836:(DCA) is increased in the colonic contents of humans in response to a high fat diet. In populations with a high incidence of colorectal cancer, fecal concentrations of bile acids are higher, and this association suggests that increased colonic exposure to bile acids could play a role in the development of cancer. In one particular comparison, the fecal DCA concentrations in Native Africans in South Africa (who eat a low fat diet) compared to African Americans (who eat a higher fat diet) was 7.30 vs. 37.51 nmol/g wet weight stool. Native Africans in South Africa have a low incidence rate of colon cancer of less than 1:100,000, compared to the high incidence rate for male African Americans of 72:100,000.
578:
subsequent removal of the 7α hydroxyl group by intestinal bacteria will then result in a less toxic but still-functional dihydroxy bile acid. Over the course of vertebrate evolution, a number of positions have been chosen for placement of the third hydroxyl group. Initially, the 16α position was favored, in particular in birds. Later, this position was superseded in a large number of species selecting the 12α position. Primates (including humans) utilize 12α for their third hydroxyl group position, producing cholic acid. In mice and other rodents, 6β hydroxylation forms
493:
labeled A, B, C, and D, from the farthest to the closest to the side chain with the carboxyl group. The D-ring is smaller by one carbon than the other three. The structure is commonly drawn with A at the left and D at the right. The hydroxyl groups can be in either of two configurations: either up (or out), termed beta (β; often drawn by convention as a solid line), or down, termed alpha (α; displayed as a dashed line). All bile acids have a 3-hydroxyl group, derived from the parent molecule, cholesterol, in which the 3-hydroxyl is beta.
452:
466:
164:
497:
438:
480:
531:, from which the "cheno" portion of the name was derived (Greek: χήν = goose). The 5β in the name denotes the orientation of the junction between rings A and B of the steroid nucleus (in this case, they are bent). The term "cholan" denotes a particular steroid structure of 24 carbons, and the "24-oic acid" indicates that the carboxylic acid is found at position 24, at the end of the side-chain. Chenodeoxycholic acid is made by many species, and is the prototypic functional bile acid.
308:. The added solubility of conjugated bile salts aids in their function by preventing passive re-absorption in the small intestine. As a result, the concentration of bile acids/salts in the small intestine is high enough to form micelles and solubilize lipids. "Critical micellar concentration" refers to both an intrinsic property of the bile acid itself and amount of bile acid necessary to function in the spontaneous and dynamic formation of micelles. Bile acid-containing micelles aid
396:
424:
410:
4889:
382:
523:. There are multiple steps in bile acid synthesis requiring 14 enzymes in all. These result in the junction between the first two steroid rings (A and B) being altered, making the molecule bent; in this process, the 3-hydroxyl is converted to the α orientation. The simplest 24-carbon bile acid has two hydroxyl groups at positions 3α and 7α. This is 3α,7α-dihydroxy-5β-cholan-24-oic acid, or, as more usually known,
784:, or from bile stasis. Lower concentrations of bile acids or phospholipids in bile reduce cholesterol solubility and lead to microcrystal formation. Oral therapy with chenodeoxycholic acid and/or ursodeoxycholic acid has been used to dissolve cholesterol gallstones. Stones may recur when treatment is stopped. Bile acid therapy may be of value to prevent stones in certain circumstances such as following
4901:
560:, 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid, the most abundant bile acid in humans and many other species, was discovered before chenodeoxycholic acid. It is a tri-hydroxy-bile acid with 3 hydroxyl groups (3α, 7α and 12α). In its synthesis in the liver, 12α hydroxylation is performed by the additional action of
258:
of the unconjugated bile acids are between 5 and 6.5, and the pH of the duodenum ranges between 3 and 5, so when unconjugated bile acids are in the duodenum, they are almost always protonated (HA form), which makes them relatively insoluble in water. Conjugating bile acids with amino acids lowers the
492:
Bile salts constitute a large family of molecules, composed of a steroid structure with four rings, a five- or eight-carbon side-chain terminating in a carboxylic acid, and several hydroxyl groups, the number and orientation of which is different among the specific bile salts. The four rings are
319:
Synthesis of bile acids is a major route of cholesterol metabolism in most species other than humans. The body produces about 800 mg of cholesterol per day and about half of that is used for bile acid synthesis producing 400–600 mg daily. Human adults secrete between 12 and 18 g of
589:
Many other bile acids have been described, often in small amounts, resulting from bacterial enzymatic or other modifications. The "iso-" epimers have the 3-hydroxyl group in the β position. The "allo-" epimers have the 5α configuration, which changes the relative position of the A and B rings.
577:
Different vertebrate families have evolved to use modifications of most positions on the steroid nucleus and side-chain of the bile acid structure. To avoid the problems associated with the production of lithocholic acid, most species add a third hydroxyl group to chenodeoxycholic acid. The
652:
are tightly regulated. Activation of FXR in the liver inhibits synthesis of bile acids, and is one mechanism of feedback control when bile acid levels are too high. Secondly, FXR activation by bile acids during absorption in the intestine increases transcription and synthesis of
886:). Deoxycholic acid as an injectable has received FDA approval to dissolve submental fat. Phase III trials showed significant responses although many subjects had mild adverse reactions of bruising, swelling, pain, numbness, erythema, and firmness around the treated area.
259:
pKa of the bile-acid/amino-acid conjugate to between 1 and 4. Thus conjugated bile acids are almost always in their deprotonated (A-) form in the duodenum, which makes them much more water-soluble and much more able to fulfil their physiologic function of emulsifying fats.
2707:
Singh S, Khanna S, Pardi DS, Loftus EV, Talwalkar JA (2013). "Effect of ursodeoxycholic acid use on the risk of colorectal neoplasia in patients with primary sclerosing cholangitis and inflammatory bowel disease: a systematic review and meta-analysis".
716:
bind bile acids in the gut, preventing reabsorption. In so doing, more endogenous cholesterol is shunted into the production of bile acids, thereby lowering cholesterol levels. The sequestered bile acids are then excreted in the feces.
209:
in a multi-step process. Approximately 600 mg of bile salts are synthesized daily to replace bile acids lost in the feces, although, as described below, much larger amounts are secreted, reabsorbed in the gut and recycled.
542:), expressed in liver, and also in macrophages and other tissues. CYP27A1 contributes significantly to total bile acid synthesis by catalyzing sterol side chain oxidation, after which cleavage of a three-carbon unit in the
2873:"Efficacy, patient-reported outcomes and safety profile of ATX-101 (deoxycholic acid), an injectable drug for the reduction of unwanted submental fat: results from a phase III, randomized, placebo-controlled study"
320:
bile acids into the intestine each day, mostly after meals. The bile acid pool size is between 4–6 g, which means that bile acids are recycled several times each day. About 95% of bile acids are reabsorbed by
779:
The relationship of bile acids to cholesterol saturation in bile and cholesterol precipitation to produce gallstones has been studied extensively. Gallstones may result from increased saturation of cholesterol or
363:. They bind less specifically to some other receptors and have been reported to regulate the activity of certain enzymes and ion channels and the synthesis of diverse substances including endogenous fatty acid
2339:
Reddy BS, Hanson D, Mangat S, et al. (September 1980). "Effect of high-fat, high-beef diet and of mode of cooking of beef in the diet on fecal bacterial enzymes and fecal bile acids and neutral sterols".
1573:
Kulkarni AV, Tevethia HV, Arab JP, Candia R, Premkumar M, Kumar P, Sharma M, Reddy DN, Padaki NR (May 2021). "Efficacy and safety of obeticholic acid in liver disease-A systematic review and meta-analysis".
564:. As this had already been described, the discovery of chenodeoxycholic acid (with 2 hydroxyl groups) made this new bile acid a "deoxycholic acid" in that it had one fewer hydroxyl group than cholic acid.
570:
is formed from cholic acid by 7-dehydroxylation, resulting in 2 hydroxyl groups (3α and 12α). This process with chenodeoxycholic acid results in a bile acid with only a 3α hydroxyl group, termed
3797:
1933:
Allen L, Stobie D, Mauldin GN, Baer KE (January 1999). "Clinicopathologic features of dogs with hepatic microvascular dysplasia with and without portosystemic shunts: 42 cases (1991-1996)".
142:
546:
leads to formation of a C24 bile acid. Minor pathways initiated by 25-hydroxylase in the liver and 24-hydroxylase in the brain also may contribute to bile acid synthesis. 7α-hydroxylase (
632:. Many of their functions as signaling molecules in the liver and the intestines are by activating FXR, whereas TGR5 may be involved in metabolic, endocrine and neurological functions.
160:
It is to be noted that bile acid synthesis is the only manner in which humans or other mammals may excrete excess cholesterol, as the parent compound of all bile acids is cholesterol.
606:, 6α-ethyl-chenodeoxycholic acid, is a semi-synthetic bile acid with greater activity as an FXR agonist, which has been developed as a pharmaceutical agent in certain liver diseases.
