535:
InChI=1S/C59H79N15O21S6/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-/m0/s1
493:
414:
391:
31:
823:
819:(R-S-S-R) bonds it contains, which are between Cys and Cys, between Cys and Cys, and between Cys and Cys; these are shown in exaggerated fashion in the line-angle graphic showing the chemical bonds within and between each amino acid (and their stereochemistries, see the infobox, above right), and are represented using a one-letter abbreviations in the following additional schematic:
2427:
896:
and
Microbia, Forest would pay $ 70 million in licensing fees towards the development of linaclotide, with profits shared between the two companies in the US; Forest obtained exclusive rights to market in Canada and Mexico. By 2010, Microbia had changed its name to Ironwood Pharmaceuticals and had
1677:
843:. The study also reported that solution-phase oxidation (disulfide formation) was advisable over solid-supported synthesis for linaclotide, and that the Cys–Cys disulfide bridge was the most favored energetically.
2447:
236:
L-Cysteinyl-L-cysteinyl-L-glutamyl-L-tyrosyl-L-cysteinyl-L-cysteinyl-L-asparaginyl-L-prolyl-L-alanyl-L-cysteinyl-L-threonylglycyl-L-cysteinyl-L-tyrosine cyclo(1-6),(2-10),(5-13)-tris(disulfide)
675:
The US label has a black box warning to not use linaclotide in children less than six years old and to avoid in people from 6 to 18 years old, due to the risk of serious dehydration.
1776:
1669:
1222:
140:
1892:
1870:
551:
731:
2321:
515:
O=C(O)(NC(=O)4NC(=O)CNC(=O)(NC(=O)2NC(=O)(NC(=O)5N(C(=O)(NC(=O)1NC(=O)(NC(=O)(NC(=O)(NC(=O)(NC(=O)(N)CSSC1)CSSC2)CCC(=O)O)Cc3ccc(O)cc3)CSSC4)CC(=O)N)CCC5)C)(O)C)Cc6ccc(O)cc6
1080:
1933:
915:. Allergan acquired rights from Almirall in 2015, and in 2017, acquired remaining rights in most of the rest of the world, excluding North America, Japan, and China.
64:
507:
863:
to commercialize the lab's know-how and inventions related to microbial pathogens and biology. In 2002 the company hired Mark Currie who had worked at the
1299:
829:
A study in discovery synthesis reported that 2 of 14 strategies available to synthesize linaclotide were successful—the successful ones involving
726:
cells. Linaclotide is minimally absorbed and it is undetectable in the systemic circulation at therapeutic doses. Activation of GC-C increases
1809:
678:
More than 10% of people taking linaclotide have diarrhea. Between 1% and 10% of people have decreased appetite, dehydration, low potassium,
957:
1768:
1110:
1973:
1840:
1214:
2457:
1899:
1862:
527:
1742:
1568:
1072:
588:
228:
170:
96:
1925:
1429:
Love BL, Johnson A, Smith LS (July 2014). "Linaclotide: a novel agent for chronic constipation and irritable bowel syndrome".
1252:
1136:
929:
730:(cGMP). Elevated cGMP stimulates secretion of chloride and bicarbonate and water into the intestinal lumen, mainly by way of
727:
1029:
2417:
1305:
640:
was the originator. In 2021, it was the 246th most commonly prescribed medication in the United States, with more than 1
330:
115:
1863:"Press release: Allergan Acquires Rights To Ironwoods Constella (Linaclotide) From Almirall In More Than 40 Countries"
370:
2452:
2283:
1646:
1379:"Linaclotide: A new drug for the treatment of chronic constipation and irritable bowel syndrome with constipation"
852:
657:
637:
580:
682:, nausea, vomiting, urgent need to defecate, fecal incontinence, and bleeding in the colon, rectum, and anus.
