Grundinformationen
- Standard-SMILES
CC(O)CN1CCN(CC(=O)[O-])CCN(CC(=O)[O-])CCN(CC(=O)[O-])CC1.[Gd+3]- InChIKey
DPNNNPAKRZOSMO-UHFFFAOYSA-K- Summenformel
- C17H29GdN4O7
- Durchschnittliche Molmasse
- 558,7 g/mol
- Monoisotopische Masse
- 559,12774
Namen und Bezeichner
- Bevorzugter Name
- Gadoteridol
- IUPAC
- 2-[4,7-bis(carboxylatomethyl)-10-(2-hydroxypropyl)-1,4,7,10-tetrazacyclododec-1-yl]acetate;gadolinium(3+)
- Englischer Name
- Gadoteridol
- Summenformel
- C17H28GdN4O7
- Molmasse
- 557.68
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
120066-54-8- PubChem CID
- 60714
- UNII
- 0199MV609F
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 154 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 11
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 471
Experimentelle und physikochemische Eigenschaften
Solubility
In water, 737 mg/mL
Solubility (mg/mL): methanol 119, isopropanol 41, dimethylformamide 10.1, acetonitrile 6.1, methylene chloride 5.2, ethyl acetate 0.5, acetone 0.4, hexane 0.2, toluene 0.3
Physikochemische Eigenschaften
- Schmelzpunkt
- 188 · 188-193 °C
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- PBS (pH 7.2): 10 mg/ml
- Aggregatzustand
- A solid
- Farbe
- White to off-white
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C17H31N4O7.Gd/c1-14(22)10-18-2-4-19(11-15(23)24)6-8-21(13-17(27)28)9-7-20(5-3-18)12-16(25)26;/h14H,2-13H2,1H3,(H,23,24)(H,25,26)(H,27,28);/q-1;+4/p-3
- InChIKey
- JOJFJDKAWWEUPD-UHFFFAOYSA-K
- SMILES
- CC1CN23CCN45CCN67CCN8(CC2)CC(=O)[O-][Gd+3]3486([O-]C(=O)C5)([O-]C(=O)C7)O1
Sicherheit und Regulatorisches
Gefahrenhinweise
FDA Requirements
The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including gadoteridol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Sicherheit und Schutzausrüstung
Disposal Methods
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: The elements of the lanthanide series typically occur as the +3 ion either in solution or in compounds(1). Based on the Gd3+/Gd reduction potential of -2.28 V(1), gadolinium(III) ions do not undergo oxidation-reduction reactions under normal environmental conditions(SRC). Gadolinium ions are likely to adsorb to soils(SRC). In general, metal cations in solution are attracted to the negatively charged surfaces of soil particles(2). The extent of adsorption of metal ions to soils depends on the pH, the mineral content, and organic content of the soil(2). Gadolinium compounds do not volatilize from dry or moist soil surfaces due to their ionic character(SRC).
Toxicity Summary
IDENTIFICATION AND USE: Gadoteridol is used as injectable contrast medium for Magnetic Resonance Imaging (MRI). HUMAN EXPOSURE AND TOXICITY: Gadolinium-based contrast agents (GBCAs) increase the risk for nephrogenic systemic fibrosis (NSF) among patients with impaired elimination of the drugs. Avoid use of GBCAs in these patients unless the diagnostic information is essential and not available with non-contrasted MRI or other modalities. NSF may result in fatal or debilitating systemic fibrosis affecting the skin, muscle and internal organs. The risk for NSF appears highest among patients with: chronic, severe kidney disease , or acute kidney injury. Screen patients for acute kidney injury and other conditions that may reduce renal function. For patients at risk for chronically reduced renal function (older than 60 years, hypertension or diabetes), estimate the glomerular filtration rate (GFR) through laboratory testing. For patients at highest risk for NSF, do not exceed the recommended ProHance dose and allow a sufficient period of time for elimination of the drug from the body prior to re-administration. The possibility of a reaction, including serious, life threatening, or fatal, anaphylactic or cardiovascular reactions, or other idiosyncratic reactions, should always be considered, especially in those patients with a history of a known clinical hypersensitivity or a history of asthma or other allergic respiratory disorders. The literature describe a case of vasovagal response and anaphylactoid reaction during iv administration of gadoteridol. In an in vitro test, gadoteridol did not demonstrate any potential to hemolyze human erythrocytes when incubated in high concentrations with whole blood, suggesting there is little probability gadoteridol will cause hemolysis in vivo. ANIMAL STUDIES: Gadopentetate dimeglumine (Magnevist), gadoteridol (ProHance), gadodiamide (Omniscan), and gadoversetamide (Optimark) were evaluated at standard concentration and compared wi
