6-[(3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (BioDeep_00000913916)
代谢物信息卡片
6-[(3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
化学式: C24H32O9 (464.2046222)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CCC2(O)OC4C(C(C(C(O4)C(=O)O)O)O)O)CCC5=C3C=CC(=C5)O
InChI: InChI=1S/C24H32O9/c1-23-8-6-14-13-5-3-12(25)10-11(13)2-4-15(14)16(23)7-9-24(23,31)33-22-19(28)17(26)18(27)20(32-22)21(29)30/h3,5,10,14-20,22,25-28,31H,2,4,6-9H2,1H3,(H,29,30)
描述信息
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
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代谢反应
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在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Yu-Meng Jia, Ting Zhu, Huan Zhou, Jin-Zi Ji, Ting Tai, Hong-Guang Xie. Multidrug Resistance-Associated Protein 3 Is Responsible for the Efflux Transport of Curcumin Glucuronide from Hepatocytes to the Blood.
Drug metabolism and disposition: the biological fate of chemicals.
2020 10; 48(10):966-971. doi:
10.1124/dmd.119.089193. [PMID: 31900255] - Gwenaëlle Conseil, May Arama-Chayoth, Yossi Tsfadia, Susan P C Cole. Structure-guided probing of the leukotriene C4 binding site in human multidrug resistance protein 1 (MRP1; ABCC1).
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2019 10; 33(10):10692-10704. doi:
10.1096/fj.201900140r. [PMID: 31268744] - Mingxiang Liao, Qing Zhu, Andy Zhu, Christopher Gemski, Bingli Ma, Emily Guan, Albert P Li, Guangqing Xiao, Cindy Q Xia. Comparison of uptake transporter functions in hepatocytes in different species to determine the optimal model for evaluating drug transporter activities in humans.
Xenobiotica; the fate of foreign compounds in biological systems.
2019 Jul; 49(7):852-862. doi:
10.1080/00498254.2018.1512017. [PMID: 30132394] - Alexandra Crowe, Wei Zheng, Jonathan Miller, Sonia Pahwa, Khondoker Alam, Kar-Ming Fung, Erin Rubin, Feng Yin, Kai Ding, Wei Yue. Characterization of Plasma Membrane Localization and Phosphorylation Status of Organic Anion Transporting Polypeptide (OATP) 1B1 c.521 T>C Nonsynonymous Single-Nucleotide Polymorphism.
Pharmaceutical research.
2019 May; 36(7):101. doi:
10.1007/s11095-019-2634-3. [PMID: 31093828] - Guillermo Nicolás Tocchetti, Agostina Arias, Maite Rocío Arana, Juan Pablo Rigalli, Camila Juliana Domínguez, Felipe Zecchinati, María Laura Ruiz, Silvina Stella Maris Villanueva, Aldo Domingo Mottino. Acute regulation of multidrug resistance-associated protein 2 localization and activity by cAMP and estradiol-17β-D-glucuronide in rat intestine and Caco-2 cells.
Archives of toxicology.
2018 Feb; 92(2):777-788. doi:
10.1007/s00204-017-2092-9. [PMID: 29052767] - Mayukh Banerjee, Vanessa Marensi, Gwenaëlle Conseil, X Chris Le, Susan P C Cole, Elaine M Leslie. Polymorphic variants of MRP4/ABCC4 differentially modulate the transport of methylated arsenic metabolites and physiological organic anions.
Biochemical pharmacology.
2016 Nov; 120(?):72-82. doi:
10.1016/j.bcp.2016.09.016. [PMID: 27659809] - Moritz Gruetz, Heinrich Sticht, Hartmut Glaeser, Martin F Fromm, Jörg König. Analysis of amino acid residues in the predicted transmembrane pore influencing transport kinetics of the hepatic drug transporter organic anion transporting polypeptide 1B1 (OATP1B1).
Biochimica et biophysica acta.
2016 Nov; 1858(11):2894-2902. doi:
10.1016/j.bbamem.2016.08.018. [PMID: 27594653] - Nisreen Hoosain, Brendon Pearce, Clifford Jacobs, Mongi Benjeddou. Mapping SLCO1B1 Genetic Variation for Global Precision Medicine in Understudied Regions in Africa: A Focus on Zulu and Cape Admixed Populations.