299:
1966:
679:
664:
126:
409:
2278:
2137:
1951:
1466:"Advances in the management of constipation-predominant irritable bowel syndrome: the role of linaclotide"
1163:"Advances in the management of constipation-predominant irritable bowel syndrome: the role of linaclotide"
886:
988:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
2104:
712:
290:
777:
peptide) with the sequence CCEYCCNPACTGCY by one-letter abbreviation, or by three-letter abbreviation:
836:
of all cysteines, or trityl protection of all cysteines except Cys and Cys, which were protected with
987:
716:
610:
1513:
Braga Emidio N, Tran HN, Andersson A, Dawson PE, Albericio F, Vetter I, Muttenthaler M (June 2021).
386:
2288:
2225:
2215:
2185:
2175:
893:
856:
245:
133:
1799:
2315:
2195:
2066:
2018:
1959:
1804:
1724:
1670:"Xconomy: Renewables Aren't Just for Biofuels: Microbia Makes Industrial Chemicals a Bit Greener"
1599:
770:
965:
939:
for 30 pills; Allergan and
Ironwood increased the price of linaclotide to around $ 414 in 2018.
39:
ring of terminal tyrosine (Y) is in the lower left corner. Exaggerated bond lengths emphasize 3
35:
Linaclotide structure. A 2D line-angle schematic of linaclotide (sequence CCEYCCNPACTGCY). The
2303:
2200:
2180:
2036:
1716:
1591:
1544:
1495:
1446:
1408:
1359:
1192:
1102:
875:. Currie directed the efforts that led to the discovery of linaclotide, which was based on an
592:
319:
185:
54:
685:
It has not been tested in pregnant women and it is unknown if it is excreted in breast milk.
2341:
2152:
2099:
1708:
1583:
1567:
Góngora-Benítez M, Tulla-Puche J, Paradís-Bas M, Werbitzky O, Giraud M, Albericio F (2011).
1534:
1526:
1485:
1477:
1438:
1398:
1390:
1349:
1182:
1174:
881:
864:
833:
426:
254:
1832:
339:
2431:
2235:
2210:
2190:
2061:
2056:
902:
413:
390:
2379:
2230:
2051:
2000:
1746:
1539:
1514:
1490:
1465:
1403:
1378:
1354:
1337:
1187:
1162:
816:
629:
822:
815:
However, the actual structure of linaclotide is not fully specified without the three
30:
2441:
2119:
2084:
1728:
1607:
785:
402:
279:
198:
88:
1603:
1338:"Treatment of Chronic Constipation: Prescription Medications and Surgical Therapies"
2389:
2374:
1991:
1638:
1274:
1132:
932:
which raised sales by 21%; campaigns in 2015 and 2016 raised sales by 27% and 30%.
603:
599:
in children in the US; the most common adverse effects in others include diarrhea.
584:
153:
148:
74:
1712:
1244:
1530:
2384:
2346:
2142:
1025:
876:
860:
766:
755:
738:
activation. This results in increased intestinal fluid and accelerated transit.
735:
704:
663:
In June 2023, the indication was expanded in the US to include the treatment of
596:
82:
1569:"Optimized Fmoc solid-phase synthesis of the cysteine-rich peptide linaclotide"
2404:
2336:
2041:
837:
793:
774:
759:
723:
697:
465:
310:
1481:
1394:
1178:
2399:
2394:
2351:
2331:
2326:
2258:
2170:
2165:
2109:
2031:
2026:
1987:
805:
720:
653:
68:
40:
22:
1720:
1699:
Hornby PJ (2015). "Drug discovery approaches to irritable bowel syndrome".
1595:
1548:
1499:
1450:
1412:
1363:
1196:
2311:
2293:
2268:
2240:
2219:
2205:
2160:
2129:
2094:
2089:
2076:
2008:
1983:
912:
898:
872:
868:
789:
781:
762:
700:
633:
618:
614:
110:
1833:"From Actavis to Allergan: One pharma company's wild dealmaking journey"
908:
It was approved in the United States and in the
European Union in 2012.
