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targets (3) enzymes (4)
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Identification
Name Edetic Acid
Accession Number DB00974 (APRD01327)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
CaEDTA
Calcium Disodium Edetate (JAN)
Calcium Disodium Versenate
Calcium disodium versenate (TN)
Edetate Calcium
Edetate calcium disodium (USP)
EDT
EDTA
Salts Not Available
Brand names
Name Company
Cheladrate
Endrate
Havidote
Titriplex
Versenate
Brand mixtures Not Available
Categories
  • Anticoagulants
  • Chelating Agents
  • Food Additives
CAS number 62-33-9
Weight Average: 292.2426
Monoisotopic: 292.090665498
Chemical Formula C10H16N2O8
InChI Key InChIKey=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)
Plain Text
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
Plain Text
Mass Spec show (10.2 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
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.
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.
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
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.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Graceway pharmaceuticals llc
  • Watson laboratories inc
  • 3m pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intramuscular
Injection, solution Intravenous drip
Prices
Unit description Cost Unit
Endrate 150 mg/ml ampul 1.44 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility 1000000 mg/L at 25 °C MEYLAN,WM et al. (1996)
logP -2.6 Not Available
Predicted Properties
Property Value Source
water solubility 9.26e+00 g/l ALOGPS
logP -1.2 ALOGPS
logP -5.2 ChemAxon
logS -1.5 ALOGPS
pKa (strongest acidic) 1.49 ChemAxon
pKa (strongest basic) 8.13 ChemAxon
physiological charge -3 ChemAxon
hydrogen acceptor count 10 ChemAxon
hydrogen donor count 4 ChemAxon
polar surface area 155.68 ChemAxon
rotatable bond count 11 ChemAxon
refractivity 62.35 ChemAxon
polarizability 25.64 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00571 Link_out
PubChem Compound 6049 Link_out
PubChem Substance 46508301 Link_out
ChemSpider 5826 Link_out
Therapeutic Targets Database DNC000594 Link_out
PharmGKB PA449439 Link_out
HET EDT Link_out
RxList http://www.rxlist.com/cgi/generic2/canaversenate.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/EDTA Link_out
ATC Codes
  • V03AB03
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Lead

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;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

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 Jan 3. Pubmed

3. manganese

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. Epub 2010 Mar 29. Pubmed
Enzymes

1. Adenosine deaminase

Actions: inhibitor

Adenosine + H(2)O = inosine + NH(3)

UniProt ID: P00813 Link_out
Gene: ADA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: inhibitor

Has very limited arylesterase and no paraoxonase activities but rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents (By similarity)

UniProt ID: Q15166 Link_out
Gene: PON3 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Catalyzes the formation of aromatic C18 estrogens from C19 androgens

UniProt ID: P11511 Link_out
Gene: CYP19A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19