Detail

Gadobutrol

Description

Name: Gadobutrol
Type: small molecule
Groups: approved
Indication: For diagnostic use only. Indicated for adults and children age 2 and over for contrast enhancement during cranial and spinal MRI, and for contrast-enhanced magnetic resonance angiography (CE-MRA). Gadobutrol is particularly suited for the detection of very small lesions and for the visualization of tumors that do not readily take up contrast media. It may be a desired agent when the exclusion or demonstration of an additional pathology may influence the choice of therapy or patient management. It may also be suitable for perfusion studies in the diagnosis of stroke, detection of focal cerebral ischemia, and in studies of tumor perfusion.
Accession Number: DB06703 ( DB06703)
Description: Intravenous gadobutrol is a second-generation extracellular non-ionic macrocyclic GBCA (gadolinium-based contrast agent) used in magnetic resonance imaging (MRI) in adults and children older than 2 years of age. It may help visualize and detect vascular abnormalities in the blood brain barrier (BBB) and central nervous system (CNS). In patients with impaired renal function, gadolinium based contrast agents increase the risk of nephrogenic systemic fibrosis (NSF). A physician should be contacted if symptoms of NSF are encountered, such as dark or red patches on the skin; stiffness in joints; trouble moving, bending or straightening arms, hands, legs or feet; burning, itching, swelling, scaling, hardening and tightening of skin; pain in hip bones or ribs; or muscle weakness. Common adverse reactions that may be experienced include headache, nausea, feeling hot, abnormal taste, and warmth, burning or pain local to the injection site. General precautions should be taken in patients who are pregnant or breastfeeding, or who have a history of allergic reaction to contrast media, bronchial asthma or an allergic respiratory disorder.
Structure:
Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Gadavistinjection604.72 mg/mLintravenous14-03-2011US
Gadovist 1.0solution604.72 mgintravenous30-01-2004Canada

Generic Prescription Products: Not Available
Over the Counter Products: Not Available
International Brands
  • No Brands

Brand Names
  • No Brands

Brand Mixtures
Brand NameIngredients
GadavistGadobutrol
Gadovist 1.0Gadobutrol

Categories
  • Contrast Media

Pharmacology

Indication: For diagnostic use only. Indicated for adults and children age 2 and over for contrast enhancement during cranial and spinal MRI, and for contrast-enhanced magnetic resonance angiography (CE-MRA). Gadobutrol is particularly suited for the detection of very small lesions and for the visualization of tumors that do not readily take up contrast media. It may be a desired agent when the exclusion or demonstration of an additional pathology may influence the choice of therapy or patient management. It may also be suitable for perfusion studies in the diagnosis of stroke, detection of focal cerebral ischemia, and in studies of tumor perfusion.
Pharmacodynamics: Not Available
Mechanism of action: MRI tissue visualization is dependent, in part, on variations in intensity of radiofrequency signals which occur due to differences in proton density, differences of the spin-lattice or longitudinal relaxation times (T1), and differences in the spin-spin or transverse relaxation times (T2). Gadolinium shortens T1 and T2 relaxation times. Greater signal enhancement is achieved with increased shortening of T1 and T2. The extent to which Gadolinium can shorten T1 and T2 is influenced by concentration in tissue, MRI field strength, and the relative ratio of transverse and longitudinal relaxation times. The recommended dose produced the greatest sensitivity of T1 shortening effect in T1-weighted magnetic resonance sequences. In T2-weighted sequences, the large magnetic moment of gadolinium induced local magnetic field inhomogenenities. At high concentrations used during bolus injections, T2-weighted sequences show a signal decrease.
Absorption: With normal renal function, the AUC is 1.1 ± 0.1 mmol·h/L.
Volume of distribution:
    Rapid distribution to extracellular space occurs after intravenous administration. After a dose of 0.1mmol/kg body weight, an average plasma level of 0.59 mmol/L was measured 2 minutes post injection, and 0.3mmol/L 60 minutes post injection.