2263:
2046:
1442:
809:
801:
797:
747:
708:
606:
265:
1587:
830:
751:
625:
36:
1300:"FDA approves first treatment for pediatric functional constipation"
359:
2250:
2114:
1769:"Microbia, Forest Laboratories Announce Linaclotide Collaboration"
492:
483:
693:
Systemic absorption of the globular tetradecapeptide is minimal.
660:
with constipation and chronic constipation with no known cause.
350:
207:
179:
1955:
192:
105:
2273:
995:
821:
621:. It was approved in the US and the European Union in 2012.
375:
2448:
Drugs acting on the gastrointestinal system and metabolism
1026:"UK label: Linaclotide Summary of Product Characteristics"
911:
Forest was acquired in 2014 and eventually became part of
1515:"Improving the Gastrointestinal Stability of Linaclotide"
928:
In 2014, Ironwood and Forest then
Allergan began running
892:
Under a partnership agreement announced in 2007, between
1745:
MUSC Foundation for
Research Development. Archived from
558:
935:
In 2017, the list price for linaclotide in the US was
2415:
897:
licensed rights to distribute the drug in Europe to
2362:
2302:
2249:
2151:
2128:
2075:
2017:
1999:
1215:"How Allergan Continues to Make Drug Prices Insane"
1028:. Electronic Medicines Compendium. September 2017.
732:
cystic fibrosis transmembrane conductance regulator
719:(GC-C). The medication binds to the surface of the
481:
464:
425:
420:
401:
369:
349:
329:
309:
298:
289:
264:
244:
219:
169:
164:
139:
125:
95:
81:
63:
53:
48:
1800:"Drug for Irritable Bowel Achieves Goals in Trial"
1336:Hussain ZH, Everhart K, Lacy BE (February 2015).
1831:Jones S, Burdette K, Wieczner J (30 July 2015).
1632:
1630:
1628:
278:
253:
1331:
1329:
1327:
1325:
1073:"Linzess- linaclotide capsule, gelatin coated"
889:. The company started Phase I trials in 2004.
1967:
8:
1562:
1560:
1558:
114:
21:
1898:. Ironwood. 31 January 2017. Archived from
1208:
1206:
1156:
1154:
1974:
1960:
1952:
1431:American Journal of Health-System Pharmacy
1067:
958:"Macrocycle Milestone for Ironwood Pharma"
758:(STa) and the endogenous peptide hormones
412:
389:
318:
1538:
1489:
1402:
1353:
1186:
1065:
1063:
1061:
1059:
1057:
1055:
1053:
1051:
1049:
1047:
1020:
1018:
1016:
1014:
1012:
338:
1470:Therapeutic Advances in Gastroenterology
1383:United European Gastroenterology Journal
1167:Therapeutic Advances in Gastroenterology
1133:"Linaclotide - Ironwood Pharmaceuticals"
589:chronic constipation with no known cause
43:(-S—S-) bonds between 6 cysteines (C's).
2422:
1926:"How DTC got things moving for Linzess"
948:
532:
512:
385:
233:
87:
2186:Magnesium hydroxide (milk of magnesia)
1843:from the original on 27 September 2020
1743:"Director profile: Mark Currie, Ph.D."
1643:Paradigm Magazine, Whitehead Institute
680:dizziness when standing up too quickly
403:
20:
1812:from the original on 20 December 2011
1798:Pollack, Andrew (13 September 2010).
1424:
1422:
1275:"Linaclotide - Drug Usage Statistics"
73:
7:
1377:Corsetti M, Tack J (February 2013).
