24:
42:
33:
1410:
1387:
481:
300:
741:
736:
2198:
956:
1616:
1623:
1444:
Trientine tetrahydrochloride (brand name
Cuprior) was approved for medical use in the European Union in September 2017. It is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy.
1448:
Trientine dihydrochloride (brand name
Cufence) was approved for medical use in the European Union in July 2019. It is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy.
749:
716:
1230:
2153:
Utsuno S, Sakai Y, Yoshikawa Y, Yamatera H (1985). "Three
Isomers of the Trans -Diammine-[N,N′-bis(2-Aminoethyl)-1,2-Ethanediamine]-Cobalt(III) Complex Cation".
803:
1560:
1499:
developed a generic, which patients and doctors expected to be cheaper, but when it was introduced in
February 2018, Teva's price was $ 18,375 for 100 pills.
1185:
23:
969:
1986:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1949:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1097:
520:
1503:, who studies drug pricing at Harvard Medical School, said that drug companies price the product at what they think the market will bear.
1022:, older samples assume a yellowish color due to impurities resulting from air-oxidation. It is soluble in polar solvents. The branched
1765:
32:
41:
1898:
1872:
1846:
964:
1486:
1062:
curing. TETA, like other aliphatic amines, react quicker and at lower temperatures than aromatic amines due to less negative
1033:
derivatives may also be present in commercial samples of TETA. The hydrochloride salts are used medically as a treatment for
1523:. This process gives a variety of amines, especially ethylene amines which are separated by distillation and sublimation.
2174:
2108:
1134:
1004:
495:
95:
976:
1441:
Trientine hydrochloride (brand name
Syprine) was approved for medical use in the United States in November 1985.
1294:
1215:
1115:
935:
870:
2137:
1667:
2233:
2056:
1405:
789:
420:
295:
229:
1997:
1438:. Some recommend trientine as first-line treatment, but experience with penicillamine is more extensive.
1366:
459:
799:
363:
2188:
740:
1817:"Trientine dihydrochloride Tillomed 250 mg capsules, hard - Summary of Product Characteristics (SmPC)"
221:
2238:
2223:
1971:
1934:
307:
1489:
raised the price of its
Syprine brand of TETA from $ 625 to $ 21,267 for 100 pills over five years.
1382:
476:
357:
2218:
1739:
1683:
1171:
1087:
1026:
1588:
2092:
1536:
1348:
1107:
735:
249:
2228:
763:
728:
644:
161:
2084:
1966:
1929:
1496:
1464:(inflammation of the duodenum, the part of the gut leading out of the stomach), and severe
437:
429:
257:
137:
54:
8:
1431:
1178:
129:
119:
1409:
1386:
480:
299:
193:
2126:
2100:
2061:
2030:
1710:
1491:
1145:
1055:
912:
201:
173:
1816:
1791:
2170:
2133:
2104:
2085:
2022:
1663:
1338:
1267:
1254:
1242:
1066:
since the linear nature of the molecule provides it the ability to rotate and twist.
884:
2162:
2096:
2012:
1655:
1500:
1198:
1012:
1008:
807:
668:
633:
543:
2034:
393:
2202:
1423:
1051:
1034:
907:
385:
326:
1792:"Cuprior 150 mg film-coated tablets - Summary of Product Characteristics (SmPC)"
1050:
The reactivity and uses of TETA are similar to those for the related polyamines
2166:
1539:, where it is referred to as trien. Octahedral complexes of the type M(trien)L
1063:
947:
781:
657:
838:
2212:
1659:
1593:
1565:
1435:
1398:
1327:
693:
622:
612:
288:
2017:
2026:
1512:
1193:
1075:
814:
1320:
277:
1461:
1030:
571:
308:
240:
1561:"Health product highlights 2021: Annexes of products approved in 2021"
1650:
Eller K, Henkes E, Rossbacher R, Höke H (2005). "Amines, Aliphatic".
1457:
1101:
773:
448:
946:
Except where otherwise noted, data are given for materials in their
1734:
1732:
1520:
1469:
1311:
1129:
346:
268:
2057:"Patients Eagerly Awaited a Generic Drug. Then They Saw the Price"
1354:
160:
1516:
1495:
said that this "egregious" price increase caused public outrage.
1465:
777:
602:
372:
1729:
1532:
1453:
1427:
1023:
1018:. The pure freebase is a colorless oily liquid, but, like many
917:
795:
212:
1059:
1019:
404:
184:
150:
2152:
2091:(Seventh ed.). Oxford: Butterworth-Heinemann. pp.