Protein binding: No particular protein binding is displayed.
Metabolism: Not Available
Route of elimination: Excreted unchanged via glomerular filtration by the kidneys. Extrarenal elimination is negligible.
Half life: 1.81 hours (1.33-2.13 hours).
Clearance: Not Available
Toxicity: Lethality was observed in rodents after a single intravenous administration of 20 mmol/kg. This represents a dose of at least 2 orders of magnitude higher than the standard single diagnostic dose in humans (0.1 mmol/kg). No carcinogenicity studies have been conducted. No mutagenesis was observed in vitro in reverse mutation tests in bacteria, or in the HGPRT (hypoxanthine-guanine phosphoribosyl transferase) test using Chinese hamster V79 cells. Similarly, no mutagenesis was seen in chromosome abberation tests of human peripheral blood lymphocytes. It was also negative in in-vivo micronucleus tests in mice following a 0.5mmol/kg intravenous injection. No fertility or reproductive impairment was observed in male and female rates given doses 12.2 times human equivalent doses, based on body surface area. Intolerance reactions local to the injection site have been observed in rabbits after paravenous administration, and are associated with the infiltration of inflammatory cells, suggesting the possibility of local irritation if the contrast medium leaks around veins in a clinical setting.
Affected organisms
  • Not Available

SNP Mediated Adverse Drug Reactions
  • Not Available

Pharmacoeconomics

Manufacturers:
  • Not Available

Packagers:
  • Not Available

Dosage forms
FormRouteStrength
Injectionintravenous604.72 mg/mL
Solutionintravenous604.72 mg

Prices
Unit descriptionCostUnit

Patents
CountryPatent NumberApprovedExpires (estimated)
5980864United States2011-03-142016-11-09

Interactions

Drug Interactions
DrugInteraction

Food Interactions:
  • Not affected by food.

Taxonomy

Kingdom: Organic compounds
Super Class: Not Available
Class: Not Available
Sub Class: Not Available
Direct Parent: Not Available
Alternative Parents:
  • 1,2-aminoalcohols
  • 1,2-diols
  • 1,3-aminoalcohols
  • Azacyclic compounds
  • Carbonyl compounds
  • Carboxylic acid salts
  • Carboxylic acids
  • Hydrocarbon derivatives
  • Organic salts
  • Organic zwitterions
  • Primary alcohols
  • Secondary alcohols
  • Trialkylamines
  • Tricarboxylic acids and derivatives

substituent:
  • 1,2-aminoalcohol
  • 1,2-diol
  • 1,3-aminoalcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
  • Alpha-amino acid
  • Amine
  • Azacycle
  • Carbonyl group
  • Carboxylic acid
  • Carboxylic acid salt
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Polyol
  • Primary alcohol
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Tricarboxylic acid or derivatives

References

Synthesis Reference: Orlin Petrov, Peter Blaszkiewicz, "Process for mono- and 1,7-bis-N-.beta.-hydroxyalkylation of cyclene; N-.beta.-hydroxyalkyl-1,4,7,10-tetraazacyclododecane-lithium-salt complexes and the use of the complexes for the production of gadobutrol and analogs." U.S. Patent US5994536, issued May, 1998.
General Reference: # Scott LJ: Gadobutrol: a review of its use for contrast-enhanced magnetic resonance imaging in adults and children. Clin Drug Investig. 2013 Apr;33(4):303-14. doi: 10.1007/s40261-013-0066-0. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23435930 # Wack C, Steger-Hartmann T, Mylecraine L, Hofmeister R: Toxicological safety evaluation of gadobutrol. Invest Radiol. 2012 Nov;47(11):611-23. doi: 10.1097/RLI.0b013e318263f128. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23011188 # Kunnemeyer J, Terborg L, Nowak S, Scheffer A, Telgmann L, Tokmak F, Gunsel A, Wiesmuller G, Reichelt S, Karst U: Speciation analysis of gadolinium-based MRI contrast agents in blood plasma by hydrophilic interaction chromatography/electrospray mass spectrometry. Anal Chem. 2008 Nov 1;80(21):8163-70. doi: 10.1021/ac801264j. Epub 2008 Sep 27. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18821778
External Links:
ResourceLink
RxListhttp://www.rxlist.com/gadavist-drug.htm
Drugs.comhttp://www.drugs.com/international/gadavist.html

ATC Codes:
  • Array

AHFS Codes:
  • Not Available

MSDS: Download
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