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Identification
NameEdetic Acid
Accession NumberDB00974  (APRD01327)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
(Ethylenedinitrilo)tetraacetic acid, ion(4-)Not AvailableNot Available
{[-(bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-acetic acidNot AvailableNot Available
2,2',2'',2'''-(ethane-1,2-diyldinitrilo)tetraacetateNot AvailableNot Available
Acide edetiqueNot AvailableNot Available
Acide ethylenediaminetetracetiqueNot AvailableNot Available
Acido edeticoNot AvailableNot Available
Acidum edeticumNot AvailableNot Available
Edetic acidNot AvailableNot Available
EDTANot AvailableNot Available
EDTA, ion(4-)Not AvailableNot Available
EthylenediaminetetraacetateNot AvailableNot Available
Ethylenediaminetetraacetic acidNot AvailableNot Available
H4EdtaNot AvailableNot Available
N,N'-1,2-Ethane diylbis-(N-(carboxymethyl)glycine)Not AvailableNot Available
Salts
Name/CAS Structure Properties
Edetate calcium disodium
Thumb
  • InChI Key: SHWNNYZBHZIQQV-UHFFFAOYSA-J
  • Monoisotopic Mass: 374.001495875
  • Average Mass: 374.268
DBSALT000837
Edetate disodium
Thumb
  • InChI Key: ZGTMUACCHSMWAC-UHFFFAOYSA-L
  • Monoisotopic Mass: 336.054554784
  • Average Mass: 336.2063
DBSALT000838
Brand names
NameCompany
CheladratePharmex
Diso-TateO'Neal, Jones
EndrateBersworth
Uni WashUnited
Brand mixturesNot Available
Categories
CAS number62-33-9
WeightAverage: 292.2426
Monoisotopic: 292.090665498
Chemical FormulaC10H16N2O8
InChI KeyKCXVZYZYPLLWCC-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
Mass Specshow(10.2 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsTertiary Amines; Polyols; Polyamines; Enolates; Carboxylic Acids
Substituentspolyol; tertiary amine; enolate; polyamine; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Pharmacology
IndicationFor 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.
PharmacodynamicsEdetate 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 actionThe 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.
AbsorptionPoorly absorbed from the gastrointestinal tract. Well absorbed following intramuscular injection.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Almost none of the compound is metabolized.

Route of eliminationIt 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 lifeThe half life of edetate calcium disodium is 20 to 60 minutes.
ClearanceNot Available
ToxicityInadvertent 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.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.8668
Blood Brain Barrier - 0.7126
Caco-2 permeable - 0.5739
P-glycoprotein substrate Substrate 0.6377
P-glycoprotein inhibitor I Non-inhibitor 0.9296
P-glycoprotein inhibitor II Non-inhibitor 0.972
Renal organic cation transporter Non-inhibitor 0.8473
CYP450 2C9 substrate Non-substrate 0.8457
CYP450 2D6 substrate Non-substrate 0.8271
CYP450 3A4 substrate Non-substrate 0.7616
CYP450 1A2 substrate Non-inhibitor 0.8959
CYP450 2C9 substrate Non-inhibitor 0.9225
CYP450 2D6 substrate Non-inhibitor 0.9306
CYP450 2C19 substrate Non-inhibitor 0.9174
CYP450 3A4 substrate Non-inhibitor 0.9288
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9891
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.7715
Biodegradation Not ready biodegradable 0.8307
Rat acute toxicity 1.8974 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8158
hERG inhibition (predictor II) Non-inhibitor 0.9341
Pharmacoeconomics
Manufacturers
  • Graceway pharmaceuticals llc
  • Watson laboratories inc
  • 3m pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntramuscular
Injection, solutionIntravenous drip
Prices
Unit descriptionCostUnit
Endrate 150 mg/ml ampul1.44USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point237 °CNot Available
water solubility1000000 mg/L at 25 °CMEYLAN,WM et al. (1996)
logP-2.6Not Available
Predicted Properties
PropertyValueSource
water solubility9.26e+00 g/lALOGPS
logP-1.2ALOGPS
logP-5.2ChemAxon
logS-1.5ALOGPS
pKa (strongest acidic)1.49ChemAxon
pKa (strongest basic)8.13ChemAxon
physiological charge-3ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count4ChemAxon
polar surface area155.68ChemAxon
rotatable bond count11ChemAxon
refractivity62.35ChemAxon
polarizability25.64ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MS
References
Synthesis Reference

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

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00571
PubChem Compound6049
PubChem Substance46508301
ChemSpider5826
Therapeutic Targets DatabaseDNC000594
PharmGKBPA449439
HETEDT
RxListhttp://www.rxlist.com/cgi/generic2/canaversenate.htm
WikipediaEDTA
ATC CodesV03AB03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Lead

Kind: small molecule

Organism: Human

Pharmacological action: yes

Actions: chelator

Components

Name UniProt ID Details

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;26(5):1295-302. Pubmed
  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. 2010 Dec 13. Pubmed
  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. 2010 Dec 17. Pubmed

2. Iron

Kind: small molecule

Organism: Human

Pharmacological action: unknown

Actions: chelator

Components

Name UniProt ID Details

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 Jan 3. Pubmed

3. Manganese cation

Kind: small molecule

Organism: Human

Pharmacological action: unknown

Actions: chelator

Components

Name UniProt ID Details

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. Epub 2010 Mar 29. Pubmed

Enzymes

1. Adenosine deaminase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Adenosine deaminase P00813 Details

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

2. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

3. Serum paraoxonase/lactonase 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Serum paraoxonase/lactonase 3 Q15166 Details

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

4. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

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
  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
  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
  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. Epub 2008 Apr 20. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 16, 2014 14:02