NAV

Edetate calcium disodium

Identification

Summary

Edetate calcium disodium is a chelating agent used to treat lead poisoning.

Brand Names
Calcium Disodium Versenate
Generic Name
Edetate calcium disodium anhydrous
Commonly known or available as Edetate calcium disodium
DrugBank Accession Number
DB14598
Background

Edetate calcium disodium is a metal ion chelator used to reduce blood concentrations and depot stores of lead from the body.7 It is on the World Health Organization Model List of Essential Medicines.5

Edetate calcium disodium was granted FDA approval on 16 July 1953.7

Type
Small Molecule
Groups
Approved
Structure
Similar Structures
Weight
Average: 374.268
Monoisotopic: 374.001495875
Chemical Formula
C10H12CaN2Na2O8
Synonyms
  • Edetate calcium disodium (anhydrous)
  • Edetic acid calcium disodium salt
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Pharmacology

Indication

Edetate calcium disodium is indicated to reduce blood levels and depot stores of lead in acute and chronic lead poisoning.7

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in treatment ofPoisoning, lead•••••••••••••••••• ••••••••••••••••••
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Pharmacodynamics

Edetate calcium disodium is a polyvalent ion chelator used to remove lead from the body after lead poisoning.7 It has a wide therapeutic index, as overdoses must be well in excess of the therapeutic dose to show symptoms.7 It has a long duration of action, as doses are given at least a day apart.7 Patients should be counselled regarding the risk of increased intracranial pressure with intravenous infusions.7

Mechanism of action

Edetate calcium disodium distributes into tissues, such as the kidney and bone, where it chelates lead ions.1,3 The lead ions are then eliminated in the normal urinary excretion of edetate.1,2 Lead in certain tissues such as the liver and bone, redistribute to other tissues after edetate calcium disodium treatment, but lead levels do not decrease to levels seen in unexposed patients.2

TargetActionsOrganism
ULead
chelator
Humans
UIron
chelator
Humans
UManganese cation
chelator
Humans
Absorption

Calcium edetate disodium's Cmax and AUC are dependant on renal function.4 5% of an oral dose is absorbed from the gastrointestinal tract.6

Volume of distribution

The volume of distribution of edetate calcium disodium is 0.19±0.10L/kg.3

Protein binding

Not Available

Metabolism

Edetate calcium disodium is almost completely unmetabolized in vivo.6,7

Route of elimination

Edetate calcium disodium is 95% eliminated in the urine within 24 hours.3,7 An oral dose in rats was 88.32% recovered in the feces and 10.30% recovered in the urine.6

Half-life

The half life of edetate calcium disodium is 20-60 minutes.7

Clearance

The mean clearance of edetate in 1 month olds is 54.6mL/min/1.73m2.6 2-17 year olds have a mean clearance of 113.9±24.4mL/min/1.73m2.6

Adverse Effects
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Toxicity

Patients experiencing an overdose may present with similar symptoms to severe lead poisoning such as cerebral edema and renal tubular necrosis.7 Overdose can be managed through the administration of mannitol, zinc level monitoring, and maintenance of urinary output.7

Pathways
Not Available
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Not Available

Interactions

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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
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interactions in your software
Technetium Tc-99m oxidronateEdetate calcium disodium anhydrous may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Edetate calcium disodium25IH6R4SGF6766-87-6JCQNARRMQCMKAN-UHFFFAOYSA-J
Active Moieties
NameKindUNIICASInChI Key
Edetic acidunknown9G34HU7RV060-00-4KCXVZYZYPLLWCC-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Calcium Disodium VersenateInjection200 mg/1mLIntramuscular3M Pharmaceuticals2009-07-092015-12-31US flag
Calcium Disodium VersenateInjection200 mg/1mLIntramuscular; IntravenousBausch Health US, LLC2013-06-21Not applicableUS flag
Calcium Disodium VersenateInjection200 mg/1mLIntramuscularGraceway Pharmaceuticals, LLC2009-07-092015-12-31US flag
Calcium Disodium VersenateInjection200 mg/1mLIntramuscularGraceway Pharmaceuticals, LLC2009-07-092007-09-19US flag
Calcium Disodium Versenate Liq 200mg/mlLiquid200 mg / mLIntramuscular; Intravenous; Subcutaneous3 M Pharmaceuticals, A Division Of 3 M Canada Company1993-12-312006-07-24Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Edetate Calcium DisodiumInjection200 mg/1mLIntramuscular; IntravenousRising Pharmaceuticals, Inc.2023-05-03Not applicableUS flag
Edetate Calcium DisodiumInjection200 mg/1mLIntramuscular; IntravenousCasper Pharma Llc2023-05-03Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Calcium Edetate de SodiumEdetate calcium disodium anhydrous (50 mg/1mL)SolutionIntravenousBtg International Inc2022-10-21Not applicableUS flag

