1086:
45:
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36:
27:
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crypt cells on a scale of 0–4. Mice not undergoing tumorigenesis had crypt 8-oxo-dG at levels 0 to 2 (panel A shows level 1) while mice progressing to colonic tumors had 8-oxo-dG in colonic crypts at levels 3 to 4 (panel B shows level 4) Tumorigenesis was induced by adding deoxycholate to the mouse diet to give a level of deoxycholate in the mouse colon similar to the level in the colon of humans on a high fat diet. The images were made from original photomicrographs.
3743:
647:
1016:. According to these publications, a sufficient amount of deoxycholic acid in the human body would correspond with a good immune reaction of the non-specific immune system. Clinical studies conducted in the 1970s and 1980s confirm the expectation that deoxycholic acid is involved in the natural healing processes of local
2439:
Erikka
Loftfield, PhD, MPH, Roni T Falk, MS, Joshua N Sampson, PhD, Wen-Yi Huang, PhD, Autumn Hullings, MPH, Gwen Murphy, PhD, MPH, Stephanie J Weinstein, PhD, Demetrius Albanes, MD, Neal D Freedman, PhD, MPH, Rashmi Sinha, PhD, Prospective Associations of Circulating Bile Acids and Short-Chain Fatty
1103:
ratio of secondary bile acids to primary bile acids than sedentary rats in their feces. There is a positive association of exercise and physical activity with cancer prevention, tolerance to cancer-directed therapies (radiation and chemotherapy), reduction in recurrence, and improvement in survival.
1102:
Exercise decreases deoxycholate in the colon. Humans whose level of physical activity placed them in the top third had a 17% decrease in fecal bile acid concentration compared to those whose level of physical activity placed them in the lowest third. Rats provided with an exercise wheel had a lower
1036:
Deoxycholate and other secondary bile acids cause DNA damage. Secondary bile acids increase intracellular production of reactive oxygen and reactive nitrogen species resulting in increased oxidative stress and DNA damage. As shown in the figure below, deoxycholate added to the diet of mice increased
1072:
A number of factors, including diet, obesity, and exercise, affect the level of deoxycholate in the human colon. When humans were switched from their usual diet to a meat, egg and cheese based diet for five days, deoxycholate in their feces increased by factors of 2 to 10 fold. Rats fed diets with
1056:
In humans, higher levels of colonic deoxycholate are associated with higher frequencies of colon cancer. As an example, the fecal deoxycholate concentrations in
African Americans (who eat a relatively high fat diet) is more than five times higher than fecal deoxycholate of Native Africans in South
1052:
was added to the diet alongside deoxycholate, only 18% of the mice developed colon cancer. Chlorogenic acid is a component of common foods and beverages; coffee contains an average of 53.8 mg chlorogenic acid per 100 ml. Therefore, to consume the level of chlorogenic acid used in the study, a
1089:
Colonic epithelium from a mouse not undergoing colonic tumorigenesis (A), and a mouse that is undergoing colonic tumorigenesis (B). Cell nuclei are stained dark blue with hematoxylin (for nucleic acid) and immunostained brown for 8-oxo-dG. The level of 8-oxo-dG was graded in the nuclei of colonic
1081:
to the rats' high fat (30% beef tallow) diet reduced the deoxycholate in their feces to levels comparable to levels seen in the rats on a low fat diet. Curcumin is a component of the spice turmeric, and caffeic acid is a component high in some fruits and spices. Caffeic acid is also a digestive
1094:
In addition to fats, the type or amount of protein in the diet may also affect bile acid levels. Switching from a diet with protein provided by casein to a diet with protein provided by salmon protein hydrolysate led to as much as a 6-fold increase in levels of bile acids in the blood plasma of
1047:
When deoxycholate was added to the food of mice so that their feces contained deoxycholate at about the same level present in feces of human on a high fat diet, 45% to 56% of the mice developed colon cancer over the next 10 months, while none of the mice on a diet without deoxycholate developed
1098:
Obesity has been linked to cancer, and this link is in part through deoxycholate. In obese people, the relative proportion of
Firmicutes (Gram-positive bacteria) in gut microbiota is increased resulting in greater conversion of the non-genotoxic primary bile acid, cholic acid, to carcinogenic
1057:
Africa (who eat a low fat diet). Male
African Americans have a high incidence of colon cancer of 72 per 100,000, while Native Africans in South Africa have a low incidence rate of colon cancer of less than 1 per 100,000, a more than 72-fold difference in rates of colon cancer.
131:
1641:
Fredriksen JH, Rosenqvist E, Wedege E, Bryn K, Bjune G, Frøholm LO, et al. (December 1991). "Production, characterization and control of MenB-vaccine "Folkehelsa": an outer membrane vesicle vaccine against group B meningococcal disease".
2517:
Han Y, Haraguchi T, Iwanaga S, Tomotake H, Okazaki Y, Mineo S, et al. (September 2009). "Consumption of some polyphenols reduces fecal deoxycholic acid and lithocholic acid, the secondary bile acids of risk factors of colon cancer".
1301:
934:
Deoxycholates and bile acid derivatives in general are actively being studied as structures for incorporation in nanotechnology. They also have found application in microlithography as photoresistant components.
1041:, an oxidative DNA damage, in the colonic epithelium of mice. When the level of deoxycholate-induced DNA damage is high, DNA repair enzymes that ordinarily reverse DNA damage may not be able to keep up.
1215:
1120:
2935:
Hagio M, Matsumoto M, Yajima T, Hara H, Ishizuka S (September 2010). "Voluntary wheel running exercise and dietary lactose concomitantly reduce proportion of secondary bile acids in rat feces".
392:
InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
402:
InChI=1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1
901:. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry, but it is no longer common. Outside the body it is used in experimental basis of
604:
1073:
30% beef tallow (high fat) had almost 2-fold more deoxycholate in their feces than rats fed 5% beef tallow (low fat). In the same study, adding the further dietary elements of
1053:
human on a "standard" 2000-calorie daily diet (416 g/d; 250g carbs, 100g protein, 66g fat) would need to consume roughly 55 mL of coffee each day, or just under 2 fluid ounces.
