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 (267.0967)
中文名称: 3′-叠氮-3′-脱氧胸苷
谱图信息:
最多检出来源 Homo sapiens(blood) 0.93%
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A dideoxynucleoside compound in which the 3-hydroxy group on the sugar moiety has been replaced by an azido group.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
23 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; Zidovudine; Zidovudine
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:10110
- KEGG: C07210
- KEGGdrug: D00413
- KEGGdrug: D88500
- PubChem: 35370
- PubChem: 5726
- HMDB: HMDB0014638
- Metlin: METLIN3066
- DrugBank: DB00495
- ChEMBL: CHEMBL129
- Wikipedia: Zidovudine
- MeSH: Zidovudine
- MetaCyc: CPD-15110
- chemspider: 32555
- CAS: 30516-87-1
- PMhub: MS000002882
- PubChem: 9419
- PDB-CCD: AZZ
- NIKKAJI: J20.566D
- medchemexpress: HY-17413
- KNApSAcK: 10110
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)
- Zidovudine Action Pathway:
Adenosine triphosphate ⟶ Adenosine monophosphate + Pyrophosphate
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
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The lancet. HIV.
2019 08; 6(8):e518-e530. doi:
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Acta medica Indonesiana.
2019 Jul; 51(3):253-257. doi:
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International journal of antimicrobial agents.
2019 Jul; 54(1):55-61. doi:
10.1016/j.ijantimicag.2019.04.011. [PMID: 31034939] - Ya-Si Huang, Yan Lu, Chin-Ho Chen, Kuo-Hsiung Lee, Dao-Feng Chen. Potent Anti-HIV Ingenane Diterpenoids from Euphorbia ebracteolata.
Journal of natural products.
2019 06; 82(6):1587-1592. doi:
10.1021/acs.jnatprod.9b00088. [PMID: 31184480] - Nongodo Firmin Kaboré, Armel Poda, Jacques Zoungrana, Ollo Da, Laura Ciaffi, Aoua Semdé, Issouf Yaméogo, Adrien B Sawadogo, Eric Delaporte, Nicolas Meda, Sophie Limou, Amandine Cournil. Chronic kidney disease and HIV in the era of antiretroviral treatment: findings from a 10-year cohort study in a west African setting.
BMC nephrology.
2019 05; 20(1):155. doi:
10.1186/s12882-019-1335-9. [PMID: 31064340] - Kentaro Konishi, Tsuyoshi Minematsu, Yasuhisa Nagasaka, Kenji Tabata. Application of a physiologically based pharmacokinetic model for the prediction of mirabegron plasma concentrations in a population with severe renal impairment.
Biopharmaceutics & drug disposition.
2019 May; 40(5-6):176-187. doi:
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Journal of acquired immune deficiency syndromes (1999).
2019 04; 80(4):467-473. doi:
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Journal of pharmacological sciences.
2019 Apr; 139(4):275-279. doi:
10.1016/j.jphs.2018.11.016. [PMID: 30928089] - Haifeng Wu, Guoxu Ma, Qinwen Yang, Yindi Zhu, Li Huang, Yu Tian, Xiaoming Yang, Menghan Zhang, Chin-Ho Chen, Susan L Morris-Natschke, Meihua Yang, Xudong Xu, Kuo-Hsiung Lee. Discovery and synthesis of novel beesioside I derivatives with potent anti-HIV activity.
European journal of medicinal chemistry.
2019 Mar; 166(?):159-166. doi:
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Journal of pharmacy practice.
2019 Feb; 32(1):9-18. doi:
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Journal of natural products.
2019 01; 82(1):27-34. doi:
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Journal of the International Association of Providers of AIDS Care.
2019 Jan; 18(?):2325958219856579. doi:
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Electrophoresis.
2019 01; 40(2):336-342. doi:
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Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS).
2018 Dec; 50(?):240-248. doi:
10.1016/j.jtemb.2018.07.002. [PMID: 30262286] - Maria Loose, Kurt G Naber, Yanmin Hu, Anthony Coates, Florian M E Wagenlehner. Serum bactericidal activity of colistin and azidothymidine combinations against mcr-1-positive colistin-resistant Escherichia coli.
International journal of antimicrobial agents.
2018 Dec; 52(6):783-789. doi:
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AIDS research and human retroviruses.
2018 11; 34(11):912-915. doi:
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BMC pharmacology & toxicology.
2018 Oct; 19(1):66. doi:
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European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2018 Sep; 122(?):22-30. doi:
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AIDS (London, England).
2018 09; 32(14):2084-2085. doi:
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Journal of acquired immune deficiency syndromes (1999).
2018 09; 79(1):126-134. doi:
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European journal of medicinal chemistry.
2018 Aug; 156(?):618-627. doi:
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Journal of neurovirology.
2018 08; 24(4):523-525. doi:
10.1007/s13365-018-0627-3. [PMID: 29532443] - Abdul Rahim, Yohei Saito, Katsunori Miyake, Masuo Goto, Chin-Ho Chen, Gemini Alam, Susan Morris-Natschke, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto. Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita.
Journal of natural products.
2018 07; 81(7):1619-1627. doi:
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Biosensors & bioelectronics.
2018 Jul; 111(?):82-89. doi:
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The Journal of biological chemistry.
2018 06; 293(23):8722-8733. doi:
10.1074/jbc.m117.809889. [PMID: 29628445] - Ana Santos-Llamas, Maria J Monte, Jose J G Marin, Maria J Perez. Dysregulation of autophagy in rat liver with mitochondrial DNA depletion induced by the nucleoside analogue zidovudine.
