Gadodiamide hydrate (CHEM019883)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:36:16 UTC
Update Date2016-11-09 01:16:05 UTC
Accession NumberCHEM019883
Identification
Common NameGadodiamide hydrate
ClassSmall Molecule
DescriptionGadodiamide is only found in individuals that have used or taken this drug. It 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. [Wikipedia]Based 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Gadolinium 5,8-bis(carboxylatomethyl)-11-[2-(methylamino)-2-oxoethyl]-3-oxo-2,5,8,11-tetraazatridecan-13-OateHMDB
Gadolinium [bis(2-{(carboxylatomethyl)[2-(methylamino)-2-oxoethyl]amino}ethyl)amino]acetateHMDB
Gadolinium 5,8-bis(carboxylatomethyl)-11-[2-(methylamino)-2-oxoethyl]-3-oxo-2,5,8,11-tetraazatridecan-13-Oic acidHMDB
2-[Bis[2-[carboxylatomethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid;gadolinium(3+)HMDB
Gadolinium [bis(2-{(carboxylatomethyl)[2-(methylamino)-2-oxoethyl]amino}ethyl)amino]acetic acidHMDB
Amersham brand OF gadodiamideHMDB
GD-DTPA bis-(methylamide)HMDB
GD-DTPA-bmaHMDB
Nycomed brand OF gadodiamideHMDB
OmniscanHMDB
Omniscan unique softpackHMDB
Sanofi winthrop brand OF gadodiamideHMDB
Gadolinium(7+) ion 2-[bis({2-[(carboxymethyl)[(methylcarboximidato)methyl]amino]ethyl})amino]acetic acidHMDB
Chemical FormulaC16H28GdN5O9
Average Molecular Mass591.680 g/mol
Monoisotopic Mass592.113 g/mol
CAS Registry Number122795-43-1
IUPAC Name3,13-bis(methylamino)-16,19,22-trioxo-2lambda4,14lambda4,15,20,23-pentaoxa-5lambda5,8lambda5,11lambda5-triaza-1-gadolinaheptacyclo[6.6.3.3^{1,5}.3^{1,11}.0^{1,5}.0^{1,8}.0^{1,11}]tricosa-2,13-diene-2,5,8,11,14-pentakis(ylium)-1-uide
Traditional Name3,13-bis(methylamino)-16,19,22-trioxo-2lambda4,14lambda4,15,20,23-pentaoxa-5lambda5,8lambda5,11lambda5-triaza-1-gadolinaheptacyclo[6.6.3.3^{1,5}.3^{1,11}.0^{1,5}.0^{1,8}.0^{1,11}]tricosa-2,13-diene-2,5,8,11,14-pentakis(ylium)-1-uide
SMILES[Gd+3]1234567[N](CC(=[O]1)NC)(CC[N]2(CC(=O)[O-]3)CC[N]4(CC(=[O]5)NC)CC(=O)[O-]6)CC(=O)[O-]7.[H]O[H]
InChI IdentifierInChI=1S/C16H29N5O8.Gd.H2O/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);;1H2/q;+3;/p-3
InChI KeyXPCLDSMKWNNKOM-UHFFFAOYSA-K
Chemical Taxonomy
Description 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
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid salt
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP-5.1ChemAxon
pKa (Strongest Acidic)10.63ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area171.24 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity122.25 m³·mol⁻¹ChemAxon
Polarizability40.75 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0014370
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGadodiamide
Chemspider ID54756
ChEBI ID31642
PubChem Compound ID60754
Kegg Compound IDC13106
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available