Raloxifene (BioDeep_00001867796)

Main id: BioDeep_00000002326

 

PANOMIX_OTCML-2023


代谢物信息卡片


Raloxifene

化学式: C28H27NO4S (473.1660702000001)
中文名称: 雷洛昔芬
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CCN(CC1)CCOc1ccc(cc1)C(=O)c1c2ccc(cc2sc1c1ccc(cc1)O)O
InChI: InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2

描述信息

G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03X - Other sex hormones and modulators of the genital system > G03XC - Selective estrogen receptor modulators
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D020847 - Estrogen Receptor Modulators
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
D050071 - Bone Density Conservation Agents
C1892 - Chemopreventive Agent
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Raloxifene (Keoxifene) is a benzothiophene-derived selective estrogen receptor modulator (SERM). Raloxifene has estrogen-agonistic effects on bone and lipids and estrogen-antagonistic effects on the breast and uterus. Raloxifene is used for breast cancer and osteoporosis research[1].

同义名列表

5 个代谢物同义名

Raloxifene; Keoxifene; LY156758 (free base); LY139481; Raloxifene



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

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。

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文献列表

  • Victoria O Oyanna, Baron J Bechtold, Katherine D Lynch, M Ridge Call, Tyler N Graf, Nicholas H Oberlies, John D Clarke. Green Tea Catechins Decrease Solubility of Raloxifene In Vitro and Its Systemic Exposure in Mice. Pharmaceutical research. 2024 Mar; 41(3):557-566. doi: 10.1007/s11095-024-03662-w. [PMID: 38302834]
  • Saurabh Chugh, Prabhakar Tiwari, Charu Suri, Sonu Kumar Gupta, Padam Singh, Rania Bouzeyen, Saqib Kidwai, Mitul Srivastava, Nagender Rao Rameshwaram, Yashwant Kumar, Shailendra Asthana, Ramandeep Singh. Polyphosphate kinase-1 regulates bacterial and host metabolic pathways involved in pathogenesis of Mycobacterium tuberculosis. Proceedings of the National Academy of Sciences of the United States of America. 2024 Jan; 121(2):e2309664121. doi: 10.1073/pnas.2309664121. [PMID: 38170746]
  • Anjali Pant, Gajanand Sharma, Sumant Saini, Gurjeet Kaur, Atul Jain, Anil Thakur, Bhupinder Singh. QbD-driven development of phospholipid-embedded lipidic nanocarriers of raloxifene: extensive in vitro and in vivo evaluation studies. Drug delivery and translational research. 2023 Sep; ?(?):. doi: 10.1007/s13346-023-01427-3. [PMID: 37768530]
  • Shalvi Sinai Kunde, Sarika Wairkar. Folic acid anchored urchin-like raloxifene nanoparticles for receptor targeting in breast cancer: Synthesis, optimisation and in vitro biological evaluation. International journal of pharmaceutics. 2022 Jul; 623(?):121926. doi: 10.1016/j.ijpharm.2022.121926. [PMID: 35716974]
  • Mohammad Khaksari, Alireza Raji-Amirhasani, Hamideh Bashiri, Mohammad Navid Ebrahimi, Hossein Azizian. Protective effects of combining SERMs with estrogen on metabolic parameters in postmenopausal diabetic cardiovascular dysfunction: The role of cytokines and angiotensin II. Steroids. 2022 07; 183(?):109023. doi: 10.1016/j.steroids.2022.109023. [PMID: 35358567]
  • Daniela Iaconis, Licia Bordi, Giulia Matusali, Carmine Talarico, Candida Manelfi, Maria Candida Cesta, Mara Zippoli, Francesca Caccuri, Antonella Bugatti, Alberto Zani, Federica Filippini, Laura Scorzolini, Marco Gobbi, Marten Beeg, Arianna Piotti, Monica Montopoli, Veronica Cocetta, Silvia Bressan, Enrico M Bucci, Arnaldo Caruso, Emanuele Nicastri, Marcello Allegretti, Andrea R Beccari. Characterization of raloxifene as a potential pharmacological agent against SARS-CoV-2 and its variants. Cell death & disease. 2022 May; 13(5):498. doi: 10.1038/s41419-022-04961-z. [PMID: 35614039]
