47:
360:
228:
826:
38:
1903:
1638:
647:
821:
The most common side effects include peripheral neuropathy (nerve damage in the hands and feet), diarrhea, nausea (feeling sick), acid reflux (stomach acid flowing up into the mouth), esophagitis (inflammation of the food pipe), jaundice (yellowing of the skin and eyes), skin problems (lesions) and
796:
Cholic acid FGK (Kolbam) was approved for medical use in the
European Union in November 2015. It is indicated for the treatment of inborn errors of primary bile acid synthesis, in infants from one month of age for continuous lifelong treatment through adulthood, encompassing the following single
125:
1494:
Alan F. Hofmann; Johnson L. Thistle; Peter D. Klein; Patricia A. Szczepanik; Paulina Y. S. Yu (1978). "Chenotherapy for
Gallstone Dissolution, II. Induced Changes in Bile Composition and Gallstone Response".
1167:
855:
770:, is approved for use in the United States and is indicated as a treatment for children and adults with bile acid synthesis disorders due to single enzyme defects, and for peroxisomal disorders (such as
383:
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
393:
InChI=1/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
604:
578:
494:
660:
1459:
Iser JH, Dowling H, Mok HY, Bell GD (August 1975). "Chenodeoxycholic acid treatment of gallstones. A follow-up report and analysis of factors influencing response to therapy".
1714:
782:
745:(rate-limiting step in bile acid synthesis), and cholesterol does the opposite. This is why chenodeoxycholic acid, and not cholic acid, can be used to treat
409:
1686:
Text was copied from this source which is under copyright of the
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1338:
Text was copied from this source which is under copyright of the
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1611:
561:
1207:
895:
1210:
898:
1180:
868:
1357:
1707:
1179:
867:
1373:
Bennion LJ, Ginsberg RL, Gernick MB, Bennett PH (January 1976). "Effects of oral contraceptives on the gallbladder bile of normal women".
1198:
886:
718:. These two major bile acids are roughly equal in concentration in humans. Derivatives are made from cholyl-CoA, which exchanges its
1214:
902:
790:
756:
are the most important human bile acids. Other species may synthesize different bile acids as their predominant primary bile acids.
574:
374:
1200:
888:
1287:
1211:
899:
1700:
589:
542:
805:
1177:
865:
742:
261:
1213:
1193:
1187:
1182:
901:
881:
875:
870:
1205:
1185:
893:
873:
811:
1893:
667:
1617:
1587:
1237:
1178:
866:
317:
1196:
1195:
1174:
884:
883:
862:
338:
1215:
1204:
1191:
1190:
1189:
903:
892:
879:
878:
877:
1208:
1194:
896:
882:
1212:
1209:
900:
897:
1671:
1581:
1323:
1192:
880:
556:
1218:
1217:
1175:
1171:
906:
905:
863:
859:
1216:
1206:
1203:
1202:
1201:
1186:
1184:
1183:
1181:
1173:
1172:
1170:
904:
894:
891:
890:
889:
874:
872:
871:
869:
861:
860:
858:
1199:
1188:
1176:
887:
876:
864:
1197:
885:
476:
1623:
223:
46:
1865:
165:
1938:
1801:
1749:
801:
753:
703:
69:
59:
1791:
1764:
1923:
825:
355:
91:
777:
It was approved for use in the
European Union in September 2013, and is sold under the brand name
1835:
1769:
771:
515:
37:
1796:
1933:
1880:
1563:
1512:
1476:
1441:
1390:
1353:
617:
1318:
1759:
1553:
1543:
1504:
1468:
1431:
1421:
1382:
735:
731:
432:
185:
1666:
781:. It is indicated for the treatment of inborn errors in primary bile-acid synthesis due to
326:
1928:
1907:
1532:"Bile salts of vertebrates: structural variation and possible evolutionary significance"
359:
227:
145:
101:
1558:
1531:
1436:
1409:
793:
deficiency in infants, children and adolescents aged one month to 18 years and adults.