Omics : a journal of integrative biology.
2016 09; 20(9):546-54. doi:
10.1089/omi.2016.0115. [PMID: 27631194] - Feng Deng, Noora Sjöstedt, Heidi Kidron. The Effect of Albumin on MRP2 and BCRP in the Vesicular Transport Assay.
PloS one.
2016; 11(10):e0163886. doi:
10.1371/journal.pone.0163886. [PMID: 27706255] - Gloria Wissel, Pavel Kudryavtsev, Leo Ghemtio, Päivi Tammela, Peter Wipf, Marjo Yliperttula, Moshe Finel, Arto Urtti, Heidi Kidron, Henri Xhaard. Exploring the structure-activity relationships of ABCC2 modulators using a screening approach.
Bioorganic & medicinal chemistry.
2015 Jul; 23(13):3513-25. doi:
10.1016/j.bmc.2015.04.029. [PMID: 25935289] - Saki Izumi, Yoshitane Nozaki, Kazuya Maeda, Takafumi Komori, Osamu Takenaka, Hiroyuki Kusuhara, Yuichi Sugiyama. Investigation of the impact of substrate selection on in vitro organic anion transporting polypeptide 1B1 inhibition profiles for the prediction of drug-drug interactions.
Drug metabolism and disposition: the biological fate of chemicals.
2015 Feb; 43(2):235-47. doi:
10.1124/dmd.114.059105. [PMID: 25414411] - E van de Steeg, R Greupink, M Schreurs, I H G Nooijen, K C M Verhoeckx, R Hanemaaijer, D Ripken, M Monshouwer, M L H Vlaming, J DeGroot, M Verwei, F G M Russel, M T Huisman, H M Wortelboer. Drug-drug interactions between rosuvastatin and oral antidiabetic drugs occurring at the level of OATP1B1.
Drug metabolism and disposition: the biological fate of chemicals.
2013 Mar; 41(3):592-601. doi:
10.1124/dmd.112.049023. [PMID: 23248200] - Anett Engel, Stefan Oswald, Werner Siegmund, Markus Keiser. Pharmaceutical excipients influence the function of human uptake transporting proteins.
Molecular pharmaceutics.
2012 Sep; 9(9):2577-81. doi:
10.1021/mp3001815. [PMID: 22808947] - Lei Qin, Shui-Pang Tam, Roger G Deeley. Effect of multiple cysteine substitutions on the functionality of human multidrug resistance protein 1 expressed in human embryonic kidney 293 cells: identification of residues essential for function.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Jul; 40(7):1403-13. doi:
10.1124/dmd.112.044867. [PMID: 22511347] - Heidi Kidron, Gloria Wissel, Nenad Manevski, Marika Häkli, Raimo A Ketola, Moshe Finel, Marjo Yliperttula, Henri Xhaard, Arto Urtti. Impact of probe compound in MRP2 vesicular transport assays.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2012 May; 46(1-2):100-5. doi:
10.1016/j.ejps.2012.02.016. [PMID: 22406294] - Dirk R de Waart, Koen van de Wetering, Cindy Kunne, Suzanne Duijst, Coen C Paulusma, Ronald P J Oude Elferink. Oral availability of cefadroxil depends on ABCC3 and ABCC4.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Mar; 40(3):515-21. doi:
10.1124/dmd.111.041731. [PMID: 22166395] - Rick Greupink, Lieve Dillen, Mario Monshouwer, Maarten T Huisman, Frans G M Russel. Interaction of fluvastatin with the liver-specific Na+ -dependent taurocholate cotransporting polypeptide (NTCP).
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2011 Nov; 44(4):487-96. doi:
10.1016/j.ejps.2011.09.009. [PMID: 21945488] - Maria Ulvestad, Petter Björquist, Espen Molden, Anders Asberg, Tommy B Andersson. OATP1B1/1B3 activity in plated primary human hepatocytes over time in culture.
Biochemical pharmacology.
2011 Nov; 82(9):1219-26. doi:
10.1016/j.bcp.2011.07.076. [PMID: 21787759] - Megan Roth, Juan J Araya, Barbara N Timmermann, Bruno Hagenbuch. Isolation of modulators of the liver-specific organic anion-transporting polypeptides (OATPs) 1B1 and 1B3 from Rollinia emarginata Schlecht (Annonaceae).