267:
Once secreted into the lumen of the intestine, bile salts are modified by gut bacteria. They are partially dehydroxylated. Their glycine and taurine groups are removed to give the
3878:
614:
Bile acids also act as steroid hormones, secreted from the liver, absorbed from the intestine and having various direct metabolic actions in the body through the nuclear receptor
4823:
2220:
Uy MC, Talingdan-Te MC, Espinosa WZ, Daez ML, Ong JP (December 2008). "Ursodeoxycholic acid in the prevention of gallstone formation after bariatric surgery: a meta-analysis".
2181:"Ursodeoxycholic acid alone or with chenodeoxycholic acid for dissolution of cholesterol gallstones: a randomized multicentre trial. The British-Italian Gallstone Study group"
343:), emulsifying fat-soluble vitamins to enable their absorption, and aiding in motility and the reduction of the bacteria flora found in the small intestine and biliary tract.
1224:
Fiorucci S, Mencarelli A, Palladino G, Cipriani S (November 2009). "Bile-acid-activated receptors: targeting TGR5 and farnesoid-X-receptor in lipid and glucose disorders".
4099:
4089:
1170:"The intraluminal phase of fat digestion in man: the lipid content of the micellar and oil phases of intestinal content obtained during fat digestion and absorption"
843:, causing oxidative stress, and also increase DNA damage. Mice fed a diet with added DCA mimicking colonic DCA levels in humans on a high fat diet developed colonic
685:
279:. Cholic acid is converted into deoxycholic acid and chenodeoxycholic acid into lithocholic acid. All four of these bile acids are recycled, in a process known as
2753:"High-dose ursodeoxycholic acid is associated with the development of colorectal neoplasia in patients with ulcerative colitis and primary sclerosing cholangitis"
1371:
Nagahashi M, Takabe K, Liu R, Peng K, Wang X, Wang Y, Hait NC, Wang X, Allegood JC, Yamada A, Aoyagi T, Liang J, Pandak WM, Spiegel S, Hylemon PB, Zhou H (2015).
3914:
4104:
2494:
O'Keefe SJ, Kidd M, Espitalier-Noel G, Owira P (May 1999). "Rarity of colon cancer in
Africans is associated with low animal product consumption, not fiber".
2751:
Eaton JE, Silveira MG, Pardi DS, Sinakos E, Kowdley KV, Luketic VA, Harrison ME, McCashland T, Befeler AS, Harnois D, Jorgensen R, Petz J, Lindor KD (2011).
684:
Bile acids bind to some other proteins in addition to their hormone receptors (FXR and TGR5) and their transporters. Among these protein targets, the enzyme
3871:
4084:
3792:
2540:
839:
Experimental studies also suggest mechanisms for bile acids in colon cancer. Exposure of colonic cells to high DCA concentrations increase formation of
339:
Bile acids have other functions, including eliminating cholesterol from the body, driving the flow of bile to eliminate certain catabolites (including
4753:
3641:
3442:
3119:
3003:
725:
Tests for bile acids are useful in both human and veterinary medicine, as they aid in the diagnosis of a number of conditions, including types of
3864:
3827:
3807:
1474:"Structure of Human N-Acylphosphatidylethanolamine-Hydrolyzing Phospholipase D: Regulation of Fatty Acid Ethanolamide Biosynthesis by Bile Acids"
600:, which has been used medicinally for centuries. Its structure resembles chenodeoxycholic acid but with the 7-hydroxyl group in the β position.
3954:
3787:
3262:
3136:
4124:
3929:
3126:
862:
The effects of ursodeoxycholic acid (UDCA) in modifying the risk of colorectal cancer has been looked at in several studies, particularly in
4773:
3061:
114:, are also found, with derivatives of cholic, chenodeoxycholic and deoxycholic acids accounting for over 90% of human biliary bile acids.
4265:
4144:
4024:
3812:
3524:
4748:
4445:
4385:
2109:
Danzinger RG, Hofmann AF, Schoenfield LJ, Thistle JL (January 1972). "Dissolution of cholesterol gallstones by chenodeoxycholic acid".
712:
As bile acids are made from endogenous cholesterol, disruption of the enterohepatic circulation of bile acids will lower cholesterol.
4533:
4139:
4054:
3802:
3716:
2304:
Degirolamo C, Modica S, Palasciano G, Moschetta A (2011). "Bile acids and colon cancer: Solving the puzzle with nuclear receptors".
4195:
336:
of bile acids allows a low rate of synthesis, only about 0.3 g/day, but with large amounts being secreted into the intestine.
511:
The initial step in the classical pathway of hepatic synthesis of bile acids is the enzymatic addition of a 7α hydroxyl group by
2144:
Thistle JL, Hofmann AF (September 1973). "Efficacy and specificity of chenodeoxycholic acid therapy for dissolving gallstones".
4926:
574:(litho = stone) having been identified first in a gallstone from a calf. It is poorly water-soluble and rather toxic to cells.
106:) are the major bile salts. They are roughly equal in concentration. The salts of their 7-alpha-dehydroxylated derivatives,
3619:
758:
730:
1275:"The function of bile salts in fat absorption. The solvent properties of dilute micellar solutions of conjugated bile salts"
3634:
3435:
2996:
1898:
Davidson MH (2011). "A systematic review of bile acid sequestrant therapy in children with familial hypercholesterolemia".
1524:
Margheritis, E, Castellani B, Magotti P, Peruzzi S, Romeo E, Natali F, Mostarda S, Gioiello A, Piomelli D, Garau G (2016).
695:) that play important roles in several physiological pathways including stress and pain responses, appetite, and lifespan.
629:
625:
360:
1660:
Parks DJ, Blanchard SG, Bledsoe RK, et al. (May 1999). "Bile acids: natural ligands for an orphan nuclear receptor".
1080:
Carey, MC.; Small, DM. (Oct 1972). "Micelle formation by bile salts. Physical-chemical and thermodynamic considerations".
2802:"Risk modification of colorectal adenoma by CYP7A1 polymorphisms and the role of bile acid metabolism in carcinogenesis"
2062:"Intrahepatic cholestasis of pregnancy: a randomized controlled trial comparing dexamethasone and ursodeoxycholic acid"
1373:"Conjugated bile acid-activated S1P receptor 2 is a key regulator of sphingosine kinase 2 and hepatic gene expression"
3898:
2447:"Association between low colonic short-chain fatty acids and high bile acids in high colon cancer risk populations"
586:(3α,6α,7α-trihydroxy-5β-cholanoic acid), and other species have a hydroxyl group on position 23 of the side-chain.
238:
Prior to secreting any of the bile acids (primary or secondary, see below), liver cells conjugate them with either
4673:
2021:"A multicenter, controlled trial of ursodiol for the treatment of primary biliary cirrhosis. UDCA-PBC Study Group"
3627:
3428:
2989:
1617:
Makishima M, Okamoto AY, Repa JJ, et al. (May 1999). "Identification of a nuclear receptor for bile acids".
738:
512:
222:
520:
503:
recommended ring lettering (left) and atom numbering (right) of the steroid skeleton. The four rings A-D form a
465:
451:
4355:
863:
754:
2537:
859:), unlike mice fed a control diet producing one-tenth the level of colonic DCA who had no colonic neoplasia.
4865:
3844:
870:, with varying results partly related to dosage. Genetic variation in the key bile acid synthesis enzyme,
741:
in dogs. Structural or functional abnormalities of the biliary system result in an increase in bilirubin (
217:
in synthesis is the addition of a hydroxyl group of the 7th position of the steroid nucleus by the enzyme
4400:
4094:
3887:
304:
regions, conjugated bile salts sit at the lipid/water interface and, above the right concentration, form
4879:
867:
471:
457:
255:
99:
95:
17:
4175:
4170:
437:
1798:"Differential regulation of bile acid homeostasis by the farnesoid X receptor in liver and intestine"
750:
333:
280:
4658:
4205:
4044:
4783:
4698:
2970:
2656:
Prasad AR, Prasad S, Nguyen H, Facista A, Lewis C, Zaitlin B, Bernstein H, Bernstein C (Jul 2014).
805:
516:
137:, which encapsulate nutrients, facilitating their absorption. These micelles are suspended in the
2849:
840:
809:
479:
125:). An increased secretion of bile acids produces an increase in bile flow. Bile acids facilitate
2966:
4345:
3974:
3777:
3772:
3593:
817:
395:
3649:
620:
3782:
3701:
3529:
3477:
2976:
989:
713:
524:
443:
198:
103:
4190:
4180:
423:
409:
4528:
4500:
4490:
4109:
3675:
3650:
3519:
3492:
1669:
1626:
762:
615:
593:
356:
150:
4185:
874:, influenced the effectiveness of UDCA in colorectal adenoma prevention in a large trial.
8:
4931:
4921:
4330:
4230:
4154:
3856:
1796:
Kim, I; Ahn, SH; Inagaki, T; Choi, M; Ito, S; Guo, GL; Kliewer, SA; Gonzalez, FJ (2007).
