U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H13N2O8.3Na
Molecular Weight 358.1881
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDETATE TRISODIUM

SMILES

[Na+].[Na+].[Na+].OC(=O)CN(CCN(CC([O-])=O)CC([O-])=O)CC([O-])=O

InChI

InChIKey=QZKRHPLGUJDVAR-UHFFFAOYSA-K
InChI=1S/C10H16N2O8.3Na/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;3*+1/p-3

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H13N2O8
Molecular Weight 289.2188
Charge -3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Edetic acid (EDTA) is a chelating agent. The U.S. Food and Drug Administration (FDA) approved edetic acid chelation therapy as a treatment for lead and heavy metal poisoning. Edetic acid in form of disodium salt was withdrawn from the market due to death resulting from hypocalcemia during chelation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
18.3 null [pKd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Calcium disodium versenate

Approved Use

Edetate calcium disodium is indicated 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.

Launch Date

-5.19523205E11
Curative
Calcium Disodium Versenate

Approved Use

Edetate calcium disodium is indicated 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.

Launch Date

-5.19523205E11
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
51 μg/mL
1 g single, intramuscular
dose: 1 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
EDETATE CALCIUM DISODIUM serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
60 min
unknown, unknown
EDETATE CALCIUM DISODIUM plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
25 mg/kg 2 times / day multiple, intravenous
Recommended
Dose: 25 mg/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / day
Co-administed with::
2,3-dimercapto-1-propanol, i.v(3 mg/kg; 6/day; 5 days)
Sources:
unhealthy, 1-8
n = 130
Health Status: unhealthy
Condition: Plumbism
Age Group: 1-8
Sex: M+F
Population Size: 130
Sources:
Disc. AE: Acute renal failure...
Other AEs: Nephrotoxicity...
AEs leading to
discontinuation/dose reduction:
Acute renal failure (3%)
Other AEs:
Nephrotoxicity (mild, 13%)
Sources:
160 mg/kg single, intravenous
Studied dose
Dose: 160 mg/kg
Route: intravenous
Route: single
Dose: 160 mg/kg
Sources: Page: p.361
unhealthy, 49
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Multiple myeloma
Age Group: 49
Sex: F
Population Size: 1
Sources: Page: p.361
Disc. AE: Hypocalcemia...
AEs leading to
discontinuation/dose reduction:
Hypocalcemia
Sources: Page: p.361
400 mg/kg 1 times / day multiple, intravenous (max)
Highest studied dose
Dose: 400 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg/kg, 1 times / day
Sources: Page: p.360
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Breast cancer
Age Group: 58
Sex: F
Population Size: 1
Sources: Page: p.360
Disc. AE: Restlessness, Hypocalcemia...
AEs leading to
discontinuation/dose reduction:
Restlessness
Hypocalcemia
Sources: Page: p.360
400 mg/kg 1 times / day multiple, intravenous (max)
Highest studied dose
Dose: 400 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg/kg, 1 times / day
Sources: Page: p.360
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Breast cancer
Age Group: 58
Sex: F
Population Size: 1
Sources: Page: p.360
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache
Sources: Page: p.360
AEs