1255:from the original on 15 January 2024
859:in 1998 by postdocs from the lab of
152:
1779:from the original on 20 August 2016
1649:from the original on 28 August 2021
1139:from the original on 7 October 2017
579:elsewhere) is a drug used to treat
358:
269:
1936:from the original on 15 April 2018
1873:from the original on 15 April 2018
1680:from the original on 16 April 2018
1225:from the original on 15 April 2018
1083:from the original on 29 March 2021
1032:from the original on 15 April 2018
14:
1342:Gastroenterology & Hepatology
1113:from the original on 22 June 2021
901:and had licensed Asian rights to
855:, which had been spun out of the
2425:
1701:Expert Opinion on Drug Discovery
1668:Timmerman L (23 February 2009).
1464:Yu SW, Rao SS (September 2014).
1161:Yu SW, Rao SS (September 2014).
443:
437:
29:
1637:Withers M (22 September 2004).
540:Key:KXGCNMMJRFDFNR-WDRJZQOASA-N
1519:Journal of Medicinal Chemistry
930:direct-to-consumer advertising
728:cyclic guanosine monophosphate
632:) in the United states and by
455:
449:
431:
1:
1713:10.1517/17460441.2015.1049528
1310:(Press release). 12 June 2023
575:in the US and Mexico, and as
571:, (sold under the brand name
1531:10.1021/acs.jmedchem.1c00380
1306:Food and Drug Administration
879:produced by some strains of
1213:Nocera J (9 January 2018).
851:The drug was discovered at
2474:
2284:Sodium lauryl sulfoacetate
595:about the risk of serious
421:Chemical and physical data
2458:Drugs developed by AbbVie
1107:European Medicines Agency
548:
523:
503:
224:
28:
1982:Drugs for constipation (
1482:10.1177/1756283X14537882
1395:10.1177/2050640612474446
1179:10.1177/1756283X14537882
976:– via CENBlog.org.
956:Oh SA (17 August 2011).
746:Linaclotide is a hybrid
658:irritable bowel syndrome
638:Ironwood Pharmaceuticals
581:irritable bowel syndrome
665:functional constipation
644:million prescriptions.
2077:Bulk-forming laxatives
841:-butylsulphenyl groups
826:
696:Linaclotide, like the
2105:Polycarbophil calcium
1775:. 17 September 2007.
1245:"The Top 300 of 2021"
871:and then had gone to
825:
773:tetradecapeptide (14
713:cell surface receptor
2279:Sodium laurilsulfate
717:guanylate cyclase 2C
611:guanylate cyclase 2C
2216:Polyethylene glycol
2176:Magnesium carbonate
2130:Lubricant laxatives
2019:Stimulant laxatives
1869:. 27 October 2015.
1613:on 11 February 2017
968:on 27 November 2018
919:Society and culture
894:Forest Laboratories
887:traveler's diarrhea
857:Whitehead Institute
711:that activates the
613:and remains in the
188:(Prescription only)
25:
2316:Oxycodone/naloxone
2304:Opioid antagonists
2196:Magnesium peroxide
2067:Sodium picosulfate
1805:The New York Times
1443:10.2146/ajhp130575
1079:. 31 August 2021.
827:
624:It is marketed by
617:after it is taken
2453:Tetradecapeptides
2413:
2412:
2201:Magnesium sulfate
2181:Magnesium citrate
2153:Osmotic laxatives
1588:10.1002/bip.21480
1525:(12): 8384–8390.
1437:(13): 1081–1091.
