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Identification
- Summary
Edetate disodium is a polyvalent ion chelator indicated for emergency treatment of hypercalcemia and digitalis toxicity associated ventricular arrhythmias.
- Brand Names
- Endrate
- Generic Name
- Edetate disodium anhydrous
Commonly known or available as Edetate disodium - DrugBank Accession Number
- DB14600
- Background
Edetate disodium anhydrous is a polyvalent chelating agent used to treat hypercalcemia and digitalis toxicity associated ventricular arrhythmias.1
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Edetate disodium anhydrous (DB14600)
- Weight
- Average: 336.2063
Monoisotopic: 336.054554784 - Chemical Formula
- C10H14N2Na2O8
- Synonyms
- Anhydrous disodium edetate
- Disodium EDTA, anhydrous
- Edetate disodium, anhydrous
- EDTA disodium salt (anhydrous)
Pharmacology
- Indication
Edetate disodium is indicated for emergency treatment of hypercalcemia and digitalis toxicity associated ventricular arrhythmias.2
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Hypercalcemia •••••••••••• ••••••••• Treatment of Arrhythmia of ventricular origin •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
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Edetate disodium anhydrous is a polyvalent ion chelator that reduces blood concentrations of calcium or digitalis.2,3 It has a long duration of action as patients are generally given 1 daily dose.2,3 The therapeutic index is wide, as high doses are generally well tolerated.2,3 Patients should be counselled regarding the risk of postural hypotension, effects of myocardial contractility, hypokalemia, hypomagnesemia, and hypoglycemia.2,3
- Mechanism of action
Edetate disodium anhydrous chelates divalent and trivalent ions such as magnesium, zinc, and calcium.3 The chelate is excreted in the urine, reducing concentrations of these ions in the blood.3
Target Actions Organism ALead chelatorHumans UIron chelatorHumans UManganese cation chelatorHumans - Absorption
Not Available
- Volume of distribution
Data regarding the volume of distribution of edetate disodium anhydrous is not readily available.1
- Protein binding
Not Available
- Metabolism
- Route of elimination
After intravenous administration, 95% of the dose is recovered in the urine after 24 hours.2,3 Oral administration in rats leads to 5.3% recovery in urine and 88.5% recovery in feces.1
- Half-life
Not Available
- Clearance
The mean clearance of edetate in 1 month olds is 54.6mL/min/1.73m2.1 2-17 year olds have a mean clearance of 113.9 ± 24.4 mL/min/1.73m2.1
- Adverse Effects
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Patients experiencing an overdose may present with calcium deficiency.2 Treat overdose with symptomatic and supportive treatment, which may include intravenous calcium gluconate.2
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareTechnetium Tc-99m oxidronate Edetate disodium anhydrous may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Edetate disodium 7FLD91C86K 6381-92-6 OVBJJZOQPCKUOR-UHFFFAOYSA-L - Active Moieties
Name Kind UNII CAS InChI Key Edetic acid unknown 9G34HU7RV0 60-00-4 KCXVZYZYPLLWCC-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Endrate Injection, solution 150 mg/1mL Intravenous UNSPECIFIED 2006-05-11 Not applicable US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Clinplant Gel, dentifrice 24 g/100g Dental Nibec Co., Ltd 2018-06-20 Not applicable US Clinplant Floss Gel, dentifrice 17 g/100g Dental Nibec Co., Ltd 2018-06-20 2018-09-20 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Miin Foot Edetate disodium (0.05 g/100g) + Aloe vera leaf (0.5 g/100g) + Glycerin (8 g/100g) + Urea (4 g/100g) Liquid Topical Lydia Co., Ltd. 2019-08-22 Not applicable US Miracle FootCream Lavender Edetate disodium (0.05 g/100g) + Aloe vera leaf (0.5 g/100g) + Glycerin (8 g/100g) + Urea (4 g/100g) Cream Topical Aloe Vera Korea Co.,Ltd. 2019-08-22 Not applicable US Miracle FootCream Lemon Edetate disodium (0.05 g/100g) + Aloe vera leaf (0.5 g/100g) + Glycerin (8 g/100g) + Urea (4 g/100g) Cream Topical Aloe Vera Korea Co.,Ltd. 2022-03-29 Not applicable US รีเวทเทียร์ Edetate disodium (0.05 g) + Boric acid (0.19 g) + Sodium chloride (0.65 g) Liquid Ophthalmic บริษัท ยูเมด้า จำกัด 2015-05-25 2020-08-23 Thailand 
