Adefovir Dipivoxil (BioDeep_00000033257)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate

化学式: C20H32N5O8P (501.1988402)
中文名称: 阿德福韦酯
谱图信息: 最多检出来源 Homo sapiens(blood) 96.88%

分子结构信息

SMILES: CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C
InChI: InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)

描述信息

Adefovir Dipivoxil is only found in individuals that have used or taken this drug.Adefovir dipivoxil, previously called bis-POM PMEA, with trade names Preveon and Hepsera, is an orally-administered nucleotide analog reverse transcriptase inhibitor (ntRTI) used for treatment of hepatitis B. It is a failed treatment for HIV. [Wikipedia]Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA. The inhibition constant (Ki) for adefovir diphosphate for HBV DNA polymerase was 0.1 μM. Adefovir diphosphate is a weak inhibitor of human DNA polymerases alpha and gamma with Ki values of 1.18 μM and 0.97μM, respectively.
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors
C471 - Enzyme Inhibitor > C1589 - Reverse Transcriptase Inhibitor > C97452 - Nucleoside Reverse Transcriptase Inhibitor
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors
D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
C254 - Anti-Infective Agent > C281 - Antiviral Agent
Adefovir dipivoxil, an adenosine analogue, is an oral proagent of the nucleoside reverse transcriptase inhibitor Adefovir. Adefovir dipivoxil inhibits both the wild type and HBV Lamivudine-resistant strains[1][2]. Adefovir dipivoxil shows anti-orthopoxvirus activity.

同义名列表

14 个代谢物同义名

[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate; 9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine; Adefovir Dipivoxil; Adefovir depivoxil; Adefovir pivoxil; Adefovirdipivoxl; Bis-pom pmea; ADEFOVIR; Preveon; Hepsera; GS-840; PMEA; ADV; GS 0840



数据库引用编号

9 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

1 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(1)

