569:
546:
690:
InChI=1S/C54H69N11O10S2/c1-29(2)45-54(75)63-44(53(74)65-46(30(3)66)47(57)68)28-77-76-27-43(62-48(69)38(56)23-32-15-18-33-10-4-5-11-34(33)22-32)52(73)60-41(24-31-16-19-36(67)20-17-31)50(71)61-42(25-35-26-58-39-13-7-6-12-37(35)39)51(72)59-40(49(70)64-45)14-8-9-21-55/h4-7,10-13,15-20,22,26,29-30,38,40-46,58,66-67H,8-9,14,21,23-25,27-28,55-56H2,1-3H3,(H2,57,68)(H,59,72)(H,60,73)(H,61,71)(H,62,69)(H,63,75)(H,64,70)(H,65,74)/t30-,38-,40+,41+,42-,43+,44+,45+,46+/m1/s1
648:
31:
1950:
897:
as somatostatin, although with higher affinity to peripheral receptors, and has similar activity. However, while somatostatin is quickly broken down in the body (within minutes), lanreotide has a much longer half-life, and produces far more prolonged effects.
922:
Lanreotide has been shown to spontaneously self-assemble into monodisperse nanotubes of 24.4 nm diameter and has been thereafter used as a fruitful and versatile model system in several biophysical studies.
1279:
233:
948:
818:
In
December 2014, the US FDA approved lanreotide for the treatment of people with unresectable, well or moderately differentiated, locally advanced or metastatic gastroenteropancreatic
133:
188:
706:
1107:
1272:
801:. In the United States and Canada, lanreotide is only indicated for the treatment of acromegaly. In the United Kingdom, it is also indicated in the treatment of
79:
1288:
662:
1265:
1176:
1926:
1005:
1628:
940:
1980:
769:. It is available in several countries, including the United Kingdom, Australia and Canada, and was approved for sale in the United States by the
1202:
Valéry C, Paternostre M, Robert B, Gulik-Krzywicki T, Narayanan T, Dedieu JC, Keller G, Torres ML, Cherif-Cheikh R, Calvo P, Artzner F (2003).
1708:
682:
129:
970:
906:
Lanreotide is available in two formulations: a sustained release formulation (sold under the trade name 'Somatuline LA'), which is
1111:
1975:
1663:
343:
218:
97:
1451:
1031:
Kvols L, Woltering E (2006). "Role of somatostatin analogs in the clinical management of non-neuroendocrine solid tumors".
670:
C((C(=O)N)NC(=O)1CSSC(C(=O)N(C(=O)N(C(=O)N(C(=O)N(C(=O)N1)C(C)C)CCCCN)Cc2cc3c2cccc3)Cc4ccc(cc4)O)NC(=O)(Cc5ccc6ccccc6c5)N)O
351:
3-(2-naphthyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-L-threoninamide (2->7)-disulfide
1940:
974:
770:
465:
882:
525:
116:
910:
every ten or fourteen days, and an extended release formulation (UK trade name 'Somatuline
Autogel', or 'Somatuline
66:
829:
It is used for polycystic liver disease. It has also been shown that it reduces the volume by 264mls on average.
1970:
1361:
1351:
1180:
1009:
414:
1309:
907:
177:
170:
564:
1341:
842:
514:
303:
287:
181:
57:
1568:
1985:
1466:
894:
838:
812:
405:
1608:
1386:
1911:
1887:
1336:
1215:
1133:
Rens-Domiano S, Reisine T (1992). "Biochemical and functional properties of somatostatin receptors".