อลิซ คอมฟอร์ท มัลติ-เพอพัส โซลูชั่น Edetate disodium (0.1 g/100ml) + Boric acid (0.175 g/100ml) + Hypromellose (0.15 g/100ml) + Poloxamer 407 (0.05 g/100ml) + Polyaminopropyl biguanide (0.00015 g/100ml) + Sodium borate (0.079 g/100ml) + Sodium chloride (0.83 g/100ml) Solution Ophthalmic บริษัท อลิซไลฟ์ จำกัด จำกัด 2017-02-02 2020-09-29 Thailand - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Clinplant Edetate disodium (24 g/100g) Gel, dentifrice Dental Nibec Co., Ltd 2018-06-20 Not applicable US Clinplant Floss Edetate disodium (17 g/100g) Gel, dentifrice Dental Nibec Co., Ltd 2018-06-20 2018-09-20 US Miracle FootCream Lavender Edetate disodium (0.05 g/100g) + Aloe vera leaf (0.5 g/100g) + Glycerin (8 g/100g) + Urea (4 g/100g) Cream Topical Aloe Vera Korea Co.,Ltd. 2019-08-22 Not applicable US Miracle FootCream Lemon Edetate disodium (0.05 g/100g) + Aloe vera leaf (0.5 g/100g) + Glycerin (8 g/100g) + Urea (4 g/100g) Cream Topical Aloe Vera Korea Co.,Ltd. 2022-03-29 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Tetracarboxylic acids and derivatives
- Direct Parent
- Tetracarboxylic acids and derivatives
- Alternative Parents
- Alpha amino acids / Trialkylamines / Carboxylic acid salts / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic zwitterions / Organic sodium salts / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Aliphatic acyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid / Carboxylic acid salt / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- organic sodium salt (CHEBI:64734)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 8NLQ36F6MM
- CAS number
- 139-33-3
- InChI Key
- ZGTMUACCHSMWAC-UHFFFAOYSA-L
- InChI
- InChI=1S/C10H16N2O8.2Na/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;2*+1/p-2
- IUPAC Name
- disodium 2-({2-[bis(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetate
- SMILES
- [Na+].[Na+].OC(=O)CN(CCN(CC(O)=O)CC([O-])=O)CC([O-])=O
References
- General References
- Lanigan RS, Yamarik TA: Final report on the safety assessment of EDTA, calcium disodium EDTA, diammonium EDTA, dipotassium EDTA, disodium EDTA, TEA-EDTA, tetrasodium EDTA, tripotassium EDTA, trisodium EDTA, HEDTA, and trisodium HEDTA. Int J Toxicol. 2002;21 Suppl 2:95-142. doi: 10.1080/10915810290096522. [Article]
- Dailymed: Endrate Edetate Disodium Anhydrous Intravenous Injection (Discontinued) [Link]
- Medsafe New Zealand Approved Drug Products: Edetate Disodium Injection [Link]
- External Links
- KEGG Drug
- D03945
- PubChem Compound
- 8759
- ChemSpider
- 8429
- ChEBI
- 64734
- ChEMBL
- CHEMBL1749
- Wikipedia
- Ethylenediaminetetraacetic_acid
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Recruiting Treatment Critical Limb Ischemia (CLI) / Diabetes 1 somestatus stop reason just information to hide 1, 2 Terminated Diagnostic Kidney Diseases / Renal Insufficiency,Chronic 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel, dentifrice Dental 24 g/100g Gel, dentifrice Dental 17 g/100g Injection Intravenous Injection, solution Intravenous 150 mg/1mL Liquid Topical Cream Topical Liquid Ophthalmic Solution Ophthalmic - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 240 Lanigan, 2002 boiling point (°C) 252 Lanigan, 2002 - Predicted Properties