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Gadolinium-based contrast agents (GBCAs) increase the risk for nephrogenic systemic fibrosis (NSF) among patients with impaired elimination of the drugs. Avoid use of GBCAs in these patients unless the diagnostic information is essential and not available with non-contrasted MRI or other modalities. NSF may result in fatal or debilitating systemic fibrosis affecting the skin, muscle and internal organs. The risk for NSF appears highest among patients with: chronic, severe kidney disease (GFR <30 mL/min/1.73 sq m), or acute kidney injury. Screen patients for acute kidney injury and other conditions that may reduce renal function. For patients at risk for chronically reduced renal function (e.g. age > 60 years, hypertension or diabetes), estimate the glomerular filtration rate (GFR) through laboratory testing. For patients at highest risk for NSF, do not exceed the recommended ProHance dose and allow a sufficient period of time for elimination of the drug from the body prior to re-administration.
/SIGNS AND SYMPTOMS/ The possibility of a reaction, including serious, life threatening, or fatal, anaphylactic or cardiovascular reactions, or other idiosyncratic reactions, should always be considered, especially in those patients with a history of a known clinical hypersensitivity or a history of asthma or other allergic respiratory disorders.
/CASE REPORTS/ ... The authors describe a case of vasovagal response and anaphylactoid reaction during iv administration of gadoteridol. MR users should be aware of the potential for adverse effects to occur in association with use of gadoteridol and be prepared by implementing appropriate observation procedures for patients receiving this as well as other MR contrast agents. In addition, physiologic monitoring devices and resuscitation equipment should be readily available in the clinical MR setting for proper treatment of patients who may experience moderate to severe adverse reactions.
/CASE REPORTS/ ... A case of a life-threatening anaphylactoid reaction to gadoteridol /is reported/. The reaction resulted in hospitalization but did respond to medical treatment. Resuscitation equipment and properly trained personnel should be available if these agents are being administered.
/ALTERNATIVE and IN VITRO TESTS/ In an in vitro test, gadoteridol did not demonstrate any potential to hemolyze human erythrocytes when incubated in high concentrations with whole blood, suggesting there is little probability gadoteridol will cause hemolysis in vivo.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Gadoteridol
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ ... Gadopentetate dimeglumine (Magnevist), gadoteridol (ProHance), gadodiamide (Omniscan), and gadoversetamide (Optimark) were evaluated at standard concentration and compared with a control (physiologic saline) and the conventional ionic radiographic contrast medium meglumine diatrizoate (Renografin 60). Each mouse received a sc injection in the hindlimb of 0.3 mL of contrast or saline. There were 6 experimental groups, with 15 animals in each group. ... Of the four MR contrast agents, gadopentetate dimeglumine caused the greatest tissue damage, and gadoteridol and gadodiamide-the two lowest osmolar agents-the least. The difference was statistically significant in terms of both inflammation (P=0.0008 for gadoteridol, and P=0.006 for gadodiamide) and necrosis (P=0.0067 for gadoteridol, and P=0.031 for gadodiamide), when these agents were compared with gadopentetate dimeglumine. In regard to the control experiments, for all three variables (necrosis, edema, and inflammation), there was no statistically significant difference between the results with gadoteridol or gadodiamide and those with saline. ... The risk of tissue damage due to extravasation is not widely appreciated for the gadolinium chelates. Care should be exercised during contrast injection, to avoid inadvertent extravasation and its deleterious consequences, in particular with the two higher osmolar agents (gadopentetate dimeglumine and gadoversetamide).
/LABORATORY ANIMALS: Acute Exposure/ In mice, the acute iv LD50 for gadoteridol (0.5 M) injection was 11 to 14 mmol/kg, and the iv minimal lethal dose in rats was greater than 10 mmol/kg.
