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Chemistry

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Also known as: 2809-21-4, Etidronate, 1-hydroxyethylidene-1,1-diphosphonic acid, Hedp, Ehdp, Etidronsaeure
Molecular Formula
C2H8O7P2
Molecular Weight
206.03  g/mol
InChI Key
DBVJJBKOTRCVKF-UHFFFAOYSA-N
FDA UNII
M2F465ROXU

Etidronic Acid
A diphosphonate which affects calcium metabolism. It inhibits ectopic calcification and slows down bone resorption and bone turnover.
Etidronic acid is a Bisphosphonate.
1 2D Structure

Etidronic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1-hydroxy-1-phosphonoethyl)phosphonic acid
2.1.2 InChI
InChI=1S/C2H8O7P2/c1-2(3,10(4,5)6)11(7,8)9/h3H,1H3,(H2,4,5,6)(H2,7,8,9)
2.1.3 InChI Key
DBVJJBKOTRCVKF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(O)(P(=O)(O)O)P(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
M2F465ROXU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (1-hydroxyethylene)diphosphonic Acid

2. (1-hydroxyethylene)diphosphonic Acid, Tetrapotassium Salt

3. 1 Hydroxyethane 1,1 Diphosphonate

4. 1 Hydroxyethylidene 1,1 Bisphosphonate

5. 1,1 Hydroxyethylenediphosphonate

6. 1,1-hydroxyethylenediphosphonate

7. 1-hydroxyethane-1,1-diphosphonate

8. 1-hydroxyethylene Diphosphonate, Disodium

9. 1-hydroxyethylidene-1,1-bisphosphonate

10. Dicalcium Ehdp

11. Dicalcium Etidronate

12. Didronel

13. Diphosphonate, Disodium 1-hydroxyethylene

14. Diphosphonic Acid, Hydroxyethylidene

15. Disodium 1 Hydroxyethylene Diphosphonate

16. Disodium 1-hydroxyethylene Diphosphonate

17. Disodium Etidronate

18. Ehdp

19. Ehdp, Dicalcium

20. Ethanehydroxydiphosphonate

21. Ethanehydroxyphosphate

22. Etidronate

23. Etidronate Disodium

24. Etidronate, Dicalcium

25. Etidronate, Disodium

26. Etidronate, Sodium

27. Etidronate, Tetrapotassium Salt

28. Hedp

29. Hedspa

30. Hydroxyethanediphosphonate

31. Hydroxyethylidene Diphosphonic Acid

32. Phosphonic Acid, (1-hydroxyethylidene)bis-, Disodium Salt

33. Salt Etidronate, Tetrapotassium

34. Sodium Etidronate

35. Tetrapotassium Salt Etidronate

36. Xidifon

37. Xidiphon

38. Xydiphone

2.3.2 Depositor-Supplied Synonyms

1. 2809-21-4

2. Etidronate

3. 1-hydroxyethylidene-1,1-diphosphonic Acid

4. Hedp

5. Ehdp

6. Etidronsaeure

7. Acetodiphosphonic Acid

8. Hydroxyethanediphosphonic Acid

9. Turpinal Sl

10. Oxyethylidenediphosphonic Acid

11. Didronel

12. Dequest 2015

13. Dequest Z 010

14. Phosphonic Acid, (1-hydroxyethylidene)bis-

15. Acido Etidronico

16. Ferrofos 510

17. Acide Etidronique

18. 1-hydroxyethane-1,1-diphosphonate

19. 1-hydroxyethane-1,1-diphosphonic Acid

20. Diphosphonate (base)

21. (1-hydroxyethane-1,1-diyl)diphosphonic Acid

22. 1-hydroxyethanediphosphonic Acid

23. Dequest 2010

24. (1-hydroxyethylidene)diphosphonic Acid

25. 1-hydroxyethane-1,1-bisphosphonic Acid

26. Ethane-1-hydroxy-1,1-diphosphonic Acid

27. (hydroxyethylidene)diphosphonic Acid

28. Ethane-1-hydroxy-1,1-diphosphonate

29. (1-hydroxyethylene)diphosphonic Acid

30. Acide Etidronique [inn-french]

31. Acido Etidronico [inn-spanish]

32. Acidum Etidronicum [inn-latin]

33. 1,1,1-ethanetriol Diphosphonate

34. 1-hydroxyethylidene-1,1-bisphosphonate

35. 1-hydroxy-1,1-diphosphonoethane

36. (1-hydroxyethylidene)bis(phosphonic Acid)

