ipriflavone (BioDeep_00000398658)
代谢物信息卡片
ipriflavone
化学式: C18H16O3 (280.10993859999996)
中文名称: 依普黄酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)OC1=CC2=C(C=C1)C(=O)C(=CO2)C3=CC=CC=C3
InChI: InChI=1S/C18H16O3/c1-12(2)21-14-8-9-15-17(10-14)20-11-16(18(15)19)13-6-4-3-5-7-13/h3-12H,1-2H3
描述信息
M - Musculo-skeletal system > M05 - Drugs for treatment of bone diseases > M05B - Drugs affecting bone structure and mineralization
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.328
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.329
同义名列表
1 个代谢物同义名
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:31719
- KEGGdrug: D01338
- KEGGdrug: D70301
- PubChem: 3747
- Metlin: METLIN84971
- DrugBank: DB13618
- ChEMBL: CHEMBL165790
- CAS: 35212-22-7
- MoNA: FiehnHILIC002017
- MoNA: FiehnHILIC000446
- MoNA: BML81467
- MoNA: BML81465
- MoNA: BML01781
- MoNA: BML01770
- MoNA: BML01759
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。
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
- Hiroshi Koike, Yoshihiro Nishida, Tamayuki Shinomura, Bisei Ohkawara, Kinji Ohno, Lisheng Zhuo, Koji Kimata, Takahiro Ushida, Shiro Imagama. Possible Repositioning of an Oral Anti-Osteoporotic Drug, Ipriflavone, for Treatment of Inflammatory Arthritis via Inhibitory Activity of KIAA1199, a Novel Potent Hyaluronidase.
International journal of molecular sciences.
2022 Apr; 23(8):. doi:
10.3390/ijms23084089. [PMID: 35456905] - Xiao Wang, Ao Zheng, Xian Zhen Xin, Ling Jie Peng, Jie Wang, Ling Yan Cao, Xin Quan Jiang. Osteogenic Induction of Low-dose Ipriflavone on Bone Marrow Mesenchymal Stem Cells Extracted from Osteoporosis Rats.
The Chinese journal of dental research.
2021 Sep; 24(3):153-158. doi:
10.3290/j.cjdr.b1965039. [PMID: 34491009] - 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] - Rania A Gad, Eman S Abdel-Reheim, Gaber M G Shehab, Hani S Hafez, Abdelaziz S A Abuelsaad. Evaluation of Insulin Resistance Induced Brain Tissue Dysfunction in Obese Dams and their Neonates: Role of Ipriflavone Amelioration.
Combinatorial chemistry & high throughput screening.
2021; 24(6):767-780. doi:
10.2174/1386207323666200808181148. [PMID: 32772909] - Nashwa W Yassa, Sofia Khalil, Samar R Saleh, Doaa A Ghareeb, Maha A El Demellawy, Mohamed M El-Sayed. Ipriflavone and Ipriflavone loaded albumin nanoparticles reverse lipopolysaccharide induced neuroinflammation in rats.
PloS one.
2020; 15(8):e0237929. doi:
10.1371/journal.pone.0237929. [PMID: 32822403] - 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] - Violetta Mohos, Tímea Bencsik, Gabriella Boda, Eszter Fliszár-Nyúl, Beáta Lemli, Sándor Kunsági-Máté, Miklós Poór. Interactions of casticin, ipriflavone, and resveratrol with serum albumin and their inhibitory effects on CYP2C9 and CYP3A4 enzymes.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2018 Nov; 107(?):777-784. doi:
10.1016/j.biopha.2018.08.068. [PMID: 30142539] - Nishikant Wase, Boqiang Tu, James W Allen, Paul N Black, Concetta C DiRusso. Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
Plant physiology.
2017 Aug; 174(4):2146-2165. doi:
10.1104/pp.17.00433. [PMID: 28652262] - Bing Lin, Jun-Fei Huang, Xiong-Wei Liu, Xi-Tao Ma, Xiong-Li Liu, Yi Lu, Ying Zhou, Feng-Min Guo, Ting-Ting Feng. Rapid, microwave-accelerated synthesis and anti-osteoporosis activities evaluation of Morusin scaffolds and Morusignin L scaffolds.