911:
819:
790:
739:
310:
1733:
1493:
1326:
541:
1882:
1668:
1548:
1331:
360:
1728:
1593:
1204:"Biomimetic organization: Octapeptide self-assembly into nanotubes of viral capsid-like dimension"
1618:
1528:
1508:
1441:
1406:
1396:
1366:
1301:
1158:
747:
743:
144:
1788:
1673:
1613:
1498:
1416:
1411:
1376:
1867:
1862:
1845:
1835:
1793:
1658:
1648:
1603:
1558:
1518:
1513:
1483:
1426:
1877:
1738:
1698:
1356:
1243:
1150:
1089:
1048:
805:
259:
246:
43:
1901:
1896:
1578:
1573:
1768:
1763:
1758:
1753:
1583:
1553:
1488:
1233:
1223:
1142:
1079:
1040:
789:
and non-pituitary growth hormone-secreting tumors, and the management of symptoms caused by
581:
369:
269:
474:
454:
1954:
794:
786:
297:
277:
978:
568:
545:
1219:
1346:
1298:
1146:
1044:
878:
858:
1238:
1203:
1964:
1257:
861:
have been associated with use of lanreotide, particularly over long periods of time.
557:
1162:
1830:
1563:
1381:
870:
811:
Lanreotide also shows activity against non-endocrine tumors, and, along with other
751:
201:
196:
394:
89:
1850:
1808:
1803:
1798:
1783:
1688:
1683:
1543:
1503:
1431:
1371:
1208:
Proceedings of the
National Academy of Sciences of the United States of America
1840:
1825:
1813:
1778:
1743:
1678:
1588:
1538:
1533:
1401:
802:
782:
755:
735:
731:
620:
445:
1855:
1820:
1228:
1084:
1067:
841:
of lanreotide treatment are mild to moderate pain at the injection site and
325:
83:
1247:
1093:
1052:
22:
1154:
1653:
1391:
890:
854:
846:
425:
111:
434:
1748:
886:
874:
823:
762:
380:
30:
1773:
850:
798:
505:
1008:. electronic Medicines Compendium. 17 September 2003. Archived from
1068:"Rationale for the use of somatostatin analogs as antitumor agents"
494:
766:
647:
638:
914:' in the US), which is administered subcutaneously once a month.
1179:. electronic Medicines Compendium. 12 April 2007. Archived from
485:
240:
1261:
253:
123:
106:
877:
which blocks the release of several other hormones, including
530:
227:
155:
815:, is being studied as a possible general antitumor agent.
808:, a rare tumor of the pituitary gland which secretes TSH.
1467:
971:"FDA Approves New Drug to Treat Rare Disease, Acromegaly"
1629:
713:
1452:
1938:
1912:
1293:
1910:
1709:
1707:
1627:
1465:
1308:
636:
619:
580:
575:
556:
524:
504:
484:
464:
444:
424:
413:
404:
379:
359:
334:
324:
309:
296:
286:
276:
268:
217:
212:
187:
169:
143:
96:
78:
52:
42:
37:
1362:Placental growth hormone (growth hormone variant)
1108:"FDA Approves Lanreotide Injection for GEP-NETs"
393:
941:"Mytolac (Amdipharm Mercury Australia Pty Ltd)"
368:
128:
1273:
8:
115:
21:
1280:
1266:
1258:
567:
544:
453:
29:
1237:
1227:
1083:
473:
1000:
998:
996:
1945:
932:
781:Lanreotide is used in the treatment of
687:
667:
540:
433:
348:
1457:Tooltip Growth hormone-binding protein
1310:
1289:
945:Therapeutic Goods Administration (TGA)
869:Lanreotide is a synthetic analogue of
558:
20:
951:from the original on 13 November 2022
513:
88:
70:
7:
200:
873:, a naturally occurring inhibitory
493:
384:
1147:10.1111/j.1471-4159.1992.tb10938.x
1045:10.1097/01.cad.0000210335.95828.ed
14:
1948:
977:. 30 August 2007. Archived from
598:
592:
893:. Lanreotide binds to the same
695:Key:PUDHBTGHUJUUFI-SCTWWAJVSA-N
1981:Systemic hormonal preparations
1402:Somatrogon (MOD-4023; hGH-CTP)
610:
604:
586:
1:
61:
1066:Susini C, Buscail L (2006).
