45:
340:
221:
715:(USFDA) determined zinc-DTPA and calcium-DTPA to be safe and effective for treatment of those who have breathed in or otherwise been contaminated internally by plutonium, americium, or curium. The recommended treatment is for an initial dose of calcium-DTPA, as this salt of DTPA has been shown to be more effective in the first 24 hours after internal contamination by plutonium, americium, or curium. After that time has elapsed both calcium-DTPA and zinc-DTPA are similarly effective in reducing internal contamination with
554:
819:. It is unclear to what extent does DTPA really contribute to protect dissolved Fe against air oxidation and if the Fe(III)-DTPA complex cannot also be directly assimilated by aquatic plants simply because of its enhanced solubility. Under natural conditions,
1449:
Kahn, Daniel; J. Christopher Austin; Robert T Maguire; Sara J Miller; Jack
Gerstbrein; Richard D Williams (1999). "A Phase II Study of Yttrium-Capromab Pendetide in the Treatment of Men with Prostate Cancer Recurrence Following Radical Prostatectomy".
1288:
Colodette, J. L. (1987). Factors affecting hydrogen peroxide stability in the brightening of mechanical and chemi-mechanical pulps (Doctoral dissertation, State
University of New York College of Environmental Science and
1202:(2) Brown, M. A.; Paulenova, A.; Gelis, A. V. "Aqueous Complexation of Thorium(IV), Uranium(IV), Neptunium(IV), Plutonium(III/IV), and Cerium(III/IV) with DTPA" Inorganic Chemistry 2012, volume 51, 7741-7748.
1240:
Caravan, Peter; Ellison, Jeffrey J.; McMurry, Thomas J. ; Lauffer, Randall B. "Gadolinium(III) Chelates as MRI Contrast Agents: Structure, Dynamics, and
Applications" Chem. Revs. 1999, volume 99, pp.
637:, DTPA wraps around a metal ion by forming up to eight bonds. Its complexes can also have an extra water molecule that coordinates the metal ion. Transition metals, however, usually form less than eight
1092:
Moeller, T.; Thompson, L. C. Observations on the rare earths—LXXV(1): The stabilities of diethylenetriaminepentaacetic acid chelates. Journal of
Inorganic and Nuclear Chemistry 1962, 24, 499.
138:
692:
salt (Ca or Zn-DTPA), since these ions are readily displaced by more highly charged cations and mainly to avoid to depleting them in the organism. DTPA forms complexes with
1298:
Burnett, L. C. "Final Report on the Safety
Assessment of Pentasodium Pentetate and Pentetic Acid as Used in Cosmetics" International Journal of Toxicology 2008, 27, 71-92.
1128:"Spectroscopic and Computational Characterization of Diethylenetriaminepentaacetic Acid/Transplutonium Chelates: Evidencing Heterogeneity in the Heavy Actinide(III) Series"
1254:
Cohen, Gerald; Lewis, David; Sinet, Pierre M. (1981). "Oxygen consumption during the Fenton-type reaction between hydrogen peroxide and a ferrous-chelate (Fe-DTPA)".
965:
Compounds that are structurally related to DTPA are used in medicine, taking advantage of the high affinity of the triaminopentacarboxylate scaffold for metal ions.
870:
in the chlorine-free process of paper making. Several thousands tons of DTPA are produced annually for this purpose in order to limit the non-negligible losses of H
1308:
Fisher, Anna E.O.; Maxwell, Suzette C.; Naughton, Declan P. (2004). "Superoxide and hydrogen peroxide suppression by metal ions and their EDTA complexes".
1106:
J. Roger Hart "Ethylenediaminetetraacetic Acid and
Related Chelating Agents" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
645:. For example, in its complex with copper(II), DTPA binds in a hexadentate manner utilizing the three amine centres and three of the five carboxylates.
567:
815:
of iron for aquatic plants. It contributes so to maintain iron under a dissolved form (probably a mix of Fe(II) and Fe(III) DTPA complexes) in the
1083:
Anonymous
Pentetic Acid. In Dictionary of Organic Compounds, Sixth Edition; Buckingham, J., Macdonald, F., Eds.; CRC Press: 1996; Vol. 5, pp 1188.
953:
ions in the chlorine-free Kraft pulping processes (total chlorine free (TCF) and environmental chlorine free (ECF) processes). DTPA decreases the
727:, and zinc-DTPA is less likely to deplete the body's normal levels of zinc and other metals essential to health. Each drug can be administered by
363:
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)
823:, in the absence of complexing DTPA, Fe is more easily assimilated by most organisms, because of its 100-fold higher solubility than that of Fe.