  • Hae Won Lee, Woo Youl Kang, Wookjae Jung, Mi-Ri Gwon, Kyunghee Cho, Backhwan Lee, Sook Jin Seong, Young-Ran Yoon. Pharmacokinetic Drug Interaction Between Raloxifene and Cholecalciferol in Healthy Volunteers. Clinical pharmacology in drug development. 2022 05; 11(5):623-631. doi: 10.1002/cpdd.1062. [PMID: 34984851]
  • Anju Sharma, Jarriaun Streets, Priyanka Bhatt, Pranav Patel, Vijaykumar Sutariya, Sheeba Varghese Gupta. Formulation and Characterization of Raloxifene Nanostructured Lipid Carriers for Permeability and Uptake Enhancement Applications. Assay and drug development technologies. 2022 May; 20(4):164-174. doi: 10.1089/adt.2022.004. [PMID: 35617693]
  • Atul Jain, Teenu Sharma, Rajendra Kumar, O P Katare, Bhupinder Singh. Raloxifene-loaded SLNs with enhanced biopharmaceutical potential: QbD-steered development, in vitro evaluation, in vivo pharmacokinetics, and IVIVC. Drug delivery and translational research. 2022 05; 12(5):1136-1160. doi: 10.1007/s13346-021-00990-x. [PMID: 33966178]
  • Guilherme L Alves, Fernanda V Teixeira, Priscila Bianca Rodrigues da Rocha, Anna Paula Krawczyk-Santos, Lígia Marquez Andrade, Marcilio Cunha-Filho, Ricardo N Marreto, Stephânia F Taveira. Preformulation and characterization of raloxifene-loaded lipid nanoparticles for transdermal administration. Drug delivery and translational research. 2022 03; 12(3):526-537. doi: 10.1007/s13346-021-00949-y. [PMID: 33682031]
  • Francesco Caruso, Jens Z Pedersen, Sandra Incerpi, Sarjit Kaur, Stuart Belli, Radu-Mihai Florea, Miriam Rossi. Mechanism of Caspase-1 Inhibition by Four Anti-inflammatory Drugs Used in COVID-19 Treatment. International journal of molecular sciences. 2022 Feb; 23(3):. doi: 10.3390/ijms23031849. [PMID: 35163769]
  • Richa Mishra, Lalita Mohan Behera, Soumendra Rana. Binding of raloxifene to human complement fragment 5a (hC5a): a perspective on cytokine storm and COVID19. Journal of biomolecular structure & dynamics. 2022 02; 40(3):982-994. doi: 10.1080/07391102.2020.1820381. [PMID: 32930050]
  • Marcello Allegretti, Maria Candida Cesta, Mara Zippoli, Andrea Beccari, Carmine Talarico, Flavio Mantelli, Enrico M Bucci, Laura Scorzolini, Emanuele Nicastri. Repurposing the estrogen receptor modulator raloxifene to treat SARS-CoV-2 infection. Cell death and differentiation. 2022 01; 29(1):156-166. doi: 10.1038/s41418-021-00844-6. [PMID: 34404919]
  • Nisha Mahey, Rushikesh Tambat, Nishtha Chandal, Dipesh Kumar Verma, Krishan Gopal Thakur, Hemraj Nandanwar. Repurposing Approved Drugs as Fluoroquinolone Potentiators to Overcome Efflux Pump Resistance in Staphylococcus aureus. Microbiology spectrum. 2021 12; 9(3):e0095121. doi: 10.1128/spectrum.00951-21. [PMID: 34908453]
  • Xinhui Du, Na Gao, Xiaoyong Song. Bioadhesive polymer/lipid hybrid nanoparticles as oral delivery system of raloxifene with enhancive intestinal retention and bioavailability. Drug delivery. 2021 Dec; 28(1):252-260. doi: 10.1080/10717544.2021.1872742. [PMID: 33501870]
  • Hao-Yang Ma, Shuang Chen, Ling-Ling Lu, Wei Gong, Ai-Hua Zhang. Raloxifene in the Treatment of Osteoporosis in Postmenopausal Women with End-Stage Renal Disease: A Systematic Review and Meta-Analysis. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2021 Nov; 53(11):730-737. doi: 10.1055/a-1655-4362. [PMID: 34740274]