707:it mimics, is an
593:black box warning
566:
565:
494:Interactive image
371:CompTox Dashboard
211:
196:
183:
108:
2465:
2430:
2429:
2428:
2421:
2342:Methylnaltrexone
2289:Sodium phosphate
2226:Sodium phosphate
2062:Senna glycosides
1976:
1969:
1962:
1953:
1946:
1945:
1943:
1941:
1921:
1915:
1914:
1912:
1910:
1905:on 15 April 2018
1904:
1897:
1889:
1883:
1882:
1880:
1878:
1859:
1853:
1852:
1850:
1848:
1828:
1822:
1821:
1819:
1817:
1795:
1789:
1788:
1786:
1784:
1765:
1759:
1758:
1756:
1754:
1749:on 16 April 2018
1739:
1733:
1732:
1696:
1690:
1689:
1687:
1685:
1665:
1659:
1658:
1656:
1654:
1634:
1623:
1622:
1620:
1618:
1612:
1606:. Archived from
1573:
1564:
1553:
1552:
1542:
1510:
1504:
1503:
1493:
1461:
1455:
1454:
1426:
1417:
1416:
1406:
1374:
1368:
1367:
1357:
1333:
1320:
1319:
1317:
1315:
1296:
1290:
1289:
1287:
1285:
1271:
1265:
1264:
1262:
1260:
1241:
1235:
1234:
1232:
1230:
1210:
1201:
1200:
1190:
1158:
1149:
1148:
1146:
1144:
1129:
1123:
1122:
1120:
1118:
1103:"Constella EPAR"
1099:
1093:
1092:
1090:
1088:
1069:
1042:
1041:
1039:
1037:
1022:
1007:
1006:
1004:
1002:
992:nctr-crs.fda.gov
984:
978:
977:
975:
973:
964:. Archived from
953:
938:
882:Escherichia coli
643:
562:
561:
554:
496:
476:
474:
457:
451:
445:
439:
433:
416:
405:
394:
393:
379:
377:
362:
342:
322:
302:
282:
272:
271:
257:
209:
206:
201:
194:
191:
181:
178:
156:
118:
107:
104:
91:
77:
33:
26:
24:
2473:
2472:
2468:
2467:
2466:
2464:
2463:
2462:
2438:
2437:
2436:
2426:
2424:
2416:
2414:
2409:
2358:
2298:
2245:
2236:Sodium tartrate
2211:Pentaerythritol
2191:Magnesium oxide
2147:
2138:Liquid paraffin
2124:
2100:Methylcellulose
2071:
2057:Phenolphthalein
2013:
2001:Stool softeners
1995:
1980:
1950:
1949:
1939:
1937:
1923:
1922:
1918:
1908:
1906:
1902:
1895:
1891:
1890:
1886:
1876:
1874:
1861:
1860:
1856:
1846:
1844:
1830:
1829:
1825:
1815:
1813:
1797:
1796:
1792:
1782:
1780:
1767:
1766:
1762:
1752:
1750:
1741:
1740:
1736:
1698:
1697:
1693:
1683:
1681:
1667:
1666:
1662:
1652:
1650:
1636:
1635:
1626:
1616:
1614:
1610:
1571:
1566:
1565:
1556:
1512:
1511:
1507:
1463:
1462:
1458:
1428:
1427:
1420:
1376:
1375:
1371:
1335:
1334:
1323:
1313:
1311:
1298:
1297:
1293:
1283:
1281:
1273:
1272:
1268:
1258:
1256:
1243:
1242:
1238:
1228:
1226:
1212:
1211:
1204:
1160:
1159:
1152:
1142:
1140:
1135:. AdisInsight.
1131:
1130:
1126:
1116:
1114:
1109:. 24 May 2023.
1101:
1100:
1096:
1086:
1084:
1071:
1070:
1045:
1035:
1033:
1024:
1023:
1010:
1000:
998:
986:
985:
981:
971:
969:
955:
954:
950:
945:
936:
926:
921:
903:Astellas Pharma
849:
744:
691:
673:
671:Adverse effects
652:Linaclotide is
650:
641:
557:
555:
552:(what is this?)