The Journal of pharmacology and experimental therapeutics.
2011 Nov; 339(2):624-32. doi:
10.1124/jpet.111.184564. [PMID: 21846839] - Maciej J Zamek-Gliszczynski, Jeffrey S Day, Kathleen M Hillgren, Diane L Phillips. Efflux transport is an important determinant of ethinylestradiol glucuronide and ethinylestradiol sulfate pharmacokinetics.
Drug metabolism and disposition: the biological fate of chemicals.
2011 Oct; 39(10):1794-800. doi:
10.1124/dmd.111.040162. [PMID: 21708882] - Vandana Megaraj, Tianyong Zhao, Christian M Paumi, Phillip M Gerk, Richard B Kim, Mary Vore. Functional analysis of nonsynonymous single nucleotide polymorphisms of multidrug resistance-associated protein 2 (ABCC2).
Pharmacogenetics and genomics.
2011 Aug; 21(8):506-15. doi:
10.1097/fpc.0b013e328348c786. [PMID: 21691255] - Lei Gong, Nelly Aranibar, Yong-Hae Han, Youcai Zhang, Lloyd Lecureux, Vasanthi Bhaskaran, Purnima Khandelwal, Curtis D Klaassen, Lois D Lehman-McKeeman. Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles.
Toxicological sciences : an official journal of the Society of Toxicology.
2011 Aug; 122(2):587-97. doi:
10.1093/toxsci/kfr114. [PMID: 21561886] - Pablo Martinez-Becerra, Oscar Briz, Marta R Romero, Rocio I R Macias, Maria J Perez, Carlos Sancho-Mateo, Maria P Lostao, Jose M Fernandez-Abalos, Jose J G Marin. Further characterization of the electrogenicity and pH sensitivity of the human organic anion-transporting polypeptides OATP1B1 and OATP1B3.
Molecular pharmacology.
2011 Mar; 79(3):596-607. doi:
10.1124/mol.110.069971. [PMID: 21173039] - Asier Vallejo, Aresatz Usobiaga, Maren Ortiz-Zarragoitia, Miren P Cajaraville, Luis A Fernández, Olatz Zuloaga. Focused ultrasound-assisted acceleration of enzymatic hydrolysis of alkylphenols and 17β-oestradiol glucuronide in fish bile.
Analytical and bioanalytical chemistry.
2010 Nov; 398(5):2307-14. doi:
10.1007/s00216-010-4156-z. [PMID: 20835815] - Chunshan Gui, Bruno Hagenbuch. Cloning/characterization of the canine organic anion transporting polypeptide 1b4 (Oatp1b4) and classification of the canine OATP/SLCO members.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2010 Apr; 151(3):393-9. doi:
10.1016/j.cbpc.2010.01.005. [PMID: 20079461] - P Sharma, V E Holmes, R Elsby, C Lambert, D Surry. Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions.
Xenobiotica; the fate of foreign compounds in biological systems.
2010 Jan; 40(1):24-37. doi:
10.3109/00498250903351013. [PMID: 19919292] - Dirk R de Waart, Maria L H Vlaming, Cindy Kunne, Alfred H Schinkel, Ronald P J Oude Elferink. Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2.
Drug metabolism and disposition: the biological fate of chemicals.
2009 Aug; 37(8):1698-702. doi:
10.1124/dmd.108.026146. [PMID: 19443695] - M-K Choi, H Kim, Y-H Han, I-S Song, C-K Shim. Involvement of Mrp2/MRP2 in the species different excretion route of benzylpenicillin between rat and human.
Xenobiotica; the fate of foreign compounds in biological systems.
2009 Feb; 39(2):171-81. doi:
10.1080/00498250802642256. [PMID: 19255943] - Fernando A Crocenzi, Enrique J Sánchez Pozzi, María Laura Ruiz, Andrés E Zucchetti, Marcelo G Roma, Aldo D Mottino, Mary Vore. Ca(2+)-dependent protein kinase C isoforms are critical to estradiol 17beta-D-glucuronide-induced cholestasis in the rat.
