IDPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomy
Targets (1)
Targets (1)Biointeractions (1)

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Identification
NameGadopentetate dimeglumine
Accession NumberDB00789  (APRD00991)
TypeSmall Molecule
GroupsApproved
Description

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)

Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Diethylenetriaminepentaacetic acid dimeglumine salt gadolinium chelate
Dimeglumine-gadolinium-dtpa
Gadopentetic acid dimeglumine salt
Gd-DTPA
Magnevist
Meglumine gadopentetate
External IDs SH L 451 A / SHL-451A
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Gadopentetate DimeglumineInjection469.01 mg/mLIntravenousAlvogen, Inc.2014-02-24Not applicableUs
Gadopentetate Dimeglumine Injection, USPSolution469 mgIntravenousJubilant Draximage IncNot applicableNot applicableCanada
MagnevistInjection469.01 mg/mLIntravenousBayer2010-12-14Not applicableUs
MagnevistSolution469 mgIntravenousBayer1992-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIRH248G8V27
CAS number86050-77-3
WeightAverage: 938.0
Monoisotopic: 938.260314726
Chemical FormulaC28H54GdN5O20
InChI KeyLGMLJQFQKXPRGA-VPVMAENOSA-K
InChI
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
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
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
Pharmacology
Indication

For use with magnetic resonance imaging (MRI) in adults, and pediatric patients (2 years of age and older) to visualize lesions with abnormal vascularity in the brain (intracranial lesions), spine and associated tissues as well as lesions with abnormal vascularity in the head and neck. Also used to facilitate the visualization of lesions with abnormal vascularity in the body (excluding the heart).

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

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.

TargetKindPharmacological actionActionsOrganismUniProt ID
6-phosphogluconate dehydrogenase, decarboxylatingProteinunknown
inhibitor
HumanP52209 details
Related Articles
AbsorptionNot Available
Volume of distribution
  • 266 ± 43 mL/kg
Protein bindingNot Available
Metabolism

No detectable biotransformation or decomposition.

Route of elimination

Gadopentetate is exclusively eliminated in the urine with 83 ± 14% (mean ± SD) of the dose excreted within 6 hours and 91 ± 13% (mean ± SD) by 24 hours, post-injection.