Bioorganic & medicinal chemistry letters.
2017 06; 27(11):2389-2396. doi:
10.1016/j.bmcl.2017.04.018. [PMID: 28427808] - Miki Fujimori, Kazunori Kadota, Kouki Kato, Yoshiki Seto, Satomi Onoue, Hideyuki Sato, Hiroshi Ueda, Yuichi Tozuka. Low hygroscopic spray-dried powders with trans-glycosylated food additives enhance the solubility and oral bioavailability of ipriflavone.
Food chemistry.
2016 Jan; 190(?):1050-1055. doi:
10.1016/j.foodchem.2015.06.081. [PMID: 26213075] - Changhong Yun, Li Ding, Ye Leng, He Zhu, Aidong Wen, Lin Yang. Determination of ipriflavone in human plasma by LC-MS and its application in a pharmacokinetic study.
Biomedical chromatography : BMC.
2012 Jan; 26(1):123-8. doi:
10.1002/bmc.1641. [PMID: 21594876] - Shirin Hooshmand, Dania A Khalil, Genoveva Murillo, Keith Singletary, Savitri K Kamath, Bahram H Arjmandi. The combination of genistin and ipriflavone prevents mammary tumorigenesis and modulates lipid profile.
Clinical nutrition (Edinburgh, Scotland).
2008 Aug; 27(4):643-8. doi:
10.1016/j.clnu.2008.04.012. [PMID: 18571816] - H J Chung, I Lee, M G Lee. Effects of water deprivation for 72 h on the pharmacokinetics of ipriflavone in rats.
Research in veterinary science.
2008 Aug; 85(1):149-55. doi:
10.1016/j.rvsc.2007.08.010. [PMID: 17919668] - J Yao, J Zhang, J-F Hou. Effects of ipriflavone on caged layer bone metabolism in vitro and in vivo.
Poultry science.
2007 Mar; 86(3):503-7. doi:
10.1093/ps/86.3.503. [PMID: 17297162] - Alice A Cotter, Kevin D Cashman. The effect of two dietary and a synthetic phytoestrogen on transepithelial calcium transport in human intestinal-like Caco-2 cells.
European journal of nutrition.
2005 Mar; 44(2):72-8. doi:
10.1007/s00394-004-0495-x. [PMID: 15309423] - Farzad Deyhim, Brenda J Smith, Do Y Soung, Shanil Juma, Latha Devareddy, Bahram H Arjmandi. Ipriflavone modulates IGF-I but is unable to restore bone in rats.
Phytotherapy research : PTR.
2005 Feb; 19(2):116-20. doi:
10.1002/ptr.1615. [PMID: 15852487] - Ben Seaver, Jerry Robert Smith. Inhibition of COX isoforms by nutraceuticals.
Journal of herbal pharmacotherapy.
2004; 4(2):11-8. doi:
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Journal of veterinary science.
2003 Aug; 4(2):151-4. doi:
10.4142/jvs.2003.4.2.151. [PMID: 14610368] - Masaki Miyake, Norie Arai, Shimpei Ushio, Kanso Iwaki, Masao Ikeda, Masashi Kurimoto. Promoting effect of kaempferol on the differentiation and mineralization of murine pre-osteoblastic cell line MC3T3-E1.
Bioscience, biotechnology, and biochemistry.
2003 Jun; 67(6):1199-205. doi:
10.1271/bbb.67.1199. [PMID: 12843643] - H J Kang, R Ansbacher, M M Hammoud. Use of alternative and complementary medicine in menopause.
International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics.
2002 Dec; 79(3):195-207. doi:
10.1016/s0020-7292(02)00297-7. [PMID: 12445983] - A V Kropotov, O L Kolodnyak, V M Koldaev. Effects of Siberian ginseng extract and ipriflavone on the development of glucocorticoid-induced osteoporosis.
Bulletin of experimental biology and medicine.