1338:
1194:
1235:
1268:
951:
3023:
1290:
1060:
A prospective human study investigating the relationship between microbial metabolites and cancer found a strong correlation between circulating deoxycholic acid and
1216:
https://www.ebs.tga.gov.au/servlet/xmlmillr6?dbid=ebs/PublicHTML/pdfStore.nsf&docid=6CC2E7A2D27AA7C5CA2585D80042A1CC&agid=(PrintDetailsPublic)&actionid=1
842:. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are
2397:
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".
541:
2376:
1131:
950:
fat, deoxycholic acid helps destroy (adipocytes) fat cells, which are metabolized by the body over the course of several months. Kybella is produced by
660:
1560:
1085:
3016:
1701:"Structure of human N-acylphosphatidylethanolamine-hydrolyzing phospholipase D: regulation of fatty acid ethanolamide biosynthesis by bile acids"
1620:
702:
3140:
418:
2599:
1944:
Bernstein H, Bernstein C, Payne CM, Dvorakova K, Garewal H (January 2005). "Bile acids as carcinogens in human gastrointestinal cancers".
2444:
3773:
3009:
1803:. 2nd Symp. on Prevention and Treatment of Viral Infections. Bechyne Castle: Institute f. Hygiene and Epidemiology, Prag. p. 56.
1326:
2615:"Nutritional regulation of bile acid metabolism is associated with improved pathological characteristics of the metabolic syndrome"
1183:
1227:
1420:
1260:
2557:
1677:
1044:
DNA damage has frequently been proposed as a major cause of cancer. DNA damage can give rise to cancer by causing mutations.
1164:
1530:
Kim JB, Lee BW, Yun HJ, Kwon YG (2000). "193-nm
Photoresists Based on Norbornene Copolymers with Derivatives of Bile Acid".
1048:
cancer. Thus, exposure of the colon to deoxycholate may cause cancer in mice. However, this same study reported that, when
739:
655:
270:
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rats. In humans, adding high protein to a high fat diet raised the level of deoxycholate in the plasma by almost 50%.
931:
injections to produce lipolysis, and has been used as an alternative to surgical excision in the treatment of lipomas.
1396:
383:
1860:
Vlcek B, Reif A, Budský F (1970). "Toxicity of deoxycholate at pH below 7.3 as a potential cancerostatic property".
2325:"Association between low colonic short-chain fatty acids and high bile acids in high colon cancer risk populations"
1594:
667:
720:
589:
912:
In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The
913:
2372:
67:
854:, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as
1568:
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326:
247:
783:
347:
189:
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1038:
985:. These bioactive signaling molecules play important roles in several physiological pathways including
504:
962:
Its function as a detergent and isolating agent for membrane proteins also suits it for production of
3704:
3559:
2578:
Clifford M (1999). "Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden".
1297:
3482:
3375:
2225:
Bernstein C, Holubec H, Bhattacharyya AK, Nguyen H, Payne CM, Zaitlin B, Bernstein H (August 2011).
1495:
3438:
1616:
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Duncan D, Rotunda AM (July 2011). "Injectable therapies for localized fat loss: state of the art".
799:
364:
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David LA, Maurice CF, Carmody RN, Gootenberg DB, Button JE, Wolfe BE, et al. (January 2014).
3635:
3366:
2274:
Jeon JS, Kim HT, Jeong IH, Hong SR, Oh MS, Yoon MH, Shim JH, Jeong JH, Abd El-Aty AM (May 2019).
692:
523:
149:
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1490:
986:
963:
885:
Deoxycholic acid has been used since its discovery in various fields of human medicine. In the
765:
923:
to lyse cells and solubilise cellular and membrane components. Sodium deoxycholate mixed with
3473:
3219:
3160:
2886:
Wertheim BC, Martínez ME, Ashbeck EL, Roe DJ, Jacobs ET, Alberts DS, Thompson PA (May 2009).
2664:
Bortolotti M, Kreis R, Debard C, Cariou B, Faeh D, Chetiveaux M, et al. (October 2009).
1841:
Bradna J, Poliklinik, Kutna Hora (1983). "Treatment of herpes zoster with deoxycholic acid".
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209:
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2803:
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1953:
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8:
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1699:
Magotti P, Bauer I, Igarashi M, Babagoli M, Marotta R, Piomelli D, Garau G (March 2015).
982:
938:
In the United States, deoxycholic acid, under the brand name
Kybella, is approved by the
924:
97:
2807:
2591:
2477:
2100:
2087:
Ames BN (May 1979). "Identifying environmental chemicals causing mutations and cancer".
1957:
919:
Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological
826:
803:
712:
368:
251:
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107:
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2013:
1988:
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break-down product of chlorogenic acid, high in coffee and some fruits and vegetables.
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2018:
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2143:
2132:"Involvement of oxidatively damaged DNA and repair in cancer development and aging"
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2008:
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1500:
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966:(OMP) vaccines such as MenB, a Norwegian vaccine developed in the early 1990s. The
851:
552:
493:
441:
315:
2903:
2863:
2846:
2554:"Phenol-Explorer: Showing all foods in which the polyphenol Caffeic acid is found"
1228:"Prescription medicines: registration of new chemical entities in Australia, 2016"
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1005:
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680:
1965:
44:
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3033:
2291:
2276:"Contents of chlorogenic acids and caffeine in various coffee-related products"
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638:
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10.1002/(sici)1097-0010(19990301)79:3<362::aid-jsfa256>3.0.co;2-d
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1801:
Deoxycholic acid – Therapy of viral infections and a toxicological inquiry
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943:
928:
863:
850:. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid
843:
2815:
2485:
1543:
866:. When pure, it exists in a white to off-white crystalline powder form.
