Gadoteridol

HCID 60714CAS 120066-54-8

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

GADOTERIDOLProHance120066-54-8Gadolinium-HP-DO3AProhance MultipackDTXSID2048662GD-HP-DO 3ASQ-32692Gd-HPDO3AGd-HP-DO3AGadolinium-HP-Do 3ADTXCID5028588
Weitere Namen anzeigen
ICG-MaleimideGadolinolICG-Hydrazide0))-ICG HZgadotridol
0199MV609FNSC-760055HSDB 7549SQ 32,692SQ 32692CHEBI:31643gadolinium 2,2',2''-[10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]triacetate(+-)-(10-(2-Hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetato(3-))gadolinium

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

Experimentelle und physikochemische Eigenschaften

LogPlog Kow = -3.68 (octanol/water); logP = -1.98 (butanol/water), at pH 7
DensityOsmolality (37 °C): 630 mOsM/kg water; viscosity (cP): 2.0 (20 °C), 1.3 (37 °C); density at 25 °C 1.140. /Gadoteridol injection/
Color/FormWhite solid obtained as an aggregate clump of fine needle-like micro-crystals from methanol/acetone
Solubility · 2 Einträge

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

Melting Point>225 °C
Other Experimental PropertiesHydrophilic

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)

Sicherheit und Regulatorisches

Gefahrenhinweise

FDA Requirements · 1 Eintrag

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

Storage ConditionsProHance (Gadoteridol) Injection should be stored at 25 °C (77 °F) excursions permitted to 15-30 °C (59- 86 °F). Protect from light. Do not freeze.
Disposal Methods · 1 Eintrag

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 · 1 Eintrag

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 · 1 Eintrag

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 · 5 Einträge

/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.

Artificial Pollution SourcesGadoteriol's use as a contrast agent in magnetic resonance imaging (MRI) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Gadolinium-containing MRI contrast media are not biodegradable and these complexes are stable enough to pass through municipal sewage treatment plants(1).
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Gadoteridol

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Regulatorische Informationen

FDA Requirements · 1 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

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

Protein BindingIt is unknown if protein binding of gadoteridol occurs in vivo.
Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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 · 3 Einträge

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 · 2 Einträge

It is unknown if biotransformation or decomposition of gadoteridol occurs in vivo.

It is unkown if biotransformation or decomposition of gadoteridol occur in vivo.

Verwendung und Herstellung

Uses · 5 Einträge

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

Methods of ManufacturingPreparation: M. F. Tweedle et al, European Patent Office patent 292689; eidem, United States of America patent 4885363 (1988, 1989, both to Squibb).
Formulations/PreparationsProHance (Gadoteridol) Injection is a clear, colorless to slightly yellow solution containing 279.3 mg/mL of gadoteridol in rubber stoppered vials.

Anwendungen

VerwendenGadoteridol is used as an MRI contrast chelating agent.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
河北凡博医药科技有限公司15588346797
珠海奥博凯生物医药技术有限公司400-0628126
天津始加生物医药科技有限公司15022261580 · [email protected]
湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]

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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