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

  • Shady M Abd El-Halim, Ghada A Abdelbary, Maha M Amin, Mohamed Y Zakaria, Hesham A Shamsel-Din, Ahmed B Ibrahim. Stabilized oral nanostructured lipid carriers of Adefovir Dipivoxil as a potential liver targeting: Estimation of liver function panel and uptake following intravenous injection of radioiodinated indicator. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2020 Dec; 28(2):517-532. doi: 10.1007/s40199-020-00355-8. [PMID: 32564282]
  • Linli Sun, Dan Yi, Wei Sun, Chunjiang Wang. Retrospective analysis of the clinical characteristics of adefovir dipivoxil-induced Fanconi's syndrome in the Chinese population. Journal of clinical pharmacy and therapeutics. 2020 Aug; 45(4):722-728. doi: 10.1111/jcpt.13154. [PMID: 32406123]
  • Qian Xiang, Zhiyan Liu, Yanyan Yu, Hanxu Zhang, Qiufen Xie, Guangyan Mu, Jianhua Zhang, Xinan Cen, Yimin Cui. Osteomalacia and renal failure due to Fanconi syndrome caused by long-term low-dose Adefovir Dipivoxil: a case report. BMC pharmacology & toxicology. 2020 06; 21(1):43. doi: 10.1186/s40360-020-00421-6. [PMID: 32503675]
  • Xiao-Ke Li, Ming-Xiang Zhang, Feng-Zhen Shao, Da-Qiao Zhou, Jing-Dong Xue, Tie-Jun Liu, Xiao-Ling Chi, Bing-Jiu Lu, Xian-Bo Wang, Qin Li, Jun Li, De-Wen Mao, Hua-Sheng Yang, Hong-Zhi Yang, Wen-Xia Zhao, Yong Li, Guo-Liang Zhang, Yi-Ming Zhao, Jian-Dong Zou, Meng-Yang Liu, Ke-Ke Zhang, Xian-Zhao Yang, Da-Nan Gan, Ying Li, Peng Zhang, Zhi-Guo Li, Shuo Li, Yong-An Ye. Adefovir Dipivoxil plus Chinese Medicine in HBeAg-Positive Chronic Hepatitis B Patients: A Randomized Controlled 48-Week Trial. Chinese journal of integrative medicine. 2020 May; 26(5):330-338. doi: 10.1007/s11655-020-3250-0. [PMID: 31919749]
  • Kazumoto Murata, Senko Tsukuda, Futoshi Suizu, Akihiro Kimura, Masaya Sugiyama, Koichi Watashi, Masayuki Noguchi, Masashi Mizokami. Immunomodulatory Mechanism of Acyclic Nucleoside Phosphates in Treatment of Hepatitis B Virus Infection. Hepatology (Baltimore, Md.). 2020 05; 71(5):1533-1545. doi: 10.1002/hep.30956. [PMID: 31529730]
  • Christina Trueck, Chih-Hsuan Hsin, Oliver Scherf-Clavel, Elke Schaeffeler, Rebekka Lenssen, Malaz Gazzaz, Marleen Gersie, Max Taubert, Maria Quasdorff, Matthias Schwab, Martina Kinzig, Fritz Sörgel, Marc S Stoffel, Uwe Fuhr. A Clinical Drug-Drug Interaction Study Assessing a Novel Drug Transporter Phenotyping Cocktail With Adefovir, Sitagliptin, Metformin, Pitavastatin, and Digoxin. Clinical pharmacology and therapeutics. 2019 12; 106(6):1398-1407. doi: 10.1002/cpt.1564. [PMID: 31247117]
  • Lung-Yi Mak, Sze-Hang Liu, Desmond Yat-Hin Yap, Wai-Kay Seto, Danny Ka-Ho Wong, James Fung, Tak-Mao Chan, Ching-Lung Lai, Man-Fung Yuen. In Vitro and In Vivo Renoprotective Effects of Telbivudine in Chronic Hepatitis B Patients Receiving Nucleotide Analogue. Digestive diseases and sciences. 2019 12; 64(12):3630-3641. doi: 10.1007/s10620-019-05717-0. [PMID: 31280390]
  • Ming-Chun Lai, Jiang-Shan Lian, Wen-Jin Zhang, Jun Xu, Lin Zhou, Shu-Sen Zheng. Compare with safety and efficacy of entecavir and adefovir dipivoxil combination therapy and tenofovir disoproxil fumarate monotherapy for chronic hepatitis B patient with adefovir-resistant. Mathematical biosciences and engineering : MBE. 2019 10; 17(1):627-635. doi: 10.3934/mbe.2020032. [PMID: 31731368]
  • Parisa Seyed Dorraji, Marzieh Noori, Lida Fotouhi. Voltammetric determination of adefovir dipivoxil by using a nanocomposite prepared from molecularly imprinted poly(o-phenylenediamine), multi-walled carbon nanotubes and carbon nitride. Mikrochimica acta. 2019 06; 186(7):427. doi: 10.1007/s00604-019-3538-y. [PMID: 31187299]
  • Meng-Lan Wang, Rong Deng, En-Qiang Chen, Chuan-Min Tao, Juan Liao, Tao-You Zhou, Juan Wang, Hong Tang. Performance of serum HBcrAg in chronic hepatitis B patients with 8-year nucleos(t)ide analogs therapy. Clinics and research in hepatology and gastroenterology. 2019 06; 43(3):301-309. doi: 10.1016/j.clinre.2018.10.020. [PMID: 30497844]
  • Tomohisa Kunii, Toshie Iijima, Teruo Jojima, Masanori Shimizu, Masato Kase, Shintaro Sakurai, Takahiko Kogai, Isao Usui, Yoshimasa Aso. Denosumab improves clinical manifestations of hypophosphatemic osteomalacia by adefovir-induced Fanconi syndrome: a case report. Journal of medical case reports. 2019 Apr; 13(1):99. doi: 10.1186/s13256-019-2018-7. [PMID: 31003599]