Hepatology (Baltimore, Md.).
2008 Dec; 48(6):1885-95. doi:
10.1002/hep.22532. [PMID: 18972403] - Chunshan Gui, Yi Miao, Lucas Thompson, Bret Wahlgren, Melissa Mock, Bruno Stieger, Bruno Hagenbuch. Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3.
European journal of pharmacology.
2008 Apr; 584(1):57-65. doi:
10.1016/j.ejphar.2008.01.042. [PMID: 18321482] - Jessica X Jia, Kishor M Wasan. Effects of monoglycerides on rhodamine 123 accumulation, estradiol 17 beta-D-glucuronide bidirectional transport and MRP2 protein expression within Caco-2 cells.
Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques.
2008; 11(3):45-62. doi:
10.18433/j33s3z. [PMID: 18801307] - Alexander Treiber, Ralph Schneiter, Stephanie Häusler, Bruno Stieger. Bosentan is a substrate of human OATP1B1 and OATP1B3: inhibition of hepatic uptake as the common mechanism of its interactions with cyclosporin A, rifampicin, and sildenafil.
Drug metabolism and disposition: the biological fate of chemicals.
2007 Aug; 35(8):1400-7. doi:
10.1124/dmd.106.013615. [PMID: 17496208] - Flavia I Carreras, Guillermo L Lehmann, Domenico Ferri, Mariana F Tioni, Giuseppe Calamita, Raúl A Marinelli. Defective hepatocyte aquaporin-8 expression and reduced canalicular membrane water permeability in estrogen-induced cholestasis.
American journal of physiology. Gastrointestinal and liver physiology.
2007 Mar; 292(3):G905-12. doi:
10.1152/ajpgi.00386.2006. [PMID: 17110522] - Markus Grube, Sebastian Reuther, Henriette Meyer Zu Schwabedissen, Kathleen Köck, Katrin Draber, Christoph A Ritter, Christoph Fusch, Gabriele Jedlitschky, Heyo K Kroemer. Organic anion transporting polypeptide 2B1 and breast cancer resistance protein interact in the transepithelial transport of steroid sulfates in human placenta.
Drug metabolism and disposition: the biological fate of chemicals.
2007 Jan; 35(1):30-5. doi:
10.1124/dmd.106.011411. [PMID: 17020956] - Wen-Jen Lu, Ikumi Tamai, Jun-ichi Nezu, Ming-Liang Lai, Jin-Ding Huang. Organic anion transporting polypeptide-C mediates arsenic uptake in HEK-293 cells.
Journal of biomedical science.
2006 Jul; 13(4):525-33. doi:
10.1007/s11373-006-9071-0. [PMID: 16479312] - Naoki Ishiguro, Kazuya Maeda, Wataru Kishimoto, Asami Saito, Akiko Harada, Thomas Ebner, Willy Roth, Takashi Igarashi, Yuichi Sugiyama. Predominant contribution of OATP1B3 to the hepatic uptake of telmisartan, an angiotensin II receptor antagonist, in humans.
Drug metabolism and disposition: the biological fate of chemicals.
2006 Jul; 34(7):1109-15. doi:
10.1124/dmd.105.009175. [PMID: 16611857] - Maki Shimizu, Kaori Fuse, Kazuho Okudaira, Ryuichiro Nishigaki, Kazuya Maeda, Hiroyuki Kusuhara, Yuichi Sugiyama. Contribution of OATP (organic anion-transporting polypeptide) family transporters to the hepatic uptake of fexofenadine in humans.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Oct; 33(10):1477-81. doi:
10.1124/dmd.105.004622. [PMID: 16014768] - M Yamazaki, B Li, S W Louie, N T Pudvah, R Stocco, W Wong, M Abramovitz, A Demartis, R Laufer, J H Hochman, T Prueksaritanont, J H Lin. Effects of fibrates on human organic anion-transporting polypeptide 1B1-, multidrug resistance protein 2- and P-glycoprotein-mediated transport.
Xenobiotica; the fate of foreign compounds in biological systems.
2005 Jul; 35(7):737-53. doi:
10.1080/00498250500136676. [PMID: 16316932] - Masakazu Hirouchi, Hiroshi Suzuki, Yuichi Sugiyama. Treatment of hyperbilirubinemia in Eisai hyperbilirubinemic rat by transfecting human MRP2/ABCC2 gene.