975:Food and Drug Administration
771:Food and Drug Administration
726:, sold under the brand name
1439:Antisense oligonucleotides:
883:thyroid-stimulating hormone
318:2 hours (immediate release)
2002:
918:Self-assembling properties
773:(FDA) on August 30, 2007.
761:Lanreotide (as lanreotide
734:used in the management of
576:Chemical and physical data
320:5 days (sustained release)
703:
678:
658:
339:
28:
1352:Human placental lactogen
908:injected intramuscularly
1976:Somatostatin inhibitors
1229:10.1073/pnas.1730609100
738:and symptoms caused by
65:), Lanreotide acetate (
1744:Examorelin (hexarelin)
1110:. 2014. Archived from
973:(Press release). U.S.
845:disturbances, such as
813:somatostatin analogues
746:. It is a long-acting
1085:10.1093/annonc/mdl105
947:. 28 September 2022.
820:neuroendocrine tumors
791:neuroendocrine tumors
765:) is manufactured by
740:neuroendocrine tumors
1799:Pralmorelin (GHRP-2)
1342:Eftansomatropin alfa
1183:on 28 September 2007
1177:"Somatuline Autogel"
1012:on 24 September 2006
857:. Isolated cases of
56:Lanreotide acetate (
1841:Ibutamoren (MK-677)
1669:Modified GRF (1-29)
1569:Somatostatin (1-28)
1564:Somatostatin (GHIH)
1332:Bovine somatotropin
1220:2003PNAS..10010258V
859:gallstone formation
730:among others, is a
249:(Prescription only)
236:(Prescription only)
25:
16:Pharmaceutical drug
744:carcinoid syndrome
1936:
1935:
1918:
1891:
1715:
1635:
1609:Cyclosomatostatin
1473:
1449:Binding proteins:
1357:Lonapegsomatropin
1316:
721:
720:
649:Interactive image
526:CompTox Dashboard
282:Approximately 80%
257:
244:
231:
159:
126:
109:
73:
64:
1993:
1953:
1952:
1951:
1944:
1916:
1914:
1889:
1713:
1711:
1633:
1631:
1471:
1469:
1458:
1454:
1387:Somatropin pegol
1314:
1312:
1295:
1291:
1282:
1275:
1268:
1259:
1252:
1251:
1241:
1231:
1214:(18): 10258–62.
1199:
1193:
1192:
1190:
1188:
1173:
1167:
1166:
1130:
1124:
1123:
1121:
1119:
1104:
1098:
1097:
1087:
1063:
1057:
1056:
1033:Anticancer Drugs
1028:
1022:
1021:
1019:
1017:
1002:
991:
990:
988:
986:
981:on 10 April 2021
967:
961:
960:
958:
956:
937:
843:gastrointestinal
795:carcinoid tumors
717:
716:
709:
651:
631:
629:
612:
606:
600:
594:
588:
571:
560:
549:
548:
534:
532:
517:
497:
477:
457:
437:
417:
397:
387:
386:
372:
330:Mostly bile duct
314:
255:
252:
242:
239:
229:
226:
204:
157:
154:
136:
125:
122:
119:
108:
105:
92:
72:
69:
63:
60:
33:
26:
24:
2001:
2000:
1996:
1995:
1994:
1992:
1991:
1990:
1971:Cyclic peptides
1961:
1960:
1959:
1949:
1947:
1939:
1937:
1932:
1915:
1906:
1712:
1703:
1632:
1623:
1470:
1461:
1456:
1337:Efpegsomatropin
1313:
1304:
1286:
1256:
1255:
1201:
1200:
1196:
1186:
1184:
1175:
1174:
1170:
1132:
1131:
1127:
1117:
1115:
1114:on 26 June 2019
1106:
1105:
1101:
1078:(12): 1733–42.
1065:
1064:
1060:
1030:
1029:
1025:
1015:
1013:
1006:"Somatuline LA"
1004:
1003:
994:
984:
982:
969:
968:
964:
954:
952:
939:
938:
934:
929:
920:
904:
867:
835:
793:, particularly
779:
742:, most notably
712:
710:
707:(what is this?)