  • Hongying Li, Vinayak S Jamdade. Raloxifene impedes cisplatin-induced nephrotoxicity through inhibition of Proinflammatory cytokines in female wistar rats. Pakistan journal of pharmaceutical sciences. 2021 Nov; 34(6):2141-2147. doi: . [PMID: 35034874]
  • Yan Sun, Ying Xiong, Yong Liang Meng, Heitor O Santos, Felipe L Athayde, Ivan G O de Souza, Ling Yang. Effects of raloxifene administration on serum levels of insulin-like growth factor-1 and insulin-like growth factor-binding protein 3 levels: A systematic review and meta-analysis of randomized controlled trials. Growth hormone & IGF research : official journal of the Growth Hormone Research Society and the International IGF Research Society. 2021 Oct; 60-61(?):101421. doi: 10.1016/j.ghir.2021.101421. [PMID: 34384975]
  • Rodrigo R R Duarte, Dennis C Copertino, Luis P Iñiguez, Jez L Marston, Yaron Bram, Yuling Han, Robert E Schwartz, Shuibing Chen, Douglas F Nixon, Timothy R Powell. Identifying FDA-approved drugs with multimodal properties against COVID-19 using a data-driven approach and a lung organoid model of SARS-CoV-2 entry. Molecular medicine (Cambridge, Mass.). 2021 09; 27(1):105. doi: 10.1186/s10020-021-00356-6. [PMID: 34503440]
  • Hong Shi, Heitor O Santos, Ivan G O de Souza, Gilles Jadd Hoilat, Carlos E C Martins, Hamed Kord Varkaneh, Joud Amer Alkhwildi, Aljawhara Talal Hejji, Faisal Almuqayyid, Ahmed Abu-Zaid. The Effect of Raloxifene Treatment on Lipid Profile in Elderly Individuals: A Systematic Review and Meta-analysis of Randomized Clinical Trials. Clinical therapeutics. 2021 09; 43(9):297-317. doi: 10.1016/j.clinthera.2021.07.017. [PMID: 34462124]
  • Ka-Ying Wong, Liping Zhou, Wenxuan Yu, Christina Chui-Wa Poon, Huihui Xiao, Chi-On Chan, Daniel Kam-Wah Mok, Man-Sau Wong. Water extract of Er-xian decoction selectively exerts estrogenic activities and interacts with SERMs in estrogen-sensitive tissues. Journal of ethnopharmacology. 2021 Jul; 275(?):114096. doi: 10.1016/j.jep.2021.114096. [PMID: 33823166]
  • Takashi Hara, Yasukazu Hijikata, Yukiko Matsubara, Norio Watanabe. Pharmacological interventions versus placebo, no treatment or usual care for osteoporosis in people with chronic kidney disease stages 3-5D. The Cochrane database of systematic reviews. 2021 Jul; 7(?):CD013424. doi: 10.1002/14651858.cd013424.pub2. [PMID: 34231877]
  • Aditi Sharma, Lalit Sharma, Reena V Saini, Ashwani Kumar, Rohit Goyal. Pinus roxburghii alleviates bone porosity and loss in postmenopausal osteoporosis by regulating estrogen, calcium homeostasis and receptor activator of nuclear factor-κB, osteoprotegerin, cathepsin bone markers. The Journal of pharmacy and pharmacology. 2021 Jun; 73(7):901-915. doi: 10.1093/jpp/rgaa014. [PMID: 33769535]
  • Rašković Aleksandar, Paut Kusturica Milica, Mitić Gorana, Milijašević Boris, Stojšić-Milosavljević Anastazija, Lalić-Popović Mladena, Stević Snežana, Stilinović Nebojša, Gigov Slobodan. Interaction between apigenin and sodium deoxycholate with raloxifene: A potential risk for clinical practice. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2021 Jun; 161(?):105809. doi: 10.1016/j.ejps.2021.105809. [PMID: 33741473]
  • Shao-Hua Ping, Fa-Ming Tian, Hao Liu, Qi Sun, Li-Tao Shao, Qiang-Qiang Lian, Liu Zhang. Raloxifene inhibits the overexpression of TGF-β1 in cartilage and regulates the metabolism of subchondral bone in rats with osteoporotic osteoarthritis. Bosnian journal of basic medical sciences. 2021 Jun; 21(3):284-293. doi: 10.17305/bjbms.2020.5142. [PMID: 33259777]