Pharmaceutical research.
2005 Apr; 22(4):661-6. doi:
10.1007/s11095-005-2502-1. [PMID: 15846474] - Cuiping Chen, Rouchelle J Mireles, Scott D Campbell, Jian Lin, Jessica B Mills, Jinghai J Xu, Teresa A Smolarek. Differential interaction of 3-hydroxy-3-methylglutaryl-coa reductase inhibitors with ABCB1, ABCC2, and OATP1B1.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Apr; 33(4):537-46. doi:
10.1124/dmd.104.002477. [PMID: 15616150] - Joachim Geyer, Barbara Döring, Klaus Failing, Ernst Petzinger. Molecular cloning and functional characterization of the bovine (Bos taurus) organic anion transporting polypeptide Oatp1a2 (Slco1a2).
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology.
2004 Mar; 137(3):317-29. doi:
10.1016/j.cbpc.2003.12.004. [PMID: 15050519] - Young-Joo Lee, Hiroyuki Kusuhara, Yuichi Sugiyama. Do multidrug resistance-associated protein-1 and -2 play any role in the elimination of estradiol-17 beta-glucuronide and 2,4-dinitrophenyl-S-glutathione across the blood-cerebrospinal fluid barrier?.
Journal of pharmaceutical sciences.
2004 Jan; 93(1):99-107. doi:
10.1002/jps.10521. [PMID: 14648640] - Kenichi Nunoya, Caroline E Grant, Dawei Zhang, Susan P C Cole, Roger G Deeley. Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1).
Drug metabolism and disposition: the biological fate of chemicals.
2003 Aug; 31(8):1016-26. doi:
10.1124/dmd.31.8.1016. [PMID: 12867490] - Zhe-Sheng Chen, Robert W Robey, Martin G Belinsky, Irina Shchaveleva, Xiao-Qin Ren, Yoshikazu Sugimoto, Douglas D Ross, Susan E Bates, Gary D Kruh. Transport of methotrexate, methotrexate polyglutamates, and 17beta-estradiol 17-(beta-D-glucuronide) by ABCG2: effects of acquired mutations at R482 on methotrexate transport.
Cancer research.
2003 Jul; 63(14):4048-54. doi:
. [PMID: 12874005] - Noam Zelcer, Maarten T Huisman, Glen Reid, Peter Wielinga, Pauline Breedveld, Annemieke Kuil, Puck Knipscheer, Jan H M Schellens, Alfred H Schinkel, Piet Borst. Evidence for two interacting ligand binding sites in human multidrug resistance protein 2 (ATP binding cassette C2).
The Journal of biological chemistry.
2003 Jun; 278(26):23538-44. doi:
10.1074/jbc.m303504200. [PMID: 12702717] - Zhe-Sheng Chen, Elizabeth Hopper-Borge, Martin G Belinsky, Irina Shchaveleva, Elena Kotova, Gary D Kruh. Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10).
Molecular pharmacology.
2003 Feb; 63(2):351-8. doi:
10.1124/mol.63.2.351. [PMID: 12527806] - M A Serrano, J E Bayón, L Pascolo, C Tiribelli, J D Ostrow, J Gonzalez-Gallego, J J G Marin. Evidence for carrier-mediated transport of unconjugated bilirubin across plasma membrane vesicles from human placental trophoblast.
Placenta.
2002 Aug; 23(7):527-35. doi:
10.1053/plac.2002.0838. [PMID: 12175967] - Rémon A M H van Aubel, Pascal H E Smeets, Janny G P Peters, René J M Bindels, Frans G M Russel. The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP.
Journal of the American Society of Nephrology : JASN.
2002 Mar; 13(3):595-603. doi:
10.1681/asn.v133595. [PMID: 11856762] - Makoto Sasaki, Hiroshi Suzuki, Kousei Ito, Takaaki Abe, Yuichi Sugiyama. Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and Multidrug resistance-associated protein 2 (MRP2/ABCC2).
The Journal of biological chemistry.