229:
3715:
3660:
3650:
3610:
3456:
3342:
3200:
3176:
3125:
3110:
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3084:
1873:
1184:"Belkyra (deoxycholic acid solution for injection) Product Information"
1013:
978:
902:
886:
469:
260:
200:
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3615:
3517:
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3420:
3332:
3099:
3071:
1989:"Bile acid dysregulation, gut dysbiosis, and gastrointestinal cancer"
1505:
1004:
Some publications point towards the effect of deoxycholic acid as an
920:
906:
898:
839:
706:
637:
Except where otherwise noted, data are given for materials in their
3620:
3585:
3575:
3555:
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3195:
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2224:
1074:
994:
974:
734:
290:
220:
26:
1905:"Evidence of the participation of deoxycholate in cancer immunity"
771:
130:
2704:
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in the United States as of April 2021, sold under the brand name
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160:
120:
2612:
1840:
1698:
977:, which catalyzes the release of the endogenous cannabinoid
788:
352:
3215:
3031:
2663:
2516:
990:
281:
2885:
2173:
1782:
973:
Deoxycholic acid binds and activates the membrane enzyme
894:
2934:
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2129:
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1250:
916:for deoxycholic acid is approximately 2.4–4 mM.
314:
2036:Ajouz H, Mukherji D, Shamseddine A (May 2014).
1859:
1561:"FDA approves treatment for fat below the chin"
1372:
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1435:
970:vaccine was produced using the same method.
738:
1896:
1807:
1634:
1614:
1476:
905:and is also in use to prevent and dissolve
3024:
3010:
2746:
2744:
2670:The American Journal of Clinical Nutrition
2520:Journal of Agricultural and Food Chemistry
2180:World Journal of Gastrointestinal Oncology
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1813:
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2012:
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1514:
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957:
334:
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1084:
2750:
2741:
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798:
426:C(CCC(=O)O)1CC21((C32CC43(CC(C4)O)C)O)C
363:
228:
3756:
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2164:
1591:"ATX-101 – Kythera Biopharmaceuticals"
1555:
1553:
1327:"Deoxycholic acid: FDA-Approved Drugs"
1232:Therapeutic Goods Administration (TGA)
816:
623:
241:
61:3α,12α-Dihydroxy-5β-cholan-24-oic acid
3136:Selenium disulfide (selenium sulfide)
3005:
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1779:
1747:
1692:
1068:Factors affecting deoxycholate levels
1031:
944:moderate-to-severe fat below the chin
764:
729:
711:
611:
395:Key: KXGVEGMKQFWNSR-LLQZFEROSA-N
188:
168:
2086:
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1291:"Active substance: deoxycholic acid"
1154:
770:
551:
2619:The Journal of Biological Chemistry
2510:
1608:
1550:
1307:from the original on 28 August 2021
1148:
869:Deoxycholic acid is available as a
405:Key: KXGVEGMKQFWNSR-LLQZFEROBK
305:
289:
76:)-4-phenanthren-1-yl]pentanoic acid
13:
2042:World Journal of Surgical Oncology
1680:from the original on 27 April 2021
1670:"MeNZB – Use science not opinion!"
1238:from the original on 10 April 2023
1012:, activating its main actors, the
14:
3790:
3774:Microbiological media ingredients
3146:Zinc pyrithione (pyrithione zinc)
2375:. American Cancer Society. 2009.
1993:Experimental Biology and Medicine
1362:SLMB – Schweizer Lebensmittelbuch
1341:from the original on 24 June 2021
1271:from the original on 24 June 2021
1197:from the original on 25 June 2021
1157:Handbook of Chemistry and Physics
858:. Deoxycholic acid is soluble in
598:
574:
3741:
2411:10.1111/j.1572-0241.1999.01089.x
1909:Zeitschrift für Naturforschung B
1567:. April 29, 2015. Archived from
889:deoxycholic acid is used in the
645:
453:
43:
34:
25:
3106:Ciclopirox olamine (ciclopirox)
2971:
2949:10.1152/japplphysiol.00777.2009
2928:
2879:
2838:
2787:
2698:
2606:
2571:
2560:from the original on 2017-10-19
2546:
2453:
2433:
2390:
2379:from the original on 2012-09-13
2365:
2316:
2267:
2218:
2123:
2029:
1980:
1937:
1853:
1834:
1792:
1773:
1760:
1741:
1662:
1623:from the original on 2016-10-31
1597:from the original on 2016-10-31
1583:
1523:
1470:
1413:
880:
641:(at 25 °C , 100 kPa).
1650:(2): 67–79, discussion 79–80.
1353:
1319:
1283:
1220:
1209:
1113:
914:critical micelle concentration
459:
447:
1:
2937:Journal of Applied Physiology
2904:10.1158/1055-9965.EPI-08-1187
2864:10.1158/0008-5472.CAN-13-3501
1381:Guide to Protein Purification
1106:
2341:10.1080/01635581.2012.630164
2280:Journal of Advanced Research
1615:Christensen J (2015-05-01).
1565:Food and Drug Administration
1389:10.1016/0076-6879(90)82020-3
1333:Food and Drug Administration
940:Food and Drug Administration
7:
1966:10.1016/j.mrrev.2004.08.001
1593:. Kythera.com. 2014-06-20.
10:
3795:
2373:"Cancer Facts and Figures"
2292:10.1016/j.jare.2019.01.002
1444:Clinics in Plastic Surgery
952:Kythera Biopharmaceuticals
3779:Drugs developed by AbbVie
3538:
3472:
3439:Potassium channel openers
3365:
3313:
3290:
3262:
3045:
2243:10.1007/s00204-011-0648-7
1717:10.1016/j.str.2014.12.018
1456:10.1016/j.cps.2011.02.005
1300:(EMA). 10 December 2020.