1093:
734:
4524:
1673:
1630:
914:"Bile salts of vertebrates: structural variation and possible evolutionary significance"
800:. It is commonly found when the ileum is abnormal or has been surgically removed, as in
4803:
4558:
4359:
3890:
3667:
3563:
3497:
2945:
2897:
2872:
2826:
2801:
2777:
2752:
2733:
2684:
2657:
2633:
2608:
2584:
2557:
2519:
2471:
2446:
2245:
2091:
1996:
1969:
1875:
1842:
1773:
1748:
1599:
1550:
1525:
1498:
1473:
1451:
1397:
1372:
1348:
1323:
1299:
1274:
1054:
1027:
940:
913:
801:
699:
orchestrates a direct cross-talk between lipid amide signals and bile acid physiology.
673:
500:
214:
1721:
1704:
1194:
1169:
4508:
4215:
3608:
2937:
2902:
2831:
2782:
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2507:
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2197:
2180:
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2126:
2083:
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2001:
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1819:
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1726:
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1603:
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1503:
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1402:
1353:
1304:
1241:
1199:
1147:
1097:
1059:
993:
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829:
785:
2949:
2737:
2095:
4793:
4513:
4395:
4325:
4210:
4200:
4114:
3964:
3756:
3731:
3659:
3487:
3354:
3166:
3083:
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2628:
2620:
2579:
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2523:
2503:
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2458:
2419:
2384:
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2313:
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2118:
2073:
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1991:
1981:
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1716:
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1472:
Magotti P, Bauer I, Igarashi M, Babagoli M, Marotta R, Piomelli D, Garau G (2015).
1433:
1392:
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1294:
1286:
1233:
1189:
1181:
1137:
1089:
1049:
1039:
985:
976:
Russell DW (2003). "The enzymes, regulation, and genetics of bile acid synthesis".
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833:
797:
603:
571:
567:
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225:
by cholic acid, up-regulated by cholesterol and is inhibited by the actions of the
126:
111:
107:
87:
83:
2933:
2410:
Cheah PY (1990). "Hypotheses for the etiology of colorectal cancer--an overview".
1946:
1681:
1638:
381:
163:
4905:
4470:
4365:
4245:
3186:
3161:
3156:
3078:
3073:
2721:
2544:
2462:
2317:
1587:
1258:'Essentials of Medical Biochemistry, Lieberman, Marks and Smith, eds, p432, 2007'
1142:
1125:
579:
328:
and recycled back to the liver for further secretion into the biliary system and
202:
79:
2157:
2122:
2037:
2020:
1749:"Bile acid receptors FXR and TGR5 signaling in fatty liver diseases and therapy"
4893:
4818:
4738:
4608:
4465:
4320:
4285:
3944:
3420:
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3362:
3209:
3181:
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1911:
1814:
1797:
1541:
1420:
Wiemuth D, Sahin H, Falkenburger BH, Lefevre CM, Wasmuth HE, Grunder S (2012).
1237:
1044:
852:
583:
528:
3282:
3277:
2624:
2423:
2233:
1489:
882:
Bile acids may be used in subcutaneous injections to remove unwanted fat (see
496:
4915:
4758:
4633:
4518:
4480:
4375:
4340:
4275:
4074:
4034:
3934:
3746:
3598:
3272:
3267:
3257:
3114:
2658:"Novel diet-related mouse model of colon cancer parallels human colon cancer"
1866:
1764:
649:
582:(α or β depending on the 7 hydroxyl position). Pigs have 6α hydroxylation in
535:
364:
118:
27:
Steroid acid found predominantly in the bile of mammals and other vertebrates
2353:
4843:
4813:
4788:
4743:
4688:
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4668:
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4653:
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3141:
2941:
2906:
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Ascher B, Hoffmann K, Walker P, Lippert S, Wollina U, Havlickova B (2014).
2835:
2786:
2729:
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2642:
2593:
2538:
http://www.cancer.org/Research/CancerFactsFigures/cancer-facts-figures-2009
2515:
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2005:
1986:
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1507:
1447:
1406:
1357:
1308:
1245:
1203:
1151:
1063:
997:
949:
666:
313:
117:
Bile acids comprise about 80% of the organic compounds in bile (others are
2431:
2396:
2361:
2165:
2130:
2046:
1954:
1339:
1101:
4828:
4798:
4778:
4728:
4603:
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4019:
3924:
3514:
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3482:
3393:
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3240:
3190:
3131:
3066:
2981:
2768:
2281:
2264:
1858:
1838:
1438:
1422:"BASIC--a bile acid-sensitive ion channel highly expressed in bile ducts"
1421:
1126:"The continuing importance of bile acids in liver and intestinal disease"
883:
745:) and in bile acids in the blood. Bile acids are related to the itching (
726:
689:
557:
543:
387:
329:
301:
297:
206:
194:
168:
122:
91:
2800:
Wertheim BC, Smith JW, Fang C, Alberts DS, Lance P, Thompson PA (2012).
2574:
930:
4808:
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4703:
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3583:
3544:
3539:
3534:
3409:
3388:
3344:
3109:
3102:
2920:
Wollina U, Goldman A (2015). "ATX-101 for reduction of submental fat".
774:
692:
669:
641:
551:
534:
An alternative (acidic) pathway of bile acid synthesis is initiated by
186:
134:
49:
2888:
2558:"Bile acids as endogenous etiologic agents in gastrointestinal cancer"
2078:
2061:
1388:
1290:
1185:
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4119:
4049:
4039:
3984:
3822:
3726:
3706:
3603:
3573:
3568:
2607:
Bernstein C, Holubec H, Bhattacharyya AK, et al. (August 2011).
1753:
American
Journal of Physiology. Gastrointestinal and Liver Physiology
781:
645:
597:
340:
1705:"Endogenous bile acids are ligands for the nuclear receptor FXR/BAR"
624:. Another bile acid receptor is the cell membrane receptor known as
4888:
4638:
4618:
4588:
4460:
4420:
4270:
4260:
4134:
3696:
3235:
3228:
2493:
2303:
1223:
844:
746:
742:
696:
352:
305:
232:
2108:
1836:
351:
Bile acids have metabolic actions in the body resembling those of
4848:
4833:
4763:
4225:
3949:
3320:
3056:
3049:
3012:
2265:"Recent advances in the understanding of bile acid malabsorption"
848:
688:(NAPE-PLD) generates bioactive lipid amides (e.g. the endogenous
539:
504:
309:
243:
239:
229:
146:
130:
61:
57:
34:
2060:
Glantz A, Marschall HU, Lammert F, Mattsson LA (December 2005).
1837:
Shapiro, Hagit; Kolodziejczyk, Aleksandra A.; Halstuch, Daniel;
796:
Excess concentrations of bile acids in the colon are a cause of
665:
Emerging evidence associates FXR activation with alterations in
3030:
1419:
871:
856:
813:
561:
547:
218:
154:
45:
2059:
1703:
Wang H, Chen J, Hollister K, Sowers LC, Forman BM (May 1999).
3554:
2606:
2555:
2179:
Petroni ML, Jazrawi RP, Pazzi P, et al. (January 2001).
1523:
765:
has been used for many years in these cholestatic disorders.
654:
325:
226:
138:
53:
1471:
3461:
2870:
1795:
1324:"Bile acid signaling in metabolic disease and drug therapy"
804:, or cause a condition that resembles diarrhea-predominant
41:
37:
3886:
2556:
Bernstein H, Bernstein C, Payne CM, Dvorak K (July 2009).
2219:
2018:
1572:
828:
Bile acids may have some importance in the development of
648:, bile acids are potentially toxic to cells, and so their
2750:
2655:
2536:
American Cancer
Society. Cancer Facts and Figures 2009.
3899:
2799:
2609:"Carcinogenicity of deoxycholate, a secondary bile acid"
1843:"Bile acids in glucose metabolism in health and disease"
686:
N-acyl phosphatidylethanolamine-specific phospholipase D
657:, which then inhibits bile acid synthesis in the liver.
2445:
Ou J, DeLany JP, Zhang M, Sharma S, O'Keefe SJ (2012).
1702:
1576:
Clinics and
Research in Hepatology and Gastroenterology
554:, which may be further converted in the liver to CDCA.
250:. These conjugated bile acids are often referred to as
2706:
2019:
Poupon RE, Balkau B, Eschwège E, Poupon R (May 1991).
1932:
1370:
149:
actions throughout the body, particularly through the
4877:
1659:
911:
1616:
912:
Hofmann AF, Hagey LR, Krasowski MD (February 2010).
749:) which is common in cholestatic conditions such as
312:
to digest lipids and bring them near the intestinal
2444:
2178:
2375:Hill MJ (May 1990). "Bile flow and colon cancer".
1519:
1517:
2338:
2262:
4913:
3450:
1167:
376:The structures of the principal human bile acids
1742:
1740:
1514:
2919:
2143:
1268:
1266:
1264:
1219:
1217:
1215:
1213:
1163:
1161:
1119:
1117:
1115:
1113:
1111:
1021:
1019:
1017:
1015:
1013:
1011:
1009:
1007:
971:
969:
967:
965:
963:
961:
959:
907:
905:
903:
901:
899:
823:
808:(IBS-D). This condition of bile acid diarrhea/
3872:
3635:
3436:
2997:
1746:
527:. This bile acid was first isolated from the
355:, acting through two specific receptors, the
3676:
3651:
2913:
2793:
2744:
2700:
2297:
2213:
2172:
2053:
1961:
1891:
1737:
1696:
1653:
1610:
1566:
1413:
1364:
1315:
52:. Diverse bile acids are synthesized in the
4155:
2137:
2102:
2012:
1926:
1897:
1261:
1210:
1158:
1108:
1004:
956:
896:
316:membrane, which results in fat absorption.