  • Bruce Schultz, Andrea Zaliani, Christian Ebeling, Jeanette Reinshagen, Denisa Bojkova, Vanessa Lage-Rupprecht, Reagon Karki, Sören Lukassen, Yojana Gadiya, Neal G Ravindra, Sayoni Das, Shounak Baksi, Daniel Domingo-Fernández, Manuel Lentzen, Mark Strivens, Tamara Raschka, Jindrich Cinatl, Lauren Nicole DeLong, Phil Gribbon, Gerd Geisslinger, Sandra Ciesek, David van Dijk, Steve Gardner, Alpha Tom Kodamullil, Holger Fröhlich, Manuel Peitsch, Marc Jacobs, Julia Hoeng, Roland Eils, Carsten Claussen, Martin Hofmann-Apitius. A method for the rational selection of drug repurposing candidates from multimodal knowledge harmonization. Scientific reports. 2021 05; 11(1):11049. doi: 10.1038/s41598-021-90296-2. [PMID: 34040048]
  • Gengqi Wang, Wenqiang Xu, Junjie Zhang, Tian Tang, Jing Chen, Changchun Fan. Induction of Bone Remodeling by Raloxifene-Doped Iron Oxide Functionalized with Hydroxyapatite to Accelerate Fracture Healing. Journal of biomedical nanotechnology. 2021 May; 17(5):932-941. doi: 10.1166/jbn.2021.3068. [PMID: 34082878]
  • Nur-Vaizura Mohamad, Soelaiman Ima-Nirwana, Kok-Yong Chin. Therapeutic potential of annatto tocotrienol with self-emulsifying drug delivery system in a rat model of postmenopausal bone loss. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111368. doi: 10.1016/j.biopha.2021.111368. [PMID: 33582449]
  • Keiko Imamura, Yasuteru Sakurai, Takako Enami, Ran Shibukawa, Yohei Nishi, Akira Ohta, Tsugumine Shu, Jitsutaro Kawaguchi, Sayaka Okada, Thomas Hoenen, Jiro Yasuda, Haruhisa Inoue. iPSC screening for drug repurposing identifies anti-RNA virus agents modulating host cell susceptibility. FEBS open bio. 2021 05; 11(5):1452-1464. doi: 10.1002/2211-5463.13153. [PMID: 33822489]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Fang Yang, Nana Li, Mihnea-Alexandru Gaman, Ning Wang. Raloxifene has favorable effects on the lipid profile in women explaining its beneficial effect on cardiovascular risk: A meta-analysis of randomized controlled trials. Pharmacological research. 2021 04; 166(?):105512. doi: 10.1016/j.phrs.2021.105512. [PMID: 33617974]
  • Eman M Alfadhli. Management of Primary Hyperparathyroidism With Severe Hypercalcemia During the COVID-19 Pandemic. Clinical therapeutics. 2021 04; 43(4):711-719. doi: 10.1016/j.clinthera.2021.02.003. [PMID: 33752899]
  • Katarzyna Szurkowska, Paulina Kazimierczak, Joanna Kolmas. Mg,Si-Co-Substituted Hydroxyapatite/Alginate Composite Beads Loaded with Raloxifene for Potential Use in Bone Tissue Regeneration. International journal of molecular sciences. 2021 Mar; 22(6):. doi: 10.3390/ijms22062933. [PMID: 33805785]
  • Yuan Ma, Yan Zheng, Yanli Ji, Xiuli Wang, Baoxian Ye. Raloxifene, identified as a novel LSD1 inhibitor, suppresses the migration of renal cell carcinoma. Future medicinal chemistry. 2021 03; 13(6):533-542. doi: 10.4155/fmc-2020-0323. [PMID: 33527838]
  • Subin Hong, JuOae Chang, Kwiwan Jeong, Wonsik Lee. Raloxifene as a treatment option for viral infections. Journal of microbiology (Seoul, Korea). 2021 Feb; 59(2):124-131. doi: 10.1007/s12275-021-0617-7. [PMID: 33527314]
  • Patricia Gomez-Gutierrez, Juan J Perez. Discovery of a Bradykinin B2 Partial Agonist Profile of Raloxifene in a Drug Repurposing Campaign. International journal of molecular sciences. 2020 Dec; 22(1):. doi: 10.3390/ijms22010257. [PMID: 33383825]