/LABORATORY ANIMALS: Acute Exposure/ ...Anesthetized beagles were instrumented to record the electrocardiogram and to measure arterial blood pressure. In part 1, each animal was injected with gadoversetamide at rates of 1.0, 3.0, and 10 mL/sec. In part 2, each animal was injected with gadoversetamide, gadopentetate dimeglumine, gadodiamide, and gadoteridol at a dose of 0.6 mmol/kg delivered at a rate of 3.0 mL/sec. ... IV administration of gadoversetamide caused transient decreases in both heart rate and blood pressure. The rate of injection did not affect the magnitude of the heart rate or blood pressure changes. Administration of gadoversetamide, gadopentetate dimeglumine, and gadodiamide elicited equivalent changes in cardiovascular function. Injection of gadoteridol caused a similar degree of hypotension, but the changes lasted longer. ...
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In 2-week studies with gadoteridol, no serious effects were observed in mice given 3 mmol/kg or dogs given 1.5 mmol/kg daily.
For more Non-Human Toxicity Excerpts (Complete) data for GADOTERIDOL (9 total), please visit the HSDB record page.
Populations at Special Risk
Gadolinium-based contrast agents (GBCAs) increase the risk for nephrogenic systemic fibrosis (NSF) among patients with impaired elimination of the drugs. Avoid use of GBCAs in these patients unless the diagnostic information is essential and not available with non-contrasted MRI or other modalities. NSF may result in fatal or debilitating systemic fibrosis affecting the skin, muscle and internal organs. The risk for NSF appears highest among patients with: chronic, severe kidney disease (GFR <30 mL/min/1.73 sq m), or acute kidney injury. Screen patients for acute kidney injury and other conditions that may reduce renal function. For patients at risk for chronically reduced renal function (e.g. age > 60 years, hypertension or diabetes), estimate the glomerular filtration rate (GFR) through laboratory testing. For patients at highest risk for NSF, do not exceed the recommended ProHance dose and allow a sufficient period of time for elimination of the drug from the body prior to re-administration.
The possibility of a reaction, including serious, life threatening, or fatal, anaphylactic or cardiovascular reactions, or other idiosyncratic reactions, should always be considered, especially in those patients with a history of a known clinical hypersensitivity or a history of asthma or other allergic respiratory disorders.
Probable Routes of Human Exposure
Occupational exposure to gadolinium compounds may occur through dermal contact with these compounds at workplaces where gadolinium is produced or used. Monitoring data indicate that the general population may be exposed to gadolinium compounds via ingestion of contaminated drinking water. Limited monitoring data indicate that exposure may occur via ingestion of contaminated food and inhalation. Direct exposure to gadolinium compounds among the general population will also be to those administered contrast agents containing gadolinium prior to MRI procedures. (SRC)
Environmental Water Concentrations
While data specific to gadoteridol were not located(SRC, 2014), the literature suggests that some contrast agents originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2).
Regulatorische Informationen
FDA Requirements
The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including gadoteridol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Sicherheitsdaten
- wgk
- WGK 3
- hs_code
- 2942000000
- risk_code
- 22-25-36-50-43-41
- hazard_code
- Xn,T,N,Xi
- safety_code
- 45-26-61-36/37-39
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 120066-54-8(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
V08CA04
V - Various;V08 - Contrast media;V08C - Magnetic resonance imaging contrast media;V08CA - Paramagnetic contrast media;V08CA04 - Gadoteridol
QV - Various;QV08 - Contrast media;QV08C - Magnetic resonance imaging contrast media;QV08CA - Paramagnetic contrast media;QV08CA04 - Gadoteridol
Pharmacodynamics
Gadoteridol affects proton relaxation times and consequently the MR signal. Signal intensity is affected by the dose and relaxivity of the gadoteridol molecule. Consistently, for all gadolinium-based contrast agents, the relaxivity of gadoteridol decreases with the increase of the magnetic field strength used in clinical MRI (0.2 –3.0T). Disruption of the blood-brain barrier or abnormal vascularity allows the accumulation of gadoteridol in lesions such as neoplasms, abscesses, and subacute infarcts. The pharmacokinetics of gadoteridol in various lesions is not known.