1298:European Medicines Agency
814:
782:
754:
749:
719:
701:
691:
686:
635:
534:
434:
414:
379:
90:
82:
66:
56:
51:
42:
33:
24:
2055:10.1186/1477-7819-12-164
2005:10.1177/1535370214538743
3636:Glycopyrronium tosylate
3551:Aminobenzoate potassium
3483:5α-Reductase inhibitors
3431:Topilutamide (fluridil)
3376:5α-Reductase inhibitors
3351:Topical corticosteroids
3248:Topical corticosteroids
2765:10.1515/hmbci-2013-0063
2719:10.1515/hmbci-2014-0046
2683:10.3945/ajcn.2008.27296
2632:10.1074/jbc.M111.234732
1477:Christensen JB (2001).
524:Magnetic susceptibility
3631:Glycopyrronium bromide
3474:Hair growth inhibitors
3161:Calcineurin inhibitors
2556:. Phenol-explorer.eu.
2231:Archives of Toxicology
2193:10.4251/wjgo.v6.i7.225
2109:10.1126/science.373122
1816:Casopis Lekaru Ceskych
1091:
964:outer membrane protein
958:Research in immunology
897:for absorption in the
3220:urea-containing cream
1922:10.1515/znb-1971-0509
1421:"Sodium deoxycholate"
1088:
1020:, different types of
946:. When injected into
848:chenodeoxycholic acid
68:Systematic IUPAC name
3696:Pregnenolone acetate
3397:Saw palmetto extract
2329:Nutrition and Cancer
1849:. Bratislava: 77–86.
1766:Chyle M., Chyle P.:
1010:innate immune system
856:ursodeoxycholic acid
3513:Cyproterone acetate
3416:Cyproterone acetate
3367:Alopecia treatments
3315:Anti-inflammatories
3096:Cetrimonium bromide
3067:Cyproterone acetate
2816:10.1038/nature12404
2808:2013Natur.499...37D
2592:1999JSFA...79..362C
2486:10.1038/nature12820
2478:2014Natur.505..559D
2101:1979Sci...204..587A
1958:2005MRRMR.589...47B
1544:10.1246/cl.2000.414
1450:(3): 489–501, vii.
1431:on 7 February 2012.
983:N-acylethanolamines
925:phosphatidylcholine
683:
607:(Prescription only)
494:Solubility in water
477: g·mol
21:
2580:J. Sci. Food Agric
2447:2022-07-02 at the
1874:10.1007/BF02232545
1121:"Deoxycholic acid"
1092:
1032:Research in cancer
871:generic medication
679:
668:Infobox references
19:
3729:
3728:
3666:Magnesium sulfate
3646:Hydrogen peroxide
3581:Calcium gluconate
3240:Lithium succinate
3235:Lithium gluconate
3131:Piroctone olamine
2986:(6): 585–6, 588.
2532:10.1021/jf900393k
1946:Mutation Research
1532:Chemistry Letters
1166:978-0-8493-0594-8
1062:colorectal cancer
833:
832:
784:CompTox Dashboard
732:
676:Chemical compound
674:
673:
627:
615:
602:
578:
530:-272.0·10 cm/mol
348:CompTox Dashboard
132:Interactive image
20:Deoxycholic acid
3786:
3746:
3745:
3744:
3737:
3606:Deoxycholic acid
3596:Cromoglicic acid
3047:Anti-seborrheics
3026:
3019:
3012:
3003:
3002:
2996:
2995:
2975:
2969:
2968:
2932:
2926:
2925:
2915:
2883:
2877:
2876:
2866:
2842:
2836:
2835:
2791:
2785:
2784:
2748:
2739:
2738:
2702:
2696:
2695:
2685:
2661:
2655:
2654:
2644:
2634:
2625:(32): 28382–95.
2610:
2604:
2603:
2575:
2569:
2568:
2566:
2565:
2550:
2544:
2543:
2514:
2508:
2507:
2497:
2472:(7484): 559–63.
2457:
2451:
2437:
2431:
2430:
2394:
2388:
2387:
2385:
2384:
2369:
2363:
2362:
2352:
2320:
2314:
2313:
2303:
2271:
2265:
2264:
2254:
2222:
2216:
2215:
2205:
2195:
2171:
2162:
2161:
2151:
2127:
2121:
2120:
2095:(4393): 587–93.
2084:
2078:
2077:
2067:
2057:
2033:
2027:
2026:
2016:
1999:(11): 1489–504.
1984:
1978:
1977:
1941:
1935:
1934:
1924:
1900:
1894:
1893:
1857:
1851:
1850:
1838:
1832:
1831:
1811:
1805:
1804:
1796:
1790:
1789:
1777:
1771:
1764:
1758:
1757:
1745:
1739:
1738:
1728:
1696:
1690:
1689:
1687:
1685:
1676:. 10 June 2005.
1666:
1660:
1659:
1638:
1632:
1631:
1629:
1628:
1612:
1606:
1605:
1603:
1602:
1587:
1581:
1580:
1578:
1576:
1557:
1548:
1547:
1527:
1521:
1520:
1518:
1508:
1506:10.3390/60100047
1498:
1474:
1468:
1467:
1439:
1433:
1432:
1427:. Archived from
1417:
1411:
1410:
1376:
1370:
1369:
1357:
1351:
1350:
1348:
1346:
1323:
1317:
1316:
1314:
1312:
1306:
1295:
1287:
1281:
1280:
1278:
1276:
1257:
1248:
1247:
1245:
1243:
1234:. 21 June 2022.
1224:
1218:
1213:
1207:
1206:
1204:
1202:
1188:
1180:
1171:
1170:
1155:Lide DR (1998).
