Edetate disodium

Identification

Name
Edetate disodium anhydrous
Commonly known or available as Edetate disodium
Accession Number
DB14600
Description

Edetate disodium anhydrous is a polyvalent chelating agent used to treat hypercalcemia and digitalis toxicity associated ventricular arrhythmias.1

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 336.2063
Monoisotopic: 336.054554784
Chemical Formula
C10H14N2Na2O8
Synonyms
  • Anhydrous disodium edetate
  • Disodium EDTA, anhydrous
  • Edetate disodium, anhydrous
  • EDTA disodium salt (anhydrous)

Pharmacology

Indication

Edetate disodium is indicated for emergency treatment of hypercalcemia and digitalis toxicity associated ventricular arrhythmias.2

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Edetate disodium anhydrous is a polyvalent ion chelator that reduces blood concentrations of calcium or digitalis.2,3 It has a long duration of action as patients are generally given 1 daily dose.2,3 The therapeutic index is wide, as high doses are generally well tolerated.2,3 Patients should be counselled regarding the risk of postural hypotension, effects of myocardial contractility, hypokalemia, hypomagnesemia, and hypoglycemia.2,3

Mechanism of action

Edetate disodium anhydrous chelates divalent and trivalent ions such as magnesium, zinc, and calcium.3 The chelate is excreted in the urine, reducing concentrations of these ions in the blood.3

TargetActionsOrganism
ALead
chelator
Humans
UIron
chelator
Humans
UManganese cation
chelator
Humans
Absorption
Not Available
Volume of distribution

Data regarding the volume of distribution of edetate disodium anhydrous is not readily available.1

Protein binding
Not Available
Metabolism

Edetate is almost completely unmetabolized in vivo.1,2

Route of elimination

After intravenous administration, 95% of the dose is recovered in the urine after 24 hours.2,3 Oral administration in rats leads to 5.3% recovery in urine and 88.5% recovery in feces.1

Half-life
Not Available
Clearance

The mean clearance of edetate in 1 month olds is 54.6mL/min/1.73m2.1 2-17 year olds have a mean clearance of 113.9 ± 24.4 mL/min/1.73m2.1

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with calcium deficiency.2 Treat overdose with symptomatic and supportive treatment, which may include intravenous calcium gluconate.2

Affected organisms
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
Technetium Tc-99m oxidronateEdetate disodium anhydrous may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Edetate disodium7FLD91C86K6381-92-6OVBJJZOQPCKUOR-UHFFFAOYSA-L
Active Moieties
NameKindUNIICASInChI Key
Edetic acidunknown9G34HU7RV060-00-4KCXVZYZYPLLWCC-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EndrateInjection, solution150 mg/1mLIntravenousUNSPECIFIED2006-05-11Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ClinplantGel, dentifrice24 g/100gDentalNibec Co., Ltd2018-06-20Not applicableUs
Clinplant FlossGel, dentifrice17 g/100gDentalNibec Co., Ltd2018-06-202018-09-20Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Miin FootEdetate disodium (0.05 g/100g) + Aloe Vera Leaf (0.5 g/100g) + Glycerin (8 g/100g) + Urea (4 g/100g)LiquidTopicalLydia Co., Ltd.2019-08-22Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClinplantEdetate disodium (24 g/100g)Gel, dentifriceDentalNibec Co., Ltd2018-06-20Not applicableUs
Clinplant FlossEdetate disodium (17 g/100g)Gel, dentifriceDentalNibec Co., Ltd2018-06-202018-09-20Us

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Tetracarboxylic acids and derivatives
Direct Parent
Tetracarboxylic acids and derivatives
Alternative Parents
Alpha amino acids / Trialkylamines / Carboxylic acid salts / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic zwitterions / Organic sodium salts / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid / Carboxylic acid salt / Hydrocarbon derivative
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
organic sodium salt (CHEBI:64734)

Chemical Identifiers

UNII
8NLQ36F6MM
CAS number
139-33-3
InChI Key
ZGTMUACCHSMWAC-UHFFFAOYSA-L
InChI
InChI=1S/C10H16N2O8.2Na/c13-7(14)3-11(4-8(15)16)1-2-12(5-9(17)18)6-10(19)20;;/h1-6H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20);;/q;2*+1/p-2
IUPAC Name
disodium 2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetate
SMILES
[Na+].[Na+].OC(=O)CN(CCN(CC(O)=O)CC([O-])=O)CC([O-])=O

