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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H16N2O8
Molecular Weight 292.2426
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDETIC ACID

SMILES

OC(=O)CN(CCN(CC(O)=O)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

Molecular Formula C10H16N2O8
Molecular Weight 292.2426
Charge 0
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 Edetic acid in form of disodium salt was withdrawn from the market due to death resulting from hypocalcemia during chelation.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
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
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
Hydroxyl radical footprinting of proteins using metal ion complexes.
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
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
Histidine--rich glycoprotein in the blood of the bivalve Mytilus edulis: role in cadmium speciation and cadmium transfer to the kidney.
2001 Apr
Fructose-6-phosphate aldolase is a novel class I aldolase from Escherichia coli and is related to a novel group of bacterial transaldolases.
2001 Apr 6
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
Characterization of a protease responsible for truncated actin increase in neutrophils of patients with Behçet's disease.
2001 Feb
Binding sites for progastrin-derived peptides in colonic crypts.
2001 Feb
Pharmacological characterization and antithrombotic effect of agkistin, a platelet glycoprotein Ib antagonist.
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
Progression of diabetic nephropathy.
2001 Feb
Ammonia concentration in human preovulatory ovarian follicles.
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
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
Immunological assay for the determination of procarboxypeptidase U antigen levels in human plasma.
2001 Jan
Use of an orally administered combined sugar solution to evaluate intestinal absorption and permeability in cats.
2001 Jan
The value of MnDPDP enhancement during MR guided laser interstitial thermoablation of liver tumors.
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
Molecular cloning and expression of an alpha-mannosidase gene in Mycobacterium tuberculosis.
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
Decreased in situ insulin receptor dephosphorylation in hyperglycemia-induced insulin resistance in rat adipocytes.
2001 Jan
Pretreatment of whole blood for use in immunochromatographic assays for hepatitis B virus surface antigen.
2001 Jan
Intraluminal acid and gastric mucosal integrity: the importance of blood-borne bicarbonate.
2001 Jan
Intestinal permeability in Behçet's syndrome.
2001 Jan
Inhibition of CaT1 channel activity by a noncompetitive IP3 antagonist.
2001 Jan 12
Non-oxidative mechanisms are responsible for the induction of mutagenesis by reduction of Cr(VI) with cysteine: role of ternary DNA adducts in Cr(III)-dependent mutagenesis.
2001 Jan 16
Environmental lead exposure and progressive renal insufficiency.
2001 Jan 22
Prevention of the photodamage in the hairless mouse dorsal skin by kojic acid as an iron chelator.
2001 Jan 5
Detection of bile duct leaks using MR cholangiography with mangfodipir trisodium (Teslascan).
2001 Jan-Feb
Chelating agents.
2001 Jan-Feb
Proteolytic action of Bothrops jararaca venom upon its own constituents.
2001 Jun
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
Two new modes of smooth muscle myosin regulation by the interaction between the two regulatory light chains, and by the S2 domain.
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
Noncovalent interactions of the Apple 4 domain that mediate coagulation factor XI homodimerization.
2001 Mar 2
Epilysin, a novel human matrix metalloproteinase (MMP-28) expressed in testis and keratinocytes and in response to injury.
2001 Mar 30
Characterization of phosphatidylserine transport to the locus of phosphatidylserine decarboxylase 2 in permeabilized yeast.
2001 Mar 9
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 16 16:02:54 UTC 2022
Edited
by admin
on Fri Dec 16 16:02:54 UTC 2022
Record UNII
9G34HU7RV0
Record Status Validated (UNII)
Record Version
  • Download
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 [WHO-DD]
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
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 Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
DSLD 1018 (Number of products:49)
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
NDF-RT N0000175962
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
NCI_THESAURUS C360
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
FDA ORPHAN DRUG 495615
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
EPA PESTICIDE CODE 39101
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
EU-Orphan Drug EU/3/16/1668
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
NDF-RT N0000175963
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
NDF-RT N0000175980
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
NCI_THESAURUS C263
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
WHO-ATC V03AB03
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
CFR 21 CFR 176.170
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
Code System Code Type Description
NDF-RT
N0000008556
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY Decreased Coagulation Factor Activity [PE]
MERCK INDEX
M4835
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY Merck Index
PUBCHEM
6049
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
DAILYMED
9G34HU7RV0
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
DRUG BANK
DB00974
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
CAS
60-00-4
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
DRUG CENTRAL
987
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
RXCUI
1370600
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
ALTERNATIVE
CHEBI
42191
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
ChEMBL
CHEMBL858
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
RS_ITEM_NUM
1233508
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
WIKIPEDIA
Ethylenediaminetetraacetate
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
INN
534
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
FDA UNII
9G34HU7RV0
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
EVMPD
SUB06456MIG
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
NCI_THESAURUS
C61742
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
MESH
D004492
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
RXCUI
3755
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-449-4
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
EPA CompTox
DTXSID6022977
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
HSDB
809
Created by admin on Fri Dec 16 16:02:54 UTC 2022 , Edited by admin on Fri Dec 16 16:02:54 UTC 2022
PRIMARY
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