1152:
1146:
1145:
1143:
1142:
1136:
1130:. Archived from
1125:
1117:
1050:chlorogenic acid
852:lithocholic acid
836:Deoxycholic acid
829:
818:
807:
806:
792:
790:
774:
768:
742:
740:Deoxycholic_acid
731:
728:
715:
697:Kybella, Belkyra
684:
682:
681:Deoxycholic acid
678:
658:
652:
649:
648:
625:
622:
613:
610:
600:
597:
576:
573:
555:
476:
461:
455:
449:
442:Chemical formula
372:
371:
356:
354:
338:
318:
307:
293:
273:
254:
243:
232:
212:
192:
172:
152:
134:
110:
47:
38:
29:
22:
18:
3794:
3793:
3789:
3788:
3787:
3785:
3784:
3783:
3754:
3753:
3752:
3742:
3740:
3732:
3730:
3725:
3691:Povidone-iodine
3641:Hyaluronic acid
3566:Benzoylperoxide
3534:
3468:
3361:
3309:
3286:
3264:Skin lightening
3258:
3041:
3030:
3000:
2999:
2976:
2972:
2933:
2929:
2884:
2880:
2851:Cancer Research
2843:
2839:
2792:
2788:
2749:
2742:
2703:
2699:
2662:
2658:
2611:
2607:
2576:
2572:
2563:
2561:
2552:
2551:
2547:
2526:(18): 8587–90.
2515:
2511:
2458:
2454:
2449:Wayback Machine
2438:
2434:
2395:
2391:
2382:
2380:
2371:
2370:
2366:
2321:
2317:
2272:
2268:
2223:
2219:
2172:
2165:
2128:
2124:
2085:
2081:
2034:
2030:
1985:
1981:
1942:
1938:
1901:
1897:
1858:
1854:
1839:
1835:
1812:
1808:
1797:
1793:
1778:
1774:
1765:
1761:
1746:
1742:
1697:
1693:
1683:
1681:
1668:
1667:
1663:
1639:
1635:
1626:
1624:
1613:
1609:
1600:
1598:
1589:
1588:
1584:
1574:
1572:
1559:
1558:
1551:
1528:
1524:
1496:10.1.1.362.1034
1475:
1471:
1440:
1436:
1419:
1418:
1414:
1399:
1377:
1373:
1358:
1354:
1344:
1342:
1325:
1324:
1320:
1310:
1308:
1304:
1293:
1289:
1288:
1284:
1274:
1272:
1259:
1258:
1251:
1241:
1239:
1226:
1225:
1221:
1214:
1210:
1200:
1198:
1186:
1182:
1181:
1174:
1167:
1153:
1149:
1140:
1138:
1134:
1123:
1119:
1118:
1114:
1109:
1070:
1064:risk in women.
1034:
1024:, and possibly
1006:immunostimulant
960:
883:
810:
786:
778:
745:
677:
670:
665:
664:
663: ?)
654:
650:
646:
642:
631:
584:
567:
564:
544:
527:
513:
496:
474:
464:
458:
452:
444:
430:
427:
422:
421:
410:
407:
406:
403:
397:
396:
393:
387:
386:
375:
357:
350:
341:
321:
308:
296:
276:
263:
235:
215:
195:
175:
155:
137:
124:
113:
100:
86:
78:
77:
62:
17:
12:
11:
5:
3792:
3782:
3781:
3776:
3771:
3766:
3751:
3750:
3727:
3726:
3724:
3723:
3718:
3713:
3708:
3698:
3693:
3688:
3683:
3678:
3673:
3668:
3663:
3658:
3653:
3648:
3643:
3638:
3633:
3628:
3618:
3613:
3608:
3603:
3598:
3593:
3588:
3583:
3578:
3573:
3568:
3563:
3553:
3548:
3542:
3540:
3536:
3535:
3533:
3532:
3527:
3526:
3525:
3523:Spironolactone
3520:
3515:
3510:
3498:
3497:
3496:
3491:
3478:
3476:
3470:
3469:
3467:
3466:
3465:
3464:
3459:
3449:
3448:
3447:
3435:
3434:
3433:
3428:
3426:Spironolactone
3423:
3418:
3413:
3401:
3400:
3399:
3394:
3389:
3384:
3371:
3369:
3363:
3362:
3360:
3359:
3356:hydrocortisone
3346:
3345:
3340:
3335:
3330:
3328:Gamolenic acid
3325:
3319:
3317:
3311:
3310:
3308:
3307:
3302:
3296:
3294:
3292:Skin darkening
3288:
3287:
3285:
3284:
3279:
3274:
3268:
3266:
3260:
3259:
3257:
3256:
3253:hydrocortisone
3244:
3243:
3242:
3237:
3225:
3224:
3223:
3213:
3208:
3206:Salicylic acid
3203:
3198:
3186:
3181:
3180:
3179:
3174:
3169:
3157:
3154:Antihistamines
3150:
3149:
3148:
3143:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3093:
3081:
3080:
3079:
3077:Spironolactone
3074:
3069:
3064:
3051:
3049:
3043:
3042:
3036:preparations (
3034:dermatological
3029:
3028:
3021:
3014:
3006:
2998:
2997:
2970:
2927:
2878:
2837:
2802:(7456): 37–8.
2786:
2740:
2697:
2676:(4): 1002–10.
2656:
2605:
2570:
2545:
2509:
2452:
2432:
2405:(5): 1373–80.
2389:
2364:
2315:
2266:
2217:
2163:
2122:
2079:
2028:
1979:
1936:
1895:
1852:
1833:
1822:(40): 1226–9.
1806:
1791:
1772:
1759:
1740:
1711:(3): 598–604.
1691:
1661:
1633:
1607:
1582:
1571:on May 1, 2015
1549:
1522:
1469:
1434:
1412:
1397:
1371:
1352:
1318:
1282:
1249:
1219:
1208:
1172:
1165:
1147:
1111:
1110:
1108:
1105:
1099:deoxycholate.
1069:
1066:
1033:
1030:
959:
956:
891:emulsification
882:
879:
877:among others.