638:
1258:
1241:
1228:
1917:
1870:
1642:
1508:
465:
216:
1166:
854:
1850:
1776:
1724:
749:(because decreasing bile acid synthesis would supersaturate the stones even more).
505:
500:
306:
1786:
1781:
1472:
1386:
715:
695:
1692:
1426:
1860:
1855:
1816:
1811:
1806:
839:
Click on genes, proteins and metabolites below to link to respective articles.
719:
455:
251:
176:
17:
1875:
1845:
1840:
1743:
746:
707:
687:
1567:
1445:
1480:
1394:
1348:
Colleen Smith; Lieberman, Michael; Marks, Dawn B.; Allan D. Marks (2007).
698:), it is a white crystalline substance. Salts of cholic acid are called
1516:
243:
235:
196:
1548:
205:
727:
723:
691:
293:
156:
637:
Except where otherwise noted, data are given for materials in their
281:
1826:
1612:"FDA approves Cholbam to treat rare bile acid synthesis disorders"
824:
711:
136:
124:
114:
1641:
This article incorporates text from this source, which is in the
829:
Structure of cholic acid showing relationship to other bile acids
1733:
623:
560:
551:
272:
1696:
611:
568:
1165:
853:
343:
1256:
The interactive pathway map can be edited at WikiPathways:
598:
527:
470:
200 to 201 °C (392 to 394 °F; 473 to 474 K)
655:
1891:
1352:. Hagerstwon, MD: Lippincott Williams & Wilkins.
236:
1530:
Hofmann AF, Hagey LR, Krasowski MD (February 2010).
817:
cholesterol 7 alpha-hydroxylase (CYP7A1) deficiency.
1825:
1732:
1282:
1280:
260:
305:
1313:
1311:
1309:
1169:
857:
100:
1661:
1659:
1657:
1655:
1653:
1651:
1622:(Press release). 17 March 2015. Archived from
573:
1708:
8:
1715:
1701:
1693:
684:3α,7α,12α-trihydroxy-5β-cholan-24-oic acid
358:
226:
184:
63:3α,7α,12α-Trihydroxy-5β-cholan-24-oic acid
29:
1557:
1547:
1435:
1425:
417:C(CCC(=O)O)1CC21((C32(C43(CC(C4)O)C)O)O)C
325:
1898:
1276:
1249:
766:Cholic acid, sold under the brand name
690:that is insoluble in water (soluble in
414:
379:
354:
204:
812:2- (or alpha-) methylacyl-CoA racemase
217:
1410:"Bile acids: regulation of synthesis"
1350:Marks' essential medical biochemistry
386:Key: BHQCQFFYRZLCQQ-OELDTZBJSA-N
164:
144:
7:
504:
1461:The New England Journal of Medicine
396:Key: BHQCQFFYRZLCQQ-OELDTZBJBZ
296:
280:
78:)-6-phenanthren-1-yl]heptanoic acid
25:
1901:
1636:
1582:"Cholbam (cholic acid) Capsules"
1509:10.1001/jama.1978.03280390034017
645:
45:
36:
714:, where it is synthesized from
641:(at 25 °C , 100 kPa).
1288:"Cholbam- cholic acid capsule"
806:cerebrotendinous xanthomatosis
1:
1618:Food and Drug Administration
1588:Food and Drug Administration
1473:10.1056/NEJM197508212930804
1387:10.1056/NEJM197601222940403
791:Δ-3-oxosteroid-5β-reductase
743:cholesterol-7-α-hydroxylase
702:. Cholic acid, along with
1955:
1427:10.1194/jlr.R900010-JLR200
1408:Chiang JY (October 2009).
822:malaise (feeling unwell).