549:
544:
541:
536:
531:
530:
519:
516:
511:
510:
499:
472:
470:
460:
454:
448:
442:
436:
397:
373:
365:
345:
325:
305:
285:
268:
260:
240:
237:
232:
231:
215:
199:
160:
128:
121:
44:
17:
12:
11:
5:
2471:
2469:
2461:
2460:
2455:
2450:
2440:
2439:
2435:
2434:
2411:
2410:
2408:
2407:
2402:
2397:
2392:
2387:
2382:
2380:Oxyphenisatine
2377:
2372:
2366:
2364:
2360:
2359:
2357:
2356:
2355:
2354:
2349:
2344:
2339:
2334:
2329:
2319:
2308:
2306:
2300:
2299:
2297:
2296:
2291:
2286:
2281:
2276:
2271:
2266:
2261:
2255:
2253:
2247:
2246:
2244:
2243:
2238:
2233:
2231:Sodium sulfate
2228:
2223:
2213:
2208:
2203:
2198:
2193:
2188:
2183:
2178:
2173:
2168:
2163:
2157:
2155:
2149:
2148:
2146:
2145:
2140:
2134:
2132:
2126:
2125:
2123:
2122:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2081:
2079:
2073:
2072:
2070:
2069:
2064:
2059:
2054:
2052:Oxyphenisatine
2049:
2044:
2039:
2034:
2029:
2023:
2021:
2015:
2014:
2012:
2011:
2005:
2003:
1997:
1996:
1981:
1979:
1978:
1971:
1964:
1956:
1948:
1947:
1930:BioPharma Dive
1916:
1884:
1854:
1823:
1790:
1760:
1734:
1707:(8): 809–824.
1691:
1660:
1624:
1554:
1505:
1476:(5): 193–205.
1456:
1418:
1369:
1348:(2): 104–114.
1321:
1291:
1266:
1236:
1219:Bloomberg News
1202:
1173:(5): 193–205.
1150:
1124:
1094:
1043:
1008:
979:
947:
946:
944:
941:
925:
922:
920:
917:
848:
845:
750:design of the
743:
740:
690:
687:
672:
669:
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387:DTXSID90234256
382:
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34:
15:
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2:
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2221:
2217:
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2209:
2207:
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2179:
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2169:
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2159:
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2154:
2150:
2144:
2141:
2139:
2136:
2135:
2133:
2131:
2127:
2121:
2120:Syrup of figs
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2085:Dietary fiber
2083:
2082:
2080:
2078:
2074:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
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2024:
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2010:
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2002:
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1989:
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1609:
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1309:
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1216:
1209:
1207:
1203:
1198:
1194:
1189:
1184:
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1168:
1164:
1157:
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1134:
1128:
1125:
1112:
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1098:
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1078:
1074:
1068:
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1064:
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1044:
1031:
1027:
1021:
1019:
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983:
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967:
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959:
952:
949:
942:
940:
933:
931:
923:
918:
916:
914:
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904:
900:
895:
890:
888:
884:
883:
878:
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862:
858:
854:
853:Microbia, Inc
846:
844:
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835:
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824:
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799:
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783:
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764:
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749:
741:
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733:
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488:
485:
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469:
467:
463:
430:
428:
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419:
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411:
408:
406:
404:ECHA InfoCard
400:
392:
388:
384:
383:
381:
372:
368:
361:
357:
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354:
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348:
341:
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234:
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218:
212: Rx-only
205:
202:
190:
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177:
176:
174:
172:
168:
163:
155:
150:
147:
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144:
142:
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117:
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100:
98:
94:
90:
86:
84:
80:
76:
72:
70:
66:
62:
58:
56:
52:
49:Clinical data
47:
42:
38:
32:
27:
19:
2390:Prucalopride
2375:Lubiprostone
2369:
1938:. Retrieved
1929:
1919:
1907:. Retrieved
1900:the original
1887:
1875:. Retrieved
1866:
1857:
1845:. Retrieved
1836:
1826:
1816:14 September
1814:. Retrieved
1803:
1793:
1783:15 September
1781:. Retrieved
1772:
1763:
1751:. Retrieved
1747:the original
1737:
1704:
1700:
1694:
1682:. Retrieved
1673:
1663:
1651:. Retrieved
1642:
1639:"Druhunters"
1615:. Retrieved
1608:the original
1582:(1): 69–80.
