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2D Structure
Also known as: Diethylenetriaminepentaacetic acid, 67-43-6, Dtpa, Detapac, Detarex, Complexon v
Molecular Formula
C14H23N3O10
Molecular Weight
393.35  g/mol
InChI Key
QPCDCPDFJACHGM-UHFFFAOYSA-N
FDA UNII
7A314HQM0I

An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.
Pentetic acid is a Lead Chelator. The mechanism of action of pentetic acid is as a Lead Chelating Activity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid
2.1.2 InChI
InChI=1S/C14H23N3O10/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27)
2.1.3 InChI Key
QPCDCPDFJACHGM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CN(CC(=O)O)CC(=O)O)N(CCN(CC(=O)O)CC(=O)O)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
7A314HQM0I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ca-dtpa

2. Cadtpa

3. Calcium Trisodium Pentetate

4. Cana-dtpa

5. Detapac

6. Diethylenetriamine Pentaacetic Acid

7. Dtpa

8. Indium Dtpa

9. Indium-dtpa

10. Mn-dtpa

11. Pentaacetic Acid, Diethylenetriamine

12. Pentacin

13. Pentacine

14. Pentaind

15. Pentetate Calcium Trisodium

16. Pentetate Zinc Trisodium

17. Pentetate, Calcium Trisodium

18. Pentetates

19. Penthanil

20. Sn-dtpa

21. Zinc Dtpa

22. Zinc-dtpa

2.3.2 Depositor-Supplied Synonyms

1. Diethylenetriaminepentaacetic Acid

2. 67-43-6

3. Dtpa

4. Detapac

5. Detarex

6. Complexon V

7. Titriplex V

8. Perma Kleer

9. Monaquest Cai

10. Hamp-ex Acid

11. Penthanil

12. Dabeersen 503

13. Chel 330 Acid

14. Diethylenetriamine Pentaacetic Acid

15. Pentacarboxymethyldiethylenetriamine

16. Chel Dtpa

17. Pentetate

18. Penthamil

19. Acidum Penteticum

20. H5dtpa

21. (diethylenetrinitrilo)pentaacetic Acid

22. Diethylenetriamine-n,n,n',n'',n''-pentaacetic Acid

23. Detpa

24. 2-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]acetic Acid

25. Glycine, N,n-bis(2-(bis(carboxymethyl)amino)ethyl)-

26. Monaquest

27. 1,1,4,7,7-diethylenetriaminepentaacetic Acid

28. Dtp-a

29. N,n-bis{2-[bis(carboxymethyl)amino]ethyl}glycine

30. Diethylene Triamine Pentaacetic Acid

31. Nsc 7340

32. Glycine, N,n-bis[2-[bis(carboxymethyl)amino]ethyl]-

33. Diethylenetriaminepentacetic Acid

34. Nsc-7340

35. 3,6,9-triazaundecanedioic Acid, 3,6,9-tris(carboxymethyl)-

36. Mfcd00004289

37. N,n-bis[2-[bis(carboxymethyl)amino]ethyl]glycine

38. 7a314hqm0i

39. Chel 330

40. Diethylenetriaminepentaaceticacid

41. Acetic Acid, ((carboxymethylimino)bis(ethylenenitrilo))tetra-

42. Chebi:35739

43. Nsc7340

44. Diethylenetriaminepentaacetate

45. (diethylenetriamine)pentaacetic Acid

46. N,n-bis(2-(bis(carboxymethyl)amino)ethyl)glycine

47. N,n-bis(2-(bis-(carboxymethyl)amino)ethyl)-glycine

48. Acetic Acid, 2,2',2'',2'''-(((carboxymethyl)imino)bis(2,1-ethanediylnitrilo))tetrakis-

49. Diethylenetriaminepentaacetic Acid;dtpa

50. Cas-67-43-6

51. Ncgc00015360-05

52. (((carboxymethyl)imino)bis(ethylenenitrilo))tetraacetic Acid

53. Dissolvine D

54. Dsstox_cid_3434

55. Dsstox_rid_77025

56. Dsstox_gsid_23434

57. Penthamil (van)

58. N,n,n',n'',n''-diethylenetriaminepentaacetic Acid

59. [[(carboxymethyl)imino]bis(ethylenenitrilo)]tetraacetic Acid

60. 2-[bis({2-[bis(carboxymethyl)amino]ethyl})amino]acetic Acid

61. Acido Pentetico

62. Acide Pentetique

63. [[(carboxymethyl)imino]bis(1,2-ethanediylnitrilo)tetraacetic Acid]

