Zidovudine (BioDeep_00000002509)

 

Secondary id: BioDeep_00000397845

human metabolite blood metabolite


代谢物信息卡片


1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

化学式: C10H13N5O4 (267.09674980000005)
中文名称: 3′-叠氮-3′-脱氧胸苷
谱图信息: 最多检出来源 Mus musculus(blood) 50%

分子结构信息

SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
InChI: InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

描述信息

A dideoxynucleoside compound in which the 3-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia. [PubChem]
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
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
D009676 - Noxae > D000963 - Antimetabolites > D015224 - Dideoxynucleosides
D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
C254 - Anti-Infective Agent > C281 - Antiviral Agent
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI), widely used to treat HIV infection. Zidovudine increases CRISPR/Cas9-mediated editing frequency.

同义名列表

21 个代谢物同义名

1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione; 3-Azido-2,3-dideoxythymidine; 3 Azido 2,3 dideoxythymidine; 3 Azido 3 deoxythymidine; 3-Azido-3-deoxythymidine; AZT (antiviral); AZT, antiviral; Azidothymidine; Antiviral azt; AZT antiviral; Zidovudinum; Zidovudine; Zidovudin; NSC602670; BWA 509u; Retrovir; BW a509U; BWA-509u; BWA509u; AZT; ZDV



