 Home > Encyclopedia > Gadolinate(1-), [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-, hydrogen (1:1)

Gadolinate(1-), [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-, hydrogen (1:1)

Gadolinate(1-), [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-, hydrogen (1:1) structure

CAS No:
72573-82-1
Formula:
C16H24GdN4O8.H
Chemical Name:
Gadolinate(1-), [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-, hydrogen (1:1)
Synonyms:
Gadolinate(1-),[1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-,hydrogen (1:1);Gadolinate(1-),[1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-N1,N4,N7,N10,O1,O4,O7,O10]-,hydrogen;Gadolinate(1-),[1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-,hydrogen;1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid,gadolinium complex;1,4,7,10-Tetraazacyclododecane,gadolinate(1-) deriv.;Gadoteric acid
Categories:
Inorganic Chemistry > Silica gel

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Description

Gadoteric acid is a macrocycle-structured gadolinium-based MRI contrast agent. It is composed of the organic acid DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) used for its chelating properties, and gadolinium (Gd3+). As a paramagnetic molecule, gadoterate develops a magnetic moment when placed in a magnetic field. This magnetic moment enhances the relaxation rates of water protons in its vicinity, leading to an increase in signal intensity (brightness) of tissues. More specifically, it reduces the T1 relaxation time (and to some extent the T2 and T2* relaxation times) in NMR, which is the source of its clinical utility. Increased signal brightness allows it to be used in imaging of blood vessels and of inflamed or diseased tissue where the blood vessels become 'leaky'. Gadoteric acid, as the FDA approved product Dotarem, is indicated for intravenous use with magnetic resonance imaging (MRI) in brain (intracranial), spine and associated tissues in adult and pediatric patients (2 years of age and older) to detect and visualize areas with disruption of the blood brain barrier (BBB) and/or abnormal vascularity.

Gadolinate(1-), [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-, hydrogen (1:1) Basic Attributes

Molecular Weight：

558.6 g/mol

Exact Mass：

559.09135 g/mol

UNII：

QVF9Y6955W

ATC Code：

V - Various

Characteristics

PSA：

171 Å²

Toxicity

Toxicity Summary：

The most frequent adverse reactions in clinical studies were nausea, headache, injection site pain, injection site coldness, and burning sensation. Nephrogenic Systemic Fibrosis has occurred in patients with impaired elimination of GBCAs.

Protein Binding：

Gadoterate does not undergo protein binding in vitro.

Drug Information

Drug Indication：

Gadoteric acid is indicated for intravenous use with magnetic resonance imaging (MRI) in brain (intracranial), spine and associated tissues in adult and pediatric patients (2 years of age and older) to detect and visualize areas with disruption of the blood brain barrier (BBB) and/or abnormal vascularity.|FDA Label

Pharmacology：

Gadoterate affects proton relaxation times and consequently the MR signal, and the contrast obtained is characterized by the relaxivity of the gadoterate molecule. The relaxivity values for gadoterate are similar across the spectrum of magnetic field strengths used in clinical MRI (0.2 - 1.5 T). Gadoterate does not cross the intact blood-brain barrier and, therefore, does not enhance normal brain or lesions that have a normal blood-brain barrier, e.g. cysts, mature post-operative scars. However, disruption of the blood-brain barrier or abnormal vascularity allows distribution of gadoterate in lesions such as neoplasms, abscesses, and infarcts.

MeSH：

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)|Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

Absorption：

Gadoteric acid is excreted primarily in urine.|The volume of distribution at steady state of total gadolinium in normal subjects is 179 and 211 mL/kg in female and male subjects respectively, roughly equivalent to that of extracellular water.|In healthy subjects, the renal and total clearance rates of total gadolinium are comparable (1.27 and 1.74 mL/min/kg in females; and 1.40 and 1.64 mL/min/kg in males, respectively).

Metabolism/Metabolites：

Gadoterate is not known to be metabolized.

Biological Half-Life：

Gadoteric acid demonstrates a mean elimination half-life of about 1.4 hr and 2.0 hr in female and male subjects, respectively.

Mechanism of Action：

Gadoterate is a paramagnetic molecule that develops a magnetic moment when placed in a magnetic field. The magnetic moment enhances the relaxation rates of water protons in its vicinity, leading to an increase in signal intensity (brightness) of tissues. When placed in a magnetic field, gadoterate shortens the T1 and T2 relaxation times in target tissues.

MeSH Entry Terms：

gadolinate(1-), (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-

Computed Properties

Molecular Weight:558.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:5
Exact Mass:559.09135
Monoisotopic Mass:559.09135
Topological Polar Surface Area:171
Heavy Atom Count:29
Complexity:510
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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Guide of Gadolinate(1-), [1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetato(4-)-κN1,κN4,κN7,κN10,κO1,κO4,κO7,κO10]-, hydrogen (1:1)

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