804:deficiency (presenting as
741:Cholic acid downregulates
706:, is one of the two major
460:408.57 g/mol
1672:European Medicines Agency
1414:Journal of Lipid Research
1324:European Medicines Agency
635:
487:
425:
405:
370:
84:
68:
58:
53:
44:
35:
1723:Bile and liver therapy (
834:Interactive pathway map
787:-steroid oxidoreductase
477:Magnetic susceptibility
1866:Ornithine oxoglutarate
1259:"Statin_Pathway_WP430"
1221:
909:
830:
244:(additional chemicals)
1802:Nicotinyl methylamide
1750:Chenodeoxycholic acid
1220:
908:
828:
802:sterol 27-hydroxylase
754:chenodeoxycholic acid
704:chenodeoxycholic acid
70:Systematic IUPAC name
1792:Maralixibat chloride
1765:Ursodeoxycholic acid
1227:|alt=Statin pathway
1676:. 17 September 2018
1549:10.1194/jlr.R000042
1328:. 17 September 2018
814:(AMACR) deficiency;
607:(Prescription only)
32:
1836:Arginine glutamate
1770:Ursodoxicoltaurine
1626:on 26 January 2018
1222:
910:
831:
772:Zellweger syndrome
668:Infobox references
30:
1889:
1888:
1881:Tidiacic arginine
1503:(12): 1138–1144.
1359:978-0-7817-9340-7
676:Chemical compound
674:
673:
627:
615:
602:
571:
554:
531:
483:-282.3·10 cm/mol
339:CompTox Dashboard
126:Interactive image
16:(Redirected from
1946:
1906:
1905:
1904:
1897:
1760:Obeticholic acid
1717:
1710:
1703:
1694:
1687:
1685:
1683:
1681:
1663:
1646:
1640:
1639:
1635:
1633:
1631:
1608:
1602:
1601:
1599:
1597:
1578:
1572:
1571:
1561:
1551:
1527:
1521:
1520:
1491:
1485:
1484:
1456:
1450:
1449:
1439:
1429:
1405:
1399:
1398:
1370:
1364:
1363:
1345:
1339:
1337:
1335:
1333:
1315:
1304:
1303:
1301:
1299:
1284:
1263:
1262:
1254:
1161:
1156:
1151:
1146:
1141:
1136:
1131:
1126:
1121:
1116:
1111:
1106:
1101:
1096:
1091:
1086:
1081:
1076:
1071:
1066:
1061:
1056:
1051:
1046:
1041:
1036:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
996:
991:
986:
981:
976:
971:
966:
961:
956:
951:
946:
941:
936:
931:
926:
921:
916:
797:enzyme defects:
752:Cholic acid and
738:, respectively.
736:taurocholic acid
710:produced by the
682:, also known as
658:
652:
649:
648:
625:
622:
613:
610:
600:
597:
581:
570:
567:
564:
553:
550:
529:
526:
508:
433:Chemical formula
363:
362:
347:
345:
329:
309:
298:
284:
264:
238:
230:
219:
208:
188:
168:
148:
128:
104:
49:
40:
33:
21:
1954:
1953:
1949:
1948:
1947:
1945:
1944:
1943:
1914:
1913:
1912:
1902:
1900:
1892:
1890:
1885:
1821:
1728:
1721:
1691:
1690:
1679:
1677:
1665:
1664:
1649:
1637:
1629:
1627:
1610:
1609:
1605:
1595:
1593:
1592:. 13 April 2015
1580:
1579:
1575:
1529:
1528:
1524:
1493:
1492:
1488:
1458:
1457:
1453:
1420:(10): 1955–66.
1407:
1406:
1402:
1375:N. Engl. J. Med
1372:
1371:
1367:
1360:
1347:
1346:
1342:
1331:
1329:
1319:"Orphacol EPAR"
1317:
1316:
1307:
1297:
1295:
1286:
1285:
1278:
1273:
1268:
1267:
1266:
1257:
1255:
1251:
1246:
1245:
1244:
1240:Statin pathway
1239:
1234:
1233:
1232:
1226:
1225:
1224:
1223:
1219:
1163:
1162:
1159:
1157:
1154:
1152:
1149:
1147:
1144:
1142:
1139:
1137:
1134:
1132:
1129:
1127:
1124:
1122:
1119:
1117:
1114:
1112:
1109:
1107:
1104:
1102:
1099:
1097:
1094:
1092:
1089:
1087:
1084:
1082:
1079:
1077:
1074:
1072:
1069:
1067:
1064:
1062:
1059:
1057:
1054:
1052:
1049:
1047:
1044:
1042:
1039:
1037:
1034:
1032:
1029:
1027:
1024:
1022:
1019:
1017:
1014:
1012:
1009:
1007:
1004:
1002:
999:
997:
994:
992:
989:
987:
984:
982:
979:
977:
974:
972:
969:
967:
964:
962:
959:
957:
954:
952:
949:
947:
944:
942:
939:
937:
934:
932:
929:
927:
924:
922:
919:
917:
914:
911:
907:
836:
786:
762:
677:
670:
665:
664:
663: ?)
