Gadopentetic acid

Identification

Summary

Gadopentetic acid is a gadolinium compound used as a contrast agent in MRIs.

Brand Names
Magnevist
Generic Name
Gadopentetic acid
DrugBank Accession Number
DB00789
Background

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)

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 547.58
Monoisotopic: 548.03898
Chemical Formula
C14H20GdN3O10
Synonyms
  • Acide gadopentetique
  • ácido gadopentético
  • Acidum gadopenteticum
  • Gadolinium diethylenetriamine pentaacetic acid
  • Gadolinium DTPA
  • Gadopentetate
  • Gadopentetic acid
External IDs
  • SH L 451 A
  • SH-L-451-A
  • SHL-451A

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).

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Pharmacodynamics

Not 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.

TargetActionsOrganism
U6-phosphogluconate dehydrogenase, decarboxylating
inhibitor
Humans
Absorption

Not Available

Volume of distribution
  • 266 ± 43 mL/kg
Protein binding

Not 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]
Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirGadopentetic acid may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Gadopentetic acid which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Gadopentetate dimeglumineRH248G8V2786050-77-3LGMLJQFQKXPRGA-VPVMAENOSA-K
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gadopentetate Dimeglumine InjectionSolution469 mg / mLIntravenousAvir Pharma Inc.Not applicableNot applicableCanada flag
Gadopentetate Dimeglumine Injection, USPSolution469 mg / mLIntravenousJubilant Draximage Inc. Dba Jubilant RadiopharmaNot applicableNot applicableCanada flag
MagnevistInjection469.01 mg/1mLIntravenousBayer HealthCare Pharmaceuticals Inc.2014-06-112023-01-31US flag
MagnevistSolution469 mg / mLIntravenousBayer1992-12-31Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Gadopentetate dimeglumineInjection469.01 mg/1mLIntravenousAlvogen, Inc2014-02-242020-01-16US flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MAGNEVIST 10MLInjection, solution469 mg/mlIntravenousBAYER CO. (MALAYSIA) SDN. BHD.2017-02-042018-08-31Malaysia flag
MAGNEVIST INJECTION 100MLInjection469 mg/mlIntravenousBAYER CO. (MALAYSIA) SDN. BHD.2013-08-242018-08-31Malaysia flag
MAGNEVIST INJECTION 30MLInjection, solution469 mg/mlIntravenousBAYER CO. (MALAYSIA) SDN. BHD.2013-08-242018-08-31Malaysia flag

Categories

ATC Codes
V08CA01 — Gadopentetic acid
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
K2I13DR72L
CAS number
80529-93-7
InChI Key
IZOOGPBRAOKZFK-UHFFFAOYSA-K
InChI
InChI=1S/C14H23N3O10.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;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);/q;+3/p-3
IUPAC Name
gadolinium(3+) 2-[bis({2-[bis(carboxymethyl)amino]ethyl})amino]acetate
SMILES
[Gd+3].OC(=O)CN(CCN(CCN(CC(O)=O)CC([O-])=O)CC([O-])=O)CC([O-])=O

References

General References
Not Available
Human Metabolome Database
HMDB0014927
PubChem Compound
55466
PubChem Substance
46504878
ChemSpider
138549
RxNav
1546432
ChEBI
35778
ChEMBL
CHEMBL1200431
PharmGKB
PA164748760
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Gadopentetic_acid
FDA label
Download (102 KB)
MSDS
Download (42.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticAcute Graft Rejection / Cardiac Transplant / Chronic Graft Rejection1
4CompletedDiagnosticBrain Neoplasm1
4CompletedTreatmentDisorder of Shoulder1
4Unknown StatusDiagnosticBreast Cancer Diagnosis / Magnetic Resonance Imaging (MRI) / Positron Emission Tomography1
3CompletedDiagnosticAnatomic renal artery stenosis1

Pharmacoeconomics

Manufacturers
  • Bayer healthcare pharmaceuticals inc
Packagers
  • Bayer Healthcare
Dosage Forms
FormRouteStrength
SolutionIntravenous10 ml
SolutionIntravenous15 ml
SolutionIntravenous20 ml
Injection, solution
InjectionIntravenous
InjectionIntravenous469.01 mg/1mL
Injection, solutionIntra-articular37.6 MG/20ML
Injection, solutionIntra-articular469 MG/ML
Injection, solutionIntra-articular; Intravenous469 MG/ML
SolutionIntravenous469 mg / mL
SolutionIntravenous469 mg/1ml
Injection, solutionIntra-articular2 mmol/l
Injection, solutionIntravenous469 mg/ml
SolutionRectal
SolutionIntravenous0.5 mmol/ml
SolutionIntravenous
InjectionIntravenous469 mg/ml
SolutionIntravenous469.01 mg
Injection, solution469 MG/ML
SolutionIntravenous529 mg
SolutionOral
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)Region
US5560903No1996-10-012013-10-01US flag
US5362475No1994-11-082011-11-08US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.86 mg/mLALOGPS
logP0.05ALOGPS
logP-6.3Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.95Chemaxon
pKa (Strongest Basic)8.82Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area204.71 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity118.96 m3·mol-1Chemaxon
Polarizability35.24 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
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Kind
Protein
Organism
Humans
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
Uniprot Name
6-phosphogluconate dehydrogenase, decarboxylating
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48