Property Value Source Water Solubility 72.0 mg/mL ALOGPS logP -1 ALOGPS logP -4.9 Chemaxon logS -0.67 ALOGPS pKa (Strongest Acidic) 2.35 Chemaxon pKa (Strongest Basic) 7.73 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 161.34 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 84.02 m3·mol-1 Chemaxon Polarizability 25.41 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 153.11674 predictedDeepCCS 1.0 (2019) [M+H]+ 155.47614 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.56789 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
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Yes
Chelator
References
- Onnby L, Giorgi C, Plieva FM, Mattiasson B: Removal of heavy metals from water effluents using supermacroporous metal chelating cryogels. Biotechnol Prog. 2010 Sep-Oct;26(5):1295-302. doi: 10.1002/btpr.422. [Article]
- Chakraborty N, Banerjee A, Pal R: Accumulation of lead by free and immobilized cyanobacteria with special reference to accumulation factor and recovery. Bioresour Technol. 2011 Mar;102(5):4191-5. doi: 10.1016/j.biortech.2010.12.028. Epub 2010 Dec 13. [Article]
- 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. 2011 Mar;159(3):782-8. doi: 10.1016/j.envpol.2010.11.020. Epub 2010 Dec 18. [Article]
Unknown
Chelator
References
- Hasegawa H, Rahman IM, Kinoshita S, Maki T, Furusho Y: Separation of dissolved iron from the aqueous system with excess ligand. Chemosphere. 2011 Feb;82(8):1161-7. doi: 10.1016/j.chemosphere.2010.12.048. Epub 2011 Jan 3. [Article]
Unknown
Chelator
References
- 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. doi: 10.1039/c001458c. Epub 2010 Mar 29. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine (PubMed:16670267, PubMed:23193172, PubMed:26166670, PubMed:8452534, PubMed:9361033). Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4 (PubMed:20959412). Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion (PubMed:11772392). Enhances dendritic cell immunogenicity by affecting dendritic cell costimulatory molecule expression and cytokines and chemokines secretion (By similarity). Enhances CD4+ T-cell differentiation and proliferation (PubMed:20959412). Acts as a positive modulator of adenosine receptors ADORA1 and ADORA2A, by enhancing their ligand affinity via conformational change (PubMed:23193172). Stimulates plasminogen activation (PubMed:15016824). Plays a role in male fertility (PubMed:21919946, PubMed:26166670). Plays a protective role in early postimplantation embryonic development (By similarity)
- Specific Function
- 2'-deoxyadenosine deaminase activity
- Gene Name
- ADA
- Uniprot ID
- P00813
- Uniprot Name
- Adenosine deaminase
- Molecular Weight
- 40764.13 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. 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
- Specific Function
- Acyl-l-homoserine-lactone lactonohydrolase activity
- Gene Name
- PON3
- Uniprot ID
- Q15166
- Uniprot Name
- Serum paraoxonase/lactonase 3
- Molecular Weight
- 39607.185 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Modulator
- Curator comments
- EDTA prevents inhibition of CYP19A1.
- General Function
- A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)
- Specific Function
- Aromatase activity
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- 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. [Article]
- Bellino FL, Holben L: Placental estrogen synthetase (aromatase): evidence for phosphatase-dependent inactivation. Biochem Biophys Res Commun. 1989 Jul 14;162(1):498-504. [Article]
- 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. [Article]
- 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. doi: 10.1016/j.jsbmb.2007.11.004. Epub 2008 Apr 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation
- Specific Function
- Acyl-l-homoserine-lactone lactonohydrolase activity
- Gene Name
- PON1
- Uniprot ID
- P27169
- Uniprot Name
- Serum paraoxonase/arylesterase 1
- Molecular Weight
- 39730.99 Da
References
- 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. [Article]
Drug created at August 25, 2018 15:59 / Updated at June 12, 2020 16:53