654:
650:
646:
642:
631:
584:
537:
520:
517:
497:
480:
449:
445:
441:
435:
421:
418:
413:
412:
401:
398:
397:
394:
388:
387:
384:
378:
377:
366:
348:
341:
332:
312:
299:
287:
267:
254:
211:
191:
171:
151:
131:
118:
107:
94:
80:
79:
64:
28:
23:
22:
15:
12:
11:
5:
1952:
1950:
1942:
1941:
1936:
1931:
1926:
1916:
1915:
1911:
1910:
1887:
1886:
1884:
1883:
1878:
1873:
1868:
1863:
1858:
1853:
1848:
1843:
1838:
1832:
1830:
1823:
1822:
1820:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1773:
1772:
1767:
1762:
1757:
1752:
1739:
1737:
1730:
1729:
1722:
1720:
1719:
1712:
1705:
1697:
1689:
1688:
1647:
1603:
1573:
1522:
1486:
1451:
1400:
1365:
1358:
1340:
1305:
1294:. 12 July 2019
1275:
1274:
1272:
1269:
1265:
1264:
1248:
1247:
1236:
1235:
1164:
1158:
1153:
1148:
1143:
1138:
1133:
1128:
1123:
1118:
1113:
1108:
1103:
1098:
1093:
1088:
1083:
1078:
1073:
1068:
1063:
1058:
1053:
1048:
1043:
1038:
1033:
1028:
1023:
1018:
1013:
1008:
1003:
998:
993:
988:
983:
978:
973:
968:
963:
958:
953:
948:
943:
938:
933:
928:
923:
918:
913:
912:
852:
851:
850:
849:
847:
846:
845:
844:
843:
842:
835:
832:
819:
818:
815:
809:
789:deficiency or
784:
783:3β-hydroxy-Δ-C
761:
758:
675:
672:
671:
666:
644:
643:
639:standard state
636:
633:
632:
630:
629:
620:
608:
594:
592:
586:
585:
583:
582:
565:
547:
545:
539:
538:
536:
535:
533:
523:
521:
514:
511:
510:
498:
493:
490:
489:
485:
484:
481:
475:
472:
471:
468:
462:
461:
458:
452:
451:
447:
443:
439:
436:
431:
428:
427:
423:
422:
420:
419:
416:
408:
407:
406:
403:
402:
400:
399:
395:
392:
391:
389:
385:
382:
381:
373:
372:
371:
368:
367:
365:
364:
351:
349:
337:
334:
333:
331:
330:
322:
320:
314:
313:
311:
310:
302:
300:
292:
289:
288:
286:
285:
277:
275:
269:
268:
266:
265:
257:
255:
250:
247:
246:
240:
232:
231:
221:
213:
212:
210:
209:
201:
199:
193:
192:
190:
189:
181:
179:
173:
172:
170:
169:
161:
159:
153:
152:
150:
149:
141:
139:
133:
132:
130:
129:
121:
119:
112:
109:
108:
106:
105:
97:
95:
90:
87:
86:
82:
81:
73:
72:
66:
65:
62:
56:
55:
51:
50:
42:
41:
27:Main bile acid
26:
24:
18:Sodium cholate
14:
13:
10:
9:
6:
4:
3:
2:
1951:
1940:
1937:
1935:
1932:
1930:
1927:
1925:
1922:
1921:
1919:
1909:
1899:
1895:
1882:
1879:
1877:
1874:
1872:
1871:Phospholipids
1869:
1867:
1864:
1862:
1859:
1857:
1854:
1852:
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1833:
1831:
1828:
1824:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1747:
1746:
1745:
1741:
1740:
1738:
1735:
1731:
1726:
1718:
1713:
1711:
1706:
1704:
1699:
1698:
1695:
1675:
1673:
1668:
1667:"Kolbam EPAR"
1662:
1660:
1658:
1656:
1654:
1652:
1648:
1644:
1643:public domain
1625:
1621:
1619:
1613:
1607:
1604:
1591:
1589:
1583:
1577:
1574:
1569:
1565:
1560:
1555:
1550:
1545:
1542:(2): 226–46.
