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Gadopentetic acid
Identification
- Name
- Gadopentetic acid
- Accession Number
- DB00789
- 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)
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Gadopentetic acid (DB00789)
- 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).
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism U6-phosphogluconate dehydrogenase, decarboxylating inhibitorHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Unlock Additional DataAbacavir Gadopentetic acid may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Gadopentetic acid which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level. Aclidinium Gadopentetic acid may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Gadopentetic acid may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Gadopentetic acid which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Gadopentetate dimeglumine RH248G8V27 86050-77-3 LGMLJQFQKXPRGA-VPVMAENOSA-K - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataGadopentetate Dimeglumine Injection Solution Intravenous Avir Pharma Inc Not applicable Not applicable Canada 
Gadopentetate Dimeglumine Injection, USP Solution Intravenous Jubilant Draximage Inc Not applicable Not applicable Canada Magnevist Solution 469 mg Intravenous Bayer 1992-12-31 Not applicable Canada Magnevist Injection 469.01 mg/1mL Intravenous Bayer HealthCare Pharmaceuticals Inc. 2014-06-11 2023-01-31 US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataGadopentetate dimeglumine Injection 469.01 mg/1mL Intravenous Alvogen, Inc 2014-02-24 2020-01-16 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- V08CA01 — Gadopentetic acid
- Drug Categories
- Acetates
- Acids, Acyclic
- Amines
- Compounds used in a research, industrial, or household setting
- Contrast Media
- Diagnostic Uses of Chemicals
- Drugs that are Mainly Renally Excreted
- Fatty Acids
- Fatty Acids, Volatile
- Lipids
- Magnetic Resonance Contrast Activity
- Magnetic Resonance Imaging Contrast Media
- Miscellaneous Therapeutic Agents
- Organometallic Compounds
- Paramagnetic Contrast Agent
- Paramagnetic Contrast Media
- Polyamines
- Classification
- Not classified
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
- External Links
- Human Metabolome Database
- HMDB0014927
- PubChem Compound
- 55466
- PubChem Substance
- 46504878
- ChemSpider
- 138549
- 1546432
- ChEBI
- 35778
- ChEMBL
- CHEMBL1200431
- PharmGKB
- PA164748760
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Gadopentetic_acid
- AHFS Codes
- 92:00.00 — Miscellaneous Therapeutic Agents
- FDA label
- Download (102 KB)
- MSDS
- Download (42.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Diagnostic Breast Cancer Diagnosis / Magnetic Resonance Imaging (MRI) / Positron Emission Tomography (PET) 1 4 Completed Not Available Fibrosis / Impaired kidney function / Renal Failure 1 4 Completed Diagnostic Acute Graft Rejection / Cardiac Transplant / Chronic Graft Rejection 1 4 Completed Diagnostic Neoplasms, Brain 1 4 Completed Treatment Disorder of Shoulder 1 3 Completed Diagnostic Anatomic renal artery stenosis 1 3 Completed Diagnostic Breast Cancer 1 3 Completed Diagnostic Cardiovascular Abnormalities 1 3 Completed Diagnostic Carotid, Aortic, Renal or Peripheral Artery Disease 1 3 Completed Diagnostic Central Nervous System Diseases 1
Pharmacoeconomics
- Manufacturers
- Bayer healthcare pharmaceuticals inc
- Packagers
- Bayer Healthcare
- Dosage Forms
Form Route Strength Solution Intravenous Injection Intravenous 469.01 mg/1mL Solution Intravenous 469 mg - Prices
Unit description Cost Unit Magnevist vial 5.54USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5560903 No 1996-10-01 2013-10-01 US US5362475 No 1994-11-08 2011-11-08 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 7.86 mg/mL ALOGPS logP 0.05 ALOGPS logP -6.3 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 1.95 ChemAxon pKa (Strongest Basic) 8.82 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 204.71 Å2 ChemAxon Rotatable Bond Count 16 ChemAxon Refractivity 118.96 m3·mol-1 ChemAxon Polarizability 35.24 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9896 Blood Brain Barrier - 0.9154 Caco-2 permeable - 0.652 P-glycoprotein substrate Substrate 0.7451 P-glycoprotein inhibitor I Non-inhibitor 0.8839 P-glycoprotein inhibitor II Non-inhibitor 0.8277 Renal organic cation transporter Non-inhibitor 0.9191 CYP450 2C9 substrate Non-substrate 0.8788 CYP450 2D6 substrate Non-substrate 0.8015 CYP450 3A4 substrate Non-substrate 0.644 CYP450 1A2 substrate Non-inhibitor 0.8494 CYP450 2C9 inhibitor Non-inhibitor 0.8624 CYP450 2D6 inhibitor Non-inhibitor 0.925 CYP450 2C19 inhibitor Non-inhibitor 0.8775 CYP450 3A4 inhibitor Non-inhibitor 0.9468 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9956 Ames test Non AMES toxic 0.7974 Carcinogenicity Non-carcinogens 0.8588 Biodegradation Ready biodegradable 0.5775 Rat acute toxicity 2.2141 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7992 hERG inhibition (predictor II) Non-inhibitor 0.819
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
- 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
- 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]
- 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 August 05, 2020 23:36
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