1371:
464:
1899:"Cuvrior- trientine tetrahydrochloride tablet, film coated"
592:
337:
2083:
Brydson JA (1999). "Epoxide Resins". In
Brydson JA (ed.).
769:
1649:
1058:. It is primarily used as a crosslinker ("hardener") in
1705:
1703:
2186:
2161:. Inorganic Syntheses. Vol. 23. pp. 79–82.
1841:
1839:
1837:
1700:
1766:"Summary Basis of Decision (SBD) for Mar-Trientine"
1589:"Regulatory Decision Summary for Waymade-Trientine"
504:
InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2
2125:
1468:(inflammation in the large bowel causing pain and
1834:
2210:
392:
384:
2050:
2048:
2046:
2044:
1995:
1961:
1959:
1957:
1955:
1924:
1922:
1920:
1511:TETA is prepared by heating ethylenediamine or
1418:The hydrochloride salt of TETA, referred to as
136:
128:
1652:Ullmann's Encyclopedia of Industrial Chemistry
1434:, particularly in those who are intolerant to
1543:can adopt several diastereomeric structures.
2123:
2041:
1952:
1917:
1133:
627:266.6 °C; 511.8 °F; 539.7 K
617:−34.6 °C; −30.4 °F; 238.5 K
1847:"Syprine- trientine hydrochloride capsule"
1408:
1385:
479:
298:
256:
248:
2128:Stereochemistry of Coordination Compounds
2016:
1645:
1643:
1526:
436:
428:
1998:"A practice guideline on Wilson disease"
66:-(Ethane-1,2-diyl)di(ethane-1,2-diamine)
2082:
1989:
1381:
1326:
1319:
475:
362:
276:
2211:
2054:
1744:Therapeutic Goods Administration (TGA)
1715:Therapeutic Goods Administration (TGA)
1640:
1475:
1456:, especially when starting treatment,
1399:
1273:
1248:
819:129 °C (264 °F; 402 K)
289:
2159:-Diammine--Cobalt(III) Complex Cation
1996:Roberts EA, Schilsky ML (June 2003).
1487:Valeant Pharmaceuticals International
1452:The most common side effects include
1347:
1261:
1124:
1106:
507:Key: VILCJCGEZXAXTO-UHFFFAOYSA-N
228:
220:
200:
192:
1353:
1197:
85:-Bis(2-aminoethyl)ethane-1,2-diamine
1740:"AusPAR: Trientine dihydrochloride"
375:
345:
13:
14:
2250:
1873:"Trientine hydrochloride capsule"
1224:
1156:
1092:Syprine, Cuprior, Cufence, others
2196:
2101:10.1016/B978-075064132-6/50067-X
1622:. Huntsman. 2007. Archived from
1480:
1426:that is used to bind and remove
954:
739:
734:
561:
555:
40:
31:
22:
2146:
2117:
2076:
1891:
1865:
1809:
1069:
950:(at 25 °C , 100 kPa).
936:Ethylenediaminetetraacetic acid
1784:
1758:
1676:
1609:
1581:
1553:
1302:(2-aminoethyl)({2-ethyl})amine
1237:
879:
549:
1:
2055:Thomas K (23 February 2018).
1546:
1506:
1045:
1007:) when used medically, is an
706:376 J K mol (at 60 °C)
7:
827:or concentration (LD, LC):
10:
2255:
2167:10.1002/9780470132548.ch16
2132:. Chichester: John Wiley.
1972:European Medicines Agency
1935:European Medicines Agency
1397:
1365:
1337:
1310:
1290:
1285:
1214:
1209:
1184:
1170:
1144:
1114:
1096:
1086:
1081:
944:
893:
864:
823:
715:
710:
686:
662:<1 Pa (at 20 °C)
536:
516:
491:
112:
101:trientine dihydrochloride
72:
53:
48:
39:
30:
21:
1660:10.1002/14356007.a02_001
790:Precautionary statements
2124:von Zelewsky A (1995).
2018:10.1053/jhep.2003.50252
1654:. Weinheim: Wiley-VCH.