Archives of toxicology.
2018 06; 92(6):2109-2118. doi:
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European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2018 Mar; 115(?):109-118. doi:
10.1016/j.ejps.2018.01.024. [PMID: 29339228] - Barbara Castelnuovo, Frank Mubiru, Agnes N Kiragga, Rachel Musomba, Olive Mbabazi, Paul Gonza, Andrew Kambugu, Rosalind Parks Ratanshi. Antiretroviral treatment Long-Term (ALT) cohort: a prospective cohort of 10 years of ART-experienced patients in Uganda.
BMJ open.
2018 02; 8(2):e015490. doi:
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Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2018 Feb; 191(?):226-232. doi:
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Molecules (Basel, Switzerland).
2018 Feb; 23(2):. doi:
10.3390/molecules23020366. [PMID: 29425147] - Raquel M Alves-Paiva, Sachiko Kajigaya, Xingmin Feng, Jichun Chen, Marie Desierto, Susan Wong, Danielle M Townsley, Flávia S Donaires, Adeline Bertola, Bin Gao, Neal S Young, Rodrigo T Calado. Telomerase enzyme deficiency promotes metabolic dysfunction in murine hepatocytes upon dietary stress.
Liver international : official journal of the International Association for the Study of the Liver.
2018 01; 38(1):144-154. doi:
10.1111/liv.13529. [PMID: 28741793] - K S Joshy, S Snigdha, George Anne, Kalarikkal Nandakumar, Pothen Laly A, Thomas Sabu. Poly (vinyl pyrrolidone)-lipid based hybrid nanoparticles for anti viral drug delivery.
Chemistry and physics of lipids.
2018 01; 210(?):82-89. doi:
10.1016/j.chemphyslip.2017.11.003. [PMID: 29129570] - Chuan Zhao, Mei Wang, Yu Liu, Yongjuan Liang, Li Han, Che Chen. Effects of the combination of As2O3 and AZT on proliferation inhibition and apoptosis induction of hepatoma HepG2 cells following silencing of Egr-1.
OncoTargets and therapy.
2018; 11(?):3293-3301. doi:
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Toxicological sciences : an official journal of the Society of Toxicology.
2017 Nov; 160(1):30-46. doi:
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The AAPS journal.
2017 11; 19(6):1745-1759. doi:
10.1208/s12248-017-0130-4. [PMID: 28779379] - Fan Wang, Ming-Xing Miao, Bin-Bin Sun, Zhong-Jian Wang, Xian-Ge Tang, Yang Chen, Kai-Jing Zhao, Xiao-Dong Liu, Li Liu. Acute liver failure enhances oral plasma exposure of zidovudine in rats by downregulation of hepatic UGT2B7 and intestinal P-gp.
Acta pharmacologica Sinica.
2017 Nov; 38(11):1554-1565. doi:
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International journal of biological macromolecules.
2017 Oct; 103(?):1265-1275. doi:
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Chemistry and physics of lipids.
2017 10; 207(Pt A):24-37. doi:
10.1016/j.chemphyslip.2017.07.002. [PMID: 28698149] - Kristine M Erlandson, Suzanne P Fiorillo, Sandra Wagner Cardoso, Cynthia Riviere, Jorge Sanchez, James Hakim, Nagalingeswaran Kumarasamy, Sharlaa Badal-Faesen, Umesh Lalloo, Johnstone Kumwenda, Thomas B Campbell, Todd T Brown. Insulin-Like Growth Factor Is Associated with Changes in Body Composition with Antiretroviral Therapy Initiation.
AIDS research and human retroviruses.
2017 Sep; 33(9):929-934. doi:
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Toxicology and applied pharmacology.
2017 09; 330(?):74-83. doi:
10.1016/j.taap.2017.07.005. [PMID: 28705594] - Zufei Zhang, Jashvant D Unadkat. Development of a Novel Maternal-Fetal Physiologically Based Pharmacokinetic Model II: Verification of the model for passive placental permeability drugs.
Drug metabolism and disposition: the biological fate of chemicals.
2017 08; 45(8):939-946. doi:
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Chemico-biological interactions.
2017 Aug; 273(?):142-153. doi:
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Journal of acquired immune deficiency syndromes (1999).
2017 08; 75(4):e113-e119. doi:
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Journal of medicinal chemistry.
2017 07; 60(14):6220-6238. doi:
10.1021/acs.jmedchem.7b00416. [PMID: 28682067] - Navriti Chadha, Om Silakari. Indoles as therapeutics of interest in medicinal chemistry: Bird's eye view.
European journal of medicinal chemistry.
2017 Jul; 134(?):159-184. doi:
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Journal of natural products.
2017 06; 80(6):1798-1807. doi:
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MedChemComm.
2017 Feb; 8(2):408-414. doi:
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Oxidative medicine and cellular longevity.
2017; 2017(?):8356175. doi:
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Medicinal chemistry (Shariqah (United Arab Emirates)).
2017; 13(2):127-136. doi:
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BMC infectious diseases.
2016 Dec; 16(1):742. doi:
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Environmental toxicology and pharmacology.
2016 Sep; 46(?):217-226. doi:
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Materials science & engineering. C, Materials for biological applications.
2016 Sep; 66(?):40-50. doi:
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Paediatrics and international child health.
2016 Aug; 36(3):189-97. doi:
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Journal of acquired immune deficiency syndromes (1999).
2016 07; 72(3):246-53. doi:
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