Gadoterate meglumine
[CAS# 92943-93-6]

Identification

• Classification: API >> Other chemicals
• Name: Gadoterate meglumine
• Synonyms: Dotarem; Gadolinium-DOTA meglumine; Gd-DOTA meglumine; Magnescope; P 449
• Molecular Formula: C₁₆H₂₄GdN₄O₈.C₇H₁₇NO₅.H
• Molecular Weight: 753.86
• CAS Registry Number: 92943-93-6
• EC Number: 832-153-1
• SMILES: C[NH2+]C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1CN(CCN(CCN(CCN1CC(=O)[O-])CC(=O)[O-])CC(=O)[O-])CC(=O)[O-].O.[Gd+3]

Safety Data

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Gadoterate meglumine is a paramagnetic contrast agent used in magnetic resonance imaging (MRI) to enhance the visibility of internal structures in the body. It is composed of gadolinium, a rare earth metal, coordinated to a chelating agent, which is then formulated with meglumine, a salt of an amino acid. The compound is often marketed under brand names such as Dotarem and is primarily used for MRI procedures that require enhanced imaging of the brain, spinal cord, and other tissues.

The development of gadoterate meglumine followed the evolution of gadolinium-based contrast agents (GBCAs), which emerged in the 1980s to improve the diagnostic capabilities of MRI. Gadolinium, being a paramagnetic element, enhances the relaxation rates of protons in tissues during MRI scans, making it highly effective in increasing the contrast between different tissues, particularly when there is a need to differentiate between normal and abnormal tissue. GBCAs, including gadoterate meglumine, are injected into the bloodstream, where they are taken up by tissues, and the gadolinium atoms interact with the magnetic field of the MRI scanner, making the targeted areas appear brighter on the resulting images.

One of the key applications of gadoterate meglumine is in the diagnosis of neurological conditions, such as tumors, multiple sclerosis, and vascular diseases. The agent is particularly useful for identifying brain lesions, enhancing the visibility of abnormal tissue in the brain and spinal cord. It is also used to assess the blood-brain barrier, as gadolinium contrast agents can pass through the barrier when it is disrupted by diseases such as tumors or infections.

Gadoterate meglumine is favored for its high stability and low toxicity profile. The chelation of gadolinium with a ligand prevents the release of free gadolinium ions, which could be toxic to the body. The drug is typically administered intravenously, and the body eliminates it through the kidneys. This makes it a safe option for many patients, although care must be taken in individuals with impaired renal function, as the agent could accumulate in the body, potentially leading to nephrogenic systemic fibrosis (NSF), a rare but serious condition.

Beyond its use in neurological imaging, gadoterate meglumine is also employed in other areas of clinical diagnostics, including the assessment of cardiovascular conditions, musculoskeletal abnormalities, and abdominal or pelvic disorders. Its application extends to both adult and pediatric populations, as it provides high-quality imaging with relatively few side effects when used according to established safety guidelines.

Overall, gadoterate meglumine plays a critical role in modern diagnostic imaging, particularly in MRI, by providing enhanced visibility of tissues and aiding in the detection of a wide range of medical conditions. Its development has significantly advanced the capabilities of MRI in medical diagnostics, offering clinicians a valuable tool for accurate diagnosis and treatment planning.

References

2022. Safety profile of Gadoterate meglumine on the renal function of patients with severe kidney disease. Clinical Imaging, 91.
DOI: 10.1016/j.clinimag.2022.08.021

2022. The Effect of Magnetic Field Gradient and Gadolinium-Based MRI Contrast Agent Dotarem on Mouse Macrophages. Cells, 11(5).
DOI: 10.3390/cells11050757

2022. DOTAREM (DOTA)-Gold-Nanoparticles: Design, Spectroscopic Evaluation to Build Hybrid Contrast Agents to Applications in Nanomedecine. International Journal of Nanomedicine, 17.
DOI: 10.2147/ijn.s368458