Mechanism of Action
Gadoteridol is a paramagnetic agent and, as such, develops a magnetic moment when placed in a magnetic field. The relatively large magnetic moment produced by the paramagnetic agent results in a relatively large local magnetic field, which can enhance the relaxation rates of water protons in the vicinity of the paramagnetic agent. In MRI, visualization of normal and pathologic brain tissue depends, in part, on variations in the radiofrequency signal intensity that occur with: 1) differences in proton density; 2) differences of the spinlattice or longitudinal relaxation times (T1); and 3) differences in the spin-spin or transverse relaxation time (T2). When placed in a magnetic field, gadoteridol decreases T1 relaxation times in the target tissues. At recommended doses, the effect is observed with greatest sensitivity in the T1-weighted sequences.
Biological Half-Life
The elimination half-life (mean ± SD) is about 1.57 ± 0.08 hours. From population PK model of pediatric subjects receiving a single intravenous dose of 0.1 mmol/kg of gadoteridol, the mean distribution half-life (t<sub>1/2,alpha</sub>) was 0.14 ± 0.04 hours in pediatric subjects 2 years to 6 years of age, 0.18 ± 0.07 hours in pediatric subjects 6 years to 12 years of age, and 0.20 ± 0.07 hours in adolescent subjects older than 12 years of age. The mean elimination half-life (t<sub>1/2,beta</sub>) was 1.32 ± 0.006 hours in pediatric subjects 2 years to 6 years, 1.32 ± 0.07 hours in pediatric subjects 6 years to 12 years of age, and 1.61 ± 0.19 hours in adolescent subjects older than 12 years of age. Pharmacokinetic simulations indicate similar half-life values for gadoteridol in pediatric subjects less than 2 years of age when compared to those reported for adults. In patients with impaired renal function, the serum half-life of gadoteridol is prolonged. After intravenous injection of 0.1 mmol/kg, the elimination half-life of gadoteridol was 10.65 ± 0.06 hours in mild to moderately impaired patients (creatinine clearance 30 to 60 mL/min) and 9.10±0.26 hours in severely impaired patients not on dialysis (creatinine clearance 10 to 30 mL/min).
The pharmacokinetics of intravenously administered gadoteridol in normal subjects conforms to a two-compartment open model with mean distribution and elimination half-lives (reported as mean + or - SD) of about 0.20 + or - 0.04 hours and 1.57 + or - 0.08 hours, respectively.
... 18 healthy male volunteers ... were assigned to one of six dosing groups: 0.05, 0.1, 0.15, 0.2, 0.25, and 0.3 mmol/kg gadoteridol (0.5 M), in an ascending dose study. ...Pharmacokinetic data show that the elimination half-life and the distribution half-life were independent of the dose used. The mean distribution half-life was 0.20 +/- 0.04 hours, the mean elimination half-life was 1.57 +/- 0.08 hours... .
Metabolism/Metabolites
It is unknown if biotransformation or decomposition of gadoteridol occurs in vivo.
It is unkown if biotransformation or decomposition of gadoteridol occur in vivo.
FDA Pharmacological Classification
0199MV609F
GADOTERIDOL
Mechanisms of Action [MoA] - Magnetic Resonance Contrast Activity
Established Pharmacologic Class [EPC] - Paramagnetic Contrast Agent
Gadoteridol is a Paramagnetic Contrast Agent. The mechanism of action of gadoteridol is as a Magnetic Resonance Contrast Activity.
GADOTERIDOL
Absorption, Distribution and Excretion
From population PK model of pediatric subjects receiving a single intravenous dose of 0.1 mmol/kg of gadoteridol, the mean Cmax was 0.66 ± 0.21 mmol/L in pediatric subjects 2 years to 6 years of age, 0.58 ± 0.06 mmol/L in pediatric subjects 6 years to 12 years of age, and 0.68 ± 0.12 mmol/L in adolescent subjects older than 12 years. The mean AUC0-∞ was 0.74 ± 0.20 mmol/L*h in pediatric subjects 2 years to 6 years of age, 0.74 ± 0.09 mmol/L*h in pediatric subjects 6 years to 12 years of age, and 0.98 ± 0.09 mmol/L*h in adolescent subjects older than 12 years of age. Pharmacokinetic simulations indicate similar half-life, AUC, and Cmax values for ProHance in pediatric subjects less than 2 years of age when compared to those reported for adults.
