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Identification
NameGadoteridol
Accession NumberDB00597  (APRD00992)
TypeSmall Molecule
GroupsApproved
Description

Gadoteridol provides contrast enhancement of the brain, spine and surrounding tissues resulting in improved visualization (compared with unenhanced MRI) of lesions with abnormal vascularity or those thought to cause a disruption of the normal blood brain barrier. Gadoteridol can also be used for whole body contrast enhanced MRI including the head, neck, liver, breast, musculoskeletal system and soft tissue pathologies. n MRI, visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadoteridol shortens the T1 relaxation time in tissues where it accumulates. Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadoteridol in lesions such as neoplasms, abscesses, and subacute infarcts.

Structure
Thumb
Synonyms
Gadolinium 2,2',2''-[10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]triacetate
Gadolinium-HP-do3a
Gadoteridol
Gadoteridolum
GD-HP-do 3a
Gd-hpdo3a
External Identifiers
  • Gd-HP-DO 3A
  • SQ 32692
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Prohanceinjection, solution279.3 mg/mLintravenousBRACCO DIAGNOSTICS INC1992-11-16Not applicableUs
Prohance - Liq IV 279.3mg/mlsolution279.3 mgintravenousBracco Imaging Canada1998-09-08Not applicableCanada
Prohance Liq IV 279.3mg/mlliquid279.3 mgintravenousSquibb Diagnostics, Division Of Bristol Myers Squibb Canada Inc.1993-12-311998-07-30Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII0199MV609F
CAS number120066-54-8
WeightAverage: 558.68
Monoisotopic: 559.127724835
Chemical FormulaC17H29GdN4O7
InChI KeyInChIKey=DPNNNPAKRZOSMO-UHFFFAOYSA-K
InChI
InChI=1S/C17H32N4O7.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;/h14,22H,2-13H2,1H3,(H,23,24)(H,25,26)(H,27,28);/q;+3/p-3
IUPAC Name
gadolinium(3+) ion 2-[4,7-bis(carboxylatomethyl)-10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetate
SMILES
[Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Carboxylic acid salt
  • 1,2-aminoalcohol
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationGadoteridol is an MRI contrast agent used for contrast enhancement of the brain, spine and surrounding tissues resulting in improved visualization (compared with unenhanced MRI) of lesions with abnormal vascularity or those thought to cause a disruption of the normal blood brain barrier. Gadoteridol can also be used for whole body contrast enhanced MRI including the head, neck, liver, breast, musculoskeletal system and soft tissue pathologies.
PharmacodynamicsNot Available
Mechanism of actionBased on the behavior of protons when placed in a strong magnetic field, which is interpreted and transformed into images by magnetic resonance (MR) instruments. Paramagnetic agents have unpaired electrons that generate a magnetic field about 700 times larger than the proton's field, thus disturbing the proton's local magnetic field. When the local magnetic field around a proton is disturbed its relaxation process is altered. MR images are based on proton density and proton relaxation dynamics. MR instruments can record two different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and T2 (spin-spin or transverse relaxation time). In MRI, visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadoteridol shortens the T1 relaxation time in tissues where it accumulates. Gadoteridol does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in central nervous system (CNS) lesions that have not caused an abnormal blood-brain barrier (e.g., cysts, mature post-operative scars). Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadoteridol in lesions such as neoplasms, abscesses, and subacute infarcts.
Related Articles
AbsorptionNot Available
Volume of distribution
  • 204 ± 58 mL/kg
Protein bindingNot Available
MetabolismNot Available
Route of eliminationGadoteridol is eliminated in the urine with 94.4 ± 4.8% (mean ± SD) of the dose excreted within 24 hours post-injection.
Half lifeDistribution 12 minutes (mean), elimination 100 minutes (mean).
Clearance
  • 1.50+/- 0.35 mL/ min/kg
  • renal cl=1.41 +/- 0.33 mL/ min/kg
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8097
Blood Brain Barrier+0.6442
Caco-2 permeable-0.5567
P-glycoprotein substrateSubstrate0.7825
P-glycoprotein inhibitor INon-inhibitor0.8295
P-glycoprotein inhibitor IINon-inhibitor0.8408
Renal organic cation transporterNon-inhibitor0.8026
CYP450 2C9 substrateNon-substrate0.8605
CYP450 2D6 substrateNon-substrate0.769
CYP450 3A4 substrateNon-substrate0.6437
CYP450 1A2 substrateNon-inhibitor0.8814
CYP450 2C9 inhibitorNon-inhibitor0.8843
CYP450 2D6 inhibitorNon-inhibitor0.8737
CYP450 2C19 inhibitorNon-inhibitor0.81
CYP450 3A4 inhibitorNon-inhibitor0.908
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9838
Ames testNon AMES toxic0.7586
CarcinogenicityNon-carcinogens0.9134
BiodegradationNot ready biodegradable0.6054
Rat acute toxicity2.1688 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6113
hERG inhibition (predictor II)Non-inhibitor0.8966
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Bracco diagnostics inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous279.3 mg/mL
Solutionintravenous279.3 mg
Liquidintravenous279.3 mg
Prices
Unit descriptionCostUnit
Prohance 279.3 mg/ml vial6.81USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1341176 No2001-01-302018-01-30Canada
US5474756 No1992-12-122012-12-12Us
US5846519 No1995-12-082015-12-08Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.2 mg/mLALOGPS
logP0.36ALOGPS
logP-7.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.76ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area153.58 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity133.55 m3·mol-1ChemAxon
Polarizability39.42 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesV08CA04
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (195 KB)
MSDSDownload (60.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on June 28, 2016 01:51