704:
699:
696:
691:
686:
685:
674:
671:
666:
665:
654:
627:
625:
615:
609:
603:
597:
591:
552:
528:
520:
500:
480:
460:
440:
420:
400:
383:
375:
355:
352:
347:
346:
319:
312:
288:Protein binding
278:Bioavailability
270:Pharmacokinetic
264:
208:
172:
165:
146:
139:
17:
12:
11:
5:
1999:
1997:
1989:
1988:
1983:
1978:
1973:
1963:
1962:
1958:
1957:
1934:
1933:
1931:
1930:
1922:
1920:
1908:
1907:
1905:
1904:
1899:
1894:
1885:
1880:
1871:
1870:
1865:
1853:
1848:
1843:
1838:
1833:
1828:
1823:
1811:
1806:
1801:
1796:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1734:Cortistatin-14
1731:
1719:
1717:
1705:
1704:
1702:
1701:
1692:
1691:
1686:
1681:
1676:
1671:
1666:
1661:
1656:
1651:
1639:
1637:
1634:(somatocrinin)
1625:
1624:
1622:
1621:
1616:
1611:
1606:
1597:
1596:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1546:
1541:
1536:
1531:
1526:
1521:
1516:
1511:
1506:
1501:
1496:
1494:Cortistatin-14
1491:
1486:
1477:
1475:
1472:(somatostatin)
1463:
1462:
1460:
1459:
1445:
1444:
1435:
1434:
1429:
1420:
1419:
1414:
1409:
1404:
1399:
1394:
1389:
1384:
1379:
1374:
1369:
1364:
1359:
1354:
1349:
1347:Growth hormone
1344:
1339:
1334:
1329:
1327:Albusomatropin
1320:
1318:
1315:(somatotropin)
1306:
1305:
1287:
1285:
1284:
1277:
1270:
1262:
1254:
1253:
1194:
1168:
1141:(6): 1987–96.
1125:
1099:
1058:
1023:
992:
962:
931:
930:
928:
925:
919:
916:
903:
900:
879:growth hormone
866:
863:
834:
831:
785:, due to both
778:
775:
719:
718:
701:
700:
698:
697:
694:
692:
689:
681:
680:
679:
676:
675:
673:
672:
669:
661:
660:
659:
656:
655:
653:
652:
644:
642:
634:
633:
623:
617:
616:
613:
607:
601:
595:
589:
584:
578:
577:
573:
572:
562:
554:
553:
551:
550:
542:DTXSID60897514
537:
535:
522:
521:
519:
518:
510:
508:
502:
501:
499:
498:
490:
488:
482:
481:
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478:
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459:
458:
450:
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401:
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388:
377:
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373:
365:
363:
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332:
331:
328:
322:
321:
316:
307:
306:
300:
294:
293:
290:
284:
283:
280:
274:
273:
266:
265:
263:
262:
250:
237:
223:
221:
215:
214:
210:
209:
207:
206:
193:
191:
185:
184:
175:
173:administration
167:
166:
164:
163:
161:
151:
149:
141:
140:
138:
137:
120:
102:
100:
94:
93:
86:
76:
75:
54:
50:
49:
46:
40:
39:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
1998:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1968:
1966:
1956:
1946:
1942:
1928:
1924:
1923:
1921:
1919:
1917:(somatomedin)
1909:
1903:
1900:
1898:
1895:
1893:
1892:-LysÂł)-GHRP-6
1886:
1884:
1883:Cortistatin-8
1881:
1879:
1876:
1873:
1872:
1869:
1866:
1864:
1861:
1857:
1854:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1815:
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1724:
1721:
1720:
1718:
1716:
1706:
1700:
1697:
1694:
1693:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1644:
1641:
1640:
1638:
1636:
1626:
1620:
1617:
1615:
1612:
1610:
1607:
1605:
1602:
1599:
1598:
1595:
1592:
1590:
1587:
1585:
1582:
1580:
1577:
1575:
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1549:Pentetreotide
1547:
1545:
1542:
1540:
1537:
1535:
1532:
1530:
1527:
1525:
1522:
1520:
1517:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1497:
1495:
1492:
1490:
1487:
1485:
1482:
1479:
1478:
1476:
1474:
1464:
1455:
1450:
1447:
1446:
1443:
1440:
1437:
1436:
1433:
1430:
1428:
1425:
1422:
1421:
1418:
1415:
1413:
1410:
1408:
1405:
1403:
1400:
1398:
1395:
1393:
1390:
1388:
1385:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1353:
1350:
1348:
1345:
1343:
1340:
1338:
1335:
1333:
1330:
1328:
1325:
1322:
1321:
1319:
1317:
1307:
1303:
1300:
1297:
1283:
1278:
1276:
1271:
1269:
1264:
1263:
1260:
1249:
1245:
1240:
1235:
1230:
1225:
1221:
1217:
1213:
1209:
1205:
1198:
1195:
1182:
1178:
1172:
1169:
1164:
1160:
1156:
1152:
1148:
1144:
1140:
1136:
1129:
1126:
1113:
1109:
1103:
1100:
1095:
1091:
1086:
1081:
1077:
1073:
1069:
1062:
1059:
1054:
1050:
1046:
1042:
1038:
1034:
1027:
1024:
1011:
1007:
1001:
999:
997:
993:
980:
976:
972:
966:
963:
950:
946:
942:
936:
933:
926:
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624:
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570:
566:
563:
561:
559:ECHA InfoCard
555:
547:
543:
539:
538:
536:
527:
523:
516:
515:ChEMBL1201185
512:
511:
509:
507:
503:
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179:
178:Intramuscular
176:
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104:
103:
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77:
68:
59:
55:
51:
47:
45:
41:
38:Clinical data
36:
32:
27:
19:
1986:Octapeptides
1875:Antagonists:
1874:
1859:
1831:Capromorelin
1818:Non-peptide:
1817:
1729:Alexamorelin
1725:
1722:
1696:Antagonists:
1695:
1645:
1642:
1601:Antagonists:
1600:
1594:Veldoreotide
1523:
1480:
1448:
1438:
1424:Antagonists:
1423:
1382:Somatotropin
1323:
1211:
1207:
1197:
1185:. Retrieved
1181:the original
1171:
1138:
1134:
1128:
1116:. Retrieved
1112:the original
1102:
1075:
1071:
1061:
1039:(6): 601–8.
1036:
1032:
1026:
1014:. Retrieved
1010:the original
983:. Retrieved
979:the original
965:
953:. Retrieved
944:
935:
921:
905:
902:Formulations
871:somatostatin
868:
865:Pharmacology
839:side effects
836:
833:Side effects
828:
817:
810:
803:thyrotrophic
780:
777:Medical uses
760:
752:somatostatin
727:
723:
722:
711:
705:
311:Elimination
219:Legal status
213:Legal status
182:subcutaneous
98:License data
18:
1851:Macimorelin
1809:Tabimorelin
1804:Relamorelin
1784:Lenomorelin
1689:Tesamorelin
1684:Somatorelin
1619:Satoreotide
1544:Pasireotide
1529:NNC 26-9100
1509:Ilatreotide
1504:Edotreotide
1442:Atesidorsen
1432:Pegvisomant
1407:Somavaratan
1397:Sometribove
1372:Somapacitan
1367:Somagrebove
1135:J Neurochem
985:6 September
632: g·mol
565:100.215.992
370:108736-35-2
335:Identifiers
53:Other names
44:Trade names
1965:Categories
1826:Anamorelin
1814:Ulimorelin
1789:Livoletide
1779:Ipamorelin
1679:Sermorelin
1674:Rismorelin
1614:CYN-154806
1589:Vapreotide
1539:Octreotide
1534:Octreotate
1524:Lanreotide
1499:Depreotide
1417:Somidobove
1412:Somavubove
1377:Somatosalm
1302:modulators
927:References
783:acromegaly
756:octreotide
736:acromegaly
732:medication
728:Somatuline
724:Lanreotide
637:3D model (
621:Molar mass
475:0G3DE8943Y
446:ChemSpider
406:IUPHAR/BPS
361:CAS Number
344:IUPAC name
298:Metabolism
134:Lanreotide
117:Lanreotide
48:Somatuline
23:Lanreotide
1868:LY-444711
1863:LY-426410
1860:Unsorted:
1856:SM-130686
1846:L-692,585
1836:CP-464709
1821:Adenosine
1794:LY-444711
1723:Agonists:
1714:(ghrelin)
1659:Dumorelin
1649:ALRN-5281
1643:Agonists:
1604:BIM-23056
1559:Seglitide
1519:L-817,818
1514:L-803,087
1484:BIM-23052
1481:Agonists:
1427:G120K-hGH
1324:Agonists:
1299:signaling
1072:Ann Oncol
895:receptors
837:The main
787:pituitary
326:Excretion
313:half-life
171:Routes of
145:Pregnancy
90:Monograph
84:Drugs.com
1955:Medicine
1929:instead.