  • Ryo Koda, Masafumi Tsuchida, Noriaki Iino, Ichiei Narita. Hypophosphatemic Osteomalacia Associated with Adefovir-induced Fanconi Syndrome Initially Diagnosed as Diabetic Kidney Disease and Vitamin D Deficiency. Internal medicine (Tokyo, Japan). 2019 Mar; 58(6):821-825. doi: 10.2169/internalmedicine.1698-18. [PMID: 30333420]
  • Yanan Lv, Xiaomei Li, Shaoshan Liang, Dandan Liang, Feng Xu, Xiaodong Zhu, Caihong Zeng. The clinical and pathological features of adefovir dipivoxil-related renal impairment
. Clinical nephrology. 2019 Mar; 91(3):180-186. doi: 10.5414/cn109574. [PMID: 30614440]
  • Linye He, Zijing Xia, Junyi Shen, Xiaoyun Zhang, Wei Peng, Chuan Li, Tianfu Wen. The different effects of adefovir dipivoxil and telbivudine on the prognosis of hepatitis b virus-related hepatocellular carcinoma patients after curative resection. Medicine. 2019 Feb; 98(6):e14386. doi: 10.1097/md.0000000000014386. [PMID: 30732177]
  • Jiang-Shan Lian, Xiao-Lin Zhang, Ying-Feng Lu, Jian-Yang Chen, Yi-Min Zhang, Hong-Yu Jia, Zhe Zhang, Yi-Da Yang. Switching Lamivudine with Adefovir Dipivoxil Combination Therapy to Entecavir Monotherapy Provides Better Viral Suppression and Kidney Safety. International journal of medical sciences. 2019; 16(1):17-22. doi: 10.7150/ijms.28700. [PMID: 30662324]
  • Yan-Ying Qian, Zhi-Juan Dai, Lu-Ya Ruan, You-Jin Pan, Jian Jin, Meng-Te Shi, Yao-Xin Zhu, Chao-Ming Wu. Low-dose adefovir dipivoxil-induced hypophosphatemia osteomalacia in five chronic hepatitis B virus-infected patients. Is low-dose adefovir dipivoxil-induced nephrotoxicity completely reversible?. Drug design, development and therapy. 2019; 13(?):1127-1133. doi: 10.2147/dddt.s192632. [PMID: 31118563]
  • Takashi Makita, Hirotaka Kanzaki, Hideki Onishi, Ailee Ikeda, Akinobu Takaki, Nozomu Wada, Yasuto Takeuchi, Tetsuya Yasunaka, Fusao Ikeda, Hidenori Shiraha, Yuta Tanaka, Shigeki Nishihara, Kiminaka Murakawa, Yoshihisa Kitamura, Hiroyuki Okada, Toshiaki Sendo. [Adefovir Dipivoxil-induced Fanconi's Syndrome and Osteomalacia Following Multiple Bone Fractures in a Patient with Chronic Hepatitis B]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2019; 139(4):641-645. doi: 10.1248/yakushi.18-00170. [PMID: 30930400]
  • Ghada A Abdelbary, Maha M Amin, Mohamed Y Zakaria, Sally A El Awdan. Adefovir dipivoxil loaded proliposomal powders with improved hepatoprotective activity: formulation, optimization, pharmacokinetic, and biodistribution studies. Journal of liposome research. 2018 Dec; 28(4):259-274. doi: 10.1080/08982104.2017.1363228. [PMID: 28768431]
  • Yong Xu, Zhen-Wang Nie. Telbivudine and adefovir dipivoxil combination therapy improves renal function in patients with chronic hepatitis B: A STROBE-compliant article. Medicine. 2018 Nov; 97(48):e13430. doi: 10.1097/md.0000000000013430. [PMID: 30508954]
  • Xianghua Guo, Jushan Wu, Feili Wei, Yabo Ouyang, Qing Li, Kai Liu, Yanjun Wang, Yulin Zhang, Dexi Chen. Trends in hepatitis B virus resistance to nucleoside/nucleotide analogues in North China from 2009-2016: A retrospective study. International journal of antimicrobial agents. 2018 Aug; 52(2):201-209. doi: 10.1016/j.ijantimicag.2018.04.002. [PMID: 29654894]
  • J Xu, L Bao, Y Wang, L Yang, W T Li, Z H Zhao, Y Li. [Compare the effect of combined therapy between telbivudine plus adefovir dipivoxil and lamivudine plus adefovir dipivoxil corresponding to renal function in patients with hepatitis B virus infection]. Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology. 2018 Apr; 26(4):288-293. doi: 10.3760/cma.j.issn.1007-3418.2018.04.011. [PMID: 29996341]
  • X J Lai, J S Lian, J Y Chen, Y M Zhang, H Y Jia, L Zheng, Y D Yang. [Efficacy and safety of Entecavir monotherapy switched from Lamivudine combined Adefovir Dipivoxil for chronic hepatitis B virus-related compensated liver cirrhosis]. Zhonghua gan zang bing za zhi = Zhonghua ganzangbing zazhi = Chinese journal of hepatology. 2018 Feb; 26(2):113-118. doi: 10.3760/cma.j.issn.1007-3418.2018.02.008. [PMID: 29804377]
  • Akihiro Matsumoto, Shuhei Nishiguchi, Hirayuki Enomoto, Jong-Hon Kang, Yasuhito Tanaka, Noboru Shinkai, Masayuki Kurosaki, Masaru Enomoto, Tatsuo Kanda, Osamu Yokosuka, Hiroshi Yatsuhashi, Shinya Nagaoka, Chiaki Okuse, Tatehiro Kagawa, Tetsuya Mine, Koichi Takaguchi, Satoru Saito, Keisuke Hino, Fusao Ikeda, Shotaro Sakisaka, Daisuke Morihara, Shiho Miyase, Masataka Tsuge, Kazuaki Chayama, Naoki Hiramatsu, Yoshiyuki Suzuki, Kazumoto Murata, Eiji Tanaka. Combinational use of hepatitis B viral antigens predicts responses to nucleos(t)ide analogue/peg-interferon sequential therapy. Journal of gastroenterology. 2018 Feb; 53(2):247-257. doi: 10.1007/s00535-017-1360-z. [PMID: 28634723]
  • Sheng Zhu, Yu-Hui Yang, Rong-Wei Gao, Ran Li, Yu-Zhen Zou, Lei Feng, Bo Zhang. Clinical features of hypophosphatemic osteomalacia induced by long-term low-dose adefovir dipivoxil. Drug design, development and therapy. 2018; 12(?):41-45. doi: 10.2147/dddt.s140988. [PMID: 29343941]
  • Manuel Rodríguez, Juan Manuel Pascasio, Enrique Fraga, Javier Fuentes, Martín Prieto, Gloria Sánchez-Antolín, José Luis Calleja, Esther Molina, María Luisa García-Buey, María Ángeles Blanco, Javier Salmerón, María Lucía Bonet, José Antonio Pons, José Manuel González, Miguel Ángel Casado, Francisco Jorquera. Tenofovir vs lamivudine plus adefovir in chronic hepatitis B: TENOSIMP-B study. World journal of gastroenterology. 2017 11; 23(41):7459-7469. doi: 10.3748/wjg.v23.i41.7459. [PMID: 29151700]
  • Hong Shi, Zongping Han, Jian Liu, Jinfang Xue, Shuya Zhang, Zhe Zhu, Jinyu Xia, Mingxing Huang. Comparing Efficacy of Lamivudine, Adefovir Dipivoxil, Telbivudine, and Entecavir in Treating Nucleoside Analogues Naïve for HBeAg-Negative Hepatitis B with Medium Hepatitis B Virus (HBV) DNA Levels. Medical science monitor : international medical journal of experimental and clinical research. 2017 Nov; 23(?):5230-5236. doi: 10.12659/msm.903382. [PMID: 29095799]
  • Yan Xu, Xu Wang, Zhenhua Liu, Changyu Zhou, Wenqian Qi, Jian Jiao, Fan Yu, Honghua Guo, Ping Zhao, Jiangbin Wang. Addition of nucleoside analogues to peg-IFNα-2a enhances virological response in chronic hepatitis B patients without early response to peg-IFNα-2a: a randomized controlled trial. BMC gastroenterology. 2017 Aug; 17(1):102. doi: 10.1186/s12876-017-0657-y. [PMID: 28854883]
  • Qing Luo, Yong Deng, Feifei Cheng, Juan Kang, Shan Zhong, Dazhi Zhang, Weiqiong Zeng. Relationship between nephrotoxicity and long-term adefovir dipivoxil therapy for chronic hepatitis B: A meta-analysis. Medicine. 2016 Dec; 95(50):e5578. doi: 10.1097/md.0000000000005578. [PMID: 27977591]
  • Shu-hong Duan, Zhong-ying Bao, Xiao-dong Yuan, Lei Wang, Mei-sheng Liu. [Efficacy Observation of Yiguanjian Decoction Combined Adefovir Dipivoxil Tablet in Treating HBeAg Negative Chronic Viral Hepatitis B Active Compensated Liver Cirrhosis Patients]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2016 May; 36(5):535-8. doi: ". [PMID: 27386642]
  • Song Yang, Huichun Xing, Qi Wang, Xiaomei Wang, Shunai Liu, Jun Cheng. De novo entecavir+adefovir dipivoxil+lamivudine triple-resistance mutations resulting from sequential therapy with adefovir dipivoxil, and lamivudine. Annals of clinical microbiology and antimicrobials. 2016 Apr; 15(?):24. doi: 10.1186/s12941-016-0138-0. [PMID: 27079793]
  • John M Murray, Ognjen Stancevic, Marc Lütgehetmann, Karsten Wursthorn, Joerg Petersen, Maura Dandri. Variability in long-term hepatitis B virus dynamics under antiviral therapy. Journal of theoretical biology. 2016 Feb; 391(?):74-80. doi: 10.1016/j.jtbi.2015.12.005. [PMID: 26723531]
  • Junko Takagi, Hiroyuki Morita, Kiyoaki Ito, Tomohiko Ohashi, Sho Hirase, Tatsuo Ito, Takkan Morishima, Kazuo Otake, Masashi Yoneda. Urinary β-2 Microglobulin Levels Sensitively Altered in an Osteomalacia Patient Receiving Add-on Adefovir Dipivoxil Therapy for Hepatitis B Virus Infection. Internal medicine (Tokyo, Japan). 2016; 55(12):1599-603. doi: 10.2169/internalmedicine.55.6301. [PMID: 27301512]
  • Daniel Crean, Patricia Bellwon, Lydia Aschauer, Alice Limonciel, Konrad Moenks, Philip Hewitt, Tobias Schmidt, Karin Herrgen, Wolfgang Dekant, Arno Lukas, Frederic Bois, Anja Wilmes, Paul Jennings, Martin O Leonard. Development of an in vitro renal epithelial disease state model for xenobiotic toxicity testing. Toxicology in vitro : an international journal published in association with BIBRA. 2015 Dec; 30(1 Pt A):128-37. doi: 10.1016/j.tiv.2014.11.015. [PMID: 25536518]
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