decrease has been interpreted by assuming the validity of general acid catalysis. The protons from the H iTTHA(6-i)- species (i = 2 and 3) can be transferred to the coordinated DTPA or BOPTA in the ternary intermediates when the dissociation of the Gd3+ complexes occurs faster. The kinetic inertness of Gd(DTPA), Gd(BOPTA), and Gd(DTPA-BMA) differs very considerably; the rates of the ligand exchange reactions of Gd(DTPA-BMA), thus the rates of its dissociation, are 2 to 3 orders of magnitude higher than those of Gd(DTPA) and Gd(BOPTA). The rates of the ligand exchange reactions increase with increasing concentration of the endogenous citrate, phosphate, or carbonate ions at a pH of 7.4, but the effect of citrate and phosphate is negligible at their physiological concentrations. The increase in the reaction rates at the physiological concentration of the carbonate ion is significant (20-60%), and the effect is the largest for the Gd(DTPA-BMA) complex.