1531:TETA is a tetradentate
1519:mixtures over an oxide
1420:trientine hydrochloride
1040:
1027:tris(2-aminoethyl)amine
1684:"Triethylenetetramine"
1537:coordination chemistry
1527:Coordination chemistry
1485:In the United States,
2155:Three Isomers of the
1430:in the body to treat
17:Triethylenetetramine
2234:Tetradentate ligands
1497:Teva Pharmaceuticals
989:Triethylenetetramine
435:hydrochloride:
391:hydrochloride:
255:hydrochloride:
227:hydrochloride:
199:hydrochloride:
135:hydrochloride:
55:Preferred IUPAC name
1939:. 17 September 2018
1711:"Trientine Waymade"
1476:Society and culture
1257:(Prescription only)
1233:(Prescription only)
1078:
634:Solubility in water
579: g·mol
174:Beilstein Reference
18:
2087:Plastics Materials
2062:The New York Times
1879:. 28 February 2020
1853:. 22 December 2016
1492:The New York Times
1074:
1056:diethylenetriamine
977:Infobox references
913:Diethylenetriamine
894:Related compounds
597:Fishy, ammoniacal
16:
1772:. 23 October 2014
1717:. 25 January 2021
1416:
1415:
1367:CompTox Dashboard
1277:
1265:
1252:
1240:
1228:
1160:
1127:
999:), also known as
985:Chemical compound
983:
982:
928:Related compounds
882:
857:
851:
764:Hazard statements
587:Colorless liquid
460:CompTox Dashboard
162:Interactive image
2246:
2239:Secondary amines
2224:Chelating agents
2201:
2200:
2199:
2192:
2181:
2180:
2150:
2144:
2143:
2131:
2121:
2115:
2114:
2090:
2080:
2074:
2073:
2071:
2069:
2052:
2039:
2038:
2020:
2002:
1993:
1987:
1985:
1983:
1981:
1963:
1950:
1948:
1946:
1944:
1926:
1915:
1914:
1912:
1910:
1895:
1889:
1888:
1886:
1884:
1869:
1863:
1862:
1860:
1858:
1843:
1832:
1831:
1829:
1827:
1813:
1807:
1806:
1804:
1802:
1788:
1782:
1781:
1779:
1777:
1762:
1756:
1755:
1753:
1751:
1736:
1727:
1726:
1724:
1722:
1707:
1698:
1697:
1695:
1694:
1688:webbook.nist.gov
1680:
1674:
1673:
1647:
1638:
1637:
1635:
1634:
1628:
1621:
1617:"Ethyleneamines"
1613:
1607:
1606:
1604:
1602:
1585:
1579:
1578:
1576:
1574:
1557:
1501:Aaron Kesselheim
1432:Wilson's disease
1412:
1401:
1390:
1389:
1375:
1373:
1357:
1351:
1330:
1323:
1275:
1272:
1263:
1260:
1250:
1247:
1239:
1236:
1226:
1223:
1201:
1158:
1155:
1137:
1126:
1123:
1110:
1079:
1077:
1073:
1009:organic compound
967:
961:
958:
957:
881:
878:
855:
850:(dermal, rabbit)
849:
809:
805:
801:
797:
783:
779:
775:
771:
743:
738:
702:
687:Thermochemistry
669:Refractive index
578:
563:
557:
551:
544:Chemical formula
484:
483:
468:
466:
440:
432:
396:
388:
377:
366:
349:
327:Gmelin Reference
310:
302:
291:
280:
260:
252:
232:
224:
204:
196:
164:
140:
132:
44:
35:
26:
19:
15:
2254:
2253:
2249:
2248:
2247:
2245:
2244:
2243:
2209:
2208:
2207:
2197:
2195:
2187:
2185:
2184:
2177:
2151:
2147:
2140:
2122:
2118:
2111:
2081:
2077:
2067:
2065:
2053:
2042:
2000:
1994:
1990:
1979:
1977:
1965:
1964:
1953:
1942:
1940:
1928:
1927:
1918:
1908:
1906:
1897:
1896:
1892:
1882:
1880:
1871:
1870:
1866:
1856:
1854:
1845:
1844:
1835:
1825:
1823:
1815:
1814:
1810:
1800:
1798:
1790:
1789:
1785:
1775:
1773:
1764:
1763:
1759:
1749:
1747:
1738:
1737:
1730:
1720:
1718:
1709:
1708:
1701:
1692:
1690:
1682:
1681:
1677:
1670:
1648:
1641:
1632:
1630:
1626:
1619:
1615:
1614:
1610:
1600:
1598:
1597:. 20 April 2021
1587:
1586:
1582:
1572:
1570:
1569:. 3 August 2022
1559:
1558:
1554:
1549:
1542:
1529:
1509:
1483:
1478:
1424:chelating agent
1393:
1369:
1361:
1333:
1306:
1303:
1298:
1297:
1281:
1205:
1173:
1166:
1147:
1140:
1072:
1052:ethylenediamine
1048:
1043:
1035:copper toxicity
1017:
986:
979:
974:
973:
972: ?)