37. Acidum Etidronicum

38. (1-hydroxyethylidene)bisphosphonic Acid

39. (1-hydroxyethane-1,1-diyl)bis(phosphonic Acid)

40. Hydroxyethane-1,1-diphosphonic Acid

41. 1000sl

42. (1-hydroxyethylidene)diphoshonic Acid

43. (1-hydroxy-1-phosphonoethyl)phosphonic Acid

44. Phosphonic Acid, (1-hydroxyethylidene)di-

45. (1-hydroxy-1-phosphono-ethyl)phosphonic Acid

46. Chembl871

47. Nsc-227995

48. M2f465roxu

49. Ethane-1-hydroxy-1,1-bisphosphonic Acid

50. Chebi:4907

51. 2809-21-4 (freeacid)

52. M05ba01

53. 1-hydroxyethane 1,1-diphosphonic Acid

54. (1-hydroxy-ethylidene)diphosphonic Acid

55. (1-hydroxyethan-1,1-diyl)bis(phosphonic Acid)

56. (1-hydroxy-1,1-ethanediyl)bis(phosphonic Acid)

57. Phosphonic Acid, P,p'-(1-hydroxyethylidene)bis-

58. Etidronic Acid [usan:inn:ban]

59. Rp 61

60. Smr000038750

61. 1-hydroxyethylidene-1,1-biphosphonate

62. Hsdb 5898

63. 1-hydroxyethylidenediphosphonic Acid

64. Ncgc00159352-02

65. Einecs 220-552-8

66. Mfcd00070585

67. Phosphonic Acid, 1-hydroxy-1,1-ethanediyl Ester

68. Unii-m2f465roxu

69. Nsc 227995

70. Brn 1789291

71. Etidronicacid

72. Etidronic Acid (usan/inn)

73. Etidronic-acid

74. (1-hydroxyethylidene)bisphosphonic Acid Monohydrate

75. 1-hydroxy Ethylidene

76. Ethane-1-hydroxy-1,1-bisphosphonate

77. Hdepa

78. Hedpa

79. Oedfk

80. Oedp

81. Etidronate (didronel)

82. 1-hydroxyethylidene-1,1-diphosphonicacid

83. Prestwick0_000863

84. Prestwick1_000863

85. Prestwick2_000863

86. Prestwick3_000863

87. Dsstox_cid_3028

88. Etidronate [vandf]

89. Ec 220-552-8

90. Dsstox_rid_76837

91. Etidronic Acid [mi]

92. Dsstox_gsid_23028

93. Schembl18607

94. Bspbio_000905

95. Etidronic Acid [inn]

96. 0-02-00-00171 (beilstein Handbook Reference)

97. Mls002207267

98. Mls002695948

99. Etidronic Acid [hsdb]

100. Etidronic Acid [inci]

101. Etidronic Acid [usan]

102. Spbio_002826

103. Bpbio1_000997

104. Gtpl7184

105. Etidronic Acid [mart.]

106. Dtxsid6023028

107. Etidronic Acid [who-dd]

108. Hms3604e03

109. Hy-b0302

110. Zinc3830813

111. Tox21_200417

112. Bbl028139

113. Bdbm50115102

114. Dl-390

115. Etidronic Acid 60% Aqueous Solution

116. Nsc227995

117. S1857

118. Stk721995

119. Akos005524039

120. Etidronic Acid, 60% Aqueous Solution

121. Ccg-266618

122. Db01077

123. Hydroxyethylidene-1,1-diphosphonic Acid

124. S12329

125. Ncgc00159352-04

126. Ncgc00159352-05

127. Ncgc00159352-06

128. Ncgc00257971-01

129. 1-hydroxyethane-1,1-diyldiphosphonic Acid

130. Cas-2809-21-4

131. 1-hydroxy Ethylidene-1,1-diphosphonic Acid

132. Ft-0607934

133. Ft-0668439

134. H0587

135. (1-hydroxy-1-phosphono-ethyl)-phosphonic Acid

136. A23202

137. C07736

138. D02373

139. J-504794

140. Q2758338

141. 1-hydroxy Ethylidene-1,1-diphosphonic Acid (powder)