数据库引用编号

20 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

  • Dhananjay Singh, Nishu Mittal, Swati Verma, Anjali Singh, Mohammed Haris Siddiqui. Applications of some advanced sequencing, analytical, and computational approaches in medicinal plant research: a review. Molecular biology reports. 2023 Dec; 51(1):23. doi: 10.1007/s11033-023-09057-1. [PMID: 38117315]
  • Jiří Sedlák, Jaroslava Přibylová, Igor Koloňuk, Josef Špak, Ondřej Lenz, Matěj Semerák. Elimination of Solanum nigrum ilarvirus 1 and Apple Hammerhead Viroid from Apple Cultivars Using Antivirals Ribavirin, Rimantadine, and Zidovudine. Viruses. 2023 Aug; 15(8):. doi: 10.3390/v15081684. [PMID: 37632025]
  • Suwannee Saisin, Kanda Panthong, Sakchai Hongthong, Chutima Kuhakarn, Sariyarach Thanasansurapong, Arthit Chairoungdua, Kanoknetr Suksen, Radeekorn Akkarawongsapat, Chanita Napaswad, Samran Prabpai, Narong Nuntasaen, Vichai Reutrakul. Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity. Journal of natural products. 2023 03; 86(3):498-507. doi: 10.1021/acs.jnatprod.2c00980. [PMID: 36787536]
  • Naonobu Tanaka, Sakura Takahashi, Yuki Yoshino, Megumi Nakatani, Fakhruddin Ali Ahmed, Gazi Mosharof Hossain, Chin-Ho Chen, Kuo-Hsiung Lee, Yoshiki Kashiwada. Tigliane-Type Diterpene Esters from the Fruits of Shirakiopsis indica and Their Anti-HIV Activity. Journal of natural products. 2022 11; 85(11):2687-2693. doi: 10.1021/acs.jnatprod.2c00752. [PMID: 36378070]
  • Lem Edith Abongwa, Anthony Kebira Nyamache, Fokunang Charles, Judith Torimiro, Nshom Emmanuel, Irénée Domkam, Mbu Eyongetah, Beriyuy Jude, Fung Holgar Mua, Sama Bella, Tankou Colman Tamboh, Erna Charlene Moungang, Victorine Ngum, Paul Okemo. Risk factors of severe hepatotoxicity among HIV-1 infected individuals initiated on highly active antiretroviral therapy in the Northwest Region of Cameroon. BMC gastroenterology. 2022 Jun; 22(1):286. doi: 10.1186/s12876-022-02305-x. [PMID: 35658835]
  • Gentille Musengimana, Elysee Tuyishime, Athanase Kiromera, Samuel S Malamba, Augustin Mulindabigwi, Madjid R Habimana, Cyprien Baribwira, Muhayimpundu Ribakare, Savio D Habimana, Josh DeVos, Richard C N Mwesigwa, Eugenie Kayirangwa, Jules M Semuhore, Gallican N Rwibasira, Amitabh B Suthar, Eric Remera. Acquired HIV drug resistance among adults living with HIV receiving first-line antiretroviral therapy in Rwanda: A cross-sectional nationally representative survey. Antiviral therapy. 2022 06; 27(3):13596535221102690. doi: 10.1177/13596535221102690. [PMID: 35593031]
  • Nicholas I Paton, Joseph Musaazi, Cissy Kityo, Stephen Walimbwa, Anne Hoppe, Apolo Balyegisawa, Jesca Asienzo, Arvind Kaimal, Grace Mirembe, Abbas Lugemwa, Gilbert Ategeka, Margaret Borok, Henry Mugerwa, Abraham Siika, Eva Laker A Odongpiny, Barbara Castelnuovo, Agnes Kiragga, Andrew Kambugu. Efficacy and safety of dolutegravir or darunavir in combination with lamivudine plus either zidovudine or tenofovir for second-line treatment of HIV infection (NADIA): week 96 results from a prospective, multicentre, open-label, factorial, randomised, non-inferiority trial. The lancet. HIV. 2022 06; 9(6):e381-e393. doi: 10.1016/s2352-3018(22)00092-3. [PMID: 35460601]
  • Rosa Marlene Cuco, Osvaldo Loquiha, Adelino Juga, Aleny Couto, Bindiya Meggi, Adolfo Vubil, Esperança Sevene, Nafissa Osman, Marleen Temermam, Olivier Degomme, Mohsin Sidat, Nilesh Bhatt. Nevirapine hair and plasma concentrations and HIV-1 viral suppression among HIV infected ante-partum and post-partum women attended in a mother and child prevention program in Maputo city, Mozambique. PloS one. 2022; 17(2):e0261522. doi: 10.1371/journal.pone.0261522. [PMID: 35143515]
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  • Taklo Simeneh Yazie. Derangement of Liver Enzymes, Hyperglycemia, Anemia, and Associated Factors among HIV-Infected Patients Treated with Tenofovir Disoproxil Fumarate-Based Regimen in Ethiopia: A Prospective Cohort Study. BioMed research international. 2021; 2021(?):6613519. doi: 10.1155/2021/6613519. [PMID: 34222476]
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  • Luca Docci, Kenichi Umehara, Stephan Krähenbühl, Stephen Fowler, Neil Parrott. Construction and Verification of Physiologically Based Pharmacokinetic Models for Four Drugs Majorly Cleared by Glucuronidation: Lorazepam, Oxazepam, Naloxone, and Zidovudine. The AAPS journal. 2020 10; 22(6):128. doi: 10.1208/s12248-020-00513-5. [PMID: 33033903]
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  • Lufuno Grace Mavhandu, Hua Cheng, Yeou-Cheng Bor, Denis Manga Tebit, Marie-Louise Hammarskjold, David Rekosh, Pascal Obong Bessong. Development of a pseudovirus assay and evaluation to screen natural products for inhibition of HIV-1 subtype C reverse transcriptase. Journal of ethnopharmacology. 2020 Aug; 258(?):112931. doi: 10.1016/j.jep.2020.112931. [PMID: 32360797]
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  • Esaú C João, R Leavitt Morrison, David E Shapiro, Nahida Chakhtoura, Maria Isabel S Gouvèa, Maria de Lourdes B Teixeira, Trevon L Fuller, Blandina T Mmbaga, James S Ngocho, Boniface N Njau, Avy Violari, Ruth Mathiba, Zaakirah Essack, Jose Henrique S Pilotto, Luis Felipe Moreira, Maria Jose Rolon, Pedro Cahn, Sinart Prommas, Timothy R Cressey, Kulkanya Chokephaibulkit, Peerawong Werarak, Lauren Laimon, Roslyn Hennessy, Lisa M Frenkel, Patricia Anthony, Brookie M Best, George K Siberry, Mark Mirochnick. Raltegravir versus efavirenz in antiretroviral-naive pregnant women living with HIV (NICHD P1081): an open-label, randomised, controlled, phase 4 trial. The lancet. HIV. 2020 05; 7(5):e322-e331. doi: 10.1016/s2352-3018(20)30038-2. [PMID: 32386720]
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  • Yuan-Yuan Qin, Ping Xu, Tong Wu, Chao-Qun Qian, Yi-Lin Fan, Dong-Hao Gen, Liang Zhu, Wei-Min Kong, Han-Yu Yang, Feng Xu, Yi-Ting Yang, Li Liu, Xiao-Dong Liu. Bile duct ligation enhances AZT CNS toxicity partly by impairing the expression and function of BCRP in rat brain. Acta pharmacologica Sinica. 2020 Feb; 41(2):181-191. doi: 10.1038/s41401-019-0242-8. [PMID: 31142800]
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  • Hua-Ding Zhao, Yan Lu, Min Yan, Chin-Ho Chen, Susan L Morris-Natschke, Kuo-Hsiung Lee, Dao-Feng Chen. Rapid Recognition and Targeted Isolation of Anti-HIV Daphnane Diterpenes from Daphne genkwa Guided by UPLC-MSn. Journal of natural products. 2020 01; 83(1):134-141. doi: 10.1021/acs.jnatprod.9b00993. [PMID: 31860304]
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