1878:A-778193
1739:EP-51216
1726:Peptide:
1699:MZ-5-156
1654:CJC-1295
1646:Peptide:
1392:Somatrem
1248:12930900
1187:19 April
1163:36873846
1118:29 April
1094:16801334
1053:16917205
955:29 April
949:Archived
891:glucagon
855:vomiting
847:diarrhea
824:GEP-NETs
748:analogue
714:(verify)
426:DrugBank
304:GI tract
189:ATC code
147:category
112:DailyMed
1902:YIL-781
1897:JMV2959
1749:Ghrelin
1579:SRIF-28
1574:SRIF-14
1216:Bibcode
1155:1315373
1016:2 March
887:insulin
885:(TSH),
875:hormone
806:adenoma
799:VIPomas
763:acetate
754:, like
582:Formula
435:DB06791
381:PubChem
205:)
199: (
197:H01CB03
160: C
132::
114::
1941:Portal
1774:GHRP-6
1769:GHRP-5
1764:GHRP-4
1759:GHRP-3
1754:GHRP-1
1584:TT-232
1554:RC-160
1489:CH-275
1246:
1239:193548
1236:
1161:
1153:
1092:
1051:
851:nausea
663:SMILES
506:ChEMBL
495:D04666
260:â„ž-only
258:
245:
232:
127:
110:
1913:IGF-1
1294:IGF-1
1159:S2CID
912:Depot
767:Ipsen
683:InChI
639:JSmol
455:64450
395:71349
1927:here
1925:See
1664:GHRH
1630:GHRH
1468:GHIH
1453:GHBP
1296:axis
1244:PMID
1189:2007
1151:PMID
1120:2023
1090:PMID
1049:PMID
1018:2007
987:2007
957:2023
889:and
853:and
797:and
486:KEGG
466:UNII
415:2031
272:data
80:AHFS
67:USAN
1710:GHS
1234:PMC
1224:doi
1212:100
1143:doi
1080:doi
1041:doi
826:).
750:of
630:.33
628:096
531:EPA
385:CID
302:In
292:78%
247:POM
202:WHO
130:FDA
58:JAN
1967::
1858:;
1816:;
1311:GH
1290:GH
1242:.
1232:.
1222:.
1210:.
1206:.
1157:.
1149:.
1139:58
1137:.
1088:.
1076:17
1074:.
1070:.
1047:.
1037:17
1035:.
995:^
943:.
881:,
849:,
758:.
608:10
602:11
596:69
590:54
254:US
241:UK
234:S4
228:AU
180:,
156:AU
124:US
107:US
71:US
62:JP
1943::
1890:D
1888:(
1292:/
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1274:t
1267:v
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614:2
611:S
605:O
599:N
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587:C
533:)
529:(
256::
243::
230::
158::
82:/
74:)
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