2002 Feb; 277(8):6497-503. doi:
10.1074/jbc.m109081200. [PMID: 11748225] - E Battaglia, J Gollan. A unique multifunctional transporter translocates estradiol-17beta -glucuronide in rat liver microsomal vesicles.
The Journal of biological chemistry.
2001 Jun; 276(26):23492-8. doi:
10.1074/jbc.m102494200. [PMID: 11313362] - J Isern, B Hagenbuch, B Stieger, P J Meier, A Meseguer. Functional analysis and androgen-regulated expression of mouse organic anion transporting polypeptide 1 (Oatp1) in the kidney.
Biochimica et biophysica acta.
2001 Mar; 1518(1-2):73-8. doi:
10.1016/s0167-4781(01)00169-5. [PMID: 11267661] - H Zeng, G Liu, P A Rea, G D Kruh. Transport of amphipathic anions by human multidrug resistance protein 3.
Cancer research.
2000 Sep; 60(17):4779-84. doi:
. [PMID: 10987286] - B Stieger, K Fattinger, J Madon, G A Kullak-Ublick, P J Meier. Drug- and estrogen-induced cholestasis through inhibition of the hepatocellular bile salt export pump (Bsep) of rat liver.
Gastroenterology.
2000 Feb; 118(2):422-30. doi:
10.1016/s0016-5085(00)70224-1. [PMID: 10648470] - R A Walgren, T Walle. The influence of plasma binding on absorption/exsorption in the Caco-2 model of human intestinal absorption.
The Journal of pharmacy and pharmacology.
1999 Sep; 51(9):1037-40. doi:
10.1211/0022357991773366. [PMID: 10528987] - B D Stride, S P Cole, R G Deeley. Localization of a substrate specificity domain in the multidrug resistance protein.
The Journal of biological chemistry.
1999 Aug; 274(32):22877-83. doi:
10.1074/jbc.274.32.22877. [PMID: 10428874] - M Klein, E Martinoia, G Weissenböck. Directly energized uptake of beta-estradiol 17-(beta-D-glucuronide) in plant vacuoles is strongly stimulated by glutathione conjugates.
The Journal of biological chemistry.
1998 Jan; 273(1):262-70. doi:
10.1074/jbc.273.1.262. [PMID: 9417074] - B D Stride, C E Grant, D W Loe, D R Hipfner, S P Cole, R G Deeley. Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells.
Molecular pharmacology.
1997 Sep; 52(3):344-53. doi:
10.1124/mol.52.3.344. [PMID: 9281595] - Y Liu, L Huang, T Hoffman, M Gosland, M Vore. MDR1 substrates/modulators protect against beta-estradiol-17beta-D-glucuronide cholestasis in rat liver.
Cancer research.
1996 Nov; 56(21):4992-7. doi:
NULL. [PMID: 8895755] - D W Loe, K C Almquist, S P Cole, R G Deeley. ATP-dependent 17 beta-estradiol 17-(beta-D-glucuronide) transport by multidrug resistance protein (MRP). Inhibition by cholestatic steroids.
The Journal of biological chemistry.
1996 Apr; 271(16):9683-9. doi:
10.1074/jbc.271.16.9683. [PMID: 8621644] - R B Hakim, R H Gray, H A Zacur. Is there a need for creatinine adjustment of urinary steroid hormone levels in studies of early fetal loss?.
Clinica chimica acta; international journal of clinical chemistry.
1994 Oct; 230(2):209-14. doi:
10.1016/0009-8981(94)90273-9. [PMID: 7834871] - D Alvaro, M Angelico, A Cantafora, E Gaudio, C Gandin, M T Santini, R Masella, L Capocaccia. Improvement of estradiol 17 beta-D-glucuronide cholestasis by intravenous administration of dimethylethanolamine in the rat.
Hepatology (Baltimore, Md.).
1991 Jun; 13(6):1158-72. doi:
NULL. [PMID: 1646761] - S Teo, M Vore. Mirex exposure inhibits the uptake of estradiol-17 beta(beta-D-glucuronide), taurocholate, and L-alanine into isolated rat hepatocytes.
Toxicology and applied pharmacology.
1990 Jul; 104(3):411-20. doi:
10.1016/0041-008x(90)90163-o. [PMID: 1696754] - R H Gray, O M Campbell, R Apelo, S S Eslami, H Zacur, R M Ramos, J C Gehret, M H Labbok. Risk of ovulation during lactation.
