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

Similar Structures

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

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Gadopentetate dimeglumine	RH248G8V27	86050-77-3	LGMLJQFQKXPRGA-VPVMAENOSA-K

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Gadopentetate Dimeglumine Injection, USP	Solution	469 mg	Intravenous	Jubilant Draximage Inc	Not applicable	Not applicable
Magnevist	Injection	469.01 mg/1mL	Intravenous	Bayer	2010-12-14	Not applicable
Magnevist	Solution	469 mg	Intravenous	Bayer	1992-12-31	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Gadopentetate dimeglumine	Injection	469.01 mg/1mL	Intravenous	Alvogen, Inc.	2014-02-24	Not applicable

Categories

UNII

K2I13DR72L

CAS number

80529-93-7

Weight

Average: 547.58
Monoisotopic: 548.03898

Chemical Formula

C₁₄H₂₀GdN₃O₁₀

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

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).

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	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]

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
Abacavir	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.

Food Interactions

Not Available

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0014927
PubChem Compound: 55466
PubChem Substance: 46504878
ChemSpider: 138549
ChEBI: 35778
ChEMBL: CHEMBL1200431
PharmGKB: PA164748760
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Gadopentetic_acid

ATC Codes

V08CA01 — 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
0	Completed	Treatment	Malignant Gliomas / WHO Grade III or IV Recurrent Glioma	1
1	Completed	Diagnostic	Healthy Volunteers	1
1, 2	Not Yet Recruiting	Treatment	Abnormal 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, 2	Not Yet Recruiting	Treatment	Chronic Migraine More than15 Days Per Month, and Lasting 4 Hours a Day or Longer	1
1, 2	Not Yet Recruiting	Treatment	Congenital Immunodeficiency	1
1, 2	Not Yet Recruiting	Treatment	Increased Muscle Tone in Elbow, Wrist, Finger, and Thumb Flexors / Upper Limb Spasticity Unilaterally in Adults With History of Stroke	1
1, 2	Not Yet Recruiting	Treatment	Psoriasis Vulgaris (Plaque Psoriasis)	1
2	Completed	Diagnostic	Magnetic Resonance Angiography / Peripheral Arterial Disease (PAD) / Peripheral Vascular Disease (PVD)	1
2	Completed	Diagnostic	Myocardial Infarction	1
2	Completed	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
3	Completed	Diagnostic	Anatomic renal artery stenosis	1
3	Completed	Diagnostic	Cancer, Breast	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
3	Completed	Diagnostic	Central Nervous System Diseases / Diagnostic Self Evaluation	1
3	Completed	Diagnostic	Magnetic Resonance Imaging (MRI)	2
3	Completed	Diagnostic	Neoplasms, Brain	1
3	Completed	Diagnostic	Peripheral Vascular Disease (PVD)	2
3	Completed	Diagnostic	Stenosis	1
3	Completed	Diagnostic	Vascular Diseases	1
4	Active Not Recruiting	Diagnostic	Breast Cancer Diagnosis / Magnetic Resonance Imaging (MRI) / Positron Emission Tomography (PET)	1
4	Completed	Not Available	Fibrosis / Impaired Renal 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
Not Available	Completed	Not Available	Diagnostic Imaging	1
Not Available	Completed	Not Available	Magnetic Resonance Imaging Contrast Agents	1
Not Available	Completed	Diagnostic	Kidney (Renal Cell) Cancer / Neoplasms, Kidney / Renal Cell Adenocarcinoma	1
Not Available	Completed	Diagnostic	Menière's Disease	1
Not Available	Recruiting	Diagnostic	Neoplasms, Hepatic	1
Not Available	Terminated	Diagnostic	Adult Anaplastic Astrocytoma / Adult Anaplastic Ependymoma / Adult Anaplastic Oligodendroglioma / Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor	1
Not Available	Withdrawn	Diagnostic	Menière's Disease	1
Not Available	Withdrawn	Diagnostic	Shoulder Pain	1

Pharmacoeconomics

Manufacturers

Bayer healthcare pharmaceuticals inc

Packagers

Bayer Healthcare

Dosage forms

Form	Route	Strength
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)
US5560903	No	1996-10-01	2013-10-01
US5362475	No	1994-11-08	2011-11-08

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available

Taxonomy

Classification: Not classified

Targets

Details1. 6-phosphogluconate dehydrogenase, decarboxylating

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 April 23, 2019 12:19

Gadopentetic acid

Identification

Structure for Gadopentetic acid (DB00789)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References