4206:Allopregnanedione (5α-dihydroprogesterone)
3879:
3865:
3642:
3628:
3443:
3429:
3011:
3004:
2990:
1967:
1272:
1123:
1079:
975:
635:
370:
2969:at the U.S. National Library of Medicine
2896:
2825:
2776:
2683:
2673:
2632:
2600:
2583:
2573:
2470:
2280:
2196:
2077:
2036:
1995:
1985:
1874:
1813:
1772:
1720:
1549:
1497:
1437:
1396:
1347:
1298:
1193:
1168:Hofmann AF, Borgström B (February 1964).
1141:
1053:
1043:
1025:
939:
929:
361:G protein-coupled bile acid receptor/TGR5
3904:Tooltip Constitutive androstane receptor
3757:
3660:
2409:
1467:
1465:
1321:
990:10.1146/annurev.biochem.72.121801.161712
702:
495:
171:showing relationship to other bile acids
162:
2374:
1970:"Intrahepatic cholestasis of pregnancy"
1075:
1073:
262:
14:
4914:
4659:Pregnanedione (5β-dihydroprogesterone)
4045:Pregnanedione (5β-dihydroprogesterone)
660:
3860:
3623:
3424:
2985:
1462:
1028:"Bile acids: regulation of synthesis"
791:
759:intrahepatic cholestasis of pregnancy
731:intrahepatic cholestasis of pregnancy
679:
180:
78:result from bacterial actions in the
1747:Chiang JY, Ferrell JM (March 2020).
1094:10.1001/archinte.1972.03650040040005
1070:
626:G protein-coupled bile acid receptor
74:are those synthesized by the liver.
1526:"Bile Acid Recognition by NAPE-PLD"
618:(FXR), also known by its gene name
609:
24:
346:
291:
127:digestion of dietary fats and oils
56:. Bile acids are conjugated with
25:
4943:
2960:
707:
4899:
4887:
2508:10.1111/j.1572-0241.1999.01089.x
2198:10.1046/j.1365-2036.2001.00853.x
1847:Journal of Experimental Medicine
478:
464:
450:
436:
422:
408:
394:
380:
246:, to form a total of 8 possible
2864:
2842:
2649:
2549:
2530:
2487:
2438:
2403:
2368:
2332:
2263:Pattni, S; Walters, JR (2009).
2256:
1830:
1789:
739:hepatic microvascular dysplasia
219:cholesterol 7 alpha-hydroxylase
64:residues to give anions called
4211:Allopregnanolone (brexanolone)
2818:10.1158/1940-6207.CAPR-11-0320
1252:
877:
864:primary sclerosing cholangitis
755:primary sclerosing cholangitis
720:
519:. This is then metabolised to
185:Bile acid synthesis occurs in
13:
1:
4927:Farnesoid X receptor agonists
4866:Receptor/signaling modulators
4824:Tropanyl 3,5-dimethulbenzoate
4674:Pregnenolone 16α-carbonitrile
3845:Receptor/signaling modulators
2977:Special Issue on "Bile Acids"
2934:10.1517/14656566.2015.1019465
1947:10.2460/javma.1999.214.02.218
1722:10.1016/s1097-2765(00)80348-2
1682:10.1126/science.284.5418.1365
1639:10.1126/science.284.5418.1362
889:
768:
175:
3681:Tooltip Farnesoid X receptor
3656:Tooltip Farnesoid X receptor
2877:J Eur Acad Dermatol Venereol
2850:"Deoxycholic acid injection"
2722:10.1097/MIB.0b013e318286fa61
2463:10.1080/01635581.2012.630164
2389:10.1016/0165-1110(90)90023-5
2318:10.1016/j.molmed.2011.05.010
1588:10.1016/j.clinre.2021.101675
1143:10.1001/archinte.159.22.2647
521:7α-hydroxy-4-cholesten-3-one
286:
7:
4401:Dodecylbenzenesulfonic acid
4160:Tooltip Pregnane X receptor
3888:Xenobiotic-sensing receptor
2158:10.1056/NEJM197309272891303
2123:10.1056/NEJM197201062860101
2038:10.1056/NEJM199105303242204
1273:Hofmann AF (October 1963).
824:Bile acids and colon cancer
40:found predominantly in the
10:
4948:
2662:World J Gastrointest Oncol
1912:10.1016/j.jacl.2011.01.005
1815:10.1194/jlr.M700330-JLR200
1542:10.1021/acschembio.6b00624
1238:10.1016/j.tips.2009.08.001
1045:10.1194/jlr.R900010-JLR200
1026:Chiang JY (October 2009).
868:inflammatory bowel disease
772:
513:cholesterol 7α-hydroxylase
472:Taurochenodeoxycholic acid
458:Glycochenodeoxycholic acid
100:glycochenodeoxycholic acid
96:taurochenodeoxycholic acid
4857:
4153:
3897:
3836:
3755:
3674:
3553:
3460:
3402:
3381:
3353:
3334:
3310:
3291:
3218:
3199:
3092:
3039:
3020:
2625:10.1007/s00204-011-0648-7
2424:10.1080/01635589009514073
2234:10.1007/s11695-008-9587-7
1968:Pusl T, Beuers U (2007).
1802:Journal of Lipid Research
1490:10.1016/j.str.2014.12.018
751:primary biliary cirrhosis
334:enterohepatic circulation
281:enterohepatic circulation
4784:Testosterone isocaproate
4699:Reverse triiodothyronine
3762:Tooltip Liver X receptor
3665:Tooltip liver X receptor
3451:Bile and liver therapy (
2971:Medical Subject Headings
2922:Expert Opin Pharmacother
2269:British Medical Bulletin
2185:Aliment. Pharmacol. Ther
1765:10.1152/ajpgi.00223.2019
1322:Li T, Chiang JY (2014).
812:can be diagnosed by the
806:irritable bowel syndrome
596:was first isolated from
4176:17α-Hydroxyprogesterone
4171:17α-Hydroxypregnenolone
2806:Cancer Prev Res (Phila)
841:reactive oxygen species
810:bile acid malabsorption
636:Regulation of synthesis
538:sterol 27-hydroxylase (
371:Structure and synthesis
205:-mediated oxidation of
145:. Bile acids also have
3778:24S-Hydroxycholesterol
3773:22R-Hydroxycholesterol
3594:Ornithine oxoglutarate
2675:10.4251/wjgo.v6.i7.225
2562:World J. Gastroenterol
1987:10.1186/1750-1172-2-26
1935:J. Am. Vet. Med. Assoc
818:bile acid sequestrants
816:test and treated with
714:Bile acid sequestrants
508:
172:
157:(also known as TGR5).
3915:6,7-Dimethylesculetin
3783:27-Hydroxycholesterol
3702:Chenodeoxycholic acid
3530:Nicotinyl methylamide
3478:Chenodeoxycholic acid
2354:10.1093/jn/110.9.1880
1340:10.1124/pr.113.008201
1226:Trends Pharmacol. Sci
703:Clinical significance
525:chenodeoxycholic acid
517:7α-hydroxycholesterol
499:
444:Chenodeoxycholic acid
248:conjugated bile acids
199:chenodeoxycholic acid
166:
104:chenodeoxycholic acid
4502:Hypericum perforatum
4491:Hetacillin potassium
3520:Maralixibat chloride
3493:Ursodeoxycholic acid
2967:Bile Acids and Salts
2769:10.1038/ajg.2011.156
2757:Am. J. Gastroenterol
2496:Am. J. Gastroenterol
1859:10.1084/jem.20171965
1530:ACS Chemical Biology
1439:10.1096/fj.12-207043
763:ursodeoxycholic acid
676:, and liver growth.
616:Farnesoid X receptor
594:Ursodeoxycholic acid
357:farnesoid X receptor
269:secondary bile acids
263:Secondary bile acids
151:farnesoid X receptor
76:Secondary bile acids
4331:Cyproterone acetate
4231:Amlodipine besylate
3373:Halogenated steroid
2575:10.3748/wjg.15.3329
1974:Orphanet J Rare Dis
1674:1999Sci...284.1365P
1631:1999Sci...284.1362M
1124:Hofmann AF (1999).