2002 Mar; 133(3):252-4. doi:
10.1023/a:1015834717178. [PMID: 12360344] - So Hee Kim, Myung Gull Lee. Pharmacokinetics of ipriflavone, an isoflavone derivative, after intravenous and oral administration to rats hepatic and intestinal first-pass effects.
Life sciences.
2002 Feb; 70(11):1299-315. doi:
10.1016/s0024-3205(01)01508-9. [PMID: 11883708] - C Tsourounis. Clinical effects of phytoestrogens.
Clinical obstetrics and gynecology.
2001 Dec; 44(4):836-42. doi:
10.1097/00003081-200112000-00021. [PMID: 11600864] - Y Somekawa, M Chiguchi, T Ishibashi, K Wakana, T Aso. Efficacy of ipriflavone in preventing adverse effects of leuprolide.
The Journal of clinical endocrinology and metabolism.
2001 Jul; 86(7):3202-6. doi:
10.1210/jcem.86.7.7673. [PMID: 11443189] - A D Halpner, G Kellermann, M J Ahlgrimm, C L Arndt, N A Shaikh, J J Hargrave, P G Tallas. The effect of an ipriflavone-containing supplement on urinary N-linked telopeptide levels in postmenopausal women.
Journal of women's health & gender-based medicine.
2000 Nov; 9(9):995-8. doi:
10.1089/15246090050200024. [PMID: 11103099] - B H Arjmandi, D A Khalil, B W Hollis. Ipriflavone, a synthetic phytoestrogen, enhances intestinal calcium transport in vitro.
Calcified tissue international.
2000 Sep; 67(3):225-9. doi:
10.1007/s002230001123. [PMID: 10954777] - S Kim, J Lee, M Lee. Pharmacokinetics and tissue distribution of ipriflavone, an isoflavone derivative, after intravenous administration to rabbits.
Biopharmaceutics & drug disposition.
2000 May; 21(4):147-56. doi:
10.1002/1099-081x(200005)21:4<147::aid-bdd233>3.0.co;2-l. [PMID: 11180193] - B H Arjmandi, R S Birnbaum, S Juma, E Barengolts, S C Kukreja. The synthetic phytoestrogen, ipriflavone, and estrogen prevent bone loss by different mechanisms.
Calcified tissue international.
2000 Jan; 66(1):61-5. doi:
10.1007/s002230050012. [PMID: 10602847] - Y P Li, J J Zhou, X Y Zhang, Y Y Pei. Pharmacokinetics of intragastric ipriflavone solid dispersion in rats.
Zhongguo yao li xue bao = Acta pharmacologica Sinica.
1999 Nov; 20(11):1035-8. doi:
NULL. [PMID: 11270971] - S H Kim, J S Lee, M G Lee. Stability, blood partition and plasma protein binding of ipriflavone, an isoflavone derivative.
Biopharmaceutics & drug disposition.
1999 Oct; 20(7):355-60. doi:
10.1002/(sici)1099-081x(199910)20:7<355::aid-bdd197>3.0.co;2-x. [PMID: 10760844] - Y Sato, H Kuno, M Kaji, N Saruwatari, K Oizumi. Effect of ipriflavone on bone in elderly hemiplegic stroke patients with hypovitaminosis D.
American journal of physical medicine & rehabilitation.
1999 Sep; 78(5):457-63. doi:
10.1097/00002060-199909000-00008. [PMID: 10493456] - M D Scheiber, R W Rebar. Isoflavones and postmenopausal bone health: a viable alternative to estrogen therapy?.
Menopause (New York, N.Y.).
1999; 6(3):233-41. doi:
10.1097/00042192-199906030-00010. [PMID: 10486794] - T Fujita, Y Fujii, A Miyauchi, Y Takagi. Comparison of antiresorptive activities of ipriflavone, an isoflavone derivative, and elcatonin, an eel carbocalcitonin.
Journal of bone and mineral metabolism.
1999; 17(4):289-95. doi:
10.1007/s007740050097. [PMID: 10575594] - G G Kuiper, J G Lemmen, B Carlsson, J C Corton, S H Safe, P T van der Saag, B van der Burg, J A Gustafsson. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.
Endocrinology.