AEs

AESignificanceDosePopulation
Acute renal failure 3%
Disc. AE
25 mg/kg 2 times / day multiple, intravenous
Recommended
Dose: 25 mg/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / day
Co-administed with::
2,3-dimercapto-1-propanol, i.v(3 mg/kg; 6/day; 5 days)
Sources:
unhealthy, 1-8
n = 130
Health Status: unhealthy
Condition: Plumbism
Age Group: 1-8
Sex: M+F
Population Size: 130
Sources:
Nephrotoxicity mild, 13%
25 mg/kg 2 times / day multiple, intravenous
Recommended
Dose: 25 mg/kg, 2 times / day
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / day
Co-administed with::
2,3-dimercapto-1-propanol, i.v(3 mg/kg; 6/day; 5 days)
Sources:
unhealthy, 1-8
n = 130
Health Status: unhealthy
Condition: Plumbism
Age Group: 1-8
Sex: M+F
Population Size: 130
Sources:
Hypocalcemia Disc. AE
160 mg/kg single, intravenous
Studied dose
Dose: 160 mg/kg
Route: intravenous
Route: single
Dose: 160 mg/kg
Sources: Page: p.361
unhealthy, 49
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Multiple myeloma
Age Group: 49
Sex: F
Population Size: 1
Sources: Page: p.361
Hypocalcemia Disc. AE
400 mg/kg 1 times / day multiple, intravenous (max)
Highest studied dose
Dose: 400 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg/kg, 1 times / day
Sources: Page: p.360
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Breast cancer
Age Group: 58
Sex: F
Population Size: 1
Sources: Page: p.360
Restlessness Disc. AE
400 mg/kg 1 times / day multiple, intravenous (max)
Highest studied dose
Dose: 400 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg/kg, 1 times / day
Sources: Page: p.360
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Breast cancer
Age Group: 58
Sex: F
Population Size: 1
Sources: Page: p.360
Headache Disc. AE
400 mg/kg 1 times / day multiple, intravenous (max)
Highest studied dose
Dose: 400 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 400 mg/kg, 1 times / day
Sources: Page: p.360
unhealthy, 58
n = 1
Health Status: unhealthy
Condition: Hypercalcemia|Breast cancer
Age Group: 58
Sex: F
Population Size: 1
Sources: Page: p.360
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of ethylenediaminetetraacetic acid (EDTA) on acute mercury poisoning of toad.
1986
Inhibition of carcinogen induced c-Ha-ras and c-fos proto-oncogenes expression by dietary curcumin.
2001
Artificial iron-dependent proteases.
2001
Evaluation of Er:YAG laser and EDTAC on dentin adhesion of six endodontic sealers.
2001
Evaluation of copper availability to plants in copper-contaminated vineyard soils.
2001
Isolation and characterization of rheumatoid arthritis synovial fibroblasts from primary culture--primary culture cells markedly differ from fourth-passage cells.
2001
Chromosomal mapping, gene structure and characterization of the human and murine RAB27B gene.
2001
Brain dystrophin-glycoprotein complex: persistent expression of beta-dystroglycan, impaired oligomerization of Dp71 and up-regulation of utrophins in animal models of muscular dystrophy.
2001
Role of complement activation and mast cell degranulation in the pathogenesis of rapid intestinal ischemia/reperfusion injury in rats.
2001
Purification and characterization of a phosphoric triester hydrolase from the tufted apple bud moth, Platynota idaeusalis (Walker).
2001
Chemical speciation used to assess [S,S']-ethylenediaminedisuccinic acid (EDDS) as a readily-biodegradable replacement for EDTA in radiochemical decontamination formulations.
2001 Apr
Cloning and biochemical characterization of BglC, a beta-glucosidase from the cellulolytic actinomycete Thermobifida fusca.
2001 Apr
Quantitation of genomic DNA in plasma and serum samples: higher concentrations of genomic DNA found in serum than in plasma.
2001 Feb
Anti-Saccharomyces cerevisiae antibodies (ASCA), phenotypes of IBD, and intestinal permeability: a study in IBD families.
2001 Feb
Prolonged stability of endogenous cardiotrophin-1 in whole blood.
2001 Feb
Estimation of glomerular filtration rate in cancer patients.
2001 Feb
Radiation sensitization of mammalian cells by metal chelators.
2001 Feb
Cabbage cryoprotectin is a member of the nonspecific plant lipid transfer protein gene family.
2001 Feb
Urea is a product of ureidoglycolate degradation in chickpea. Purification and characterization of the ureidoglycolate urea-lyase.
2001 Feb
Ethylenediamine-N,N,N',N'-tetraacetic acid induces parthenogenetic activation of porcine oocytes at the germinal vesicle stage, leading to formation of blastocysts.
2001 Feb
Glycoxidation and lipid peroxidation of low-density lipoprotein can synergistically enhance atherogenesis.
2001 Feb 1
Influence of citrate and EDTA anticoagulants on plasma malondialdehyde concentrations estimated by high-performance liquid chromatography.
2001 Feb 10
Comparative effects of metal chelating agents on the neuronal cytotoxicity induced by copper (Cu+2), iron (Fe+3) and zinc in the hippocampus.
2001 Feb 16
Robustness of slope-intercept versus slope-only for measurement of glomerular filtration rate.
2001 Jan
Phagocytic response of bovine polymorphonuclear leukocytes to different incubation conditions and following exposure to some effectors of phagocytosis and different anticoagulants in vitro.
2001 Jan
Enhancement of jejunal absorption of conjugated bile acid by neurotensin in rats.
2001 Jan
Use of an orally administered combined sugar solution to evaluate intestinal absorption and permeability in cats.
2001 Jan
Flow cytometric analysis of the human articular chondrocyte phenotype in vitro.