931:10.1194/jlr.R000042
735:portosystemic shunt
661:Metabolic functions
189:, which synthesize
4804:Thonzonium bromide
4559:Methylprednisolone
4360:prasterone sulfate
3564:Arginine glutamate
3498:Ursodoxicoltaurine
2710:Inflamm. Bowel Dis
2543:2012-09-13 at the
2282:10.1093/bmb/ldp032
978:Annu. Rev. Biochem
792:Bile acid diarrhea
680:Other interactions
674:glucose metabolism
509:
296:As molecules with
215:rate-limiting step
191:primary bile acids
181:Primary bile acids
173:
143:further processing
72:Primary bile acids
4875:
4874:
4509:Indinavir sulfate
4216:Alpha-Lipoic acid
4191:Δ-Androstenedione
4181:Δ-Androstenedione
3854:
3853:
3793:Cholestenoic acid
3617:
3616:
3609:Tidiacic arginine
3418:
3417:
3403:Elements replaced
2889:10.1111/jdv.12377
2079:10.1002/hep.20952
1536:(10): 2908–2914.
1389:10.1002/hep.27592
1291:10.1042/bj0890057
1186:10.1172/JCI104909
1130:Arch. Intern. Med
830:colorectal cancer
786:bariatric surgery
761:. Treatment with
515:(CYP7A1) forming
221:. This enzyme is
129:. They serve as
16:(Redirected from
4939:
4904:
4903:
4902:
4892:
4891:
4883:
4794:Thiamylal sodium
4529:γ-linolenic acid
4525:α-Linolenic acid
4523:Linolenic acid:
4514:Lasalocid sodium
4504:(St John's wort)
4396:Docusate calcium
4326:Cyclophosphamide
4201:Allopregnanediol
4186:Δ-Androstenediol
4161:
4157:
4115:Ethinylestradiol
3965:Cyclophosphamide
3905:
3901:
3881:
3874:
3867:
3858:
3857:
3763:
3759:
3732:Obeticholic acid
3682:
3678:
3666:
3662:
3657:
3653:
3644:
3637:
3630:
3621:
3620:
3488:Obeticholic acid
3445:
3438:
3431:
3422:
3421:
3382:Elements removed
3355:Functional group
3167:Androstenetrione
3084:Estratrienetriol
3006:
2999:
2992:
2983:
2982:
2954:
2953:
2917:
2911:
2910:
2900:
2868:
2862:
2861:
2859:
2857:
2846:
2840:
2839:
2829:
2797:
2791:
2790:
2780:
2748:
2742:
2741:
2704:
2698:
2697:
2687:
2677:
2653:
2647:
2646:
2636:
2604:
2598:
2597:
2587:
2577:
2553:
2547:
2534:
2528:
2527:
2491:
2485:
2484:
2474:
2442:
2436:
2435:
2407:
2401:
2400:
2372:
2366:
2365:
2336:
2330:
2329:
2301:
2295:
2294:
2284:
2260:
2254:
2253:
2217:
2211:
2210:
2200:
2176:
2170:
2169:
2141:
2135:
2134:
2106:
2100:
2099:
2081:
2057:
2051:
2050:
2040:
2016:
2010:
2009:
1999:
1989:
1965:
1959:
1958:
1930:
1924:
1923:
1895:
1889:
1888:
1878:
1834:
1828:
1827:
1817:
1793:
1787:
1786:
1776:
1759:(3): G554–G573.
1744:
1735:
1734:
1724:
1700:
1694:
1693:
1668:(5418): 1365–8.
1657:
1651:
1650:
1625:(5418): 1362–5.
1614:
1608:
1607:
1570:
1564:
1563:
1553:
1521:
1512:
1511:
1501:
1469:
1460:
1459:
1441:
1417:
1411:
1410:
1400:
1368:
1362:
1361:
1351:
1319:
1313:
1312:
1302:
1270:
1259:
1256:
1250:
1249:
1221:
1208:
1207:
1197:
1165:
1156:
1155:
1145:
1121:
1106:
1105:
1077:
1068:
1067:
1057:
1047:
1023:
1002:
1001:
973:
954:
953:
943:
933:
909:
834:Deoxycholic acid
798:chronic diarrhea
610:Hormonal actions
604:Obeticholic acid
580:muricholic acids
572:lithocholic acid
568:Deoxycholic acid
486:Lithocholic acid
482:
468:
454:
440:
430:Deoxycholic acid
426:
416:Taurocholic acid
412:
402:Glycocholic acid
398:
384:
322:active transport
277:lithocholic acid
273:deoxycholic acid
112:lithocholic acid
108:deoxycholic acid
102:(derivatives of
90:(derivatives of
88:glycocholic acid
84:taurocholic acid
21:
4947:
4946:
4942:
4941:
4940:
4938:
4937:
4936:
4912:
4911:
4910:
4900:
4898:
4886:
4878:
4876:
4871:
4853:
4754:Suberoylanilide
4471:Fluorometholone
4366:Dibunate sodium
4246:Aurothioglucose
4159:
4149:
4085:3,17β-Estradiol
3903:
3893:
3885:
3855:
3850:
3832:
3761:
3751:
3680:
3670:
3664:
3655:
3648:
3618:
3613:
3549:
3456:
3449:
3419:
3414:
3398:
3377:
3349:
3338:
3330:
3314:
3306:
3295:
3287:
3233:Dehydrogenated:
3222:
3214:
3203:
3195:
3187:Androstadienone
3162:Androstenedione
3157:Androstanedione
3107:Dehydrogenated:
3096:
3088:
3079:Estratrienediol
3074:Estratrienolone
3054:Dehydrogenated:
3043:
3035:
3024:
3016:
3010:
2963:
2958:
2957:
2918:
2914:
2883:(12): 1707–15.
2869:
2865:
2855:
2853:
2848:
2847:
2843:
2798:
2794:
2749:
2745:
2705:
2701:
2654:
2650:
2605:
2601:
2568:(27): 3329–40.
2554:
2550:
2545:Wayback Machine
2535:
2531:
2492:
2488:
2443:
2439:
2408:
2404:
2373:
2369:
2337:
2333:
2302:
2298:
2261:
2257:
2218:
2214:
2177:
2173:
2146:N. Engl. J. Med
2142:
2138:
2111:N. Engl. J. Med
2107:
2103:
2072:(6): 1399–405.
2058:
2054:
2031:(22): 1548–54.
2025:N. Engl. J. Med
2017:
2013:
1966:
1962:
1931:
1927:
1896:
1892:
1835:
1831:
1808:(12): 2664–72.
1794:
1790:
1745:
1738:
1701:
1697:
1658:
1654:
1615:
1611:
1571:
1567:
1522:
1515:
1470:
1463:
1432:(10): 4122–30.
1418:
1414:
1369:
1365:
1320:
1316:
1271:
1262:
1257:
1253:
1222:
1211:
1174:J. Clin. Invest
1166:
1159:
1136:(22): 2647–58.
1122:
1109:
1082:Arch Intern Med
1078:
1071:
1038:(10): 1955–66.
1024:
1005:
974:
957:
910:
897:
892:
880:
853:adenocarcinomas
826:
802:Crohn's disease
794:
777:
771:
723:
710:
705:
682:
663:
638:
612:
488:
483:
474:
469:
460:
455:
446:
441:
432:
427:
418:
413:
404:
399:
390:
385:
373:
349:
347:Cell signalling
294:
292:Lipid digestion
289:
265:
203:cytochrome P450
201:in humans) via
183:
178:
28:
23:
22:
15:
12:
11:
5:
4945:
4935:
4934:
4929:
4924:
4909:
4908:
4896:
4873:
4872:
4870:
4869:
4862:
4858:
4855:
4854:
4852:
4851:
4846:
4837:
4836:
4831:
4826:
4821:
4819:Troleandomycin
4816:
4811:
4806:
4801:
4796:
4791:
4786:
4781:
4776:
4771:
4766:
4761:
4756:
4751:
4746:
4741:
4739:Spironolactone
4736:
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4621:
4616:
4611:
4609:Norelgestromin
4606:
4601:
4596:
4591:
4586:
4581:
4576:
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4531:
4521:
4516:
4511:
4506:
4498:
4493:
4488:
4483:
4478:
4473:
4468:
4466:Flucloxacillin
4463:
4458:
4453:
4448:
4443:
4438:
4433:
4428:
4423:
4418:
4413:
4408:
4403:
4398:
4393:
4388:
4383:
4378:
4373:
4368:
4363:
4353:
4343:
4338:
4333:
4328:
4323:
4321:Corticosterone
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4286:Chlorpromazine
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4243:
4238:
4233:
4228:
4223:
4218:
4213:
4208:
4203:
4198:
4193:
4188:
4183:
4178:
4173:
4164:
4162:
4151:
4150:
4148:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4107:
4105:17-Androstanol
4102:
4100:3β-Androstanol
4097:
4095:3α-Androstenol
4092:
4090:3α-Androstanol
4087:
4078:
4077:
4072:
4067:
4062:
4057:
4052:
4047:
4042:
4037:
4032:
4027:
4022:
4017:
4012:
4007:
4002:
3997:
3992:
3987:
3982:
3972:
3967:
3962:
3957:
3952:
3947:
3945:Chlorpromazine
3942:
3937:
3932:
3927:
3922:
3917:
3908:
3906:
3895:
3894:
3884:
3883:
3876:
3869:
3861:
3852:
3851:
3849:
3848:
3841:
3837:
3834:
3833:
3831:
3830:
3825:
3816:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3766:
3764:
3753:
3752:
3750:
3749:
3740:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3699:
3694:
3685:
3683:
3672:
3671:
3647:
3646:
3639:
3632:
3624:
3615:
3614:
3612:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3560:
3558:
3551:
3550:
3548:
3547:
3542:
3537:
3532:
3527:
3522:
3517:
3512:
3507:
3502:
3501:
3500:
3495:
3490:
3485:
3480:
3467:
3465:
3458:
3457:
3448:
3447:
3440:
3433:
3425:
3416:
3415:
3413:
3412:
3406:
3404:
3400:
3399:
3397:
3396:
3391:
3385:
3383:
3379:
3378:
3376:
3375:
3370:
3368:Hydroxysteroid
3365:
3363:17-Ketosteroid
3359:
3357:
3351:
3350:
3348:
3347:
3341:
3339:
3336:
3332:
3331:
3329:
3328:
3323:
3317:
3315:
3312:
3308:
3307:
3305:
3304:
3298:
3296:
3293:
3289:
3288:
3286:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3243:
3238:
3225:
3223:
3220:
3216:
3215:
3213:
3212:
3210:19-Norpregnane
3206:
3204:
3201:
3197:
3196:
3194:
3193:
3184:
3182:Androstadienol
3179:
3177:Androstenolone
3174:
3172:Androstanolone
3169:
3164:
3159:
3154:
3152:Androstenediol
3149:
3147:Androstanediol
3144:
3139:
3134:
3129:
3120:Androstatriene
3117:
3112:
3099:
3097:
3094:
3090:
3089:
3087:
3086:
3081:
3076:
3064:
3059:
3046:
3044:
3041:
3037:
3036:
3034:
3033:
3027:
3025:
3022:
3018:
3017:
3015:classification
3009:
3008:
3001:
2994:
2986:
2980:
2979:
2974:
2962:
2961:External links
2959:
2956:
2955:
2912:
2863:
2852:. Medline plus
2841:
2812:(2): 197–204.
