Edetic acid

Identification

Summary

Edetic acid is a chelating agent used to treat mercury and lead toxicity and some blood transfusion dependent anemias.

Generic Name
Edetic acid
DrugBank Accession Number
DB00974
Background

A chelating agent (chelating agents) that sequesters a variety of polyvalent cations. It is used in pharmaceutical manufacturing and as a food additive.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 292.2426
Monoisotopic: 292.090665498
Chemical Formula
C10H16N2O8
Synonyms
  • (ethylenedinitrilo)tetraacetic acid, ion(4−)
  • {[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetic acid
  • 2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetate
  • Acide edetique
  • Acide ethylenediaminetetracetique
  • Acido edetico
  • Acidum edeticum
  • Edetic acid
  • EDTA
  • EDTA, ion(4-)
  • Ethylenediaminetetraacetate
  • Ethylenediaminetetraacetic acid
  • N,N'-1,2-Ethane diylbis-(N-(carboxymethyl)glycine)

Pharmacology

Indication

For the reduction of blood levels and depot stores of lead in lead poisoning (acute and chronic) and lead encephalopathy, in both pediatric populations and adults.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofLead poisoning••••••••••••
Treatment ofLead encephalopathy••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Edetate calcium is a heavy metal chelating agent. The calcium in edetate calcium can be displaced by divalent or trivalent metals to form a stable water soluble complex that can be excreted in the urine. In theory, 1 g of edetate calcium can theoretically bind 620 mg of lead, but in reality only about 5 mg per gram is actually excreted into the urine in lead poisoned patients. In addition to chelating lead, edetate calcium also chelates and eliminates zinc from the body. Edetate calcium also binds cadmium, copper, iron and manganese, but to a much lesser extent than either lead or zinc. Edetate calcium is relatively ineffective for use in treating mercury, gold or arsenic poisoning.

Mechanism of action

The pharmacologic effects of edetate calcium disodium are due to the formation of chelates with divalent and trivalent metals. A stable chelate will form with any metal that has the ability to displace calcium from the molecule, a feature shared by lead, zinc, cadmium, manganese, iron and mercury. The amounts of manganese and iron metabolized are not significant. Copper is not mobilized and mercury is unavailable for chelation because it is too tightly bound to body ligands or it is stored in inaccessible body compartments. The excretion of calcium by the body is not increased following intravenous administration of edetate calcium disodium, but the excretion of zinc is considerably increased.

TargetActionsOrganism
ALead
chelator
Humans
UIron
chelator
Humans
UManganese cation
chelator
Humans
Absorption

Poorly absorbed from the gastrointestinal tract. Well absorbed following intramuscular injection.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Almost none of the compound is metabolized.

Route of elimination

It is excreted primarily by the kidney, with about 50% excreted in one hour and over 95% within 24 hours.2 Almost none of the compound is metabolized.

Half-life

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

Clearance

Not Available

Adverse Effects
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Toxicity

Inadvertent administration of 5 times the recommended dose, infused intravenously over a 24 hour period, to an asymptomatic 16 month old patient with a blood lead content of 56 mcg/dl did not cause any ill effects. Edetate calcium disodium can aggravate the symptoms of severe lead poisoning, therefore, most toxic effects (cerebral edema, renal tubular necrosis) appear to be associated with lead poisoning. Because of cerebral edema, a therapeutic dose may be lethal to an adult or a pediatric patient with lead encephalopathy. Higher dosage of edetate calcium disodium may produce a more severe zinc deficiency.

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
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Edetic acid.
AceclofenacThe risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Edetic acid.
AcemetacinThe risk or severity of bleeding and hemorrhage can be increased when Edetic acid is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Edetic acid is combined with Acenocoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Edetic acid.
Food Interactions
  • Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.

Products

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International/Other Brands
Cheladrate (Pharmex) / Diso-Tate (O'Neal, Jones) / Endrate (Bersworth) / Uni Wash (United)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DETTOL ANTISEPTIC CREAMEdetic acid (0.2 G/100G) + Chloroxylenol (0.3 G/100G) + Triclosan (0.3 G/100G)Creamบริษัท เรกคิทท์ เบนคีเซอร์ (ประเทศไทย) จำกัด2012-04-22Not applicableThailand flag
Dettol Moisturising Formula Antiseptic CreamEdetic acid (0.2 %w/w) + Chloroxylenol (0.3 %w/w) + Triclosan (0.3 %w/w)CreamTopicalRB (HEALTH) MALAYSIA SDN BHD2020-09-082020-12-18Malaysia flag
Foam Care Pcmx Surgical Hand ScrubEdetic acid (.2 %) + Chloroxylenol (1.5 %)LiquidTopicalBallard Medical Products1990-12-312008-09-17Canada flag
YIGANERJING SuifurSoapEdetic acid (0.0672 g/84g) + Octasulfur (0.84 g/84g) + Titanium dioxide (0.168 g/84g)SoapTopicalTAIZHOU YOUPENG IMPORT AND EXPORT TRADING CO.,LTD.2020-06-22Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
YIGANERJING SuifurSoapEdetic acid (0.0672 g/84g) + Octasulfur (0.84 g/84g) + Titanium dioxide (0.168 g/84g)SoapTopicalTAIZHOU YOUPENG IMPORT AND EXPORT TRADING CO.,LTD.2020-06-22Not 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 / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
ethylenediamine derivative, polyamino carboxylic acid, tetracarboxylic acid (CHEBI:42191)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9G34HU7RV0
CAS number
60-00-4
InChI Key
KCXVZYZYPLLWCC-UHFFFAOYSA-N
InChI
InChI=1S/C10H16N2O8/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)
IUPAC Name
2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetic acid
SMILES
OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O