1998 Oct; 139(10):4252-63. doi:
10.1210/endo.139.10.6216. [PMID: 9751507] - M Nozaki, K Hashimoto, Y Inoue, R Ogata, A Okuma, H Nakano. Treatment of bone loss in oophorectomized women with a combination of ipriflavone and conjugated equine estrogen.
International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics.
1998 Jul; 62(1):69-75. doi:
10.1016/s0020-7292(98)00068-x. [PMID: 9722129] - D Acerbi, G Poli, P Ventura. Comparative bioavailability of two oral formulations of ipriflavone in healthy volunteers at steady-state. Evaluation of two different dosage schemes.
European journal of drug metabolism and pharmacokinetics.
1998 Apr; 23(2):172-7. doi:
10.1007/bf03189335. [PMID: 9725477] - K Monostory, L Vereczkey, F Lévai, I Szatmári. Ipriflavone as an inhibitor of human cytochrome P450 enzymes.
British journal of pharmacology.
1998 Feb; 123(4):605-10. doi:
10.1038/sj.bjp.0701633. [PMID: 9517377] - C Gennari, D Agnusdei, G Crepaldi, G Isaia, G Mazzuoli, S Ortolani, L Bufalino, M Passeri. Effect of ipriflavone--a synthetic derivative of natural isoflavones--on bone mass loss in the early years after menopause.
Menopause (New York, N.Y.).
1998; 5(1):9-15. doi:
NULL. [PMID: 9689189] - S H Kim, J S Lee, M G Lee. Determination of a isoflavone derivative, ipriflavone, and its metabolites, M1 and M5, in rat plasma, urine, and tissue homogenate by high-performance liquid chromatography.
Research communications in molecular pathology and pharmacology.
1997 Dec; 98(3):313-24. doi:
NULL. [PMID: 9485525] - M Gambacciani, M Ciaponi, B Cappagli, L Piaggesi, A R Genazzani. Effects of combined low dose of the isoflavone derivative ipriflavone and estrogen replacement on bone mineral density and metabolism in postmenopausal women.
Maturitas.
1997 Sep; 28(1):75-81. doi:
10.1016/s0378-5122(97)00059-5. [PMID: 9391998] - D Agnusdei, G Crepaldi, G Isaia, G Mazzuoli, S Ortolani, M Passeri, L Bufalino, C Gennari. A double blind, placebo-controlled trial of ipriflavone for prevention of postmenopausal spinal bone loss.
Calcified tissue international.
1997 Aug; 61(2):142-7. doi:
10.1007/s002239900312. [PMID: 9236262] - D de Aloysio, M Gambacciani, P Altieri, M Ciaponi, V Ventura, M Mura, A R Genazzani, F Bottiglioni. Bone density changes in postmenopausal women with the administration of ipriflavone alone or in association with low-dose ERT.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology.
1997 Aug; 11(4):289-93. doi:
10.3109/09513599709152548. [PMID: 9272427] - S Rohatagi, J S Barrett, W Sawyers, K Yu, R J Morales. Pharmacokinetics of ipriflavone and metabolites after oral administration of a corn-oil suspension relative to the Osteofix tablet.
American journal of therapeutics.
1997 Jul; 4(7-8):229-38. doi:
10.1097/00045391-199707000-00003. [PMID: 10423615] - X H Ma, Y Xu, T P Liu. [High performance liquid chromatographic method for the determination of ipriflavone in serum and its pharmacokinetic study in healthy volunteers].
Yao xue xue bao = Acta pharmaceutica Sinica.
1997 Jun; 32(6):470-2. doi:
NULL. [PMID: 11596332] - S Rohatagi, J S Barrett. Integrated pharmacokinetic and metabolic modeling of ipriflavone and metabolites after oral administration.
American journal of therapeutics.
1997 May; 4(5-6):189-98. doi:
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Journal of the American Society of Nephrology : JASN.
1997 Feb; 8(2):260-70. doi:
10.1681/asn.v82260. [PMID: 9048345] - R Civitelli. In vitro and in vivo effects of ipriflavone on bone formation and bone biomechanics.
Calcified tissue international.