1579:
1575:
1522:
1518:
1508:
1473:
1469:
1459:
1434:
1430:
1386:
1382:
1372:
1345:
1341:
1312:. Retrieved
1303:
1294:
1282:. Retrieved
1278:
1269:
1257:. Retrieved
1248:
1239:
1227:. Retrieved
1218:
1170:
1166:
1141:. Retrieved
1127:
1115:. Retrieved
1106:
1097:
1085:. Retrieved
1076:
1034:. Retrieved
999:. Retrieved
991:
982:
970:. Retrieved
966:the original
962:The Haystack
961:
951:
934:
927:
910:
907:
891:
880:
867:division of
850:
838:
828:
814:
812:–Cys–Tyr–OH
779:
754:heat-stable
745:
695:
692:
689:Pharmacology
684:
677:
674:
662:
651:
623:
604:oligopeptide
601:
585:constipation
576:
572:
568:
567:
556:
550:
171:Legal status
165:Legal status
97:License data
18:
2385:Plecanatide
2370:Linaclotide
2347:Naldemedine
2143:Mineral oil
1924:LaMotta L.
1617:10 February
1576:Biopolymers
1389:(1): 7–20.
972:11 February
885:that cause
877:enterotoxin
861:Gerald Fink
767:uroguanylin
756:enterotoxin
736:ion channel
705:uroguanylin
648:Medical use
597:dehydration
591:. It has a
569:Linaclotide
477: g·mol
410:100.243.239
255:851199-59-2
220:Identifiers
116:Linaclotide
83:MedlinePlus
55:Trade names
23:Linaclotide
2442:Categories
2405:Ulimorelin
2337:Bevenopran
2042:Castor oil
1988:cathartics
1284:14 January
1259:14 January
1001:22 October
943:References
834:protection
775:amino acid
769:. It is a
760:endogenous
724:epithelial
721:intestinal
698:endogenous
628:(formerly
482:3D model (
466:Molar mass
340:N0TXR0XR5X
311:ChemSpider
291:IUPHAR/BPS
246:CAS Number
229:IUPAC name
2400:Tenapanor
2395:Tegaserod
2352:Naloxegol
2332:Axelopran
2327:Alvimopan
2259:Bisacodyl
2171:Laminarid
2166:Lactulose
2110:Sterculia
2095:Ispaghula
2032:Bisoxatin
2027:Bisacodyl
1984:laxatives
1729:207494271
924:Economics
817:disulfide
792:–Cys–Cys–
771:synthetic
742:Chemistry
656:to treat
654:indicated
636:in Asia;
602:It is an
577:Constella
127:Routes of
75:Monograph
69:Drugs.com
41:disulfide
2432:Medicine
2312:Naloxone
2294:Sorbitol
2269:Glycerol
2241:Sorbitol
2220:macrogol
2206:Mannitol
2161:Lactitol
2115:Triticum
2090:Ethulose
2009:Docusate
1940:15 April
1934:Archived
1909:15 April
1877:15 April
1871:Archived
1867:Allergan
1847:15 April
1841:Archived
1810:Archived
1777:Archived
1773:FDA News
1753:15 April
1721:26193876
1684:15 April
1678:Archived
1653:15 April
1647:Archived
1604:46150263
1596:20560145
1549:33979161
1500:25177366
1451:24939497
1413:24917937
1364:27099579
1279:ClinCalc
1253:Archived
1249:ClinCalc
1229:15 April
1223:Archived
1197:25177366
1143:15 April
1137:Archived
1111:Archived
1081:Archived
1077:DailyMed
1036:15 April
1030:Archived
913:Allergan
899:Almirall
873:Sepracor
869:Monsanto
763:guanylin
701:guanylin
634:Astellas
630:Allergan
619:by mouth
615:GI tract
559:(verify)
320:17314504
280:16158208
141:ATC code
134:By mouth
111:DailyMed
37:phenolic
16:Medicine
2322:PAMORAs
2264:Dantron
2047:Dantron
2037:Cascara
1837:Fortune
1674:Xconomy
1540:8237258
1491:4107700
1404:4040778
1355:4836568
1314:12 June
1188:4107700
1117:12 June
1087:12 June
937:US$ 378
847:History
748:peptide
734:(CFTR)
709:agonist
607:agonist
573:Linzess
427:Formula
266:PubChem
203:Rx-only
200:WARNING
157:)
151: (
149:A06AX04
113::
89:a613007
59:Linzess
2418:Portal
2363:Others
2251:Enemas
1727:
1719:
1602:
1594:
1547:
1537:
1498:
1488:
1449:
1411:
1401:
1362:
1352:
1195:
1185:
865:Searle
831:trityl
752:E.coli
642:
626:Abbvie
508:SMILES
360:D09355
197:
184:
109:
1903:(PDF)
1896:(PDF)
1893:"8-K"
1725:S2CID
1611:(PDF)
1600:S2CID
1572:(PDF)
1308:(FDA)
1304:U.S.