Half life

Distribution half life 12 minutes, elimination half 100 minutes

Clearance
  • 1.94 +/- 0.28 mL/min/kg [Normal subjects]
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions No interactions found.
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (102 KB)
MSDSDownload (42.2 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticHealthy Volunteers1
1, 2Not Yet RecruitingTreatmentAbnormal Head Position and Neck Pain for These 7 Muscle Groups: Splenius,Scalene,Sterno-cleido-mastoid,Levator Scapulae,Semispinalis,Trapezius,and Longissimus / Cervical Dystonia Adults 1
1, 2Not Yet RecruitingTreatmentChronic Migraine More than15 Days Per Month, and Lasting 4 Hours a Day or Longer1
1, 2Not Yet RecruitingTreatmentCongenital Immunodeficiency1
1, 2Not Yet RecruitingTreatmentIncreased Muscle Tone in Elbow, Wrist, Finger, and Thumb Flexors / Upper Limb Spasticity Unilaterally in Adults With History of Stroke1
1, 2Not Yet RecruitingTreatmentPlaque Psoriasis1
2CompletedDiagnosticMagnetic Resonance Angiography / Peripheral Arterial Disease (PAD) / Peripheral Vascular Disease (PVD)1
2CompletedDiagnosticMyocardial Infarction (MI)1
2CompletedTreatmentNon-Small-Cell Lung Carcinoma (NSCLC)1
3CompletedDiagnosticAnatomic renal artery stenosis1
3CompletedDiagnosticCancer, Breast1
3CompletedDiagnosticCardiovascular Abnormalities1
3CompletedDiagnosticCarotid, Aortic, Renal or Peripheral Artery Disease1
3CompletedDiagnosticCentral Nervous System Diseases1
3CompletedDiagnosticCentral Nervous System Diseases / Diagnostic Self Evaluation1
3CompletedDiagnosticMagnetic Resonance Imaging (MRI)2
3CompletedDiagnosticNeoplasms, Brain1
3CompletedDiagnosticPeripheral Vascular Disease (PVD)2
3CompletedDiagnosticStenosis1
3CompletedDiagnosticVascular Diseases1
4Active Not RecruitingDiagnosticBreast Cancer Diagnosis / Magnetic Resonance Imaging (MRI) / Positron Emission Tomography (PET)1
4CompletedNot AvailableFibrosis / Impaired Renal Function / Renal Failure1
4CompletedDiagnosticAcute Graft Rejection / Cardiac Transplant / Chronic Graft Rejection1
4CompletedDiagnosticNeoplasms, Brain1
4CompletedTreatmentDisorder of Shoulder1
Not AvailableCompletedNot AvailableDiagnostic Imaging1
Not AvailableCompletedDiagnosticKidney (Renal Cell) Cancer / Neoplasms, Kidney / Renal Cell Adenocarcinoma1
Not AvailableCompletedDiagnosticMenière's Disease1
Not AvailableEnrolling by InvitationDiagnosticCoronary Artery Disease / Prophylaxis of cardiomyopathy1
Not AvailableRecruitingDiagnosticNeoplasms, Hepatic1
Not AvailableTerminatedDiagnosticAdult Anaplastic Astrocytoma / Adult Anaplastic Ependymoma / Adult Anaplastic Oligodendroglioma / Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor1
Not AvailableWithdrawnDiagnosticMenière's Disease1
Not AvailableWithdrawnDiagnosticShoulder Pain1
Pharmacoeconomics
Manufacturers
  • Bayer healthcare pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
InjectionIntravenous469.01 mg/mL
SolutionIntravenous469 mg
Prices
Unit descriptionCostUnit
Magnevist vial5.54USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5362475 No1994-11-082011-11-08Us
US5560903 No1993-10-012013-10-01Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
logP-6.4ChemAxon
pKa (Strongest Acidic)0.094ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area204.71 Å2ChemAxon
Rotatable Bond Count28ChemAxon
Refractivity118.96 m3·mol-1ChemAxon
Polarizability34.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9896
Blood Brain Barrier-0.9154
Caco-2 permeable-0.652
P-glycoprotein substrateSubstrate0.7451
P-glycoprotein inhibitor INon-inhibitor0.8839
P-glycoprotein inhibitor IINon-inhibitor0.8277
Renal organic cation transporterNon-inhibitor0.9191
CYP450 2C9 substrateNon-substrate0.8788
CYP450 2D6 substrateNon-substrate0.8015
CYP450 3A4 substrateNon-substrate0.644
CYP450 1A2 substrateNon-inhibitor0.8494
CYP450 2C9 inhibitorNon-inhibitor0.8624
CYP450 2D6 inhibitorNon-inhibitor0.925
CYP450 2C19 inhibitorNon-inhibitor0.8775
CYP450 3A4 inhibitorNon-inhibitor0.9468
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9956
Ames testNon AMES toxic0.7974
CarcinogenicityNon-carcinogens0.8588
BiodegradationReady biodegradable0.5775
Rat acute toxicity2.2141 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7992
hERG inhibition (predictor II)Non-inhibitor0.819
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentPentacarboxylic acids and derivatives
Alternative ParentsHexoses / 1,3-aminoalcohols / Secondary alcohols / 1,2-aminoalcohols / Polyols / Dialkylamines / Primary alcohols / Organopnictogen compounds / Organic zwitterions / Organic salts
SubstituentsPentacarboxylic acid or derivatives / Hexose monosaccharide / Monosaccharide / 1,3-aminoalcohol / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Polyol / Secondary amine / Organic oxygen compound
Molecular FrameworkNot Available
External Descriptorsgadolinium coordination entity (CHEBI:31797 )

Targets

Details
1. 6-phosphogluconate dehydrogenase, decarboxylating
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Phosphogluconate dehydrogenase (decarboxylating) activity
Specific Function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH.
Gene Name:
PGD
Uniprot ID:
P52209
Molecular Weight:
53139.56 Da
References
  1. Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752 ]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:53