831:
830:
820:
812:
811:
809:
808:
795:
793:
780:
779:
777:
776:
760:
758:
752:
751:
747:
746:
744:
743:
725:
723:
717:
716:
709:
699:
698:
695:
689:
688:
675:
672:
671:
666:
644:
643:
639:standard state
636:
633:
632:
630:
629:
620:
608:
594:
592:
586:
585:
583:
582:
580:
570:
568:
561:
558:
557:
545:
540:
537:
536:
532:
531:
528:
522:
519:
518:
515:
511:
501:
500:
497:
492:
489:
488:
485:
479:
478:
472:
466:
465:
462:
456:
450:
445:
440:
437:
436:
432:
431:
429:
428:
425:
417:
416:
415:
412:
411:
409:
408:
404:
401:
400:
398:
394:
391:
390:
382:
381:
380:
377:
376:
374:
373:
360:
358:
346:
343:
342:
340:
339:
331:
329:
323:
322:
320:
319:
311:
309:
301:
298:
297:
295:
294:
286:
284:
278:
277:
275:
274:
266:
264:
259:
256:
255:
245:
237:
236:
234:
233:
225:
223:
217:
216:
214:
213:
205:
203:
197:
196:
194:
193:
185:
183:
177:
176:
174:
173:
165:
163:
157:
156:
154:
153:
145:
143:
139:
138:
136:
135:
127:
125:
118:
115:
114:
112:
111:
103:
101:
96:
93:
92:
88:
87:
84:
80:
79:
71:
70:
64:
63:
60:
54:
53:
49:
48:
40:
39:
31:
30:
15:
9:
6:
4:
3:
2:
3791:
3780:
3777:
3775:
3772:
3770:
3767:
3765:
3762:
3761:
3759:
3749:
3739:
3738:
3735:
3722:
3719:
3717:
3714:
3712:
3709:
3706:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3686:Oxymetazoline
3684:
3682:
3679:
3677:
3674:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3626:
3622:
3619:
3617:
3614:
3612:
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3587:
3584:
3582:
3579:
3577:
3574:
3572:
3569:
3567:
3564:
3561:
3557:
3554:
3552:
3549:
3547:
3544:
3543:
3541:
3537:
3531:
3528:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3505:
3504:
3503:
3502:Antiandrogens
3499:
3495:
3492:
3490:
3487:
3486:
3485:
3484:
3480:
3479:
3477:
3475:
3471:
3463:
3460:
3458:
3455:
3454:
3453:
3450:
3446:
3443:
3442:
3441:
3440:
3436:
3432:
3429:
3427:
3424:
3422:
3419:
3417:
3414:
3412:
3409:
3408:
3407:
3406:
3405:Antiandrogens
3402:
3398:
3395:
3393:
3390:
3388:
3385:
3383:
3380:
3379:
3378:
3377:
3373:
3372:
3370:
3368:
3364:
3357:
3353:
3352:
3348:
3347:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3320:
3318:
3316:
3312:
3306:
3303:
3301:
3300:Afamelanotide
3298:
3297:
3295:
3293:
3289:
3283:
3280:
3278:
3275:
3273:
3270:
3269:
3267:
3265:
3261:
3254:
3250:
3249:
3245:
3241:
3238:
3236:
3233:
3232:
3231:
3230:
3229:Lithium salts
3226:
3221:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3193:
3192:
3191:
3187:
3185:
3182:
3178:
3175:
3173:
3170:
3168:
3165:
3164:
3163:
3162:
3158:
3156:
3155:
3151:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3101:
3097:
3094:
3092:
3089:
3088:
3087:
3086:
3082:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3059:
3058:
3057:
3056:Antiandrogens
3053:
3052:
3050:
3048:
3044:
3039:
3035:
3027:
3022:
3020:
3015:
3013:
3008:
3007:
3004:
2993:
2989:
2985:
2981:
2974:
2966:
2962:
2958:
2954:
2950:
2946:
2942:
2938:
2931:
2923:
2919:
2914:
2909:
2905:
2901:
2898:(5): 1591–8.
2897:
2893:
2889:
2882:
2874:
2870:
2865:
2860:
2857:(7): 1885–9.
2856:
2852:
2848:
2841:
2833:
2829:
2825:
2821:
2817:
2813:
2809:
2805:
2801:
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2638:
2633:
2628:
2624:
2620:
2616:
2609:
2601:
2597:
2593:
2589:
2586:(3): 362–72.
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2555:
2549:
2541:
2537:
2533:
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2525:
2521:
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2248:
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2240:
2237:(8): 863–71.
2236:
2232:
2228:
2221:
2213:
2209:
2204:
2199:
2194:
2189:
2186:(7): 225–43.
2185:
2181:
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2168:
2159:
2155:
2150:
2145:
2142:(3): 254–84.
2141:
2137:
2133:
2126:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2090:
2083:
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2020:
2015:
2010:
2006:
2002:
1998:
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1990:
1983:
1975:
1971:
1967:
1963:
1959:
1955:
1951:
1947:
1940:
1932:
1928:
1923:
1918:
1915:(5): 419–24.
1914:
1910:
1906:
1899:
1891:
1887:
1883:
1879:
1875:
1871:
1867:
1863:
1856:
1848:
1844:
1843:Rehabilitacia
1837:
1829:
1825:
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1817:
1810:
1802:
1795:
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1611:
1596:
1592:
1586:
1570:
1566:
1562:
1556:
1554:
1545:
1541:
1538:(4): 414–15.
1537:
1533:
1526:
1517:
1512:
1507:
1502:
1497:
1492:
1489:(12): 47–51.