963:
959:
955:
951:
940:
929:
922:
908:Ethylenediamine
901:
889:
860:
842:
836:
792:
766:
752:
731:
703:
696:
679:
677:
636:
576:
566:
560:
554:
546:
532:
529:
524:
523:
512:
509:
508:
505:
499:
498:
487:
469:
462:
443:
415:
399:
378:
352:
329:
320:
283:
263:
235:
207:
176:
167:
154:
143:
122:
108:
107:
68:
67:
12:
11:
5:
2252:
2242:
2241:
2236:
2231:
2226:
2221:
2219:Ethyleneamines
2206:
2205:
2183:
2182:
2175:
2145:
2138:
2116:
2109:
2075:
2040:
2011:(6): 1475–92.
1988:
1967:"Cufence EPAR"
1951:
1930:"Cuprior EPAR"
1916:
1890:
1864:
1833:
1808:
1783:
1757:
1728:
1699:
1675:
1668:
1639:
1608:
1580:
1551:
1550:
1548:
1545:
1540:
1528:
1525:
1508:
1505:
1482:
1479:
1477:
1474:
1414:
1413:
1403:
1395:
1394:
1392:
1391:
1378:
1376:
1363:
1362:
1360:
1359:
1343:
1341:
1335:
1334:
1332:
1331:
1324:
1316:
1314:
1308:
1307:
1305:
1304:
1301:
1293:
1292:
1291:
1288:
1287:
1283:
1282:
1280:
1279:
1270:
1258:
1245:
1234:
1220:
1218:
1212:
1211:
1207:
1206:
1204:
1203:
1190:
1188:
1182:
1181:
1176:
1174:administration
1168:
1167:
1165:
1164:
1162:
1152:
1150:
1142:
1141:
1139:
1138:
1120:
1118:
1112:
1111:
1104:
1094:
1093:
1090:
1084:
1083:
1071:
1068:
1064:steric effects
1047:
1044:
1042:
1039:
1015:
984:
981:
980:
975:
953:
952:
948:standard state
945:
942:
941:
939:
938:
932:
930:
927:
924:
923:
921:
920:
915:
910:
904:
902:
900:Related amines
899:
896:
895:
891:
890:
888:
887:
875:
873:
867:
866:
862:
861:
859:
858:
852:
845:
843:
834:
832:
829:
828:
821:
820:
817:
811:
810:
804:P305+P351+P338
793:
788:
785:
784:
767:
762:
759:
758:
753:
748:
745:
744:
732:
727:
724:
723:
713:
712:
708:
707:
704:
692:
689:
688:
684:
683:
680:
675:
667:
664:
663:
660:
658:Vapor pressure
654:
653:
650:
641:
640:
637:
632:
629:
628:
625:
619:
618:
615:
609:
608:
605:
599:
598:
595:
589:
588:
585:
581:
580:
574:
568:
567:
564:
558:
552:
547:
542:
539:
538:
534:
533:
531:
530:
527:
519:
518:
517:
514:
513:
511:
510:
506:
503:
502:
494:
493:
492:
489:
488:
486:
485:
472:
470:
458:
455:
454:
451:
445:
444:
442:
441:
433:
425:
423:
417:
416:
414:
413:
409:
407:
401:
400:
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397:
389:
381:
379:
371:
368:
367:
360:
354:
353:
351:
350:
342:
340:
334:
333:
330:
325:
322:
321:
319:
318:
314:
312:
304:
303:
293:
285:
284:
282:
281:
273:
271:
265:
264:
262:
261:
253:
245:
243:
237:
236:
234:
233:
225:
217:
215:
209:
208:
206:
205:
197:
189:
187:
181:
180:
177:
172:
169:
168:
166:
165:
157:
155:
148:
145:
144:
142:
141:
133:
125:
123:
118:
115:
114:
110:
109:
106:
105:
102:
99:
92:
89:
86:
75:
74:
70:
69:
58:
57:
51:
50:
46:
45:
37:
36:
28:
27:
9:
6:
4:
3:
2:
2251:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2216:
2214:
2204:
2194:
2193:
2190:
2178:
2176:9780470132548
2172:
2168:
2164:
2160:
2156:
2149:
2141:
2135:
2130:
2129:
2120:
2112:
2110:9780750641326
2106:
2102:
2098:
2094:
2089:
2088:
2079:
2064:
2063:
2058:
2051:
2049:
2047:
2045:
2036:
2032:
2028:
2024:
2019:
2014:
2010:
2006:
1999:
1992:
1976:. 24 May 2019
1975:
1973:
1968:
1962:
1960:
1958:
1956:
1938:
1936:
1931:
1925:
1923:
1921:
1905:. 20 May 2022
1904:
1900:
1894:
1878:
1874:
1868:
1852:
1848:
1842:
1840:
1838:
1822:
1818:
1812:
1797:
1793:
1787:
1771:
1770:Health Canada
1767:
1761:
1745:
1741:
1735:
1733:
1716:
1712:
1706:
1704:
1689:
1685:
1679:
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2068:21 September
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1801:21 September
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1748:. Retrieved
1746:. 3 May 2021
1743:
1719:. Retrieved
1714:
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1631:. Retrieved
1624:the original
1611:
1599:. Retrieved
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1513:ethanolamine
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1216:Legal status
1210:Legal status
1116:License data
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405:RTECS number
113:Identifiers
82:
78:
73:Other names
63:
59:
1750:8 September
1721:8 September
1406:100.003.591
1286:Identifiers
1088:Trade names
856:(oral, rat)
839:median dose
825:Lethal dose
815:Flash point
750:Signal word
584:Appearance
537:Properties
296:100.003.591
194:CHEBI:39501
94:trientine (
2213:Categories
2139:047195599X
2005:Hepatology
1909:21 January
1693:2022-07-20
1669:3527306730
1633:2016-07-10
1547:References
1507:Production
1462:duodenitis
1339:PDB ligand
1295:IUPAC name
1046:Epoxy uses
1031:piperazine
848:550 mg kg
729:Pictograms
607:982 mg mL
572:Molar mass
528:NCCNCCNCCN
438:HC3NX54582
430:SJ76Y07H5F
241:ChemSpider
202:CHEBI:9706
149:3D model (
138:38260-01-4
120:CAS Number
1458:skin rash
1172:Routes of
1146:Pregnancy
1135:Trientine
1108:Monograph
1102:Drugs.com
1076:Trientine
1011:with the
1001:trientine
854:2.5 g kg
720:labelling
639:Miscible
449:UN number
412:YE6650000
364:Trientine
317:203-950-6
309:EC Number
222:ChEMBL609
2203:Medicine
2027:12774027
1903:DailyMed
1877:DailyMed
1851:DailyMed
1601:25 March
1573:25 March
1521:catalyst
1470:diarrhea
1312:DrugBank
1186:ATC code
1179:By mouth
1148:category
1130:DailyMed
711:Hazards
269:DrugBank
250:21106175
130:112-24-3
1517:ammonia
1466:colitis
1422:, is a
1321:DB06824
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373:PubChem
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104:MK-0681
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2035:263620
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1776:29 May
1666:
1533:ligand
1454:nausea
1428:copper
1268:℞-only
1266:
1253:
1243:℞-only
1229:
1128:
1024:isomer
1020:amines
965:verify
962:
918:Cyclam
885:℞-only
756:Danger
682:1.496
652:1.985
521:SMILES
347:C07166
332:27008
213:ChEMBL
49:Names
2157:trans
2031:S2CID
2001:(pdf)
1974:(EMA)
1937:(EMA)
1821:(emc)
1796:(emc)
1627:(PDF)
1620:(PDF)
1346:104 (
1060:epoxy
997:trien
496:InChI
453:2259
394:71433
258:64521
185:ChEBI
151:JSmol
91:trien
2171:ISBN
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2105:ISBN
2070:2020
2023:PMID
1982:2020
1945:2020
1911:2023
1885:2020
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1778:2022
1752:2021
1723:2021
1664:ISBN
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1575:2024
1349:PDBe
1098:AHFS
1054:and
1041:Uses
1029:and
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800:P280
796:P273
782:H412
778:H317
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770:H312
645:log
593:Odor
421:UNII
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338:KEGG
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