Gadobutrol - CAS 770691-21-9
Catalog number:
770691-21-9
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C18H31GdN4O9
Molecular Weight:
604.71
COA:
Certificate of Analysis-Gadobutrol 770691-21-9 B15H1014  
Targets:
Others
Description:
Gadobutrol is a nonionic, paramagnetic contrast agent developed for tissue contrast enhancement in magnetic resonance imaging (MRI). It has a macrocyclic framework and is neutral. It is a water-soluble, highly hydrophilic compound with a partition coefficient between n-butanol and buffer at pH 7.6 of ~ 0.006.
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Purity:
≥ 99.5%
Appearance:
White, odorless amorphous powder
Synonyms:
Gadograf; Gadovist; Protovist; ZK 135079; Gd-DO3A-butrol; Gallium 10-(1,3,4-trihydroxybutan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate; 770691-21-9; AK325914; gallium; 10-(1,3,4-trihydroxybutan-2-yl)-1,4,7,10-tetrazacyclododecane-1,4,7-tricarboxylate; (SA-​8-​1425362’5’)​-[rel-​10-​[(2R,​3S)​-​2-​(hydroxy-​κO)​-​3-​hydroxy-​1-​(hydroxymethyl)​propyl]​-​1,​4,​7,​10-​tetraazacyclododecan​e-​1,​4,​7-​triacetato(3-​)​-​κN1,​κN4,​κN7,​κN10,​κO1,​κO4,​κO7]​-​gadolinium;
Solubility:
Easily soluble in water, slightly soluble in methanol and ethanol, practically insoluble in chloro-form and acetone.
MSDS:
Inquire
Application:
A gadolinium-based MRI contrast agent (GBCA)
Quality Standard:
In-house standard
Quantity:
Grams-Kilos
Melting Point:
>300ºC (dec.)
InChIKey:
NMVNSVAWXBUTGC-UHFFFAOYSA-K
InChI:
1S/C15H28N4O9.Ga/c20-9-11(12(22)10-21)16-1-3-17(13(23)24)5-7-19(15(27)28)8-6-18(4-2-16)14(25)26;/h11-12,20-22H,1-10H2,(H,23,24)(H,25,26)(H,27,28);/q;+3/p-3
Canonical SMILES:
C1CN(CCN(CCN(CCN1C(CO)C(CO)O)C(=O)[O-])C(=O)[O-])C(=O)[O-].[Ga+3]
1.Gadobutrol: an alternative contrast agent for digital subtraction dacryocystography
M. Priebe, A. Mohr, J. Brossmann, M. Heller, C. Frahm. Eur Radiol (2002) 12:2083–2086
Theoretically, X-ray attenuation of gadolinium compares favorably with that of iodine, as the absorption of Xrays depends on the atomic number to the third power. With an atomic number of 64 and a k-edge of 52 keV, gadolinium has photoelectric characteristics similar to those of iodine (atomic number of 53 and k-edge of 33.2 keV); thus, a higher X-ray absorption can be expected from gadolinium. Gadobutrol has the double gadolinium concentration (1.0 mmol/l or 157.34 mg/ml) of the other gadolinium-based contrast agents, resulting in a high radiodensity which is very similar to that of iodinated contrast medium iopentol with a iodine concentration of 250 mg/ml. Due to the high concentration, the radiodensity of gadobutrol is only approximately 20% lower than the concentration of iopentol (300 mg iodine/ml). This correlates well with our impression that the image contrast of DS-DCG with gadobutrol was only slightly inferior to routine DS-DCG studies performed with iopentol.
2.Safety of contrast-enhanced MR angiography employing gadobutrol 1.0 M as contrast material
Jörn O. Balzer, Christian Loewe, Kirsten Davis. Eur Radiol (2003) 13:2067–2074
In three multicenter studies (body MRA study, peripheral MRA study, safety study) conducted in 27 centers from January to December 2000 a total of 436 patients were recruited for CE MRA employing intravenous injections of the new contrast agent 1.0-M gadobutrol (Gadovist, Schering, Berlin, Germany; Table 1). One patient did not receive the study drug and was excluded; thus, the data of 435 patients was included in order to evaluate the clinical safety of 1.0-M gadobutrol injections. Due to organizational limits, not all participating centers had the opportunity to collect data on all safety parameters during the follow-up period. Adverse events (i.e., all adverse reactions observed by the investigator or reported by the patient during the follow-up period) were evaluated in all patients, laboratory values were available from 124 patients, and vital signs (blood pressure and heart rate after at least 5 min recumbence) as well as 12-lead electrocardiogram (ECG) recordings from 93 patients.
3.Double-dose 1.0-M gadobutrol versus standard-dose 0.5-M gadopentetate dimeglumine in revealing small hypervascular hepatocellular carcinomas
Young Kon Kim, Young Hwan Lee, Chong Soo Kim. Eur Radiol (2008) 18: 70–77
Our study result from matched pairs analysis, in which superior lesion-to-liver contrast was noted by all observers for one lesion with gadopentetate dimeglumine compared with gadobutrol despite the low gadolinium concentration of the gadopentetate dimeglumine, is totally opposite to the theoretical expectation. This is because all the study conditions of the two MRIs, except for the contrast agent and the physiologic aspects were all kept constant to permit a direct comparison. In this study, even though the modified VIBE sequence with mSENSE for inducing increased temporal resolution and the resultant double arterial phases were used, as well as a test-bolus technique, two small HCCs were not clearly demonstrated with either MRI. This could be interpreted to mean that it is still difficult to accurately capture the very short enhancement period of small HCCs with MR technology in our study. In other words, under the circumstance of using the 3D-dynamic MR sequence, the accurate timing to capture the arterial phase imaging might be given much more weight for detecting HCCs than the concerns about what extracellular MR contrast agent is used. However, the potential of a more highly concentrated gadolinium chelate has to be further investigated by additional studies using ultra-fast MR equipment, where a compact bolus is advantageous, or an MR protocol such as 2D-dynamic imaging with longer data acquisition time (≈20 s).
4.Intraindividual, randomized comparison of the macrocyclic contrast agents gadobutrol and gadoterate meglumine in breast magnetic resonance imaging
Eva M. Fallenberg & Diane M. Renz & Bettina Karle & Carsten Schwenke. Eur Radiol (2015) 25:837–849
The aim of our study was to investigate whether gadobutrol and gadoterate meglumine differ not only with regard to peak enhancement, which is expected on the basis of their different T1-relaxivities, but also with regard to the time course of signal enhancement, which might be attributable to differences in electric charge. We, therefore, performed an intraindividual comparison of the signal intensity time courses after gadobutrol and gadoterate meglumine administration in women with different benign and malignant breast lesions.
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CAS 770691-21-9 Gadobutrol

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