2792:
2763:(9): 1638–45.
2743:
2699:
2648:
2599:
2548:
2529:
2502:(5): 1373–80.
2486:
2437:
2402:
2367:
2331:
2312:(10): 564–72.
2306:Trends Mol Med
2296:
2255:
2228:(12): 1532–8.
2212:
2171:
2136:
2101:
2052:
2011:
1960:
1925:
1900:J Clin Lipidol
1890:
1853:(2): 383–396.
1841:(2018-01-16).
1829:
1788:
1736:
1695:
1652:
1609:
1565:
1513:
1484:(3): 598–604.
1461:
1412:
1383:(4): 1216–26.
1363:
1328:Pharmacol. Rev
1314:
1260:
1251:
1232:(11): 570–80.
1209:
1157:
1107:
1069:
1003:
955:
894:
893:
891:
888:
879:
876:
825:
822:
793:
790:
773:Main article:
770:
767:
722:
719:
709:
708:Hyperlipidemia
706:
704:
701:
681:
678:
662:
659:
650:concentrations
637:
634:
611:
608:
584:hyocholic acid
529:domestic goose
490:
489:
484:
477:
475:
470:
463:
461:
456:
449:
447:
442:
435:
433:
428:
421:
419:
414:
407:
405:
400:
393:
391:
386:
379:
377:
372:
369:
348:
345:
293:
290:
288:
285:
264:
261:
223:down-regulated
182:
179:
177:
174:
26:
9:
6:
4:
3:
2:
4944:
4933:
4930:
4928:
4925:
4923:
4920:
4919:
4917:
4907:
4897:
4895:
4890:
4885:
4884:
4881:
4868:
4867:
4863:
4860:
4859:
4856:
4850:
4847:
4845:
4842:
4839:
4838:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4787:
4785:
4782:
4780:
4777:
4775:
4772:
4770:
4767:
4765:
4762:
4760:
4759:Sulfisoxazole
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4634:Phenobarbital
4632:
4630:
4627:
4625:
4622:
4620:
4617:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4526:
4522:
4520:
4519:Levothyroxine
4517:
4515:
4512:
4510:
4507:
4505:
4503:
4499:
4497:
4494:
4492:
4489:
4487:
4484:
4482:
4481:Guggulsterone
4479:
4477:
4474:
4472:
4469:
4467:
4464:
4462:
4459:
4457:
4454:
4452:
4449:
4447:
4444:
4442:
4439:
4437:
4434:
4432:
4429:
4427:
4424:
4422:
4419:
4417:
4414:
4412:
4409:
4407:
4404:
4402:
4399:
4397:
4394:
4392:
4389:
4387:
4384:
4382:
4379:
4377:
4376:Dicloxacillin
4374:
4372:
4369:
4367:
4364:
4361:
4357:
4354:
4351:
4347:
4344:
4342:
4341:Dexamethasone
4339:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4276:Cephaloridine
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4229:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4187:
4184:
4182:
4179:
4177:
4174:
4172:
4169:
4166:
4165:
4163:
4158:
4152:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4093:
4091:
4088:
4086:
4083:
4080:
4079:
4076:
4075:Valproic acid
4073:
4071:
4068:
4066:
4063:
4061:
4058:
4056:
4053:
4051:
4048:
4046:
4043:
4041:
4038:
4036:
4035:Phenobarbital
4033:
4031:
4028:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3980:
3976:
3973:
3971:
3968:
3966:
3963:
3961:
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3935:Carbamazepine
3933:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3910:
3909:
3907:
3902:
3896:
3892:
3889:
3882:
3877:
3875:
3870:
3868:
3863:
3862:
3859:
3847:
3846:
3842:
3839:
3838:
3835:
3829:
3828:Larsucosterol
3826:
3824:
3821:
3818:
3817:
3814:
3811:
3809:
3808:Hypocholamide
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3768:
3767:
3765:
3760:
3754:
3748:
3747:Guggulsterone
3745:
3742:
3741:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3690:
3687:
3686:
3684:
3679:
3673:
3669:
3663:
3654:
3645:
3640:
3638:
3633:
3631:
3626:
3625:
3622:
3610:
3607:
3605:
3602:
3600:
3599:Phospholipids
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3561:
3559:
3556:
3552:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3475:
3474:
3473:
3469:
3468:
3466:
3463:
3459:
3454:
3446:
3441:
3439:
3434:
3432:
3427:
3426:
3423:
3411:
3408:
3407:
3405:
3401:
3395:
3392:
3390:
3387:
3386:
3384:
3380:
3374:
3371:
3369:
3366:
3364:
3361:
3360:
3358:
3356:
3352:
3346:
3343:
3342:
3340:
3333:
3327:
3324:
3322:
3319:
3318:
3316:
3309:
3303:
3300:
3299:
3297:
3290:
3284:
3281:
3279:
3276:
3274:
3273:Pregnenedione
3271:
3269:
3268:Pregnanedione
3266:
3264:
3261:
3259:
3258:Pregnanetriol
3256:
3254:
3251:
3247:
3244:
3242:
3239:
3237:
3234:
3230:
3227:
3226:
3224:
3217:
3211:
3208:
3207:
3205:
3198:
3192:
3188:
3185:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3121:
3118:
3116:
3115:Androstadiene
3113:
3111:
3108:
3104:
3101:
3100:
3098:
3091:
3085:
3082:
3080:
3077:
3075:
3072:
3068:
3065:
3063:
3060:
3058:
3055:
3051:
3048:
3047:
3045:
3038:
3032:
3029:
3028:
3026:
3019:
3014:
3007:
3002:
3000:
2995:
2993:
2988:
2987:
2984:
2978:
2975:
2972:
2968:
2965:
2964:
2951:
2947:
2943:
2939:
2935:
2931:
2928:(5): 755–62.
2927:
2923:
2916:
2908:
2904:
2899:
2894:
2890:
2886:
2882:
2878:
2874:
2867:
2851:
2845:
2837:
2833:
2828:
2823:
2819:
2815:
2811:
2807:
2803:
2796:
2788:
2784:
2779:
2774:
2770:
2766:
2762:
2758:
2754:
2747:
2739:
2735:
2731:
2727:
2723:
2719:
2716:(8): 1631–8.
2715:
2711:
2703:
2695:
2691:
2686:
2681:
2676:
2671:
2668:(7): 225–43.
2667:
2663:
2659:
2652:
2644:
2640:
2635:
2630:
2626:
2622:
2619:(8): 863–71.
2618:
2614:
2613:Arch. Toxicol
2610:
2603:
2595:
2591:
2586:
2581:
2576:
2571:
2567:
2563:
2559:
2552:
2546:
2542:
2539:
2533:
2525:
2521:
2517:
2513:
2509:
2505:
2501:
2497:
2490:
2482:
2478:
2473:
2468:
2464:
2460:
2456:
2452:
2448:
2441:
2433:
2429:
2425:
2421:
2417:
2413:
2406:
2398:
2394:
2390:
2386:
2383:(3): 313–20.
2382:
2378:
2371:
2363:
2359:
2355:
2351:
2348:(9): 1880–7.