64. 2,2',2'',2''',2''''-(ethane-1,2-diylnitrilo)pentaacetic Acid

65. Diethylenetriaminepentaacetic Acid, 99%

66. Acide Pentetique [inn-french]

67. Acido Pentetico [inn-spanish]

68. Acidum Penteticum [inn-latin]

69. Sr-01000075826

70. Einecs 200-652-8

71. Brn 1810219

72. Unii-7a314hqm0i

73. Acetic Acid, [(carboxymethylimino)bis(ethylenenitrilo)]tetra-

74. Pentetic-acid

75. N-carboxymethyliminobis(ethylenenitrilo)tetra(acetic Acid)

76. Acetic Acid, 2,2',2'',2'''-[[(carboxymethyl)imino]bis(2,1-ethanediylnitrilo)]tetrakis-

77. Pentetic Acid [usan:usp:inn:ban]

78. Nanodtpa

79. 2,2'-(carboxymethylimino)bis(ethyliminodiessigsaeure)

80. Pentetic Acid; Dtpa

81. Dtpa (pentetic Acid)

82. Plexene D (salt/mix)

83. Syntron C (salt/mix)

84. Kiresuto P (salt/mix)

85. Tetralon B (salt/mix)

86. Prestwick0_000941

87. Prestwick1_000941

88. Prestwick2_000941

89. Prestwick3_000941

90. Lopac-d-6518

91. Pentetate [vandf]

92. Chel 330 (salt/mix)

93. Chembl780

94. Ec 200-652-8

95. Pentetic Acid (usp/inn)

96. Pentetic Acid [ii]

97. Pentetic Acid [mi]

98. Pentetic Acid [inn]

99. Lopac0_000431

100. Schembl17138

101. Bspbio_000902

102. Pentetic Acid [inci]

103. Pentetic Acid [usan]

104. 4-04-00-02454 (beilstein Handbook Reference)