1541:
1537:
1533:
1526:
1523:
1518:
1514:
1510:
1506:
1502:
1498:
1490:
1487:
1482:
1478:
1474:
1470:
1467:(8): 378–83.
1466:
1462:
1455:
1452:
1447:
1443:
1438:
1433:
1428:
1423:
1419:
1415:
1411:
1404:
1401:
1396:
1392:
1388:
1384:
1381:(4): 189–92.
1380:
1376:
1369:
1366:
1361:
1355:
1351:
1344:
1341:
1327:
1325:
1320:
1314:
1312:
1310:
1306:
1293:
1289:
1283:
1281:
1277:
1270:
1260:
1253:
1250:
1243:
1238:
1230:
1168:
856:
841:
840:
833:
827:
823:
816:
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1851:Glycyrrhizin
1777:Cyclobutyrol
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1678:. Retrieved
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1628:. Retrieved
1624:the original
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1594:. Retrieved
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590:Legal status
543:License data
166:ChEMBL205596
85:Identifiers
75:
31:Cholic acid
1787:Hymecromone
1782:Elafibranor
1755:Cholic acid
732:glycocholic
730:, yielding
716:cholesterol
696:acetic acid
680:Cholic acid
426:Properties
224:100.001.217
146:CHEBI:16359
1924:Bile acids
1918:Categories
1861:Methionine
1856:Metadoxine
1817:Seladelpar
1812:Piprozolin
1807:Odevixibat
1271:References
747:gallstones
708:bile acids
456:Molar mass
327:G1JO7801AE
252:IUPHAR/BPS
177:ChemSpider
113:3D model (
92:CAS Number
60:IUPAC name
1876:Silymarin
1846:Epomediol
1841:Citiolone
1797:Menbutone
1744:bile acid
688:bile acid
516:Pregnancy
1934:Cholanes
1908:Medicine
1568:19638645
1446:19346330
1292:DailyMed
779:Orphacol
700:cholates
532: B2
518:category
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495:ATC code
479:(χ)
237:E number
197:DrugBank
1829:therapy
1736:therapy
1559:2803226
1481:1152936
1437:2739756
1395:1244533
848:[[File:
808:, CTX);
768:Cholbam
728:taurine
724:glycine
692:alcohol
661:what is
659: (
579:Cholbam
577::
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501:A05AA03
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294:PubChem
206:DB02659
102:81-25-4
1929:Triols
1894:Portal
1680:19 May
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618:℞-only
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410:SMILES
307:221493
282:D10699
242:E1000
186:192176
157:ChEMBL
54:Names
1827:Liver
1674:(EMA)
1620:(FDA)
1616:U.S.
1596:3 May
1590:(FDA)
1586:U.S.
1332:2 May
1326:(EMA)
1298:2 May
1160:]
726:, or
712:liver
375:InChI
137:ChEBI
115:JSmol
1734:Bile
1682:2020
1632:2020
1598:2020
1564:PMID
1513:PMID
1497:JAMA
1477:PMID
1442:PMID
1391:PMID
1354:ISBN
1334:2020
1300:2020
1242:edit
1229:edit
734:and
694:and
318:UNII
273:KEGG
1725:A05
1554:PMC
1544:doi
1505:doi
1501:239
1469:doi
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1432:PMC
1422:doi
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720:CoA
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506:WHO
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297:CID
262:609
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