2347:
2343:
2335:
2327:
2323:
2319:
2315:
2311:
2307:
2300:
2292:
2288:
2283:
2278:
2274:
2270:
2266:
2259:
2251:
2247:
2243:
2239:
2235:
2231:
2227:
2223:
2216:
2208:
2204:
2199:
2194:
2190:
2186:
2182:
2175:
2167:
2163:
2159:
2155:
2152:(13): 655–9.
2151:
2147:
2140:
2132:
2128:
2124:
2120:
2116:
2112:
2105:
2097:
2093:
2089:
2085:
2080:
2075:
2071:
2067:
2063:
2056:
2048:
2044:
2039:
2034:
2030:
2026:
2022:
2015:
2007:
2003:
1998:
1993:
1988:
1983:
1979:
1975:
1971:
1964:
1956:
1952:
1948:
1944:
1941:(2): 218–20.
1940:
1936:
1929:
1921:
1917:
1913:
1909:
1905:
1901:
1894:
1886:
1882:
1877:
1872:
1868:
1864:
1860:
1856:
1852:
1848:
1844:
1840:
1833:
1825:
1821:
1816:
1811:
1807:
1803:
1799:
1792:
1784:
1780:
1775:
1770:
1766:
1762:
1758:
1754:
1750:
1743:
1741:
1732:
1728:
1723:
1718:
1715:(5): 543–53.
1714:
1710:
1706:
1699:
1691:
1687:
1683:
1679:
1675:
1671:
1667:
1663:
1656:
1648:
1644:
1640:
1636:
1632:
1628:
1624:
1620:
1613:
1605:
1601:
1597:
1593:
1589:
1585:
1582:(3): 101675.
1581:
1577:
1569:
1561:
1557:
1552:
1547:
1543:
1539:
1535:
1531:
1527:
1520:
1518:
1509:
1505:
1500:
1495:
1491:
1487:
1483:
1479:
1475:
1468:
1466:
1457:
1453:
1449:
1445:
1440:
1435:
1431:
1427:
1423:
1416:
1408:
1404:
1399:
1394:
1390:
1386:
1382:
1378:
1374:
1367:
1359:
1355:
1350:
1345:
1341:
1337:
1334:(4): 948–83.
1333:
1329:
1325:
1318:
1310:
1306:
1301:
1296:
1292:
1288:
1284:
1280:
1276:
1269:
1267:
1265:
1255:
1247:
1243:
1239:
1235:
1231:
1227:
1220:
1218:
1216:
1214:
1205:
1201:
1196:
1191:
1187:
1183:
1180:(2): 247–57.
1179:
1175:
1171:
1164:
1162:
1153:
1149:
1144:
1139:
1135:
1131:
1127:
1120:
1118:
1116:
1114:
1112:
1103:
1099:
1095:
1091:
1088:(4): 506–27.
1087:
1083:
1076:
1074:
1065:
1061:
1056:
1051:
1046:
1041:
1037:
1033:
1029:
1022:
1020:
1018:
1016:
1014:
1012:
1010:
1008:
999:
995:
991:
987:
983:
979:
972:
970:
968:
966:
964:
962:
960:
951:
947:
942:
937:
932:
927:
924:(2): 226–46.
923:
919:
915:
908:
906:
904:
902:
900:
895:
887:
885:
875:
873:
869:
865:
860:
858:
854:
850:
846:
842:
837:
835:
831:
821:
819:
815:
811:
807:
803:
799:
789:
787:
783:
776:
766:
764:
760:
756:
752:
748:
744:
740:
736:
732:
728:
718:
715:
700:
698:
694:
691:
687:
677:
675:
671:
668:
658:
656:
651:
647:
643:
633:
631:
627:
623:
622:
617:
607:
605:
601:
599:
595:
591:
587:
585:
581:
575:
573:
569:
565:
563:
559:
555:
553:
549:
545:
541:
537:
536:mitochondrial
532:
530:
526:
522:
518:
514:
506:
502:
498:
494:
487:
481:
476:
473:
467:
462:
459:
453:
448:
445:
439:
434:
431:
425:
420:
417:
411:
406:
403:
397:
392:
389:
383:
378:
375:
374:
368:
366:
365:ethanolamides
362:
358:
354:
344:
342:
337:
335:
331:
327:
323:
317:
315:
311:
307:
303:
299:
284:
282:
278:
274:
270:
260:
257:
253:
249:
245:
241:
236:
234:
231:
228:
224:
220:
216:
211:
208:
204:
200:
196:
192:
188:
170:
167:Structure of
165:
161:
158:
156:
152:
148:
144:
140:
136:
132:
128:
124:
120:
119:phospholipids
115:
113:
109:
105:
101:
97:
93:
89:
85:
82:. In humans,
81:
77:
73:
69:
67:
63:
59:
55:
51:
47:
43:
39:
36:
32:
19:
4864:
4844:Ketoconazole
4841:Antagonists:
4840:
4814:Troglitazone
4789:Tetracycline
4744:Spiroxatrine
4689:Quingestrone
4684:Progesterone
4669:Pregnenolone
4664:Pregnanolone
4654:Pregnanediol
4649:Prednisolone
4574:Mifepristone
4501:
4476:Griseofulvin
4456:Fenbendazole
4441:Famprofazone
4436:Erythromycin
4431:Epothilone B
4416:Eburnamonine
4311:Clotrimazole
4301:Clofenvinfos
4250:
4236:Antimycotics
4167:
4130:Okadaic acid
4082:Antagonists:
4081:
4070:Troglitazone
4005:Mifepristone
4000:Methoxychlor
3995:Griseofulvin
3990:Ellagic acid
3970:Cypermethrin
3960:Clotrimazole
3911:
3843:
3820:Antagonists:
3819:
3788:Abequolixron
3769:
3744:Antagonists:
3743:
3691:
3688:
3579:Glycyrrhizin
3505:Cyclobutyrol
3471:
3470:
3325:
3263:Pregnenediol
3253:Pregnanediol
3250:Substituted:
3249:
3246:Pregnatriene
3232:
3142:Androstenone
3137:Androstanone
3124:Substituted:
3123:
3106:
3071:Substituted:
3070:
3053:
2925:
2921:
2915:
2880:
2876:
2866:
2854:. Retrieved
2844:
2809:
2805:
2795:
2760:
2756:
2746:
2713:
2709:
2702:
2665:
2661:
2651:
2616:
2612:
2602:
2565:
2561:
2551:
2532:
2499:
2495:
2489:
2457:(1): 34–40.
2454:
2450:
2440:
2415:
2411:
2405:
2380:
2376:
2370:
2345:
2341:
2334:
2309:
2305:
2299:
2272:
2268:
2258:
2225:
2221:
2215:
2191:(1): 123–8.
2188:
2184:
2174:
2149:
2145:
2139:
2114:
2110:
2104:
2069:
2065:
2055:
2028:
2024:
2014:
1977:
1973:
1963:
1938:
1934:
1928:
1906:(2): 76–81.
1903:
1899:
1893:
1850:
1846:
1839:Elinav, Eran
1832:
1805:
1801:
1791:
1756:
1752:
1712:
1708:
1698:
1665:
1661:
1655:
1622:
1618:
1612:
1579:
1575:
1568:
1533:
1529:
1481:
1477:
1429:
1425:
1415:
1380:
1376:
1366:
1331:
1327:
1317:
1285:(1): 57–68.
1282:
1278:
1254:
1229:
1225:
1177:
1173:
1133:
1129:
1085:
1081:
1035:
1032:J. Lipid Res
1031:
981:
977:
921:
918:J. Lipid Res
917:
881:
861:
847:, including
838:
827:
795:
778:
724:
711:
683:
667:triglyceride
664:
639:
619:
613:
602:
592:
588:
576:
566:
556:
550:) generates
533:
510:
491:
350:
338:
318:
314:brush border
295:
268:
266:
251:
247:
237:
212:
190:
184:
159:
116:
75:
71:
70:
65:
30:
29:
4829:Zafirlukast
4799:Thiothixene
4779:Terconazole
4729:Simvastatin
4604:Nisoldipine
4599:Nilvadipine
4584:Nicardipine
4554:Metacycline
4381:Dimercaprol
4336:Demecolcine
4296:Clindamycin
4291:Ciglitazone
4241:Artemisinin
4221:Ambrisentan
4125:Nigramide J
4060:Telmisartan
4020:Nicardipine
3930:Benfuracarb
3925:Artemisinin
3515:Hymecromone
3510:Elafibranor
3483:Cholic acid
3394:Secosteroid
3302:Cardanolide
3283:5β-Pregnane
3278:5α-Pregnane
3241:Pregnadiene
3191:Etiocholane
3132:Androstenol
3127:Androstanol
3067:Estratriene
2451:Nutr Cancer
2418:(1): 5–13.