1359:
and DTPA on the characteristics and treatment of TCF (totally chlorine-free) and ECF (elementally chlorine-free) kraft pulping effluents".
379:
1606:
1577:
1126:
Deblonde, Gauthier J.-P.; Kelley, Morgan P.; Su, Jing; Batista, Enrique R.; Yang, Ping; Booth, Corwin H.; Abergel, Rebecca J. (2018).
1219:
641:. So, after forming a complex with a metal, DTPA still has the ability to bind to other reagents, as is shown by its derivative
1771:
1742:
1835:
562:
1487:"Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides"
985:
1569:
1553:
981:
354:
1788:
973:, the chelator tiuxetan is a modified version of DTPA whose carbon backbone contains an isothiocyanatobenzyl and a
630:
574:
1691:
654:
606:
44:
1599:
74:
1064:
712:
297:
216:
830:
DTPA is also used to remove dissolved ferrous and ferric ions (and other redox-active metal ions, such as
318:
1584:
1029:
1015:
745:. DTPA improves the resolution of magnetic resonance imaging (MRI) by forming a soluble complex with a
739:
489:
178:
1830:
1815:
1592:
780:
933:
An unexpected negative environmental impact of chelating agents, as DTPA, is their toxicity for the
905:
to deactivate redox-active metal ions such as Fe(II)/(III), Mn(II)/(IV) and Cu(I)/(II) perpetuating
1825:
1059:
954:
598:
335:
941:
effluents. Most of the DTPA worldwide production (several thousands of tons) is intended to avoid
1776:
1747:
1033:
1220:""FDA Approves Drugs to Treat Internal Contamination from Radioactive Elements" (press release)"
629:
assuming that each nitrogen centre and each –COO group counts as a centre for coordination. The
867:
1543:
605:
backbone with five carboxymethyl groups. The molecule can be viewed as an expanded version of
1820:
536:
57:
970:
306:
17:
198:
8:
1054:
890:
855:
758:
732:
104:
1182:
V. V. Fomenko, T. N. Polynova, M. A. Porai-Koshits, G. L. Varlamova and N. I. Pechurova
339:
220:
158:
114:
1519:
1486:
1431:
750:
662:
602:
30:
For the combined diphtheria-tetanus-acellular pertussis vaccine used in
Australia, see
1448:
1372:
1267:
764:
DTPA under the form of iron(II) chelate (Fe-DTPA, 10 – 11 wt. %) is also used as
1619:
1549:
1542:
Chowdhury, Rajat; Wilson, Iain; Rofe, Christopher; Lloyd-Jones, Graham (2013-07-08).
1524:
1506:
1467:
1423:
1415:
1376:
1333:
1325:
1271:
1165:
1157:
1149:
1019:
942:
918:
843:
1435:
269:
1514:
1498:
1459:
1407:
1368:
1317:
1263:
1203:
1187:
1139:
1107:
1049:
1036:
934:
906:
478:
402:
1757:
1623:
863:
812:
262:
92:
dtpa; Diethylenetriaminepentaacetic acid; Penta(carboxymethyl)diethylenetriamine
1782:
1502:
1321:
1025:
910:
742:
618:
545:
609:
and is used similarly. It is a white solid with limited solubility in water.
1809:
1716:
1640:
1510:
1419:
1380:
1329:
1275:
1153:
1111:
938:
776:
772:
467:
457:
209:
1668:
1528:
1471:
1463:
1427:
1337:
1184:
Crystal structure of copper (II) diethylenetriaminepentaacetate monohydrate
1169:
1144:
1127:
974:
816:
638:
1732:
1696:
1686:
1663:
1658:
765:
512:
1614:
668:
DTPA has been considered for treatment of radioactive materials such as
1573:
1393:
1191:
1011:
914:
808:
768:
746:
436:
189:
1207:
1161:
1615:
989:
950:
886:
839:
831:
827:
728:
720:
716:
701:
673:
669:
658:
642:
634:
626:
1411:
1395:
544:
Except where otherwise noted, data are given for materials in their
1708:
1394:
Milenic, Diane E.; Erik D. Brady; Martin W. Brechbiel (June 2004).
997:
957:(BOD) of activated sludges and therefore their microbial activity.
