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131069-91-5

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131069-91-5 Usage

Description

The contrast agent gadoversetamide was launched in the US as a solution for i.v. injection to be used prior to magnetic resonance imaging (MRI) in patients with anomalous blood-brain barrier or anomalous vascularity in the central nervous system or in the liver. This chelate obtained by complexation of paramagnetic gadolinium(III) ion and DTPA-bis- (methoxyethylamide) ligand enhances visualization of lesions including tumors in the brain, spine and liver due to the effect of Gd(III)-water interaction on the proton magnetic relaxation of water. The small molecular size gadoversetamide belongs to the class of extracellular contrast agents. A phase III, multicenter, double-blind, parallel group trial showed that gadoversetamide was well tolerated and as efficient as gadopentetate dimeglumine (Schering) in hepatic magnetic resonance imaging of patients with suspected liver pathology.

Originator

Mallinckrodt (US)

Uses

Different sources of media describe the Uses of 131069-91-5 differently. You can refer to the following data:
1. Diagnostic aid (paramagnetic, brain disorders; spine disorders.
2. Gadoversetamide is a gadolinium containing complex used as a contrasting imaging agent.

Definition

ChEBI: A gadolinium coordination entity that consists of Gd3+ coordinated to 3,6,9-triazaundecadiamide in which each of the amide nitrogens is substituted by a 2-methoxyethyl group and in which the nitrogens at positions 3, 6, and 9 are each ubstituted by carboxylatomethyl group. The gadolinium is coordinated to the three tertiary amino groups as well as to the carboxylate groups. A white odourless powder that is freely soluble in water, gadoversetamide has paramagnetic properties and is used s a contrast agent in magnetic resonance imaging. It distributes mainly in extracellular fluid, but does not cross the blood-brain barrier. It is used particularly in imaging the brain, spine and liver.

Manufacturing Process

A stirred suspension of diethylenetriaminepentaacetic acid dianhydride (10.8 g, 0.030 mole) in 100 ml of isopropanol was treated with 2- methoxyethylamine (5.0 g, 0.067 mole). The entire mixture was heated at 50°C for 4 hours in a water bath. The pale yellow solution was filtered through a medium porosity sintered glass funnel to remove undissolved impurities, and the filtrate was taken to dryness under reduced pressure. The resulting amorphous foam was dried (vacuum desiccator) at ambient temperature for 18 hours. The yield of the N,N"-bis[N-(2-methoxyethyl)- carbamoylmethyl]diethylenetriamine-N,N',N"-triacetic acid 14.4 g (93.5%). A mixture of gadolinium (III) oxide (3.3 g, 0.0091 mole) and N,N"-bis[N-(2- methoxyethyl)-carbamoylmethyl]diethylenetriamine-N,N',N"-triacetic acid (10.2 g, 0.020 mole) in H2O (100 ml) was heated at 60-65°C for 3 hours in a water bath. The pale yellow homogeneous solution was filtered through a fine porosity sintered glass funnel to remove undissolved impurities and the clear filtrate was poured into acetone (2 L). The heterogeneous mixture was stirred for 5 min and allowed to stand at ambient temperature for 30 min. Aqueous acetone was decanted off and the resulting gummy residue was dissolved with methanol (150 ml). The solution was concentrated under reduced pressure and the complex was precipitated from the solution by adding it to more acetone (1 L). The amorphous precipitate was collected, washed with acetone and dried. The yield of {N,N"-bis[N-(2-methoxyethyl)-carbamoylmethyl] diethylenetriamine-N,N',N"-triaceto}gadolinium (III) was 11.2 g (80.7%). The pale cream solid was crystallized from a mixture of methanol and tetrahydrofuran to give a colorless solid. It was 97.4% pure by HPLC. For {N,N"-bis[N-(2-methoxyethyl)-carbamoylmethyl]diethylenetriamine-N,N',N"- triaceto}gadolinium (III) calculated: Gd, 22.88%, found: Gd, 22.52%.

Brand name

Optimark (Mallinckrodt).

Therapeutic Function

Diagnostic aid

Check Digit Verification of cas no

The CAS Registry Mumber 131069-91-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,0,6 and 9 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 131069-91:
(8*1)+(7*3)+(6*1)+(5*0)+(4*6)+(3*9)+(2*9)+(1*1)=105
105 % 10 = 5
So 131069-91-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H37N5O10.Gd/c1-34-9-3-21-16(26)11-24(14-19(30)31)7-5-23(13-18(28)29)6-8-25(15-20(32)33)12-17(27)22-4-10-35-2;/h3-15H2,1-2H3,(H,21,26)(H,22,27)(H,28,29)(H,30,31)(H,32,33);/q;+3/p-3

131069-91-5 Well-known Company Product Price

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  • USP

  • (1287675)  Gadoversetamide  United States Pharmacopeia (USP) Reference Standard

  • 131069-91-5

  • 1287675-200MG

  • 4,326.66CNY

  • Detail

131069-91-5Downstream Products

131069-91-5Relevant articles and documents

PREPARATION OF COMPLEXING AGENTS AND METAL ION COMPLEXES IN AQUEOUS MEDIA

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Page/Page column 24, (2010/11/29)

The invention relates to methods of preparation for bis-amide complexing agents, as well as paramagnetic metal ion complexes that include such agents. To prepare these complexing agents, a reaction mixture is formed that includes a bis-anhydride, a nitrogen-containing compound, and an aqueous solvent system. The nitrogen-containing compound reacts with the bis-anhydride in the reaction mixture to form the bis-amide complexing agent. The molar ratio of water to the nitrogen containing compound in the reaction mixture is greater than 3:1, respectively. In addition, the molar ratio of the nitrogen-containing compound to the bis-anhydride in the reaction mixture is no greater than 2.5:1, respectively. In some embodiments, a base other than the nitrogen-containing compound may be included in the reaction mixture (e.g., to buffer the reaction mixture). In some embodiments, the bis-amide complexing agent may be contacted with a paramagnetic metal ion salt to form a paramagnetic metal ion complex of the invention.

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