Lancet (London, England).
1990 Jan; 335(8680):25-9. doi:
10.1016/0140-6736(90)90147-w. [PMID: 1967336] - A L Takacs, M Vore. Binding of 3H-estradiol-17 beta-(beta-D-glucuronide), a cholestatic organic anion, to rat liver plasma membranes. Evidence consonant with identification of organic anion carriers.
Molecular pharmacology.
1987 Oct; 32(4):511-8. doi:
. [PMID: 3670282] - R H Gray, O M Campbell, H A Zacur, M H Labbok, S L MacRae. Postpartum return of ovarian activity in nonbreastfeeding women monitored by urinary assays.
The Journal of clinical endocrinology and metabolism.
1987 Apr; 64(4):645-50. doi:
10.1210/jcem-64-4-645. [PMID: 3818896] - S H Andersson, T Cronholm, J Sjövall. Effects of ethanol on conjugated gonadal hormones in plasma of men.
Alcohol and alcoholism (Oxford, Oxfordshire). Supplement.
1987; 1(?):529-31. doi:
NULL. [PMID: 3426728] - H Okada, H Honjo, J Yasuda, K Otsubo, K Omori, K Tsukamoto, T Yamamoto, M Numazawa, T Nambara. Estradiol-17 beta and estradiol-17-glucosiduronate before and at delivery.
Biological research in pregnancy and perinatology.
1984; 5(2):68-73. doi:
. [PMID: 6743734] - W Slikker, M Vore, J R Bailey, M Meyers, C Montgomery. Hepatotoxic effects of estradiol-17 beta-D-glucuronide in the rat and monkey.
The Journal of pharmacology and experimental therapeutics.
1983 Apr; 225(1):138-43. doi:
. [PMID: 6300372] - A B Moore, G D Bottoms, G L Coppoc, R C Pohland, O F Roesel. Metabolism of estrogens in the gastrointestinal tract of swine. I. Instilled estradiol.
Journal of animal science.
1982 Jul; 55(1):124-34. doi:
10.2527/jas1982.551124x. [PMID: 7118738] - R C Pohland, G L Coppoc, G D Bottoms, A B Moore. Metabolism of estrogens in the gastrointestinal tract of swine. III. Estradiol-17 beta-D-glucuronide instilled into sections of intestine.
Journal of animal science.
1982 Jul; 55(1):145-52. doi:
10.2527/jas1982.551145x. [PMID: 7118739] - G L Coppoc, G D Bottoms, E Monk, A B Moore, O F Roesel. Metabolism of estrogens in the gastrointestinal tract of swine. II. Orally administered estradiol-17 beta-D-glucuronide.
Journal of animal science.
1982 Jul; 55(1):135-44. doi:
10.2527/jas1982.551135x. [PMID: 6288650] - T Nambara, K Shimada, T Ohkubo, T Niwa. Preparation and antigenic properties of estriol 16-glucuronide- and estradiol 17-glucuronide-[C-6]-bovine serum albumin conjugates.
Journal of steroid biochemistry.
1982 Apr; 16(4):533-8. doi:
10.1016/0022-4731(82)90075-9. [PMID: 7087478] - C M Branch, P O Collins, W P Collins. Ovulation prediction: changes in the concentrations of urinary estrone-3-glucuronide, estradiol-17 beta-glucuronide and estriol-16 alpha-glucuronide during conceptional cycles.
Journal of steroid biochemistry.
1982 Feb; 16(2):345-7. doi:
10.1016/0022-4731(82)90189-3. [PMID: 7078170] - I Miyakawa, F Z Stanczyk, C M March, A D March, U Goebelsmann. Urinary estradiol-17-beta-glucuronide assay for gonadotropin therapy.
Obstetrics and gynecology.
1981 Aug; 58(2):142-7. doi:
NULL. [PMID: 6789264] - T S Baker, K Jennison, A E Kellie. A possible method for the detection of ovulation and the determination of the duration of the fertile period.
Journal of steroid biochemistry.
1980 Jan; 12(?):411-5. doi:
10.1016/0022-4731(80)90300-3. [PMID: 7421226]