922:
677:
633:
for its complexes are about 100 greater than those for EDTA. As a
237:
137:
1004:
993:
882:
697:
693:
685:
622:
249:
1632:
835:
804:
754:
724:
705:
169:
1541:
680:. In theory, these complexes are more apt to be eliminated in
1737:
859:
800:
681:
281:
149:
127:
323:
1678:
1650:
1222:. United States Food and Drug Administration. 19 June 2015
946:
902:
689:
532:
228:
79:
2,2′,2′′,2′′′-{bis(ethane-2,1-diylnitrilo)}tetraacetic acid
31:
881:
DTPA chelating properties are also useful in deactivating
862:
capacity of the hydrogen peroxide stock which is used as
1125:
1307:
1186:
Journal of
Structural Chemistry, 1973, Vol. 14, 529.
731:
for those who have breathed in contamination, and by
1310:
387:C(CN(CC(=O)O)CC(=O)O)N(CCN(CC(=O)O)CC(=O)O)CC(=O)O
1807:
1351:Larisch, B.C.; Duff, S.J.B. (1997). "Effect of H
268:
261:
1253:
1003:Pentetreotide is a modified DTPA attached to a
625:. Thus, the penta-anion DTPA is potentially an
113:
1282:
893:. DTPA is used in over 150 cosmetic products.
811:of Fe and Fe ions in water, and therefore the
771:. The more soluble form of iron, Fe(II), is a
1600:
1452:Cancer Biotherapy & Radiopharmaceuticals
1396:"Antibody-targeted radiation cancer therapy"
1344:
1249:
1247:
1121:
1119:
799:O poorly soluble oxy-hydroxides after their
779:. By binding to Fe ions DTPA prevents their
1350:
1301:
992:(GYK-DTPA) is a modified DTPA containing a
1607:
1593:
1578:Centers for Disease Control and Prevention
612:
338:
219:
197:
1518:
1244:
1143:
1116:
1102:
1100:
1098:
1010:DTPA and derivatives are used to chelate
996:linker used to connect the chelate to an
648:
305:
1568:This article incorporates material from
735:for those contaminated by other routes.
1132:Angewandte Chemie International Edition
928:
334:
14:
1808:
1548:. John Wiley & Sons. p. 109.
1095:
858:mechanism). This helps preserving the
854:reduction by Fe ions according to the
838:) that otherwise would accelerate the
621:of DTPA has a high affinity for metal
462:220 °C (428 °F; 493 K)
210:
1588:
684:. It is normally administered as the
366:Key: QPCDCPDFJACHGM-UHFFFAOYSA-N
177:
157:
1212:
960:
1484:
1065:DTPA in chlorine-free Kraft pulping
925:involving redox-active metal ions.
761:and increases the images contrast.
252:
236:
24:
591:diethylenetriaminepentaacetic acid
25:
1847:
1256:Journal of Inorganic Biochemistry
1030:ventilation perfusion (V/Q) scans
657:, DTPA is predominantly used as
552:
420:
414:
43:
1535:
1478:
1442:
1387:
1292:
1060:Hydrogen peroxide decomposition
896:
713:US Food and Drug Administration
548:(at 25 °C , 100 kPa).
1576:produced by the United States
1491:Advanced Drug Delivery Reviews
1234:
1196:
1176:
1086:
1077:
945:decomposition by redox-active
426:
408:
27:DTPA: aminopolycarboxylic acid
13:
1:
1373:10.1016/S0273-1223(96)00928-6
1268:10.1016/S0162-0134(00)80298-6
1070:
472:decomposes at a higher temp.
1361:Water Science and Technology
901:DTPA is more effective than
7:
1043:
749:(Gd) ion, which alters the
10:
1852:
1836:Magnetic resonance imaging
1503:10.1016/j.addr.2008.04.006
1485:Liu, Shuang (2008-09-15).
1322:10.1016/j.bbrc.2004.02.013
1028:is chelated with DTPA for
661:agent for complexing and
68:′-{di(ethane-2,1-diyl)}bis
29:
1766:
1725:
1707:
1677:
1649:
1631:
542:
521:
506:
395:
375:
350:
97:
85:
73:
56:
51:
42:
1112:10.1002/14356007.a10_095
1018:contrast agent, such as
955:biological oxygen demand
599:aminopolycarboxylic acid
452:White crystalline solid
1034:radioisotope renography
921:. DTPA is also used in
613:Coordination properties
1464:10.1089/cbr.1999.14.99
1145:10.1002/anie.201709183
649:Chelating applications
1545:Radiology at a Glance
738:DTPA is also used as
733:intravenous injection
653:Like the more common
75:Systematic IUPAC name
971:ibritumomab tiuxetan
937:in the treatment of
929:Environmental impact
828:pulp and paper mills
711:In August, 2004 the
1400:Nat Rev Drug Discov
1055:Radiopharmaceutical
986:satumomab pendetide
878:by this mechanism.