References

Synthesis Reference

Bersworth, F.C.; U.S. Patent 2,407,645; September 17,1946; assigned to The Martin Dennis Co.

General References
Not Available
Human Metabolome Database
HMDB0015109
KEGG Drug
D00052
KEGG Compound
C00284
PubChem Compound
6049
PubChem Substance
46508301
ChemSpider
5826
BindingDB
50330325
RxNav
1370600
ChEBI
4735
ChEMBL
CHEMBL858
ZINC
ZINC000019364242
Therapeutic Targets Database
DNC000594
PharmGKB
PA449439
PDBe Ligand
EDT
RxList
RxList Drug Page
Wikipedia
Ethylenediaminetetraacetic_acid
PDB Entries
1nnf / 1zlq / 2axn / 3rnj / 3t8n / 3wfa / 4oes / 5dsg / 5fx3 / 5jhd
show 17 more

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Graceway pharmaceuticals llc
  • Watson laboratories inc
  • 3m pharmaceuticals inc
Packagers
  • Bioniche Pharma
  • Graceway Pharmaceuticals
  • Hospira Inc.
  • Merit Pharmaceuticals
  • North America Genescience LLC
  • Septodont Inc.
  • Torrance Co.
  • V Sab Medical Labs Inc.
Dosage Forms
FormRouteStrength
Cream
CreamTopical
LiquidTopical
Solution, concentrate1 G/10ML
Solution, concentrate
Injection, solution, concentrateIntravenous
SoapTopical
Prices
Unit descriptionCostUnit
Endrate 150 mg/ml ampul1.44USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)237 °CNot Available
water solubility1000000 mg/L at 25 °CMEYLAN,WM et al. (1996)
logP-2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility9.26 mg/mLALOGPS
logP-1.2ALOGPS
logP-4.9Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.35Chemaxon
pKa (Strongest Basic)7.73Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area155.68 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity62.35 m3·mol-1Chemaxon
Polarizability25.64 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8668
Blood Brain Barrier-0.7126
Caco-2 permeable-0.5739
P-glycoprotein substrateSubstrate0.6377
P-glycoprotein inhibitor INon-inhibitor0.9296
P-glycoprotein inhibitor IINon-inhibitor0.972
Renal organic cation transporterNon-inhibitor0.8473
CYP450 2C9 substrateNon-substrate0.8457
CYP450 2D6 substrateNon-substrate0.8271
CYP450 3A4 substrateNon-substrate0.7616
CYP450 1A2 substrateNon-inhibitor0.8959
CYP450 2C9 inhibitorNon-inhibitor0.9225
CYP450 2D6 inhibitorNon-inhibitor0.9306
CYP450 2C19 inhibitorNon-inhibitor0.9174
CYP450 3A4 inhibitorNon-inhibitor0.9288
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9891
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7715
BiodegradationNot ready biodegradable0.8307
Rat acute toxicity1.8974 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8158
hERG inhibition (predictor II)Non-inhibitor0.9341
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0f6x-2971000000-52370879752b5b63ccc2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-3930000000-da498c10e1988a598601
GC-MS Spectrum - GC-MSGC-MSsplash10-0f6x-2971000000-52370879752b5b63ccc2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-eec15b5cfc6def88972b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-5e2da3935f60cdedb746
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0920000000-e4633bd8216e49b18f7d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-0290000000-18fe8a8be8b2f96d3629
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-3900000000-ef29286bdeebecc8448f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-9710000000-9b8e69aab9e1c70c91eb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-170.7798687
predicted
DarkChem Lite v0.1.0
[M-H]-153.3975446
predicted
DarkChem Standard v0.1.0
[M-H]-162.24638
predicted
DeepCCS 1.0 (2019)
[M+H]+167.9805687
predicted
DarkChem Lite v0.1.0
[M+H]+159.4417095
predicted
DarkChem Standard v0.1.0
[M+H]+164.6044
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.4443687
predicted
DarkChem Lite v0.1.0
[M+Na]+170.0243687
predicted
DarkChem Lite v0.1.0
[M+Na]+170.69754
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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. [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]
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]
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

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]
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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]

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