142. (1-hydroxyethane-1,1-diyl)diphosphonic Acid Monohydrate

143. 1-hydroxyethylidenediphosphonic Acid 60% Aqueous Solution

144. 1-hydroxyethane-1,1,-diphosphonic Acid 60% Aqueous Solution

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 206.03 g/mol
Molecular Formula C2H8O7P2
XLogP3-3.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass205.97452659 g/mol
Monoisotopic Mass205.97452659 g/mol
Topological Polar Surface Area135 Ų
Heavy Atom Count11
Formal Charge0
Complexity211
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDidronel
PubMed HealthEtidronate (By mouth)
Drug ClassesCalcium Regulator
Active IngredientEtidronate disodium
Dosage FormTablet
RouteOral
Strength200mg; 400mg
Market StatusPrescription
CompanyProcter And Gamble

2 of 2  
Drug NameDidronel
PubMed HealthEtidronate (By mouth)
Drug ClassesCalcium Regulator
Active IngredientEtidronate disodium
Dosage FormTablet
RouteOral
Strength200mg; 400mg
Market StatusPrescription
CompanyProcter And Gamble

4.2 Therapeutic Uses

Chelating Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


EXPTL USE: 1-HYDROXYETHANE-1,1-DIPHOSPHONIC ACID, DICHLOROMETHANEDIPHOSPHONIC ACID OR THEIR SALTS OR ESTERS REDUCED THE INCIDENCE OF TUMOR CELL METASTASIS IN BONE IN HUMANS.

HEDGLIN WL, MARTODAM RR; ALKANEDIPHOSPHONATE INHIBITORS OF TUMOR CELL METASTASIS; BELG PATENT NUMBER 890453 3/22/82 (PROCTER AND GAMBLE CO)


BONE SCANNING AGENT WHEN LABELED WITH (99M)TECHNETIUM

CITRIN DL; TOXICITY OF HEDP IN HUMANS; J NUCL MED 17(5) 417 (1976)


CHELATING AGENT; CALCIUM REGULATING AGENT IN HUMAN MEDICINE

SRI


MEDICATION (VET): 1-HYDROXYETHANE-1,1-DIPHOSPHONIC ACID, DICHLOROMETHANEDIPHOSPHONIC ACID OR THEIR SALTS OR ESTERS REDUCED THE INCIDENCE OF TUMOR CELL METASTASIS IN BONE IN ANIMALS.

HEDGLIN WL, MARTODAM RR; ALKANEDIPHOSPHONATE INHIBITORS OF TUMOR CELL METASTASIS; BELG PATENT NUMBER 890453 3/22/82 (PROCTER AND GAMBLE CO)


4.3 Drug Indication

Etidronate is indicated to treat Paget's disease of bone, as well as the treatment and prevention of heterotropic ossification after total hip replacement of spinal cord injury.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Etidronic acid is a first generation bisphosphonate that inhibits the action of osteoclasts, preventing bone resporption. It has a wide therapeutic index as overdoses are not associated with severe toxicity and a long duration of action as it slowly releases from the bone. Patients should be counselled regarding the risk of upper gastrointestinal adverse reactions.


5.2 MeSH Pharmacological Classification

Bone Density Conservation Agents

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ETIDRONIC ACID
5.3.2 FDA UNII
M2F465ROXU
5.3.3 Pharmacological Classes
Chemical Structure [CS] - Diphosphonates
5.4 ATC Code

M - Musculo-skeletal system

M05 - Drugs for treatment of bone diseases

M05B - Drugs affecting bone structure and mineralization

M05BA - Bisphosphonates

M05BA01 - Etidronic acid


5.5 Absorption, Distribution and Excretion

Absorption

Etidronic acid has an oral bioavailability of 1-10%. Further data regarding pharmacokinetics of etidronic acid are not readily available.


Route of Elimination

Absorbed etidronic acid is eliminated in the urine, while the unabsorbed drug is eliminated in the feces.


Volume of Distribution

Etidronic acid has a volume of distribution of 0.3-1.3L/kg.


Clearance

Etidronic acid has a renal clearance of 0.09L/kg/h.


THE DISTRIBUTION OF TECHNETIUM-99M HEDP IN NORMAL HUMAN ORGANS WAS MEASURED.