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 / Organic calcium salts / Carboxylic acids / Organopnictogen compounds / Organic zwitterions / Organic sodium salts / Organic oxides
show 2 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 14 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
8U5D034955
CAS number
62-33-9
InChI Key
SHWNNYZBHZIQQV-UHFFFAOYSA-J
InChI
InChI=1S/C10H16N2O8.Ca.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;2*+1/p-4
IUPAC Name
calcium disodium 2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetate
SMILES
[Na+].[Na+].[Ca++].[O-]C(=O)CN(CCN(CC([O-])=O)CC([O-])=O)CC([O-])=O

References

General References
  1. Hammond PB, Aronson AL, Olson WC: The mechanism of mobilization of lead by ethylenediaminetetraacetate. J Pharmacol Exp Ther. 1967 Jul;157(1):196-206. [Article]
  2. Cory-Slechta DA, Weiss B, Cox C: Mobilization and redistribution of lead over the course of calcium disodium ethylenediamine tetraacetate chelation therapy. J Pharmacol Exp Ther. 1987 Dec;243(3):804-13. [Article]
  3. Bradberry S, Vale A: A comparison of sodium calcium edetate (edetate calcium disodium) and succimer (DMSA) in the treatment of inorganic lead poisoning. Clin Toxicol (Phila). 2009 Nov;47(9):841-58. doi: 10.3109/15563650903321064. [Article]
  4. Osterloh J, Becker CE: Pharmacokinetics of CaNa2EDTA and chelation of lead in renal failure. Clin Pharmacol Ther. 1986 Dec;40(6):686-93. doi: 10.1038/clpt.1986.245. [Article]
  5. Sakthithasan K, Levy P, Poupon J, Garnier R: A comparative study of edetate calcium disodium and dimercaptosuccinic acid in the treatment of lead poisoning in adults. Clin Toxicol (Phila). 2018 Nov;56(11):1143-1149. doi: 10.1080/15563650.2018.1478424. Epub 2018 Jun 11. [Article]
  6. 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. [Article]
  7. FDA Approved Drug Products: Edetate Calcium Disodium Intravenous or Intramuscular Injection [Link]
PubChem Compound
6109
ChemSpider
5883
ChEBI
4757
ChEMBL
CHEMBL1200375
Wikipedia
Sodium_calcium_edetate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4WithdrawnDiagnosticHeavy Metal Toxicity1
3CompletedDiagnosticKidney Diseases1
1RecruitingTreatmentAcute Myeloid Leukemia / Acute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Blast Phase Chronic Myelogenous Leukemia, BCR-ABL1 Positive / High-risk Myelodysplastic Syndrome (MDS) / Myelodysplastic Syndrome / Myeloproliferative Neoplasms (MPNs) / Myeloproliferative/Myelodysplastic Neoplasm / Philadelphia Chromosome Positive (Ph+) Chronic Myeloid Leukemia (CML) / Recurrent Acute Myeloid Leukemia / Recurrent Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Recurrent Myelodysplastic Syndrome / Recurrent Myelodysplastic/Myeloproliferative Neoplasm / Refractory Acute Myeloid Leukemia (AML) / Refractory Chronic Myelogenous Leukemia, BCR-ABL1 Positive / Refractory Myelodysplastic Syndromes / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Secondary Myelodysplastic Syndromes / Very High Risk Myelodysplastic Syndrome1
1, 2WithdrawnSupportive CareChronic Myeloproliferative Disorders / Infection / Leukemias / Lymphoma / Lymphoproliferative Disorders / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndrome / Myeloproliferative/Myelodysplastic Neoplasm / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedTreatmentUrological Diseases1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
InjectionIntramuscular200 mg/1mL
InjectionIntramuscular; Intravenous200 mg/1mL
LiquidIntramuscular; Intravenous; Subcutaneous200 mg / mL
SolutionIntravenous50 mg/1mL
SolutionIntramuscular; Intravenous200 mg
Injection, solutionIntramuscular; Intravenous
Injection, solutionIntramuscular; Intravenous400 mg/2ml
SolutionIntramuscular; Intravenous200 mg/1ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300Budavari, 1989
Predicted Properties
PropertyValueSource
Water Solubility23.1 mg/mLALOGPS
logP0.03ALOGPS
logP-4.9Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.35Chemaxon
pKa (Strongest Basic)7.73Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area167 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity105.69 m3·mol-1Chemaxon
Polarizability24.74 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
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-160.62097
predicted
DeepCCS 1.0 (2019)
[M+H]+163.0977
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.9228
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Lead
Kind
Small molecule
Organism
Humans
Pharmacological action
Unknown
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. [Article]
  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. [Article]
  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. [Article]
Details2. Iron
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. [Article]
Details3. Manganese cation
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. [Article]

Enzymes

Details1. Adenosine deaminase
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. [Article]
Details2. Serum paraoxonase/lactonase 3
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. [Article]
Details3. Cytochrome P450 19A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Details4. Cytochrome P450 3A4
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. [Article]
Details5. Serum paraoxonase/arylesterase 1
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. [Article]

Drug created at August 25, 2018 15:50 / Updated at February 13, 2021 10:53