2412:Nutr Cancer
884:Mesotherapy
878:Dermatology
727:cholestasis
721:Cholestasis
690:cannabinoid
642:surfactants
558:Cholic acid
544:peroxisomes
388:Cholic acid
330:gallbladder
302:hydrophilic
298:hydrophobic
207:cholesterol
195:cholic acid
187:liver cells
169:cholic acid
135:surfactants
123:cholesterol
92:cholic acid
50:vertebrates
4932:Hepatology
4922:Bile acids
4916:Categories
4809:Tianeptine
4774:Tenylidone
4769:Tacrolimus
4714:Rimexolone
4704:Rifampicin
4644:Plicamycin
4629:Paclitaxel
4614:Omeprazole
4594:Nifedipine
4569:Mevastatin
4564:Metyrapone
4544:Lovastatin
4539:Loratadine
4496:Hyperforin
4486:Haloprogin
4451:Felodipine
4426:Enzacamene
4406:Dronabinol
4371:Diclazuril
4350:prasterone
4306:Chloroxine
4281:Cephradine
4251:Bile acids
4065:Tolnaftate
4030:Permethrin
4015:Nevirapine
4010:Nefazodone
3979:prasterone
3940:Carvedilol
3920:Amiodarone
3891:modulators
3737:Tropifexor
3722:Ivermectin
3712:Fexaramine
3692:Bile acids
3668:modulators
3589:Methionine
3584:Metadoxine
3545:Seladelpar
3540:Piprozolin
3535:Odevixibat
3410:Azasteroid
3389:Norsteroid
3345:Cholestane
3110:Androstene
3103:Androstane
3062:Estradiene
2377:Mutat. Res
2117:(1): 1–8.
2066:Hepatology
1377:Hepatology
1279:Biochem. J
984:: 137–74.
890:References
775:Gallstones
769:Gallstones
693:anandamide
670:metabolism
646:detergents
552:oxysterols
252:bile salts
176:Production
66:bile salts
48:and other
31:Bile acids
18:Bile acids
4734:Sirolimus
4724:Ritonavir
4719:Riodipine
4709:Rifaximin
4694:Reserpine
4679:Proadifen
4624:Oxatomide
4579:Nafcillin
4549:Meclizine
4411:Droxidopa
4391:Docetaxel
4316:Colforsin
4266:Bumecaine
4256:Bithionol
4168:Agonists:
4145:T-0901317
4120:Meclizine
4050:Reserpine
4040:Phenytoin
4025:Octicizer
3985:Efavirenz
3912:Agonists:
3823:Efavirenz
3813:T-0901317
3770:Agonists:
3727:Nidufexor
3707:Cilofexor
3689:Agonists:
3604:Silymarin
3574:Epomediol
3569:Citiolone
3525:Menbutone
3472:bile acid
3326:Bile acid
2856:26 August
2275:: 79–93.
2250:207302960
2222:Obes Surg
1867:0022-1007
1709:Mol. Cell
1604:232242410
1478:Structure
1456:205369332
845:neoplasia
782:bilirubin
598:bear bile
341:bilirubin
287:Functions
133:-forming
4906:Medicine
4861:See also
4749:SR-12813
4639:Piperine
4619:Orlistat
4589:Nicotine
4461:Fentanyl
4446:Febantel
4421:Ecopipam
4386:Dinaline
4271:Cafestol
4261:Bosentan
4135:PK-11195
3840:See also
3697:Cafestol
3236:Pregnene
3229:Pregnane
2950:23094631
2942:25724831
2907:24605812
2836:22058145
2787:21556038
2738:39918727
2730:23665966
2694:25024814
2643:21267546
2594:19610133
2541:Archived
2516:10235221
2481:22136517
2326:21724466
2291:19900947
2242:18574646
2207:11136285
2096:19147632
2088:16317669
2006:17535422
1920:21392720
1885:29339445
1824:17720959
1783:31984784
1731:10360171
1690:10334993
1647:10334992
1596:33722778
1560:27571266
1508:25684574
1448:22735174
1407:25363242
1358:25073467
1309:14097367
1246:19758712
1204:14162533
1152:10597755
1064:19346330
998:12543708
950:19638645
849:adenomas
747:pruritus
743:jaundice
729:such as
697:NAPE-PLD
353:hormones
306:micelles
233:FGF15/19
147:hormonal
4894:Biology
4880:Portals
4849:Sesamin
4834:Zeranol
4764:Suramin
4534:LOE-908
4226:AMI-193
4140:S-07662
4055:TCPOBOP
3950:Chrysin
3803:GW-3965
3717:GW-4064
3557:therapy
3464:therapy
3321:Cholane
3057:Estrene
3050:Estrane
3013:Steroid
2898:4263247
2827:3400261
2778:3168684
2685:4092339
2634:3149672
2585:2712893
2524:6402410
2472:6844083
2432:2195469
2397:2188127
2362:7411244
2342:J. Nutr
2166:4580472
2131:5006919
2047:1674105
1997:1891276
1955:9926012
1876:5789421
1774:7099488
1670:Bibcode
1662:Science
1627:Bibcode
1619:Science
1551:5074845
1499:4351732
1426:FASEB J
1398:4376566
1349:4180336
1300:1202272
1102:4562149
1055:2739756
941:2803226
857:cancers
753:(PBC),
540:CYP27A1
505:sterane
332:. This
324:in the
310:lipases
244:taurine
240:glycine
230:hormone
141:before
131:micelle
62:glycine
58:taurine
46:mammals
35:steroid
4356:DHEA-S
4196:AA-861
3031:Gonane
2973:(MeSH)
2948:
2940:
2905:
2895:
2834:
2824:
2785:
2775:
2736:
2728:
2692:
2682:
2641:
2631:
2592:
2582:
2522:
2514:
2479:
2469:
2430:
2395:
2360:
2324:
2289:
2248:
2240:
2205:
2164:
2129:
2094:
2086:
2045:
2004:
1994:
1980:: 26.
1953:
1918:
1883:
1873:
1865:
1822:
1781:
1771:
1729:
1688:
1645:
1602:
1594:
1558:
1548:
1506:
1496:
1454:
1446:
1405:
1395:
1356:
1346:
1307:
1297:
1244:
1202:
1195:289518
1192:
1150:
1100:
1062:
1052:
996:
948:
938:
872:CYP7A1
814:SeHCAT
737:, and
562:CYP8B1
548:CYP7B1
254:. The
155:GPBAR1
94:) and
3955:CITCO
3798:DMHCA
3555:Liver
2946:S2CID
2734:S2CID
2520:S2CID
2246:S2CID
2092:S2CID
1600:S2CID
1452:S2CID
655:FGF19
628:1 or
621:NR1H4
507:core.
501:IUPAC
326:ileum
227:ileal
139:chyme
80:colon
54:liver
38:acids
4527:and
4346:DHEA
4110:AITC
3975:DHEA
3658:and
3462:Bile
2938:PMID
2903:PMID
2858:2015
2832:PMID
2783:PMID
2726:PMID
2690:PMID
2639:PMID
2590:PMID
2512:PMID
2477:PMID
2428:PMID
2393:PMID
2358:PMID
2322:PMID
2287:PMID
2238:PMID
2203:PMID
2162:PMID
2127:PMID
2084:PMID
2043:PMID
2002:PMID
1951:PMID
1916:PMID
1881:PMID
1863:ISSN
1820:PMID
1779:PMID
1727:PMID
1686:PMID
1643:PMID
1592:PMID
1556:PMID
1504:PMID
1444:PMID
1403:PMID
1354:PMID
1305:PMID
1242:PMID
1200:PMID
1148:PMID
1098:PMID
1060:PMID
994:PMID
946:PMID
866:and
851:and
630:TGR5
359:and
300:and
275:and
213:The
197:and
153:and
121:and
110:and
98:and
86:and
42:bile
33:are
4156:PXR
3900:CAR
3758:LXR
3677:FXR
3661:LXR
3652:FXR
3453:A05
2930:doi
2893:PMC
2885:doi
2822:PMC
2814:doi
2773:PMC
2765:doi
2761:106
2718:doi
2680:PMC
2670:doi
2629:PMC
2621:doi
2580:PMC
2570:doi
2504:doi
2467:PMC
2459:doi
2420:doi
2385:doi
2381:238
2350:doi
2346:110
2314:doi
2277:doi
2230:doi
2193:doi
2154:doi
2150:289
2119:doi
2115:286
2074:doi
2033:doi
2029:324
1992:PMC
1982:doi
1943:doi
1939:214
1908:doi
1871:PMC
1855:doi
1851:215
1810:doi
1769:PMC
1761:doi
1757:318
1717:doi
1678:doi
1666:284
1635:doi
1623:284
1584:doi
1546:PMC
1538:doi
1494:PMC
1486:doi
1434:doi
1393:PMC
1385:doi
1344:PMC
1336:doi
1295:PMC
1287:doi
1234:doi
1190:PMC
1182:doi
1138:doi
1134:159
1090:doi
1086:130
1050:PMC
1040:doi
986:doi
936:PMC
926:doi
757:or
644:or
640:As
256:pKa
242:or
60:or
44:of
4918::
3337:27
3313:24
3294:23
3248:;
3231::
3221:21
3202:20
3189:;
3122:;
3105::
3095:19
3069:;
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