105. Nanodtpa Component Dtpa

106. Pentetic Acid [vandf]

107. Spbio_003061

108. Pentetic Acid [mart.]

109. Bpbio1_000994

110. Pentetic Acid [usp-rs]

111. Pentetic Acid [who-dd]

112. Dtxsid2023434

113. Hms1570n04

114. Hms2094e03

115. Hms2097n04

116. Hms3261g04

117. Hms3714n04

118. Pharmakon1600-01506082

119. Hy-b1335

120. Tox21_110131

121. Tox21_500431

122. Ac-333

123. Bbl002988

124. Nsc759314

125. S4824

126. Stk373226

127. Zinc19419017

128. Pentetic Acid [usp Monograph]

129. Wln: Qv1n1vq2n1vq2n1vq1vq

130. Akos005446652

131. Tox21_110131_1

132. Ccg-204523

133. Db14007

134. Lp00431

135. Nanodtpa Zn-dtpa Component Dtpa

136. Nsc-759314

137. Sdccgsbi-0050416.p003

138. Nano-dtpa Capsule Component Dtpa

139. Ncgc00015360-01

140. Ncgc00015360-02

141. Ncgc00015360-03

142. Ncgc00015360-04

143. Ncgc00015360-06

144. Ncgc00015360-08

145. Ncgc00015360-09

146. Ncgc00015360-12

147. Ncgc00093852-01

148. Ncgc00093852-02

149. Ncgc00093852-03

150. Ncgc00261116-01

151. Vs-01284

152. Sbi-0050416.p002

153. 1,4,7,7-diethylenetriaminepentaacetic Acid

154. Ab00375916

155. Cs-0013088

156. D0504

157. Eu-0100431

158. Ft-0624901

159. D 6518

160. D05422

161. Diethylenetriaminepentaacetic Acid, P.a., 99%

162. Ab00375916-04

163. Ab00375916_05

164. Diethylenetriamine Pentaacetic Acid [vandf]

165. Diethylenetriamine-n,n',n'',n''-pentaacetic Acid

166. Glycine,n-bis[2-[bis(carboxymethyl)amino]ethyl]-

167. Q416487

168. N,n-bis {2-[bis(carboxymethyl)amino]ethyl}glycine

169. Sr-01000075826-1

170. Sr-01000075826-4

171. Brd-k40621224-001-01-8

172. Diethylenetriaminepentaacetic Acid, >=98% (titration)

173. Diethylenetriaminepentaacetic Acid, >=99% (titration)

174. N, {n-bis[2-[bis(carboxymethyl)amino]ethyl]glycine}

175. Glycine, {n,n-bis[2-[bis(carboxymethyl)amino]ethyl]-}

176. 3,9-triazaundecanedioic Acid, 3,6,9-tris(carboxymethyl)-

177. Diethylenetriamine- N,n,n',n',n''-pentaacetic Acid

178. Dtpa, Diethylenetriamine-n,n,n',n'',n''-pentaacetic Acid

179. (((carboxymethyl)imino)bis(ethylenenitrilo))-tetraacetic Acid

180. {[[(carboxymethyl)imino]bis(ethylenenitrilo)]tetraacetic} Acid

181. Acetic Acid, {[(carboxymethylimino)bis(ethylenenitrilo)]tetra-}

182. Diethylenetriaminepentaacetic Acid, For Complexometry, >=99.0%

183. Pentetic Acid, United States Pharmacopeia (usp) Reference Standard

184. Acetic Acid,2',2'',2'''-[[(carboxymethyl)imino]bis(2,1-ethanediylnitrilo)]tetrakis-

185. 1004765-76-7

186. 2,2',2'',2'''-(2,2'-(carboxymethylazanediyl)bis(ethane-2,1-diyl)bis(azanetriyl))tetraacetic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 393.35 g/mol
Molecular Formula C14H23N3O10
XLogP3-8.5
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count13
Rotatable Bond Count16
Exact Mass393.13834394 g/mol
Monoisotopic Mass393.13834394 g/mol
Topological Polar Surface Area196 Ų
Heavy Atom Count27
Formal Charge0
Complexity481
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 4  
Drug NameAn-dtpa
PubMed HealthTechnetium Tc 99m Pentetate (Injection)
Drug ClassesDiagnostic Agent, Radiopharmaceutical Imaging
Drug LabelEach kit consists of reaction vials which contain the sterile, non-pyrogenic, non-radioactive ingredients necessary to produce Technetium Tc 99m Pentetate Injection for diagnostic use by intravenous injection. Each 10 mL reaction vial contains 20 mg...
Active IngredientTechnetium tc-99m pentetate kit
Dosage FormInjectable
RouteInjection
Strengthn/a
Market StatusPrescription
CompanyJubilant Draximage

2 of 4  
Drug NameDtpa
Active IngredientTechnetium tc-99m pentetate kit
Dosage FormInjectable
RouteInjection
Strengthn/a
Market StatusPrescription
CompanyDraximage

3 of 4  
Drug NameAn-dtpa
PubMed HealthTechnetium Tc 99m Pentetate (Injection)
Drug ClassesDiagnostic Agent, Radiopharmaceutical Imaging
Drug LabelEach kit consists of reaction vials which contain the sterile, non-pyrogenic, non-radioactive ingredients necessary to produce Technetium Tc 99m Pentetate Injection for diagnostic use by intravenous injection. Each 10 mL reaction vial contains 20 mg...
Active IngredientTechnetium tc-99m pentetate kit
Dosage FormInjectable
RouteInjection
Strengthn/a
Market StatusPrescription
CompanyJubilant Draximage

4 of 4  
Drug NameDtpa
Active IngredientTechnetium tc-99m pentetate kit
Dosage FormInjectable
RouteInjection
Strengthn/a
Market StatusPrescription
CompanyDraximage

4.2 Drug Indication

DTPA is widely used in industry and medicine. As a medical agent, it is approved for its use in medical imaging and for the decorporation of internally deposited radionuclides. It is FDA approved for the treatment of individuals with known or suspected internal contamination with plutonium, americium or curium to increase the rates of elimination. Due to the pharmacokinetic elimination by the kidneys, pentetic acid conjugated with technetium Tc-99m is being used clinically to estimate physiological parameters such as glomerular filtration rat and effective renal plasma flow.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

There are reports in vivo of low stability of complexes of DPTA with uranium and neptunium which is being reported to cause deposition of the radionuclides into the tissues. In the case of plutonium, some preclinical studies have shown a very high urine elimination efficacy 1 hour after initial contamination. This efficacy is conserved for approximately 24 hours while the radiocontaminant is circulating. When the radionuclide is inhaled, it has been reported a DPTA-induced reduction of even 98% of the lung deposits. It is important to consider that pentetic acid can bind directly to other trace metals in the body which can cause deficiencies.


5.2 MeSH Pharmacological Classification

Chelating Agents

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)


Iron Chelating Agents

Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems. (See all compounds classified as Iron Chelating Agents.)


Antidotes

Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PENTETIC ACID
5.3.2 FDA UNII
7A314HQM0I
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Lead Chelator
5.4 Absorption, Distribution and Excretion

Absorption

DTPA and its trisodium salts present a very poor bioavailability after oral administration. Therefore, the normal administration of DTPA is done by slow intravenous infusion or inhalation with a nebulizer. When inhaled, the absorption is of about 20% of the administered dose.


Route of Elimination

DTPA metal complexes are quickly excreted in the urine.It is predominantly excreted by the kidney and it is not excreted by non-renal routes to any significant extent.


Volume of Distribution

The volume of distribution of DPTA is 17 L.


Clearance

Pentetic acid presents a very rapid blood clearance which explains for the short half-life. The reported clearance rate in patients with normal renal function is 80-120ml/min.


5.5 Metabolism/Metabolites

Pentetic acid and its derivatives present a very minimal metabolism in the body.


5.6 Biological Half-Life

In preclinical studies, DTPA has been shown to present a very short half-life of 18.5-31.8 min after intravenous administration.


5.7 Mechanism of Action

The calcium and zinc trisodium salts of DTPA achieve the therapeutical potential by exchanging calcium and zinc cations with transuranic radionuclides to form higher affinity complexes and then promote their elimination by glomerular filtration into the urine. DTPA as an acid acts in a very similar way by sequestering ions with its eight coordinate bond forming sites.