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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H16N2O8
Molecular Weight 292.2431
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDETIC ACID

SMILES

C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O

InChI

InChIKey=KCXVZYZYPLLWCC-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

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 Edetic acid in form of disodium salt was withdrawn from the market due to death resulting from hypocalcemia during chelation.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
Target ID: divalent and trivalent metals
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
Inhibition of carcinogen induced c-Ha-ras and c-fos proto-oncogenes expression by dietary curcumin.
2001
Hydroxyl radical footprinting of proteins using metal ion complexes.
2001
Artificial iron-dependent proteases.
2001
Attachment of human gingival fibroblasts to periodontally involved root surface following scaling and/or etching procedures: a scanning electron microscopy study.
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
Deficiency of Pten accelerates mammary oncogenesis in MMTV-Wnt-1 transgenic mice.
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
Cloning and biochemical characterization of BglC, a beta-glucosidase from the cellulolytic actinomycete Thermobifida fusca.
2001 Apr
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
Characterization of a protease responsible for truncated actin increase in neutrophils of patients with Behçet's disease.
2001 Feb
Microwave decalcification of human temporal bones.
2001 Feb
Binding sites for progastrin-derived peptides in colonic crypts.
2001 Feb
Estimation of glomerular filtration rate in cancer patients.
2001 Feb
Localization of estrogen receptor beta protein expression in adult human bone.
2001 Feb
Simultaneous determination of 226Ra and 210Pb in groundwater and soil samples by using the liquid scintillation counter-suspension gel method.
2001 Feb
Determination of glomerular filtration rate per unit renal volume using computerized tomography: correlation with conventional measures of total and divided renal function.
2001 Feb
A high signal-to-noise Ca(2+) probe composed of a single green fluorescent protein.
2001 Feb
Radiation sensitization of mammalian cells by metal chelators.
2001 Feb
Ammonia concentration in human preovulatory ovarian follicles.
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
Mucosal pathophysiology and inflammatory changes in the late phase of the intestinal allergic reaction in the rat.
2001 Feb
Glycoxidation and lipid peroxidation of low-density lipoprotein can synergistically enhance atherogenesis.
2001 Feb 1
Characterization of a model compound for the lysine tyrosylquinone cofactor of lysyl oxidase.
2001 Feb 16
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
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
Differential inhibitory mechanism of Fe2+ and Fe3+ on contraction of ileal longitudinal smooth muscle.
2001 Jan
Flow cytometric analysis of the human articular chondrocyte phenotype in vitro.
2001 Jan
Poorly controlled hypertension in a painter with chronic lead toxicity.
2001 Jan
In search of susceptibility genes for type 2 diabetes in West Africa: the design and results of the first phase of the AADM study.
2001 Jan
Electron microscopic investigation of the morphology and calcium-induced fusion of lipid vesicles with an oligomerised inner leaflet.
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
Environmental lead exposure and progressive renal insufficiency.
2001 Jan 22
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
Predicting the kinetics of peptide-antibody interactions using a multivariate experimental design of sequence and chemical space.
2001 Jan-Feb
Detection of bile duct leaks using MR cholangiography with mangfodipir trisodium (Teslascan).
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
Two new modes of smooth muscle myosin regulation by the interaction between the two regulatory light chains, and by the S2 domain.
2001 Mar
Quaternary ammoniums and other preservatives' contribution in oxidative stress and apoptosis on Chang conjunctival cells.
2001 Mar
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
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
Name Type Language
EDETIC ACID
EP   HSDB   II   INN   MART.   USP-RS   WHO-DD  
INN  
Official Name English
EDTA
INCI   MI   VANDF  
INCI  
Official Name English
EDTA [VANDF]
Common Name English
ETHYLENEDIAMINETETRAACETIC ACID
Systematic Name English
EDETIC ACID [HSDB]
Common Name English
EDETIC ACID [INN]
Common Name English
(ETHYLENEDINITRILO)TETRAACETIC ACID
Systematic Name English
EDETIC ACID [II]
Common Name English
ANTICOAGULANT ETHYLENEDIAMINE TETRAACETIC ACID (EDTA)
Common Name English
EDETIC ACID [MART.]
Common Name English
EDTA [MI]
Common Name English
EDETIC ACID [EP MONOGRAPH]
Common Name English
VERSENE ACID
Brand Name English
ANTICOAGULANT ETHYLENEDIAMINE TETRAACETIC ACID
Common Name English
ETHYLENEBIS(IMINODIACETIC ACID)
Common Name English
EDETIC ACID [WHO-DD]
Common Name English
EDTA [INCI]
Common Name English
GLYCINE, N,N'-1,2-ETHANEDIYLBIS(N-(CARBOXYMETHYL)-
Systematic Name English
EDETIC ACID [USP-RS]
Common Name English
ETHYLENEDIAMINETETRAACETATE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QV03AB03
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
DSLD 1018 (Number of products:49)
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
NDF-RT N0000175962
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
NCI_THESAURUS C360
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
FDA ORPHAN DRUG 495615
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
EPA PESTICIDE CODE 39101
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
EU-Orphan Drug EU/3/16/1668
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
NDF-RT N0000175963
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
NDF-RT N0000175980
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
NCI_THESAURUS C263
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
WHO-ATC V03AB03
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
CFR 21 CFR 176.170
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
Code System Code Type Description
NDF-RT
N0000008556
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY Decreased Coagulation Factor Activity [PE]
USP_CATALOG
1233508
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M4835
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY Merck Index
PUBCHEM
6049
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
DRUG BANK
DB00974
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
CAS
60-00-4
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
DRUG CENTRAL
987
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
RXCUI
1370600
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
ALTERNATIVE
ChEMBL
CHEMBL858
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
WIKIPEDIA
Ethylenediaminetetraacetate
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
INN
534
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
FDA UNII
9G34HU7RV0
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
EVMPD
SUB06456MIG
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
NCI_THESAURUS
C61742
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
MESH
D004492
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
RXCUI
3755
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-449-4
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
EPA CompTox
60-00-4
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY
HSDB
809
Created by admin on Fri Jun 25 21:16:20 UTC 2021 , Edited by admin on Fri Jun 25 21:16:20 UTC 2021
PRIMARY