Clomifene (BioDeep_00000002335)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine

化学式: C26H28ClNO (405.18593080000005)
中文名称: 枸橼酸恩氯米芬, 氯米芬
谱图信息: 最多检出来源 Homo sapiens(blood) 1.33%

分子结构信息

SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
InChI: InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3

描述信息

Clomifene is only found in individuals that have used or taken this drug. It is a triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. [PubChem]Clomifene has both estrogenic and anti-estrogenic properties, but its precise mechanism of action has not been determined. Clomifene appears to stumulate the release of gonadotropins, follicle-stimulating hormone (FSH), and leuteinizing hormone (LH), which leads to the development and maturation of ovarian follicle, ovulation, and subsequent development and function of the coprus luteum, thus resulting in pregnancy. Gonadotropin release may result from direct stimulation of the hypothalamic-pituitary axis or from a decreased inhibitory influence of estrogens on the hypothalamic-pituitary axis by competing with the endogenous estrogens of the uterus, pituitary, or hypothalamus. Clomifene has no apparent progestational, androgenic, or antrandrogenic effects and does not appear to interfere with pituitary-adrenal or pituitary-thyroid function.
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03G - Gonadotropins and other ovulation stimulants > G03GB - Ovulation stimulants, synthetic
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 > C1742 - Angiogenesis Inhibitor > C1971 - Angiogenesis Activator Inhibitor
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D012102 - Reproductive Control Agents > D005299 - Fertility Agents
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
C1892 - Chemopreventive Agent

同义名列表

33 个代谢物同义名

2-(4-(2-Chloro-1,2-diphenylethenyl)phenoxy)-N,N-diethylethanamine; {2-[4-(2-chloro-1,2-diphenylethenyl)phenoxy]ethyl}diethylamine; 2-(p-(beta-Chloro-alpha-phenylstyryl)phenoxy)triethylamine; 2-(p-(2-Chloro-1,2-diphenylvinyl)phenoxy)triethylamine; 2-(p-(b-Chloro-a-phenylstyryl)phenoxy)triethylamine; 2-(p-(Β-chloro-α-phenylstyryl)phenoxy)triethylamine; Racemic clomiphene citrate; Hydrochloride, clomiphene; Clomiphene citrate (Z,e); Clomiphene hydrochloride; Zuclomiphene citrate; Citrate, clomiphene; Clomiphene Citrate; Clomifene citrate; Chloramiphene; Cisclomiphene; Enclomiphene; Clostilbegit; Klostilbegit; Chloramifene; enclomifene; Chlomaphene; Clomifenum; clomiphene; Clomifeno; Serophene; Clomifene; Gravosan; Clomifen; Dyneric; Clomide; pioner; Clomid



数据库引用编号

22 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)

1 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

  • Hang Ge, Hui Chang, Yu Wang, Jing Cong, Yang Liu, Bei Zhang, Xiaoke Wu. Establishment and validation of a nomogram model for predicting ovulation in the PCOS women. Medicine. 2024 Apr; 103(14):e37733. doi: 10.1097/md.0000000000037733. [PMID: 38579058]
  • Fatima Ahmad, Abrar Ahmed, Alishba Shakeel, Hafiza A Hussain, Syed A Raza. The efficacy of Linum usitatissimum seeds to inhibit estrogen receptor as a natural therapy for PCOS: An in silico and in vitro analysis. Cell biochemistry and function. 2024 Jan; 42(1):e3897. doi: 10.1002/cbf.3897. [PMID: 38063410]
  • Yiqing He, Xi Wang, Quan Liu, Huiping Liu, Shuo Yang. Exploring the mechanism of clomiphene citrate to improve ovulation disorder in PCOS rats based on follicular fluid metabolomics. Naunyn-Schmiedeberg's archives of pharmacology. 2023 Oct; ?(?):. doi: 10.1007/s00210-023-02750-9. [PMID: 37815607]
  • M Huijben, M T W T Lock, V F de Kemp, J J H Beck, L M O De Kort, H M K van Breda. Clomiphene citrate: A potential alternative for testosterone therapy in hypogonadal males. Endocrinology, diabetes & metabolism. 2023 Mar; ?(?):e416. doi: 10.1002/edm2.416. [PMID: 36998229]
  • Zhuo Liu, Yuli Geng, Yanjing Huang, Runan Hu, Fan Li, Yufan Song, Mingmin Zhang. Letrozole Compared With Clomiphene Citrate for Polycystic Ovarian Syndrome: A Systematic Review and Meta-analysis. Obstetrics and gynecology. 2023 03; 141(3):523-534. doi: 10.1097/aog.0000000000005070. [PMID: 36735392]
  • Lijie Yang, Wanqiu Yang, Minghan Sun, Linjie Luo, Hong Ru Li, Runqing Miao, Li Pang, Yajie Chen, Kun Zou. Meta analysis of ovulation induction effect and pregnancy outcome of acupuncture & moxibustion combined with clomiphene in patients with polycystic ovary syndrome. Frontiers in endocrinology. 2023; 14(?):1261016. doi: 10.3389/fendo.2023.1261016. [PMID: 38075051]
  • Wang-Yu Cai, Xi Luo, Hong-Li Ma, Xiao-Guang Shao, Xiao-Ke Wu. Association between preconception serum lipid concentrations and treatment outcomes in women with PCOS who underwent ovulation induction. Reproductive biomedicine online. 2022 10; 45(4):805-814. doi: 10.1016/j.rbmo.2022.04.013. [PMID: 35902299]
  • Kun Ma, Yun Shi, Junqin He, Xiuxiang Teng, Rongyu Wang, Guohua Wang, Yanan Yu, Yanxia Chen, Linjuan Gong, Yuan Yuan, Huixian Zhang, Bochao Yuan, Chenhui Zhang. The effect of Bushen Culuan Decoction on anovulatory infertile women among 6 different diseases: a study protocol for a randomized, double-blinded, positively controlled, adaptive multicenter clinical trial. Trials. 2022 Jul; 23(1):563. doi: 10.1186/s13063-022-06289-7. [PMID: 35804385]
  • Scott D Lundy, Johnathan Doolittle, Nicholas J Farber, Stephanie Njemanze, Carlos Munoz-Lopez, Sarah C Vij. Follicle-stimulating hormone modestly predicts improvement in semen parameters in men with infertility treated with clomiphene citrate. Andrologia. 2022 Jul; 54(6):e14399. doi: 10.1111/and.14399. [PMID: 35187689]
  • Cindy Meun, Eline Oostingh, Yvonne Louwers, Joop Laven. The influence of ethnicity on outcomes of ovulation induction with clomifene citrate in women with PCOS. Reproductive biomedicine online. 2022 05; 44(5):874-880. doi: 10.1016/j.rbmo.2021.12.017. [PMID: 35351379]
  • Luisa Euler, Nathalie Gillard, Philippe Delahaut, Gilles Pierret, Thomas Mürdter, Matthias Schwab, Georg Döhmen, Andreas Thomas, Mario Thevis. Assessing human urinary clomiphene metabolites after consumption of eggs from clomiphene-treated laying hens using chromatographic-mass spectrometric approaches. Analytica chimica acta. 2022 Apr; 1202(?):339661. doi: 10.1016/j.aca.2022.339661. [PMID: 35341524]
  • Manlin Liu, Zhuoyao Mai, Haiyan Lin, Yu Li, Xiaoli Chen, Dongzi Yang. Does elevated luteinizing hormone level before trigger mean premature luteinizing hormone surge in advanced-aged women undergoing mild ovarian stimulation?. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2022 Apr; 38(4):314-317. doi: 10.1080/09513590.2022.2037546. [PMID: 35142255]
  • Manou Huijben, M Tycho W T Lock, Vincent F de Kemp, Laetitia M O de Kort, H M K van Breda. Clomiphene citrate for men with hypogonadism: a systematic review and meta-analysis. Andrology. 2022 03; 10(3):451-469. doi: 10.1111/andr.13146. [PMID: 34933414]
  • Evrim Ebru Kovalak, Sefik Eser Ozyurek, Ozlem Karabay Akgul, Tolga Karacan. Hormonal Changes in Clomiphene Citrate Cycles in Unexplained Infertility Can Predict Follicle Development?. Journal of the College of Physicians and Surgeons--Pakistan : JCPSP. 2022 Jan; 32(1):25-32. doi: 10.29271/jcpsp.2022.01.25. [PMID: 34983143]
  • Hongju Duan, Shihua Luo, Yang Yu, Qiaohua Yan. Image Analysis of TVCDS in Infertile Patients with Polycystic Ovary Syndrome. Contrast media & molecular imaging. 2022; 2022(?):1234983. doi: 10.1155/2022/1234983. [PMID: 35821885]
  • Shulong Zu, Dan Luo, Lili Li, Qing Ye, Rui-Ting Li, Yanan Wang, Meiling Gao, Heng Yang, Yong-Qiang Deng, Genhong Cheng. Tamoxifen and clomiphene inhibit SARS-CoV-2 infection by suppressing viral entry. Signal transduction and targeted therapy. 2021 12; 6(1):435. doi: 10.1038/s41392-021-00853-4. [PMID: 34934049]
  • Parviz K Kavoussi. Men Converting from Clomiphene Citrate to Natesto with a Desire to Maintain Spermatogenesis Should Be Followed Closely. Urology. 2021 11; 157(?):128-130. doi: 10.1016/j.urology.2021.08.028. [PMID: 34474044]
  • Luisa Seyerlein, Nathalie Gillard, Philippe Delahaut, Gilles Pierret, Andreas Thomas, Mario Thevis. Depletion of clomiphene residues in eggs and muscle after oral administration to laying hens. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Nov; 38(11):1875-1882. doi: 10.1080/19440049.2021.1949497. [PMID: 34266369]
  • Jing Wang, Fei Teng, Qiyan Wu, Yu Wu, Le Hu. Relationship between proinflammatory cytokines and clomiphene resistance in patients with polycystic ovary syndrome. Annals of palliative medicine. 2021 Nov; 10(11):11884-11890. doi: 10.21037/apm-21-3031. [PMID: 34872312]
  • Sara E Ali, Shymaa A El Badawy, Sherif H Elmosalamy, Shimaa R Emam, Asmaa A Azouz, Mona K Galal, Reham M Abd-Elsalam, Marwa Y Issa, Bardes B Hassan. Novel promising reproductive and metabolic effects of Cicer arietinum L. extract on letrozole induced polycystic ovary syndrome in rat model. Journal of ethnopharmacology. 2021 Oct; 278(?):114318. doi: 10.1016/j.jep.2021.114318. [PMID: 34111539]
  • Sean D Workman, Jonathan Day, Maya A Farha, Sara S El Zahed, Chris Bon, Eric D Brown, Michael G Organ, Natalie C J Strynadka. Structural Insights into the Inhibition of Undecaprenyl Pyrophosphate Synthase from Gram-Positive Bacteria. Journal of medicinal chemistry. 2021 09; 64(18):13540-13550. doi: 10.1021/acs.jmedchem.1c00941. [PMID: 34473495]
  • Huaying Fan, Xiaojuan Hong, Jiuzhi Zeng, Xue Wang, Jiao Chen. Differences in the individual curative effect of acupuncture for obese women with polycystic ovary syndrome based on metagenomic analysis: study protocol for a randomized controlled trial. Trials. 2021 Jul; 22(1):454. doi: 10.1186/s13063-021-05426-y. [PMID: 34266458]
  • Stylianos Vagios, Caitlin R Sacha, Karissa C Hammer, Irene Dimitriadis, Kaitlyn E James, Charles L Bormann, Irene Souter. Response to ovulation induction treatments in women with polycystic ovary syndrome as a function of serum anti-Müllerian hormone levels. Journal of assisted reproduction and genetics. 2021 Jul; 38(7):1827-1833. doi: 10.1007/s10815-021-02217-x. [PMID: 33934267]
  • Kunyan Zhou, Jing Zhang, Liangzhi Xu, Chi Eung Danforn Lim. Chinese herbal medicine for subfertile women with polycystic ovarian syndrome. The Cochrane database of systematic reviews. 2021 06; 6(?):CD007535. doi: 10.1002/14651858.cd007535.pub4. [PMID: 34085287]
  • 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]
  • Serhat Ege, Muhammet Hanifi Bademkıran, Nurullah Peker, Zinet Özgün, İhsan Bağlı, Selami Erdem, Özcan Erel, Çağdaş Özgökçe, Erdoğan Gül. Increased oxidative stress is associated with thiol/disulphide homeostasis in clomiphene citrate resistant polycystic ovary syndrome. Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology. 2021 Apr; 41(3):467-470. doi: 10.1080/01443615.2020.1786033. [PMID: 32586152]
  • Serhat Ege, Muhammet Hanifi Bademkıran, Nurullah Peker, Selami Erdem, Ruşen Köçeroğlu, Özcan Erel. Does ischaemia-modified albumin level predict clomiphene citrate resistant polycystic ovary syndrome patients?. Journal of obstetrics and gynaecology : the journal of the Institute of Obstetrics and Gynaecology. 2021 Apr; 41(3):462-466. doi: 10.1080/01443615.2020.1785407. [PMID: 32799715]
  • R Moffat, C Hansali, A Schoetzau, A Ahler, U Gobrecht, S Beutler, A Raggi, G Sartorius, C De Geyter. Randomised controlled trial on the effect of clomiphene citrate and gonadotropin dose on ovarian response markers and IVF outcomes in poor responders. Human reproduction (Oxford, England). 2021 03; 36(4):987-997. doi: 10.1093/humrep/deaa336. [PMID: 33367742]
  • Selma Amrane, Sally F Vitez, Katherine L Palmerola, Roger A Lobo. Do lipid parameters change during clomiphene citrate or letrozole therapy in women being treated for infertility? A pilot study. European journal of obstetrics, gynecology, and reproductive biology. 2021 Feb; 257(?):151-152. doi: 10.1016/j.ejogrb.2020.12.010. [PMID: 33390278]
  • Tim Sobolevsky, Brian Ahrens. High-throughput liquid chromatography tandem mass spectrometry assay as initial testing procedure for analysis of total urinary fraction. Drug testing and analysis. 2021 Feb; 13(2):283-298. doi: 10.1002/dta.2917. [PMID: 32852861]
  • Patrick Kröner, Georg Heinkele, Reinhold Kerb, Svitlana Igel, Matthias Schwab, Thomas E Mürdter. Stereoselective quantification of phase 1 and 2 metabolites of clomiphene in human plasma and urine. Talanta. 2021 Jan; 221(?):121658. doi: 10.1016/j.talanta.2020.121658. [PMID: 33076169]
  • Ava Delu, Robert J Kiltz, Vladimir A Kuznetsov, J C Trussell. Clomiphene citrate improved testosterone and sperm concentration in hypogonadal males. Systems biology in reproductive medicine. 2020 12; 66(6):364-369. doi: 10.1080/19396368.2020.1822457. [PMID: 33043679]
  • Morteza Ghasemnejad-Berenji, Sarvin Pashapour, Hojat Ghasemnejad-Berenji. Therapeutic potential for clomiphene, a selective estrogen receptor modulator, in the treatment of COVID-19. Medical hypotheses. 2020 12; 145(?):110354. doi: 10.1016/j.mehy.2020.110354. [PMID: 33129007]
  • Kenji Ezoe, Xiaowen Ni, Tamotsu Kobayashi, Keiichi Kato. Anti-Müllerian hormone is correlated with cumulative live birth in minimal ovarian stimulation with clomiphene citrate: a retrospective cohort study. BMC pregnancy and childbirth. 2020 Nov; 20(1):740. doi: 10.1186/s12884-020-03446-1. [PMID: 33246461]
  • Ahmed A Morsy, Nagwa A Sabri, Abdelrehim M Mourad, Eman M Mojahed, May A Shawki. Randomized controlled open-label study of the effect of vitamin E supplementation on fertility in clomiphene citrate-resistant polycystic ovary syndrome. The journal of obstetrics and gynaecology research. 2020 Nov; 46(11):2375-2382. doi: 10.1111/jog.14467. [PMID: 32885585]
  • Thiago Fernandes Negris Lima, Premal Patel, Ruben Blachman-Braun, Vinayak Madhusoodanan, Ranjith Ramasamy. Serum 17-Hydroxyprogesterone is a Potential Biomarker for Evaluating Intratesticular Testosterone. The Journal of urology. 2020 Sep; 204(3):551-556. doi: 10.1097/ju.0000000000001016. [PMID: 32167868]
  • Radwa Rasheedy, Hazem Sammour, Abdellatif Elkholy, Yasmine Salim. The efficacy of vitamin D combined with clomiphene citrate in ovulation induction in overweight women with polycystic ovary syndrome: a double blind, randomized clinical trial. Endocrine. 2020 08; 69(2):393-401. doi: 10.1007/s12020-020-02315-3. [PMID: 32363556]
  • Jing Feng, Xiao-Feng Zhang, Jie-Ning Ren, Yu-Hua Huang, Xin Zheng. Efficacy of clomifene citrate combined Bushen Culuan Decoction for the treatment of infertility caused by polycystic ovary syndrome: A protocol of systematic review. Medicine. 2020 Jul; 99(27):e20969. doi: 10.1097/md.0000000000020969. [PMID: 32629707]
  • Jing Zhang, Kunyan Zhou, Xiaoyan Luo, Meina Yang, Xiaoyang Shen, Liangzhi Xu. Variation of Laparoscopic Ovarian Drilling for Clomiphene Citrate-resistant Patients with Polycystic Ovary Syndrome and Infertility: A Meta-analysis. Journal of minimally invasive gynecology. 2020 Jul; 27(5):1048-1058. doi: 10.1016/j.jmig.2019.06.022. [PMID: 32289557]
  • Ranran Gao, Baojun Guo, Jun Bai, Yeke Wu, Keming Wu. Acupuncture and clomiphene citrate for anovulatory infertility: a systematic review and meta-analysis. Acupuncture in medicine : journal of the British Medical Acupuncture Society. 2020 02; 38(1):25-36. doi: 10.1136/acupmed-2017-011629. [PMID: 31581787]
  • Carla Pelusi, Flaminia Fanelli, Margherita Baccini, Vincenzo Triggiani, Nicola Bartolomeo, Matteo Domenico Carbone, Giovanni De Pergola, Guido Di Dalmazi, Uberto Pagotto, Renato Pasquali, Vito Angelo Giagulli. Effect of clomiphene citrate treatment on the Sertoli cells of dysmetabolic obese men with low testosterone levels. Clinical endocrinology. 2020 01; 92(1):38-45. doi: 10.1111/cen.14122. [PMID: 31677181]
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  • Rui Wang, Wentao Li, Esmée M Bordewijk, Richard S Legro, Heping Zhang, Xiaoke Wu, Jingshu Gao, Laure Morin-Papunen, Roy Homburg, Tamar E König, Etelka Moll, Sujata Kar, Wei Huang, Neil P Johnson, Saad A Amer, Walter Vegetti, Stefano Palomba, Angela Falbo, Ülkü Özmen, Hakan Nazik, Christopher D Williams, Grasso Federica, Jonathan Lord, Yilmaz Sahin, Siladitya Bhattacharya, Robert J Norman, Madelon van Wely, Ben Willem Mol. First-line ovulation induction for polycystic ovary syndrome: an individual participant data meta-analysis. Human reproduction update. 2019 11; 25(6):717-732. doi: 10.1093/humupd/dmz029. [PMID: 31647106]
  • Hiroyo Hashimoto, Hideaki Miyachi, Koki Kataoka, Yugo Maru, Yaei Togawa, Hiroyuki Matsue. Case of fertility treatment-induced Stevens-Johnson syndrome with a severe ocular complication. The Journal of dermatology. 2019 Nov; 46(11):1042-1045. doi: 10.1111/1346-8138.15072. [PMID: 31489686]
  • 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]
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  • Hyun-Jin Kim, Dong Young Kim, Hyae Gyeong Cheon. Clomiphene promotes browning of white adipocytes via casein kinase-2 inhibition. European journal of pharmacology. 2019 Oct; 861(?):172596. doi: 10.1016/j.ejphar.2019.172596. [PMID: 31401157]
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