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Identification
NameGadodiamide
Accession NumberDB00225  (APRD00990)
TypeSmall Molecule
GroupsApproved
Description

Gadodiamide is a gadolinium based contrast agent used in MR imaging procedures to assist in the visualization of blood vessels. It is commonly marketed under the trade name Omniscan.

Structure
Thumb
Synonyms
Gadodiamide anhydrous
External Identifiers
  • S-041
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Omniscaninjection287 mg/mLintravenousGE Healthcare Inc.2002-04-19Not applicableUs
Omniscansolution287 mgintravenousGe Healthcare Canada Inc1997-03-25Not applicableCanada
Omniscaninjection287 mg/mLintravenousGE Healthcare Inc.2005-07-29Not applicableUs
Omniscan Liq IV 287mg/mlliquid287 mgintravenousSanofi Canada, Inc.1994-12-311997-07-30Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Gadodiamide hydrate
122795-43-1
Thumb
  • InChI Key: XPCLDSMKWNNKOM-UHFFFAOYSA-K
  • Monoisotopic Mass: 592.112803052
  • Average Mass: 591.67
DBSALT000888
Categories
UNII84F6U3J2R6
CAS number131410-48-5
WeightAverage: 573.66
Monoisotopic: 574.10225
Chemical FormulaC16H26GdN5O8
InChI KeyHZHFFEYYPYZMNU-UHFFFAOYSA-K
InChI
InChI=1S/C16H29N5O8.Gd/c1-17-12(22)7-20(10-15(26)27)5-3-19(9-14(24)25)4-6-21(11-16(28)29)8-13(23)18-2;/h3-11H2,1-2H3,(H,17,22)(H,18,23)(H,24,25)(H,26,27)(H,28,29);/q;+3/p-3
IUPAC Name
SMILES
O=C1[O-][Gd+3]234567[O]=C(C[N]2(CC[N]3(CC([O-]4)=O)CC[N]5(CC(=[O]6)NC)CC(=O)[O-]7)C1)NC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Carboxylic acid
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationFor intravenous use in MRI to visualize lesions with abnormal vascularity (or those thought to cause abnormalities in the blood-brain barrier) in the brain (intracranial lesions), spine, and associated tissues.
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 2 different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and the T2 (spin-spin or transverse relaxation time). In magnetic resonance imaging (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 the T2. When placed in a magnetic field, gadodiamide shortens both the T1 and the T2 relaxation times in tissues where it accumulates. At clinical doses, gadodiamide primarily affects the T1 relaxation time, thus producing an increase in signal intensity. Gadodiamide 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 gadodiamide in lesions such as neoplasms, abscesses, and subacute infarcts.
Related Articles
AbsorptionNot Available
Volume of distribution
  • 200 ± 61 mL/kg
Protein bindingNot Available
Metabolism

There is no detectable biotransformation or decomposition of gadodiamide.

Route of eliminationGadodiamide is eliminated primarily in the urine.
Half lifeTwo-compartment model with mean distribution and elimination half-lives (reported as mean ± SD) of 3.7 ± 2.7 minutes and 77.8 ± 16 minutes, respectively.
Clearance
  • Renal cl=1.7 mL/min/kg
  • Plasma cl=1.8 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-0.9808
Blood Brain Barrier+0.62
Caco-2 permeable-0.5605
P-glycoprotein substrateSubstrate0.7041
P-glycoprotein inhibitor INon-inhibitor0.9016
P-glycoprotein inhibitor IINon-inhibitor0.9571
Renal organic cation transporterNon-inhibitor0.9031
CYP450 2C9 substrateNon-substrate0.8265
CYP450 2D6 substrateNon-substrate0.8189
CYP450 3A4 substrateNon-substrate0.5872
CYP450 1A2 substrateNon-inhibitor0.9416
CYP450 2C9 inhibitorNon-inhibitor0.9189
CYP450 2D6 inhibitorNon-inhibitor0.9566
CYP450 2C19 inhibitorNon-inhibitor0.8972
CYP450 3A4 inhibitorNon-inhibitor0.9864
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9927
Ames testNon AMES toxic0.8343
CarcinogenicityNon-carcinogens0.8563
BiodegradationNot ready biodegradable0.7604
Rat acute toxicity1.9159 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9582
hERG inhibition (predictor II)Non-inhibitor0.9424
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Ge healthcare
Packagers
Dosage forms
FormRouteStrength
Injectionintravenous287 mg/mL
Solutionintravenous287 mg
Liquidintravenous287 mg
Prices
Unit descriptionCostUnit
Omniscan prefill plus syringe7.02USD ml
Omniscan 287 mg/ml vial6.98USD ml
Omniscan 287 mg/ml bottle6.49USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1335819 No1995-06-062012-06-06Canada
US5362475 No1994-11-082011-11-08Us
US5560903 No1993-10-012013-10-01Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesV08CA03
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (56.3 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 01, 2016 20:59