1488:
1484:
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1473:
1465:
1461:
1457:
1453:
1449:
1445:
1438:
1430:
1426:
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1408:
1404:
1400:
1398:9780121820831
1394:
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1340:
1336:
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1223:
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1212:
1196:
1192:
1185:
1179:
1177:
1168:
1162:
1158:
1151:
1137:on 2020-06-06
1133:
1129:
1128:Sigma Aldrich
1122:
1116:
1112:
1104:
1100:
1096:
1087:
1083:
1080:
1076:
1065:
1063:
1058:
1054:
1051:
1045:
1042:
1040:
1037:the level of
1029:
1027:
1023:
1019:
1018:inflammations
1015:
1011:
1007:
1002:
1000:
996:
992:
988:
984:
980:
976:
971:
969:
965:
955:
953:
949:
945:
942:for reducing
941:
936:
932:
930:
927:, is used in
926:
922:
917:
915:
910:
908:
904:
900:
896:
892:
888:
878:
876:
872:
867:
865:
861:
857:
853:
849:
845:
841:
837:
828:
824:
821:
819:
817:ECHA InfoCard
813:
805:
801:
800:DTXSID0042662
797:
796:
794:
785:
781:
773:
772:RCSB PDB
767:
762:
761:
759:
757:
753:
748:
741:
736:
727:
726:
724:
722:
718:
714:
710:
708:
704:
700:
696:
694:
690:
687:Clinical data
685:
669:
662:
657:
640:
634:
628: Rx-only
621:
619:
609:
606:
596:
595:
593:
591:
588:
587:
581:
572:
571:
569:
566:
560:
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554:
549:
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543:
539:
538:
535:Pharmacology
533:
529:
525:
521:
520:
516:
510:
506:
503:
502:
498:
495:
491:
490:
486:
484:
483:Melting point
481:
480:
473:
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468:
467:
446:
443:
439:
438:
433:
424:
423:
420:
413:
399:
389:
388:
385:
378:
370:
366:
365:DTXSID0042662
362:
361:
359:
349:
345:
344:
337:
333:
332:
330:
328:
325:
324:
317:
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285:
283:
280:
279:
272:
268:
267:
265:
262:
258:
257:
253:
249:
246:
244:
242:ECHA InfoCard
239:
238:
231:
227:
226:
224:
222:
219:
218:
211:
207:
206:
204:
202:
199:
198:
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133:
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126:
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109:
105:
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94:
89:
81:
75:
69:
65:
59:
55:
50:
46:
41:
37:
32:
28:
23:
3721:Tralokinumab
3705:progesterone
3701:Progestogens
3671:Metandienone
3656:Lebrikizumab
3605:
3601:Delgocitinib
3560:testosterone
3530:Eflornithine
3508:Bicalutamide
3500:
3481:
3462:Ritlecitinib
3451:
3437:
3411:Bicalutamide
3403:
3374:
3349:
3338:Pimecrolimus
3323:Alitretinoin
3305:Melanotan II
3272:Hydroquinone
3246:
3227:
3190:Keratolytics
3188:
3184:Isotretinoin
3172:Pimecrolimus
3159:
3152:
3121:Ketoconazole
3116:Clotrimazole
3083:
3062:Bicalutamide
3054:
2983:
2979:
2973:
2943:(3): 663–8.
2940:
2936:
2930:
2895:
2891:
2881:
2854:
2850:
2840:
2799:
2795:
2789:
2759:(1): 53–61.
2756:
2752:
2710:
2706:
2700:
2673:
2669:
2659:
2622:
2618:
2608:
2583:
2579:
2573:
2562:. Retrieved
2548:
2523:
2519:
2512:
2469:
2465:
2455:
2435:
2402:
2398:
2392:
2381:. Retrieved
2367:
2335:(1): 34–40.
2332:
2328:
2318:
2283:
2279:
2269:
2234:
2230:
2220:
2183:
2179:
2139:
2135:
2125:
2092:
2088:
2082:
2045:
2041:
2031:
1996:
1992:
1982:
1952:(1): 47–65.
1949:
1945:
1939:
1912:
1908:
1898:
1868:(7): 776–8.
1865:
1861:
1855:
1846:
1845:(in Czech).
1842:
1836:
1819:
1818:(in Czech).
1815:
1809:
1800:
1794:
1785:
1781:
1775:
1767:
1762:
1753:
1752:(in Czech).
1750:Prakt. Lekar
1749:
1743:
1708:
1704:
1694:
1682:. Retrieved
1673:
1664:
1647:
1643:
1636:
1625:. Retrieved
1610:
1599:. Retrieved
1585:
1575:December 16,
1573:. Retrieved
1569:the original
1535:
1531:
1525:
1486:
1482:
1472:
1447:
1443:
1437:
1429:the original
1424:
1415:
1380:
1374:
1365:
1361:
1355:
1343:. Retrieved
1330:
1321:
1309:. Retrieved
1285:
1273:. Retrieved
1264:
1240:. Retrieved
1231:
1222:
1211:
1199:. Retrieved
1190:
1156:
1150:
1139:. Retrieved
1132:the original
1127:
1115:
1101:
1097:
1093:
1079:caffeic acid
1071:
1059:
1055:
1046:
1043:
1035:
1003:
972:
961:
937:
933:
918:
911:
884:
881:Applications
874:
868:
835:
834:
721:License data
590:Legal status
508:
190:ChEMBL406393
91:Identifiers
85:Deoxycholate
83:Other names
73:
3711:Ruxolitinib
3681:Oclacitinib
3676:Nemolizumab
3591:Crisaborole
3571:Brimonidine
3546:Abrocitinib
3494:Finasteride
3489:Dutasteride
3392:Finasteride
3387:Dutasteride
3382:Alfatradiol
3282:Monobenzone
3167:Cyclosporin
3085:Antifungals
2713:(1): 5–15.
1862:Experientia
1674:scoop.co.nz
1644:NIPH Annals
1014:macrophages
929:mesotherapy
903:cholagogues
864:acetic acid
844:cholic acid
823:100.001.344
750:Identifiers
693:Trade names
435:Properties
248:100.001.344
170:CHEBI:28834
3764:Bile acids
3758:Categories
3716:Tiratricol
3661:Lokivetmab
3651:Ivermectin
3611:Diclofenac
3457:Nepidermin
3343:Tacrolimus
3201:Resorcinol
3177:Tacrolimus
3141:Xenysalate
3126:Miconazole
3111:Climbazole
3091:Bifonazole
2564:2016-11-02
2383:2015-04-07
2048:(1): 164.