GROSSMAN LW ET AL; MEASUREMENTS OF THE DISTRIBUTION OF TECHNETIUM-99M SULFUR COLLOID AND TECHNETIUM-99M HEDP IN NORMAL HUMANS; MED PHYS 10(1) 79 (1983)


THE BONE-SEEKING AGENT (99M)TC-SN-1-HYDROXYETHYLIDENE-1,1-DIPHOSPHONIC ACID UNEXPECTEDLY BINDS TO PARTICLES OF HUMAN ARTICULAR CARTILAGE AS WELL AS CORTICAL BONE IN VITRO. MECHANISMS ADDITIONAL TO THE SIMPLE IONIC ATTRACTION BETWEEN THE PHOSPHONATE GROUPS OF HEDP & METAL CATIONS SUCH AS CA2+ ARE RESPONSIBLE FOR THE UPTAKE OF (99M)TC-HEDP BY BODY TISSUES.

EVANS CH, MEARS DC; BINDING OF THE BONE-SEEKING AGENT 99MTC-1-HYDROXYETHYLIDENE-1,1-DIPHOSPHONIC ACID TO CARTILAGE AND COLLAGEN IN VITRO AND ITS STIMULATION BY ERBIUM(3+) ION AND LOW PH; CALCIF TISSUE INT 32(2) 91 (1980)


THE AFFINITY CONSTANT WHICH CHARACTERIZES THE BINDING OF (99)TC-HYDROXYETHYLENE DIPHOSPHONATE (TC-HEDP) WITH HUMAN SERUM ALBUMIN WAS 7.8X10+4. A SINGLE SLOPE WAS OBTAINED.

DEWANJEE MK ET AL; AFFINITY CONSTANTS OF TECHNETIUM-99-PERTECHNETATE AND TECHNETIUM-CHELATES WITH HUMAN SERUM ALBUMIN; RADIOPHARM 2 (PROC INT SYMP, 2ND) 435 (1979)


5.6 Metabolism/Metabolites

Etidronic acid is not metabolized _in vivo_


5.7 Biological Half-Life

The half life of etidronate is approximately 1-6 hours.


5.8 Mechanism of Action

Bisphosphonates are taken into the bone where they bind to hydroxyapatite. Bone resorption by osteoclasts causes local acidification, releasing the bisphosphonate, which is taken into the osteoclast by fluid-phase endocytosis. Endocytic vesicles become acidified, releasing bisphosphonates into the cytosol of osteoclasts where they act. Osteoclasts mediate resorption of bone. When osteoclasts bind to bone they form podosomes, ring structures of F-actin. Disruption of the podosomes causes osteoclasts to detach from bones, preventing bone resorption. First generation bisphosphonates closely mimic the structure of pyrophosphate, which can be incorporated into ATP anologues that cannot be hydrolyzed, disrupting all ATP mediated actions of osteoclasts.


MALE RATS WERE INJECTED WITH VEHICLE (CONTROL GROUP), 0.4 OR 4.0 MG/KG/DAY OF ETHANE-1-HYDROXY-1,1-DIPHOSPHONATE (EHDP). AFTER 6 DAYS OF EHDP TREATMENT ALL RATS RECEIVED 6 SC INJECTIONS OF (3)H-THYMIDINE AT 8 HR INTERVALS. AFTER 6 DAYS OF EHDP PRE-TREATMENT THE MULTIPLE LABELING INDEX OF OSTEOPROGENITOR CELLS WAS REDUCED WITH 4.0 MG/KG/DAY DOSE OF EHDP. EHDP CAUSED INCR IN RATE OF INCORP & ACCUM OF (3)H-THYMIDINE NUCLEI IN OSTEOCLASTS. EHDP CAUSES AN ACCELERATED RATE OF OSTEOCLAST PRODN FROM PRECURSOR CELLS IN SPITE OF ITS ABILITY TO SLOW BONE RESORPTION.

MILLER SC ET AL; ETHANE-1-HYDROXY-1,1-DIPHOSPHONATE (EHDP) EFFECTS ON INCORPORATION AND ACCUMULATION OF OSTEOCLAST NUCLEI; CALCIF TISSUE RES 22(3) 243 (1977)


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19-Jan-2023
13-Apr-2024
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