ChemFOnt: Showing chemical card for Gadopentetate dimeglumine (CFc000009251)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:20 UTC

Chemfont ID

CFc000009251

Molecule Identification

Common Name

Gadopentetate dimeglumine

Definition

Gadopentetate dimeglumine is only found in individuals that have used or taken this drug. It is a complex of gadolinium with a chelating agent, diethylenetriamine penta-acetic acid (DTPA see pentetic acid), that is given to enhance the image in cranial and spinal MRIs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p706)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. MR images are based primarily on proton density and proton relaxation dynamics. MR instruments are sensitive to two different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and T2 (spin-spin or transverse relaxation time). Paramagnetic agents contain one or more unpaired electrons that enhance the T1 and T2 relaxation rates of protons in their molecular environment. The proton relaxation effect (PRE) of an unpaired electron is 700 times stronger than that of a proton itself. In MRI, visualization of normal and pathological brain tissue depends in part on variations in the radio frequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadopentetate dimeglumine shortens the T1 and T2 relaxation times in tissues where it accumulates. In the central nervous system (CNS), gadopentetate dimeglumine enhances visualization of normal tissues that lack a blood-brain barrier, such as the pituitary gland and the meninges. Gadopentetate dimeglumine does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in 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 gadopentetate dimeglumine in lesions such as neoplasms, abscesses, and subacute infarcts. Outside the CNS, gadopentetate dimeglumine rapidly reaches equilibrium in the interstitial compartment and enhances signal in all tissues as a function of delivery and size of the interstitial compartment.This compound has also been found to inhibit human erythrocyte 6-phosphogluconate dehydrogenase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Diethylenetriaminepentaacetic acid dimeglumine salt gadolinium chelate	ChEBI
Dimeglumine-gadolinium-dtpa	ChEBI
Gadopentetic acid dimeglumine salt	ChEBI
Magnevist	ChEBI
Meglumine gadopentetate	ChEBI
Diethylenetriaminepentaacetate dimeglumine salt gadolinium chelate	Generator
Diethylenetriaminepentaacetic acid dimeglumine salt gadolinium chelic acid	Generator
Gadopentetate dimeglumine salt	Generator
Meglumine gadopentetic acid	Generator
Gadopentetate	Generator
Gadopentetic acid dimeglumine	Generator
DTPA, gadolinium	MeSH
GD-DTPA	MeSH
Magnevist enteral	MeSH
Berlex brand OF gadopentetate dimeglumine	MeSH
Dimeglumine, gadopentetate	MeSH
Gadolinium dtpa	MeSH
Gadolinium dtpa dimeglumine	MeSH
Gadolinium dtpa dimeglumine salt	MeSH
GD DTPA	MeSH
Schering brand OF gadopentetate dimeglumine	MeSH
Dimeglumine, gadolinium dtpa	MeSH
Gadolinium dtpa disodium salt	MeSH
Magnograf	MeSH
Magnograf enteral	MeSH
Diethylenetriaminepenta-acetic acid, gadolinium	MeSH
Gadolinium diethylenetriaminepenta acetic acid	MeSH
Gadolinium diethylenetriaminepenta-acetic acid	MeSH
Gadopentetic acid	MeSH
Juste brand OF gadopentetate dimeglumine	MeSH
Gadopentetate dimeglumine	MeSH

Chemical Formula

C₂₈H₅₄GdN₅O₂₀

Average Molecular Weight

938.0

Monoisotopic Molecular Weight

938.260314726

IUPAC Name

gadolinium(3+) ion bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 2-[bis({2-[(carboxylatomethyl)(carboxymethyl)amino]ethyl})amino]acetate

Traditional Name

gadolinium(3+) ion H2dtpa bis(N-methyl-D(-)-glucamine)

CAS Registry Number

86050-77-3

SMILES

[Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CCN(CCN(CC(O)=O)CC([O-])=O)CC([O-])=O)CC([O-])=O

InChI Identifier

InChI=1S/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1

InChI Key

LGMLJQFQKXPRGA-VPVMAENOSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Hexose monosaccharide
Monosaccharide
1,3-aminoalcohol
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Polyol
Secondary amine
Organic oxygen compound
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Primary alcohol
Organic zwitterion
Alcohol
Aliphatic acyclic compound

Molecular Framework

Not Available

External Descriptors

gadolinium coordination entity (CHEBI:31797 )

Functional Ontology

Not Available

Not Available

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Contrast media (HMDB: HMDB0014927)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0014927)

Physical Properties

Predicted Properties

Property	Value	Source
logP	-6.4	ChemAxon
pKa (Strongest Acidic)	0.094	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	204.71 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	118.96 m³·mol⁻¹	ChemAxon
Polarizability	34.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014927

DrugBank ID

DB00789

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005174

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gadopentetic acid

METLIN ID

Not Available

PubChem Compound

55466

PDB ID

Not Available

ChEBI ID

31797

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Gadopentetate dimeglumine (CFc000009251)

MOL for CFc000009251 (Gadopentetate dimeglumine)

3D MOL for CFc000009251 (Gadopentetate dimeglumine)

3D SDF for CFc000009251 (Gadopentetate dimeglumine)

3D-SDF for CFc000009251 (Gadopentetate dimeglumine)

PDB for CFc000009251 (Gadopentetate dimeglumine)

3D PDB for CFc000009251 (Gadopentetate dimeglumine)

SMILES for CFc000009251 (Gadopentetate dimeglumine)

INCHI for CFc000009251 (Gadopentetate dimeglumine)

Structure for CFc000009251 (Gadopentetate dimeglumine)

3D Structure for CFc000009251 (Gadopentetate dimeglumine)