1627:2016-11-02
1601:2016-11-02
1311:23 January
1141:2013-10-10
1107:References
993:response,
981:and other
979:anandamide
907:gallstones
887:human body
756:PDB ligand
470:Molar mass
336:005990WHZZ
261:IUPHAR/BPS
201:ChemSpider
119:3D model (
98:CAS Number
58:IUPAC name
3625:estradiol
3621:Estrogens
3616:Dupilumab
3556:Androgens
3518:Flutamide
3445:Minoxidil
3421:Flutamide
3333:Oxaceprol
3100:cetrimide
3072:Flutamide
2735:207452705
2286:: 85–94.
1756:: 326–30.
1705:Structure
1491:CiteSeerX
1483:Molecules
1425:nzp.co.nz
948:submental
921:detergent
899:intestine
840:bile acid
713:Monograph
707:Drugs.com
563:Pregnancy
16:Bile acid
3769:Cholanes
3748:Medicine
3586:Collagen
3576:Caffeine
3277:Mequinol
3196:Coal tar
2992:23909074
2980:Oncology
2957:20616226
2922:19383885
2873:24638983
2832:12714870
2824:23803768
2781:22924768
2773:25372730
2727:25719336
2692:19710199
2651:21680746
2558:Archived
2540:19711910
2504:24336217
2445:Archived
2419:10235221
2377:Archived
2359:22136517
2310:31193351
2261:21267546
2212:25024814
2158:20589166
2074:24884764
2023:24951470
1974:15652226
1890:26829935
1735:25684574
1684:12 April
1678:Archived
1621:Archived
1595:Archived
1464:21824545
1339:Archived
1302:Archived
1269:Archived
1265:DailyMed
1242:10 April
1236:Archived
1195:Archived
1075:curcumin
1039:8-oxo-dG
999:lifespan
995:appetite
975:NAPE-PLD
735:DailyMed
579: B1
565:category
556:)
542:ATC code
526:(χ)
221:DrugBank
3703:(e.g.,
3623:(e.g.,
3558:(e.g.,
3354:(e.g.,
3251:(e.g.,
2965:7982611
2913:2743306
2804:Bibcode
2642:3151081
2588:Bibcode
2495:3957428
2474:Bibcode
2427:6402410
2350:6844083
2301:6526205
2252:3149672
2203:4092339
2149:2892402
2097:Bibcode
2089:Science
2065:4041630
2014:4357421
1954:Bibcode
1931:4398280
1882:5431154
1828:1182754
1726:4351732
1656:1812438
1619:. CNN.
1516:6236364
1407:2314239
1345:19 June
1275:20 June
1201:23 June
1008:of the
875:Kybella
860:alcohol
737::
661:what is
659: (
550: (
548:D11AX24
505:Acidity
499:0.024%
475:392.580
303:PubChem
230:DB07690
108:83-44-3
3734:Portal
3539:Others
3452:Others
3211:Sulfur
3032:Other
2990:
2963:
2955:
2920:
2910:
2871:
2830:
2822:
2796:Nature
2779:
2771:
2733:
2725:
2690:
2649:
2639:
2538:
2502:
2492:
2466:Nature
2425:
2417:
2357:
2347:
2308:
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2259:
2249:
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2146:
2117:373122
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2072:
2062:
2021:
2011:
1972:
1929:
1888:
1880:
1826:
1733:
1723:
1654:
1513:
1493:
1462:
1405:
1395:
1163:
1026:cancer
1022:herpes
997:, and
987:stress
733:
656:verify
653:
618:℞-only
616:
603:
419:SMILES
316:222528
291:C04483
210:193196
181:ChEMBL
150:B05128
142:3DMet
52:Names
2961:S2CID
2828:S2CID
2777:S2CID
2731:S2CID
2423:S2CID
1886:S2CID
1335:(FDA)
1331:U.S.
1305:(PDF)
1294:(PDF)
1187:(PDF)
1135:(PDF)
1124:(PDF)
968:MeNZB
838:is a
763:DXC (
517:6.58
384:InChI
161:ChEBI
121:JSmol
3216:Urea
2988:PMID
2953:PMID
2918:PMID
2869:PMID
2820:PMID
2769:PMID
2723:PMID
2688:PMID
2647:PMID
2536:PMID
2500:PMID
2415:PMID
2355:PMID
2306:PMID
2257:PMID
2208:PMID
2154:PMID
2113:PMID
2070:PMID
2019:PMID
1970:PMID
1927:PMID
1878:PMID
1824:PMID
1731:PMID
1686:2011
1652:PMID
1577:2019
1460:PMID
1403:PMID
1393:ISBN
1368:(3).
1347:2021
1313:2021
1277:2021
1244:2023
1203:2021
1161:ISBN
991:pain
989:and
895:fats
862:and
846:and
766:PDBe
703:AHFS
327:UNII
282:KEGG
3038:D11
2945:doi
2941:109
2908:PMC
2900:doi
2859:doi
2812:doi
2800:499
2761:doi
2715:doi
2678:doi
2637:PMC
2627:doi
2623:286
2596:doi
2528:doi
2490:PMC
2482:doi
2470:505
2407:doi
2345:PMC
2337:doi
2296:PMC
2288:doi
2247:PMC
2239:doi
2198:PMC
2188:doi
2144:PMC
2105:doi
2093:204
2060:PMC
2050:doi
2009:PMC
2001:doi
1997:239
1962:doi
1950:589
1917:doi
1870:doi
1820:114
1721:PMC
1713:doi
1540:doi
1511:PMC
1501:doi
1452:doi
1385:doi
1191:TGA
1077:or
893:of
789:EPA
553:WHO
353:EPA
306:CID
271:610
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1387::
1366:4
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1144:.
791:)
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775:)
705:/
651:N
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512:a
509:K
463:4
460:O
454:H
448:C
355:)
351:(
123:)
74:R
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