2001 Jan
Comparison of lateral condensation and thermomechanically compacted warm alpha-phase gutta-percha with a single cone for obturating curved root canals.
2001 Jan
Poorly controlled hypertension in a painter with chronic lead toxicity.
2001 Jan
The value of MnDPDP enhancement during MR guided laser interstitial thermoablation of liver tumors.
2001 Jan
Docetaxel-carboplatin as first line chemotherapy for epithelial ovarian cancer.
2001 Jan
Statistical process monitoring of WBC-reduced blood components assessed by two types of software.
2001 Jan
Long-term preservation of chilled canine semen: effect of commercial and laboratory prepared extenders.
2001 Jan 15
The occurrence of internal (1 --> 5)-linked arabinofuranose and arabinopyranose residues in arabinogalactan side chains from soybean pectic substances.
2001 Jan 15
Multifunctional antioxidant activity of HBED iron chelator.
2001 Jan 15
Expression and enzymatic activity of human disintegrin and metalloproteinase ADAM19/meltrin beta.
2001 Jan 26
Determination of metal complexes of ethylenediaminetetraacetate in the presence of organic matter by high-performance liquid chromatography.
2001 Jan 5
Detection of bile duct leaks using MR cholangiography with mangfodipir trisodium (Teslascan).
2001 Jan-Feb
Mechanism of endothelin 1 production in the cochlea of rats.
2001 Jan-Feb
Measurement of intact insulin-like growth factor-binding protein-3 in human plasma using a ligand immunofunctional assay.
2001 Mar
Duration of sample storage dramatically alters expression of the human immunodeficiency virus coreceptors CXCR4 and CCR5.
2001 Mar
Adherence of Giardia lamblia trophozoites to Int-407 human intestinal cells.
2001 Mar
Pseudomonas aeruginosa protease IV enzyme assays and comparison to other Pseudomonas proteases.
2001 Mar
Kinetic modeling of liquid-phase adsorption of reactive dyes and metal ions on chitosan.
2001 Mar
Effect of collagenase inhibitors on corneal haze after PRK.
2001 Mar
The CDTA-soluble pectic substances from soybean meal are composed of rhamnogalacturonan and xylogalacturonan but not homogalacturonan.
2001 Mar
Histamine induces exocytosis and IL-6 production from human lung macrophages through interaction with H1 receptors.
2001 Mar 15
EDTA redistribution of lead and cadmium into the soft tissues in a human with a high lead burden - should DMSA always be used to follow EDTA in such cases?
2011 Jun
Lead mobilization study and the clearance of intravenous CaNa2EDTA in a patient with end-stage renal failure on hemodialysis.
2012 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Edetic acid can be given intramuscularly at 1000 mg/m2/day
hypercalcemia: adults: 50 mg/kg/day (up to 3 g/day) administered by slow IV infusion. Frequency and duration of administration are quite variable, and should be determined based on the patient's serum calcium. Five consecutive daily doses may be administered, followed by 2 days without medication, repeating these courses as necessary to a total of 15 doses.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: Human endothelial cells (HUVEC), lung fibroblasts (CCD 18lu), mesenchymal stem cells and EPCs were harvested by rinsing with 2 mM edetic acid (EDTA) in PBS after lead exposure.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:02 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:02 UTC 2023
Record UNII
420IP921MB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EDETATE TRISODIUM
USAN   VANDF  
USAN  
Official Name English
TRISODIUM EDETATE
MART.   WHO-DD  
Systematic Name English
EDETATE TRISODIUM [USAN]
Common Name English
NSC-756746
Code English
EDTA TRISODIUM
Common Name English
TRISODIUM EDTA [INCI]
Common Name English
VERSENE-9
Brand Name English
TRISODIUM EDETATE [MART.]
Common Name English
Trisodium edetate [WHO-DD]
Common Name English
KITELOCK COMPONENT EDETATE TRISODIUM
Common Name English
LIMCLAIR
Brand Name English
EDETATE TRISODIUM [VANDF]
Common Name English
TRISODIUM ETHYLENEDIAMINETETRAACETATE
Systematic Name English
EDTA TRISODIUM SALT [MI]
Common Name English
TRISODIUM EDTA
INCI  
INCI  
Official Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 39110
Created by admin on Fri Dec 15 15:02:02 UTC 2023 , Edited by admin on Fri Dec 15 15:02:02 UTC 2023
NCI_THESAURUS C360
Created by admin on Fri Dec 15 15:02:02 UTC 2023 , Edited by admin on Fri Dec 15 15:02:02 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
205-758-8
Created by admin on Fri Dec 15 15:02:02 UTC 2023 , Edited by admin on Fri Dec 15 15:02:02 UTC 2023
PRIMARY
NSC
756746
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PRIMARY
EPA CompTox
DTXSID7020556
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PRIMARY
CHEBI
63125
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PRIMARY
FDA UNII
420IP921MB
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PRIMARY
RXCUI
105745
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PRIMARY RxNorm
NCI_THESAURUS
C76599
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PRIMARY
PUBCHEM
9008
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PRIMARY
MERCK INDEX
m4835
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PRIMARY Merck Index
DAILYMED
420IP921MB
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PRIMARY
ChEMBL
CHEMBL2028177
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PRIMARY
CAS
150-38-9
Created by admin on Fri Dec 15 15:02:02 UTC 2023 , Edited by admin on Fri Dec 15 15:02:02 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE