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Chemistry

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Also known as: 139-33-3, Edta disodium salt, Disodium edetate, Edta disodium, Titriplex iii, Disodium edta
Molecular Formula
C10H14N2Na2O8
Molecular Weight
336.21  g/mol
InChI Key
ZGTMUACCHSMWAC-UHFFFAOYSA-L

Edetate Calcium Disodium
A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.
1 2D Structure

Edetate Calcium Disodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
disodium;2-[2-[carboxylatomethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate
2.1.2 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
2.1.3 InChI Key
ZGTMUACCHSMWAC-UHFFFAOYSA-L
2.1.4 Canonical SMILES
C(CN(CC(=O)O)CC(=O)[O-])N(CC(=O)O)CC(=O)[O-].[Na+].[Na+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Acid, Edetic

2. Acid, Ethylenediaminetetraacetic

3. Acid, Ethylenedinitrilotetraacetic

4. Calcitetracemate, Disodium

5. Calcium Disodium Edetate

6. Calcium Disodium Versenate

7. Calcium Tetacine

8. Chelaton 3

9. Chromium Edta

10. Copper Edta

11. Coprin

12. Dicobalt Edta

13. Dinitrilotetraacetate, Disodium Ethylene

14. Dinitrilotetraacetate, Ethylene

15. Disodium Calcitetracemate

16. Disodium Edta

17. Disodium Ethylene Dinitrilotetraacetate

18. Disodium Versenate, Calcium

19. Distannous Edta

20. Edathamil

21. Edetate Disodium Calcium

22. Edetate, Calcium Disodium

23. Edetates

24. Edetic Acid

25. Edetic Acid, Calcium Salt

26. Edetic Acid, Calcium, Sodium Salt

27. Edetic Acid, Chromium Salt

28. Edetic Acid, Dipotassium Salt

29. Edetic Acid, Disodium Salt

30. Edetic Acid, Disodium Salt, Dihydrate

31. Edetic Acid, Disodium, Magnesium Salt

32. Edetic Acid, Disodium, Monopotassium Salt

33. Edetic Acid, Magnesium Salt

34. Edetic Acid, Monopotassium Salt

35. Edetic Acid, Monosodium Salt

36. Edetic Acid, Potassium Salt

37. Edetic Acid, Sodium Salt

38. Edta

39. Edta, Chromium

40. Edta, Copper

41. Edta, Dicobalt

42. Edta, Disodium

43. Edta, Distannous

44. Edta, Gallium

45. Edta, Magnesium Disodium

46. Edta, Potassium

47. Edta, Stannous

48. Ethylene Dinitrilotetraacetate

49. Ethylene Dinitrilotetraacetate, Disodium

50. Ethylenediaminetetraacetic Acid

51. Ethylenedinitrilotetraacetic Acid

52. Gallium Edta

53. Magnesium Disodium Edta

54. N,n'-1,2-ethanediylbis(n-(carboxymethyl)glycine)

55. Potassium Edta

56. Stannous Edta

57. Tetacine, Calcium

58. Tetracemate

59. Versenate

60. Versenate, Calcium Disodium

61. Versene

2.2.2 Depositor-Supplied Synonyms

1. 139-33-3

2. Edta Disodium Salt

3. Disodium Edetate

4. Edta Disodium

5. Titriplex Iii

6. Disodium Edta

7. Disodium Edta, Anhydrous

8. Cheladrate

9. Ethylenediaminetetraacetic Acid Disodium Salt

10. Disodium Versene

11. Endrate Disodium

12. Sodium Versenate

13. Disodium Salt Of Edta

14. Metaquest B

15. Kiresuto B

16. Chelaplex Iii

17. Complexon Iii

18. Diso-tate

19. Chelaton Iii

20. Versene Na

21. Triplex Iii

22. Chelaton 3

23. Disodium Versenate

24. Edathamil Disodium

25. Trilon Bd

26. Versene Na2

27. Disodium Sequestrene

28. Disodium Tetracemate

29. F 1 (complexon)

30. Disodium Ethylenediaminetetraacetate

31. Sequestrene Sodium 2

32. Ethylenediaminetetraacetic Acid, Disodium Salt

33. Disodium Edta Dihydrate

34. Perma Kleer Di Crystals

35. Edetic Acid Disodium Salt

36. Disodium Edetate Dihydrate

37. Disodium Dihydrogen Ethylenediaminetetraacetate

38. Disodium Ethylenediamine-n,n,n',n'-tetraacetate

39. Glycine, N,n'-1,2-ethanediylbis[n-(carboxymethyl)-, Disodium Salt

40. Edta-na2

41. Edta Disodium Salt (anhydrous)

42. Edetate Disodium Anhydrous

43. Perma Kleer 50 Crystals Disodium Salt

44. Disodium Ethylenediaminetetraacetic Acid

45. Ethylene Diamine Tetraacetic Acid, Disodium Salt

46. Disodium (ethylenedinitrilo)tetraacetate

47. Sodium Ethylenediaminetetraacetate

48. Cbc 50152966

49. Dr-16133

50. Ethylenediaminetetraacetate, Disodium Salt

51. Disodium Diacid Ethylenediaminetetraacetate

52. Mfcd00070672

53. Disodium (ethylenedinitrilo)tetraacetic Acid

54. Trilon B

55. Disodium Dihydrogen(ethylenedinitrilo)tetraacetate

56. Glycine, N,n'-1,2-ethanediylbis(n-(carboxymethyl)-, Disodium Salt

57. Endrate (tn)

58. Chelest B

59. Komplexon Iii

60. Clewat N

61. Disodium Edathamil

62. Zonon D

63. Dotite 2na

64. Selekton B 2

65. Tetracemate Disodium

66. Mavacid Ed 4

67. Na2-edta

68. Disodium Edetate Hydrate

69. Versonol 120

70. Chelest 200

71. Anhydrous Disodium Edetate

72. Veresene Disodium Salt

73. Edetate Disodium, Anhydrous

74. 8nlq36f6mm

75. Ethylenediaminetetraacetic Acid Disodium Salt Solution

76. Ethylenediaminetetraacetic Acid Disodium Salt, 0.050m Standardized Solution

77. Disodium 2-({2-[(carboxylatomethyl)(carboxymethyl)amino]ethyl}(carboxymethyl)amino)acetate

78. Chebi:64734

79. Acetic Acid, (ethylenedinitrilo)tetra-, Disodium Salt

80. Nsc-2760

81. Ccris 3658

82. E.d.t.a. Disodique [french]

83. F 1 (van)

84. E.d.t.a. Disodique

85. Nsc-759604

86. Nsc 2760

87. Einecs 205-358-3

88. Unii-8nlq36f6mm

89. Ethylenediamine Tetraacetic Acid Disodium Salt

90. Dinatrium Ethylendiamintetraacetat [czech]

91. Ai3-18049

92. Ethylenebis(iminodiacetic Acid) Disodium Salt

93. Dinatrium Ethylendiamintetraacetat

94. Hsdb 8013

95. Disodium 2-((2-((carboxylatomethyl)(carboxymethyl)amino)ethyl)(carboxymethyl)amino)acetate

96. (ethylenedinitrilo)-tetraacetic Acid Disodium Salt

97. Na2edta

98. 0.5m Sodium Edta

99. Disodium Edetate (tn)

100. Na2.edta

101. N,n'-1,2-ethanediylbis(n-(carboxymethyl)glycine) Disodium Salt

102. Ec 205-358-3

103. Edta Disodium Salt Anhydrous

104. Chembl1749

105. Dtxsid9027073

106. Disodium N,n'-1,2-ethanediylbis(n-(carboxymethyl)glycine)

107. Disodium Ethylenediamine-tetraacetate

108. Db14600

109. Sb40706

110. E386

111. Ethylenediaminetetracetic Acid Disodium Salt

112. Db-042467

113. Ethylenediaminetetra-acetic Acid Disodium Salt

114. D03945

115. P17519

116. J-007267

117. J-521348

118. Q4532977

119. Glycine, N,n'-1,2-ethanediylbis(n-(carboxymethyl)-, Sodium Salt (1:2)

120. (ethylenedinitrilo)tetraacetic Acid Disodium Salt, Edta Disodium Salt, Edta-na2

121. Disodium;2-[2-[carboxylatomethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate

122. Ethylenediaminetetraacetic Acid Disodium Salt, 0.100n (0.050m) Standardized Solution

123. Ethylenediaminetetraacetic Acid Disodium Salt, 0.115n (0.0575m) Standardized Solution

124. Ethylenediaminetetraacetic Acid Disodium Salt, 0.200n (0.1m) Standardized Solution

125. Disodium 2-({2-[(carboxylatomethyl)(carboxymethyl)amino]ethyl(carboxymethyl)amino)acetate

2.3 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 336.21 g/mol
Molecular Formula C10H14N2Na2O8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count9
Exact Mass336.05455397 g/mol
Monoisotopic Mass336.05455397 g/mol
Topological Polar Surface Area161 Ų
Heavy Atom Count22
Formal Charge0
Complexity336
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Therapeutic Uses

Anticoagulants; Chelating Agents; Food Additives

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Endrate (Edetate Disodium Injection, USP) is indicated in selected patients for the emergency treatment of hypercalcemia and for the control of ventricular arrhythmias associated with digitalis toxicity. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


Disodium edentate is also used therapeutically as an anticoagulant as it will chelate calcium and prevent the coagulation of blood in vitro. Concentrations of 0.1% w/v are used in small volumes for hematological testing and 0.3% w/v in transfusions.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 243


Disodium EDTA is used occasionally to terminate the effects of injected calcium, to antagonize digitalis toxicity, or to suppress tachyarrhythmias. /Former/

Cosmetic Ingredient Expert Review Panel; Final 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. International Journal of Toxicology 21 (S2): 95-142 (2002)


For more Therapeutic Uses (Complete) data for Disodium EDTA (8 total), please visit the HSDB record page.


4.2 Drug Warning

/BOXED WARNING/ The use of this drug in any particular patient is recommended only when the severity of the clinical condition justifies the aggressive measures associated with this type of therapy.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


Clinical studies of edetate disodium did not include sufficient numbers of patients aged 65 and over to determine whether they respond differently from younger subjects. Other reported clinical experience has not identified differences in responses between elderly and younger patients. In general, dose selection for an elderly patient should be cautious, reflecting the greater frequency of decreased hepatic, renal, or cardiac function, and of concomitant disease or other drug therapy.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


Fatal medication errors have occurred that involve confusion between edetate calcium disodium (calcium EDTA) and edetate disodium (no longer commercially available in the US). Children and adults have mistakenly received edetate disodium instead of edetate calcium disodium; at least 5 deaths have occurred as a result of inadvertent administration of edetate disodium. Although both edetate calcium disodium and edetate disodium are heavy metal antagonists, the 2 drugs were originally approved by the US Food and Drug Administration (FDA) for different uses and have different effects; edetate disodium was formerly FDA approved for use in selected patients for the emergency treatment of hypercalcemia or for the control of ventricular arrhythmias associated with cardiac glycoside toxicity. Use of edetate disodium may result in a substantial, and sometimes fatal, decrease in serum calcium concentrations. In June 2008, FDA withdrew its prior approval for edetate disodium because of safety concerns following a review of the risk-benefit profile of the drug. FDA stated that it was not considering additional action regarding edetate calcium disodium at that time; most of the fatalities following administration of an EDTA drug have involved medication errors in which edetate disodium was administered instead of edetate calcium disodium. FDA has not received reports of any fatalities resulting from the administration of edetate calcium disodium that involve a medication error.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011


Edetate Disodium Injection is contraindicated in anuric patients. It is not indicated for the treatment of generalized arteriosclerosis associated with advancing age.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


For more Drug Warnings (Complete) data for Disodium EDTA (22 total), please visit the HSDB record page.


4.3 Drug Indication

Edetate disodium is indicated for emergency treatment of hypercalcemia and digitalis toxicity associated ventricular arrhythmias.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Edetate disodium anhydrous is a polyvalent ion chelator that reduces blood concentrations of calcium or digitalis. It has a long duration of action as patients are generally given 1 daily dose. The therapeutic index is wide, as high doses are generally well tolerated. Patients should be counselled regarding the risk of postural hypotension, effects of myocardial contractility, hypokalemia, hypomagnesemia, and hypoglycemia.


5.2 MeSH Pharmacological Classification

Anticoagulants

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)


Calcium Chelating Agents

Substances that bind to and sequester CALCIUM ions. (See all compounds classified as Calcium Chelating Agents.)


Food Additives

Substances used in the processing or storage of foods or animal feed including ANTIOXIDANTS; FOOD PRESERVATIVES; FOOD COLORING AGENTS; FLAVORING AGENTS; ANTI-INFECTIVE AGENTS; EXCIPIENTS and other similarly used substances. Many of the same substances are used as PHARMACEUTIC AIDS. (See all compounds classified as Food Additives.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Calcium Chelating Activity [MoA]; Decreased Coagulation Factor Activity [PE]; Lead Chelating Activity [MoA]; Lead Chelator [EPC]; Anti-coagulant [EPC]
5.4 Absorption, Distribution and Excretion

Route of Elimination

After intravenous administration, 95% of the dose is recovered in the urine after 24 hours. Oral administration in rats leads to 5.3% recovery in urine and 88.5% recovery in feces.


Volume of Distribution

Data regarding the volume of distribution of edetate disodium anhydrous is not readily available.


Clearance

The mean clearance of edetate in 1 month olds is 54.6mL/min/1.73m2. 2-17 year olds have a mean clearance of 113.9 24.4 mL/min/1.73m2.


After intravenous administration, the chelate formed is excreted in the urine with 50% appearing in 1 hour and over 95% in 24 hours.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


Disodium edentate ... /is/ poorly absorbed from the gastrointestinal tract and /is/ associated with few adverse effects when used as an excipient in pharmaceutical preparations.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 243


Twenty male Sprague-Dawley rats were divided into four groups of five animals each. Rats in group 1 received ip injections of (14)C Disodium EDTA, group 2 received this compound on depilated skin, rats in group 3 received this compound on depilated and abraded skin (abraded every 2 or 3 cm over treated area), and group 4 was the control group. The specific activity of the (14)C Disodium EDTA was 21.6 mCi/mM and it was dissolved in saline to yield a final solution of 50 pCi/mL. Animals that received ip injections got 0.5 mL of this solution, or 25 pCi of (14)C Disodium EDTA. Animals that had the compound applied to the skin received 25 pCi of (14)C Disodium EDTA in the form of an ointment (modulan, mineral oil, petrolatum, cetyl alcohol 35:21 :25:12) spread over an area of 50 sq cm spread over a sheet of thin polyethylene. This sheet was taped to the trunk of each animal. A collar was fixed around the neck of the rats. All animals were decapitated 24 hours after treatment. The tissue distribution (per 100 mg wet organ weight) of (14)C Disodium EDTA 24 hours after ip administration was as follows: liver 577+/- 13, small intestine 631 +/- 25, large intestine 696 +/- 19, and kidney 1964 +/- 220. Twenty-four hours after application on normal skin the tissue distribution was as follows: liver 6 +/- 4, small intestine 99 +/- 22, large intestine 107 +/- 24, and kidneys 29 +/- 12. Twenty-four hours after application on abraded skin the tissue distribution was as follows: liver 139 +/- 34, small intestine 214 +/- 76, large intestine 309 +/- 115, and kidneys 222 +/- 30.

Cosmetic Ingredient Expert Review Panel; Final 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. International Journal of Toxicology 21 (S2): 95-142 (2002)


/Investigators/ reported that rats fed 0.5%, 1.0%, and 5.0% Disodium EDTA for 12 weeks excreted 82.2%, 44.5%, and 45.4%, respectively, of the ingested dose in the urine and feces. The feces contained 99.4%, 98.2%, and 97.5% of the excreted material and the urine contained 0.6%, 1.8%, and 2.5% of the material for the respective doses.

Cosmetic Ingredient Expert Review Panel; Final 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. International Journal of Toxicology 21 (S2): 95-142 (2002)


For more Absorption, Distribution and Excretion (Complete) data for Disodium EDTA (7 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Edetate is almost completely unmetabolized _in vivo_.


5.6 Biological Half-Life

After intravenous administration, the chelate formed is excreted in the urine with 50% appearing in 1 hour and over 95% in 24 hours.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


5.7 Mechanism of Action

Edetate disodium anhydrous chelates divalent and trivalent ions such as magnesium, zinc, and calcium. The chelate is excreted in the urine, reducing concentrations of these ions in the blood.


Edetate disodium injection forms chelates with the cations of calcium and many divalent and trivalent metals. Because of its affinity for calcium, edetate disodium will produce a lowering of the serum calcium level during intravenous infusion. Slow infusion over a protracted period may cause mobilization of extracirculatory calcium stores. Edetate disodium exerts a negative inotropic effect upon the heart.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006).


Edetate disodium likewise forms chelates with other polyvalent metals and produces increases in urinary excretion of magnesium, zinc and other trace elements. It does not form a chelate with potassium but may reduce the serum level and increase urinary loss of potassium.

US Natl Inst Health; DailyMed. Current Medication Information for Endrate (edetate disodium, anhydrous) injection, solution (May 2006). Available from, as of February 16, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=290c3e9c-c0c6-440a-1a9c-46e3e2b07a77


API Reference Price

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25-Aug-2021
10-Jun-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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