References

General References
  1. Lanigan RS, Yamarik TA: Final report on the safety assessment of EDTA, calcium disodium EDTA, diammonium EDTA, dipotassium EDTA, disodium EDTA, TEA-EDTA, tetrasodium EDTA, tripotassium EDTA, trisodium EDTA, HEDTA, and trisodium HEDTA. Int J Toxicol. 2002;21 Suppl 2:95-142. doi: 10.1080/10915810290096522. [PubMed:12396676]
  2. Dailymed: Endrate Edetate Disodium Anhydrous Intravenous Injection (Discontinued) [Link]
  3. Medsafe New Zealand Approved Drug Products: Edetate Disodium Injection [Link]
KEGG Drug
D03945
PubChem Compound
8759
ChemSpider
8429
ChEBI
64734
ChEMBL
CHEMBL1749
Wikipedia
Ethylenediaminetetraacetic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentCritical Limb Ischemia (CLI) / Diabetes1
1, 2TerminatedDiagnosticKidney Diseases / Renal Insufficiency,Chronic1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Gel, dentifriceDental24 g/100g
Gel, dentifriceDental17 g/100g
Injection, solutionIntravenous150 mg/1mL
LiquidTopical
SolutionOphthalmic1 mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)240Lanigan, 2002
boiling point (°C)252Lanigan, 2002
Predicted Properties
PropertyValueSource
Water Solubility72.0 mg/mLALOGPS
logP-1ALOGPS
logP-4.9ChemAxon
logS-0.67ALOGPS
pKa (Strongest Acidic)2.35ChemAxon
pKa (Strongest Basic)7.73ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area161.34 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity84.02 m3·mol-1ChemAxon
Polarizability25.41 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Small molecule
Organism
Humans
Pharmacological action
Yes
Actions
Chelator
References
  1. Onnby L, Giorgi C, Plieva FM, Mattiasson B: Removal of heavy metals from water effluents using supermacroporous metal chelating cryogels. Biotechnol Prog. 2010 Sep-Oct;26(5):1295-302. doi: 10.1002/btpr.422. [PubMed:20945486]
  2. Chakraborty N, Banerjee A, Pal R: Accumulation of lead by free and immobilized cyanobacteria with special reference to accumulation factor and recovery. Bioresour Technol. 2011 Mar;102(5):4191-5. doi: 10.1016/j.biortech.2010.12.028. Epub 2010 Dec 13. [PubMed:21195608]
  3. Tian SK, Lu LL, Yang XE, Huang HG, Brown P, Labavitch J, Liao HB, He ZL: The impact of EDTA on lead distribution and speciation in the accumulator Sedum alfredii by synchrotron X-ray investigation. Environ Pollut. 2011 Mar;159(3):782-8. doi: 10.1016/j.envpol.2010.11.020. Epub 2010 Dec 18. [PubMed:21168940]
Kind
Small molecule
Organism
Humans
Pharmacological action
Unknown
Actions
Chelator
References
  1. Hasegawa H, Rahman IM, Kinoshita S, Maki T, Furusho Y: Separation of dissolved iron from the aqueous system with excess ligand. Chemosphere. 2011 Feb;82(8):1161-7. doi: 10.1016/j.chemosphere.2010.12.048. Epub 2011 Jan 3. [PubMed:21208637]
Kind
Small molecule
Organism
Humans
Pharmacological action
Unknown
Actions
Chelator
References
  1. Broncel M, Wagner SC, Paul K, Hackenberger CP, Koksch B: Towards understanding secondary structure transitions: phosphorylation and metal coordination in model peptides. Org Biomol Chem. 2010 Jun 7;8(11):2575-9. doi: 10.1039/c001458c. Epub 2010 Mar 29. [PubMed:20485793]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 Da
References
  1. Abu-Shady MR, Elshafei AM, el-Beih FM, Mohamed LA: Properties of adenosine deaminase in extracts of Asperigillus terricola. Acta Microbiol Pol. 1994;43(3-4):305-11. [PubMed:7740980]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- ...
Gene Name
PON3
Uniprot ID
Q15166
Uniprot Name
Serum paraoxonase/lactonase 3
Molecular Weight
39607.185 Da
References
  1. Pla A, Rodrigo L, Hernandez AF, Gil F, Lopez O: Effect of metal ions and calcium on purified PON1 and PON3 from rat liver. Chem Biol Interact. 2007 Apr 5;167(1):63-70. Epub 2007 Jan 16. [PubMed:17292339]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
Curator comments
EDTA prevents inhibition of CYP19A1.
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Moslemi S, Vibet A, Papadopoulos V, Camoin L, Silberzahn P, Gaillard JL: Purification and characterization of equine testicular cytochrome P-450 aromatase: comparison with the human enzyme. Comp Biochem Physiol B Biochem Mol Biol. 1997 Sep;118(1):217-27. [PubMed:9418012]
  2. Bellino FL, Holben L: Placental estrogen synthetase (aromatase): evidence for phosphatase-dependent inactivation. Biochem Biophys Res Commun. 1989 Jul 14;162(1):498-504. [PubMed:2546553]
  3. Zhang F, Zhou D, Kao YC, Ye J, Chen S: Expression and purification of a recombinant form of human aromatase from Escherichia coli. Biochem Pharmacol. 2002 Nov 1;64(9):1317-24. [PubMed:12392814]
  4. Milczarek R, Sokolowska E, Hallmann A, Kaletha K, Klimek J: NADPH- and iron-dependent lipid peroxidation inhibit aromatase activity in human placental microsomes. J Steroid Biochem Mol Biol. 2008 Jun;110(3-5):230-5. doi: 10.1016/j.jsbmb.2007.11.004. Epub 2008 Apr 20. [PubMed:18499441]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Bournique B, Petry M, Gousset G: Usefulness of statistic experimental designs in enzymology: example with recombinant hCYP3A4 and 1A2. Anal Biochem. 1999 Dec 1;276(1):18-26. [PubMed:10585740]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxyl...
Gene Name
PON1
Uniprot ID
P27169
Uniprot Name
Serum paraoxonase/arylesterase 1
Molecular Weight
39730.99 Da
References
  1. Pla A, Rodrigo L, Hernandez AF, Gil F, Lopez O: Effect of metal ions and calcium on purified PON1 and PON3 from rat liver. Chem Biol Interact. 2007 Apr 5;167(1):63-70. Epub 2007 Jan 16. [PubMed:17292339]

Drug created on August 25, 2018 09:59 / Updated on June 12, 2020 10:53

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