  • Mohammad Navid Ebrahimi, Mohammad Khaksari, Gholamreza Sepehri, Gholamreza Asadi Karam, Alireza Raji-Amirhasani, Hossein Azizian. The effects of alone and combination tamoxifen, raloxifene and estrogen on lipid profile and atherogenic index of ovariectomized type 2 diabetic rats. Life sciences. 2020 Dec; 263(?):118573. doi: 10.1016/j.lfs.2020.118573. [PMID: 33058909]
  • Ting Du, Rongjin Sun, Li Li, Christabel Ebuzoeme, Dinh Bui, Zicong Zheng, Taijun Yin, Dong Liang, Ming Hu, Song Gao. Development and validation of ultra-high-performance liquid chromatography-mass spectrometry method for the determination of raloxifene and its phase II metabolites in plasma: Application to pharmacokinetic studies in rats. Journal of separation science. 2020 Dec; 43(24):4414-4423. doi: 10.1002/jssc.202000835. [PMID: 33119204]
  • Nimrit Kaur Soni, L J Sonali, Archu Singh, Bharti Mangla, Yub Raj Neupane, Kanchan Kohli. Nanostructured lipid carrier potentiated oral delivery of raloxifene for breast cancer treatment. Nanotechnology. 2020 Nov; 31(47):475101. doi: 10.1088/1361-6528/abaf81. [PMID: 32886644]
  • Karel Smetana, Daniel Rosel, Jan BrÁbek. Raloxifene and Bazedoxifene Could Be Promising Candidates for Preventing the COVID-19 Related Cytokine Storm, ARDS and Mortality. In vivo (Athens, Greece). 2020 Sep; 34(5):3027-3028. doi: 10.21873/invivo.12135. [PMID: 32871847]
  • Khaled M Hosny, Rahaf H Bahmdan, Nabil A Alhakamy, Mohamed A Alfaleh, Osama A Ahmed, Mohammed H Elkomy. Physically Optimized Nano-Lipid Carriers Augment Raloxifene and Vitamin D Oral Bioavailability in Healthy Humans for Management of Osteoporosis. Journal of pharmaceutical sciences. 2020 07; 109(7):2145-2155. doi: 10.1016/j.xphs.2020.03.009. [PMID: 32194094]
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  • Nermeen A Elkasabgy, Fatma S Abdel-Salam, Azza A Mahmoud, Emad B Basalious, Mohammed S Amer, Amany A Mostafa, Seham A Elkheshen. Long lasting in-situ forming implant loaded with raloxifene HCl: An injectable delivery system for treatment of bone injuries. International journal of pharmaceutics. 2019 Nov; 571(?):118703. doi: 10.1016/j.ijpharm.2019.118703. [PMID: 31536761]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Hsin-Hsueh Shen, Chien-Yi Yang, Ching-Wen Kung, Shu-Ying Chen, Hong-Min Wu, Pao-Yun Cheng, Kwok-Keung Lam, Yen-Mei Lee. Raloxifene inhibits adipose tissue inflammation and adipogenesis through Wnt regulation in ovariectomized rats and 3 T3-L1 cells. Journal of biomedical science. 2019 Aug; 26(1):62. doi: 10.1186/s12929-019-0556-3. [PMID: 31470850]
  • Sravani Adusumalli, Rohitash Jamwal, R Scott Obach, Tim F Ryder, Lorenzo Leggio, Fatemeh Akhlaghi. Role of Molybdenum-Containing Enzymes in the Biotransformation of the Novel Ghrelin Receptor Inverse Agonist PF-5190457: A Reverse Translational Bed-to-Bench Approach. Drug metabolism and disposition: the biological fate of chemicals. 2019 08; 47(8):874-882. doi: 10.1124/dmd.119.087015. [PMID: 31182423]
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  • Yukari Uemura, Shiro Tanaka, Teruhiko Miyazaki, Mayumi Tsukiyama, Teruki Sone, Akira Taguchi, Satoshi Soen, Satoshi Mori, Hiroshi Hagino, Toshitsugu Sugimoto, Masao Fukunaga, Hiroaki Ohta, Toshitaka Nakamura, Hajime Orimo, Masataka Shiraki. Study design of multi-center, open-label randomized controlled, head-to-head trial comparing minodronic acid and raloxifene: Japanese Osteoporosis Intervention Trial (JOINT)-04. Journal of bone and mineral metabolism. 2019 May; 37(3):491-495. doi: 10.1007/s00774-018-0942-z. [PMID: 30019249]
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