807:. It increases the
631:formation constants
479:Solubility in water
444: g·mol
39:
1793:Never to phase III
1192:10.1007/BF00747020
982:capromab pendetide
751:magnetic resonance
639:coordination bonds
627:octadentate ligand
603:diethylenetriamine
575:Infobox references
522:Related compounds
37:
1803:
1802:
1620:chelation therapy
1208:10.1021/ic300757k
1138:(17): 4521–4526.
961:Related compounds
943:hydrogen peroxide
935:activated sludges
919:hydrogen peroxide
907:oxidative damages
844:hydrogen peroxide
842:decomposition of
743:contrasting agent
583:Chemical compound
581:
580:
528:Related compounds
484:<0.5 g/100 mL
319:CompTox Dashboard
273: (Zinc-DTPA)
139:Interactive image
16:(Redirected from
1843:
1831:Nuclear medicine
1816:Chelating agents
1616:Chelating agents
1609:
1602:
1595:
1586:
1585:
1570:Facts about DTPA
1560:
1559:
1539:
1533:
1532:
1522:
1482:
1476:
1475:
1446:
1440:
1439:
1391:
1385:
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1348:
1342:
1341:
1305:
1299:
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1286:
1280:
1279:
1251:
1242:
1238:
1232:
1231:
1229:
1227:
1216:
1210:
1200:
1194:
1180:
1174:
1173:
1147:
1123:
1114:
1104:
1093:
1090:
1084:
1081:
1050:Nuclear medicine
1037:nuclear medicine
753:behavior of the
601:consisting of a
565:
559:
556:
555:
443:
428:
422:
416:
410:
403:Chemical formula
343:
342:
327:
325:
309:
272:
265:
254:
240:
223:
212:
201:
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161:
141:
117:
47:
40:
36:
21:
1851:
1850:
1846:
1845:
1844:
1842:
1841:
1840:
1826:Tertiary amines
1806:
1805:
1804:
1799:
1798:
1783:Clinical trials
1762:
1721:
1703:
1673:
1645:
1627:
1613:
1564:
1563:
1556:
1540:
1536:
1497:(12): 1347–70.
1483:
1479:
1447:
1443:
1412:10.1038/nrd1413
1392:
1388:
1358:
1354:
1349:
1345:
1306:
1302:
1297:
1293:
1287:
1283:
1252:
1245:
1239:
1235:
1225:
1223:
1218:
1217:
1213:
1201:
1197:
1181:
1177:
1124:
1117:
1105:
1096:
1091:
1087:
1082:
1078:
1073:
1046:
988:, the chelator
963:
931:
899:
877:
873:
864:oxidizing agent
856:Fenton reaction
853:
849:
813:bioavailability
798:
794:
790:
786:
766:aquarium plants
759:water molecules
651:
635:chelating agent
615:
584:
577:
572:
571:
570: ?)
561:
557:
553:
549:
529:
502:~1.80 (20 °C)
498:
481:
441:
431:
425:
419:
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405:
391:
388:
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371:
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328:
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184:
164:
144:
131:
120:
107:
93:
91:
81:
80:
69:
35:
28:
23:
22:
15:
12:
11:
5:
1849:
1839:
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1828:
1823:
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1797:
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1612:
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1604:
1597:
1589:
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1561:
1554:
1534:
1477:
1441:
1386:
1356:
1352:
1343:
1300:
1291:
1281:
1262:(2): 143–151.
1243:
1233:
1211:
1195:
1175:
1115:
1094:
1085:
1075:
1074:
1072:
1069:
1068:
1067:
1062:
1057:
1052:
1045:
1042:
1041:
1040:
1026:Technetium-99m
1023:
1008:
1001:
978:
962:
959:
930:
927:
898:
895:
875:
871:
851:
847:
796:
792:
788:
784:
777:aquatic plants
757:of the nearby
650:
647:
619:conjugate base
614:
611:
582:
579:
578:
573:
551:
550:
546:standard state
543:
540:
539:
530:
527:
524:
523:
519:
518:
517:Non-flammable
515:
509:
508:
504:
503:
500:
496:
486:
485:
482:
477:
474:
473:
470:
464:
463:
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429:
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401:
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386:
378:
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369:
365:
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361:
353:
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351:
348:
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344:
331:
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317:
314:
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294:
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99:
95:
94:
89:
87:
83:
82:
78:
77:
71:
70:
60:
54:
53:
49:
48:
38:Pentetic acid
26:
9:
6:
4:
3:
2:
1848:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1813:
1811:
1792:
1790:
1787:
1786:
1784:
1781:
1778:
1775:
1773:
1770:
1769:
1765:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1731:
1730:
1728:
1724:
1718:
1717:Prussian blue
1715:
1714:
1712:
1710:
1706:
1698:
1695:
1694:
1693:
1690:
1688:
1685:
1684:
1682:
1680:
1676:
1670:
1667:
1665:
1662:
1660:
1657:
1656:
1654:
1652:
1648:
1642:
1641:Penicillamine
1639:
1638:
1636:
1634:
1630:
1625:
1621:
1617:
1610:
1605:
1603:
1598:
1596:
1591:
1590:
1587:
1581:
1579:
1575:
1571:
1566:
1565:
1557:
1555:9781118691083
1551:
1547:
1546:
1538:
1530:
1526:
1521:
1516:
1512:
1508:
1504:
1500:
1496:
1492:
1488:
1481:
1473:
1469:
1465:
1461:
1458:(2): 99–111.