804:–Cys–
784:–Cys–
583:with
528:InChI
484:JSmol
1986:and
1942:2018
1911:2018
1879:2018
1849:2018
1818:2010
1785:2010
1755:2018
1717:PMID
1686:2018
1655:2018
1619:2017
1592:PMID
1545:PMID
1496:PMID
1447:PMID
1409:PMID
1360:PMID
1316:2023
1286:2024
1261:2024
1231:2018
1193:PMID
1145:2018
1119:2023
1089:2023
1038:2018
1003:2023
974:2017
839:tert
765:and
703:and
587:and
351:KEGG
331:UNII
300:5017
65:AHFS
2274:Oil
1992:A06
1990:) (
1709:doi
1584:doi
1535:PMC
1527:doi
1486:PMC
1478:doi
1439:doi
1399:PMC
1391:doi
1350:PMC
1183:PMC
1175:doi
996:FDA
810:Gly
806:Thr
802:Ala
798:Pro
794:Asn
790:Tyr
786:Glu
782:Cys
715:of
609:of
475:.73
473:526
376:EPA
270:CID
186:POM
154:WHO
2444::
1932:.
1928:.
1865:.
1839:.
1835:.
1808:.
1802:.
1771:.
1723:.
1715:.
1705:10
1703:.
1676:.
1672:.
1645:.
1641:.
1627:^
1598:.
1590:.
1580:96
1578:.
1574:.
1557:^
1543:.
1533:.
1523:64
1521:.
1517:.
1494:.
1484:.
1472:.
1468:.
1445:.
1435:71
1433:.
1421:^
1407:.
1397:.
1385:.
1381:.
1358:.
1346:11
1344:.
1340:.
1324:^
1302:.
1277:.
1251:.
1247:.
1221:.
1217:.
1205:^
1191:.
1181:.
1169:.
1165:.
1153:^
1105:.
1075:.
1046:^
1011:^
994:.
990:.
960:.
905:.
780:H–
667:.
453:21
447:15
441:79
435:59
208:EU
193:US
180:UK
106:US
2420::
2318:)
2314:(
2222:)
2218:(
1994:)
1975:e
1968:t
1961:v
1944:.
1913:.
1881:.
1851:.
1820:.
1787:.
1757:.
1731:.
1711::
1688:.
1657:.
1621:.
1586::
1551:.
1529::
1502:.
1480::
1474:7
1453:.
1441::
1415:.
1393::
1387:1
1366:.
1318:.
1288:.
1263:.
1233:.
1199:.
1177::
1171:7
1147:.
1121:.
1091:.
1040:.
1005:.
808:–
800:–
796:–
788:–
486:)
471:1
459:6
456:S
450:O
444:N
438:H
432:C
378:)
374:(
210::
195::
182::
67:/
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