1997; 61 Suppl 1(?):S12-4. doi:
10.1007/s002239900378. [PMID: 9263610] - M G Cecchini, H Fleisch, R C Mühibauer. Ipriflavone inhibits bone resorption in intact and ovariectomized rats.
Calcified tissue international.
1997; 61 Suppl 1(?):S9-11. doi:
10.1007/s002239900377. [PMID: 9263609] - M Gambacciani, B Cappagli, L Piaggesi, M Ciaponi, A R Genazzani. Ipriflavone prevents the loss of bone mass in pharmacological menopause induced by GnRH-agonists.
Calcified tissue international.
1997; 61 Suppl 1(?):S15-8. doi:
10.1007/s002239900379. [PMID: 9263611] - J Y Reginster, L Bufalino, C Christiansen, J P Devogelaer, C Gennari, B J Riis, C Roux. Design for an ipriflavone multicenter European fracture study.
Calcified tissue international.
1997; 61 Suppl 1(?):S28-32. doi:
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Calcified tissue international.
1997; 61 Suppl 1(?):S23-7. doi:
10.1007/s002239900381. [PMID: 9263613] - S Adami, L Bufalino, R Cervetti, C Di Marco, O Di Munno, L Fantasia, G C Isaia, U Serni, L Vecchiet, M Passeri. Ipriflavone prevents radial bone loss in postmenopausal women with low bone mass over 2 years.
Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA.
1997; 7(2):119-25. doi:
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Calcified tissue international.
1997; 61 Suppl 1(?):S19-22. doi:
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Calcified tissue international.
1996 Feb; 58(2):88-94. doi:
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European journal of drug metabolism and pharmacokinetics.
1996 Jan; 21(1):61-6. doi:
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Acta pharmaceutica Hungarica.
1995 Nov; 65(6):219-22. doi:
NULL. [PMID: 8742629] - T Ushiroyama, S Okamura, A Ikeda, M Ueki. Efficacy of ipriflavone and 1 alpha vitamin D therapy for the cessation of vertebral bone loss.
International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics.
1995 Mar; 48(3):283-8. doi:
10.1016/0020-7292(94)02280-c. [PMID: 7781871] - R Civitelli, S H Abbasi-Jarhomi, L R Halstead, A Dimarogonas. Ipriflavone improves bone density and biomechanical properties of adult male rat bones.
Calcified tissue international.
1995 Mar; 56(3):215-9. doi:
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Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
1995; 49(10):465-8. doi:
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La Clinica terapeutica.
1995 Jan; 146(1):13-9. doi:
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European journal of drug metabolism and pharmacokinetics.
1995 Jan; 20(1):43-7. doi:
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Bone and mineral.
1994 Jul; 26(1):19-26. doi:
10.1016/s0169-6009(08)80159-6. [PMID: 7950502] - Q Ouyang, H Li, Z Zheng, L Weng. [Experimental study on the effect of ipriflavone against osteoporosis in ovariectomized rats].
Hua xi yi ke da xue xue bao = Journal of West China University of Medical Sciences = Huaxi yike daxue xuebao.
1994 Jun; 25(2):178-82. doi:
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Calcified tissue international.
1994 May; 54(5):377-80. doi:
10.1007/bf00305522. [PMID: 8062153] - K Notoya, K Yoshida, S Taketomi, I Yamazaki, M Kumegawa. Inhibitory effect of ipriflavone on osteoclast-mediated bone resorption and new osteoclast formation in long-term cultures of mouse unfractionated bone cells.
Calcified tissue international.
1993 Sep; 53(3):206-9. doi:
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Journal of endocrinological investigation.
1993 May; 16(5):333-7. doi:
10.1007/bf03348848. [PMID: 8320424] - G B Melis, A M Paoletti, A Cagnacci, L Bufalino, A Spinetti, M Gambacciani, P Fioretti. Lack of any estrogenic effect of ipriflavone in postmenopausal women.
Journal of endocrinological investigation.
1992 Nov; 15(10):755-61. doi:
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Bone and mineral.
1992 Oct; 19 Suppl 1(?):S57-62. doi:
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