Gadoteridol is eliminated in the urine with 94.4 ± 4.8% (mean ± SD) of the dose excreted within 24 hours post-injection. Over 80% of the dose was recovered in urine for pediatric subjects after 10 hours. In patients with moderately and severely impaired renal function about 97% and 76% of the administered dose was recovered in the urine within 7 days and 14 days, respectively.
The plasma distribution volume (mean ± SD) for the non-renally impaired adults was 0.205 ± 0.025 L/kg.Following GBCA administration, gadolinium is present for months or years in the brain, bone, skin, and other organs.
The renal and plasma clearance rates (1.41 ± 0.33 mL/ min/kg and 1.50 ± 0.35 mL/ min/kg, respectively) of gadoteridol are essentially identical, indicating no alteration in elimination kinetics on passage through the kidneys and that the drug is essentially cleared through the kidney. The mean serum clearance of gadoteridol in patients with normal renal function was 116.14 ± 26.77 mL/min, compared to 37.2 ± 16.4 mL/min in patients with mild to moderate renal impairment and 16.0 ± 3.0 mL/min in patients with severe renal impairment.
... The physicochemical properties of gadoteridol, a macrocyclic nonionic gadolinium complex, were studied together with its pharmacokinetics and biodistribution in rats and dogs. ... Studies in rats were conducted after single iv injections at 0.1 or 0.35 mmol/kg using (153)Gd-labeled gadoteridol or with seven daily doses of 0.1 mmol/kg to examine the levels of residual gadolinium in organs. Nonradioactive biodistribution and excretion studies were performed in dogs following injection at 0.1 mmol/kg. ... After injection, the dose was rapidly cleared from rat blood and excreted such that more than 90% of the dose appeared in the urine within 4 hr of injection. At 7 and 14 days postinjection, only extremely low levels of gadolinium were observed in liver and bone; these levels were two to eight times lower than the levels reported after the injection of gadopentetate dimeglumine. ... Differences observed in the long-term retention of gadolinium between gadoteridol and gadopentetate dimeglumine were consistent with the reported greater in vivo resistance to transmetallation of gadolinium macrocycles compared with the linear gadolinium chelate molecules.
... To assess the safety and pharmacokinetics of gadoteridol injection (0.5 M) ... 18 healthy male volunteers ... were assigned to one of six dosing groups: 0.05, 0.1, 0.15, 0.2, 0.25, and 0.3 mmol/kg gadoteridol (0.5 M), in an ascending dose study. Physical examination, vital signs, electrocardiogram, clinical laboratory tests, and serum and urine samples were obtained at selected time points before and after administration of gadoteridol. ... No significant changes in vital signs, physical examination, clinical laboratory values, or electrocardiogram, that were believed ... to be related to the administration of the contrast agent, were observed. A single adverse event (transient hive) believed to be related to contrast agent administration was observed in one volunteer. Pharmacokinetic data show that the elimination half-life and the distribution half-life were independent of the dose used. The mean distribution half-life was 0.20 +/- 0.04 hours, the mean elimination half-life was 1.57 +/- 0.08 hours, and greater than 94% of the drug was excreted in the urine in 24 hours.
Verwendung und Herstellung
Uses
MEDICATION
Contrast Media
Injectable contrast Medium for Magnetic Resonance Imaging (MRI)
Typical contrast agents are gadolinium-based compounds that possess a higher linear attenuation coefficient than soft tissues. /Contrast agents/
Use (kg; approx.) in Germany (2009): >500;Consumption (g per capita; approx.) in Germany (2009): 0.00611;Calculated removal (%): 22
Anwendungen
VerwendenGadoteridol is used as an MRI contrast chelating agent.
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Ergänzende Hinweise
DefinitionChEBI: A non-ionic gadolinium chelate having a macrocyclic tetraamine framework. It is used as a paramagnetic contrast agent in magnetic resonance imaging (MRI).
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