1457:
1453:
1445:
1437:
1433:
1429:
1425:
1421:
1417:
1413:
1409:
1406:(6): 488–99.
1405:
1401:
1397:
1390:
1382:
1378:
1374:
1370:
1366:
1362:
1347:
1339:
1335:
1331:
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587:Pentetic acid
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975:methyl group
964:
932:
900:
897:Biochemistry
880:
825:
820:
817:water column
763:
737:
710:
676:, and other
667:
665:metal ions.
663:sequestering
652:
616:
594:
590:
586:
585:
493:
282:RTECS number
98:Identifiers
86:Other names
65:
61:
1779:from market
1697:Dexrazoxane
1664:Deferiprone
1659:Deferasirox
1014:to form an
909:induced in
868:bleach pulp
513:Flash point
449:Appearance
396:Properties
217:100.000.593
159:CHEBI:35739
1810:Categories
1574:fact sheet
1289:Forestry).
1241:2293–2342.
1071:References
1012:gadolinium
915:superoxide
809:solubility
775:needed by
769:fertilizer
747:gadolinium
708:(III/IV).
704:(IV), and
437:Molar mass
307:7A314HQM0I
190:ChemSpider
126:3D model (
105:CAS Number
58:IUPAC name
1789:Phase III
1777:Withdrawn
1626:, others)
1511:0169-409X
1420:1474-1776
1381:0273-1223
1330:0006-291X
1276:0162-0134
1154:1521-3773
1020:Magnevist
990:pendetide
951:manganese
923:bioassays
887:magnesium
860:oxidation
840:catalytic
801:oxidation
783:as Fe(OH)
729:nebulizer
721:americium
717:plutonium
702:neptunium
678:actinides
674:americium
670:plutonium
659:chelating
643:pendetide
289:MB8205000
179:ChEMBL780
1709:Thallium
1529:18538888
1472:10850293
1436:22166498
1428:15173838
1338:15003509
1226:2 August
1170:29473263
1044:See also
1007:segment.
998:antibody
889:ions in
597:) is an
507:Hazards
88:DTPA; H
1520:2539110
1367:(2–3).
1162:1426318
1005:peptide
994:peptide
883:calcium
787:, or Fe
755:protons
698:uranium
694:thorium
686:calcium
623:cations
568:what is
566: (
490:Acidity
442:393.349
270:6441444
250:PubChem
115:67-43-6
1772:WHO-EM
1633:Copper
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1152:
1039:scans.
805:oxygen
725:curium
706:cerium
700:(IV),
696:(IV),
563:verify
560:
380:SMILES
238:D05422
170:ChEMBL
52:Names
1738:BAPTA
1726:Other
1624:V03AC
1432:S2CID
911:cells
795:· n H
682:urine
355:InChI
150:ChEBI
128:JSmol
1758:EGTA
1753:DTPA
1748:DMSA
1743:DMPS
1692:EDTA
1679:Lead
1651:Iron
1572:, a
1550:ISBN
1525:PMID
1507:ISSN
1468:PMID
1424:PMID
1416:ISSN
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1334:PMID
1326:ISSN
1272:ISSN
1228:2016
1166:PMID
1158:OSTI
1150:ISSN
1032:and
984:and
949:and
947:iron
917:and
903:EDTA
885:and
821:i.e.
690:zinc
655:EDTA
617:The
607:EDTA
595:DTPA
533:EDTA
298:UNII
263:3053
229:KEGG
199:2945
32:DTPa
18:DTPA
1733:ALA
1687:BAL
1515:PMC
1499:doi
1460:doi
1408:doi
1369:doi
1318:doi
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1264:doi
1204:doi
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980:In
969:In
913:by
866:to
834:or
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253:CID
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