navuridine (BioDeep_00000668332)

   


代谢物信息卡片


1-[4-Azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

化学式: C9H11N5O4 (253.08110059999998)
中文名称: 那尿苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(OC1N2C=CC(=O)NC2=O)CO)N=[N+]=[N-]
InChI: InChI=1S/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)

描述信息

D009676 - Noxae > D000963 - Antimetabolites > D015224 - Dideoxynucleosides
3′-Azido-2′,3′-dideoxyuridine (AzdU) is a nucleoside analog of Zidovudine (HY-17413). 3′-Azido-2′,3′-dideoxyuridine is a potent inhibitor of human immunodeficiency virus (HIV) replication in human peripheral blood mononuclear cells (PBMC) with limited toxicity for human bone marrow cells (BMC)[1][2][3]. 3′-Azido-2′,3′-dideoxyuridine is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. Strain-promoted alkyne-azide cycloaddition (SPAAC) can also occur with molecules containing DBCO or BCN groups.

同义名列表

6 个代谢物同义名

1-[4-Azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione; navuridine; AzdU; AzddU; CS-87; 3′-Azido-2′,3′-dideoxyuridine



数据库引用编号

3 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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文献列表

  • Linghui Kong, John S Cooperwood, Chang H Oh, Chung K Chu, F Douglas Boudinot. Simultaneous determination of 3'-azido-2',3'-dideoxyuridine and novel prodrugs in rat plasma by liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Oct; 795(2):371-6. doi: 10.1016/s1570-0232(03)00562-2. [PMID: 14522042]
  • T N Clark, C A White, C K Chu, M G Bartlett. Determination of 3'-azido-2',3'-dideoxyuridine in maternal plasma, amniotic fluid, fetal and placental tissues by high-performance liquid chromatography. Journal of chromatography. B, Biomedical sciences and applications. 2001 May; 755(1-2):165-72. doi: 10.1016/s0378-4347(01)00054-8. [PMID: 11393701]
  • K K Manouilov, C A White, F D Boudinot, I I Fedorov, C K Chu. Lymphatic distribution of 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine in mice. Drug metabolism and disposition: the biological fate of chemicals. 1995 Jun; 23(6):655-8. doi: NULL. [PMID: 7587948]
  • Y Wang, S L Wong, R J Sawchuk. Microdialysis calibration using retrodialysis and zero-net flux: application to a study of the distribution of zidovudine to rabbit cerebrospinal fluid and thalamus. Pharmaceutical research. 1993 Oct; 10(10):1411-9. doi: 10.1023/a:1018906821725. [PMID: 8272401]
  • E M Cretton, M Y Xie, N M Goudgaon, R F Schinazi, C K Chu, J P Sommadossi. Catabolic disposition of 3'-azido-2',3'-dideoxyuridine in hepatocytes with evidence of azido reduction being a general catabolic pathway of 3'-azido-2',3'-dideoxynucleosides. Biochemical pharmacology. 1992 Sep; 44(5):973-80. doi: 10.1016/0006-2952(92)90130-b. [PMID: 1326966]
  • J M Gallo, J T Etse, K J Doshi, F D Boudinot, C K Chu. Hybrid pharmacokinetic models to describe anti-HIV nucleoside brain disposition following parent and prodrug administration in mice. Pharmaceutical research. 1991 Feb; 8(2):247-53. doi: 10.1023/a:1015808624103. [PMID: 2023876]
  • C K Chu, V S Bhadti, K J Doshi, J T Etse, J M Gallo, F D Boudinot, R F Schinazi. Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine. Journal of medicinal chemistry. 1990 Aug; 33(8):2188-92. doi: 10.1021/jm00170a023. [PMID: 2374145]
  • K J Doshi, J M Gallo, F D Boudinot, R F Schinazi, C K Chu. Comparative pharmacokinetics of 3'-azido-3'-deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (AZddU) in mice. Drug metabolism and disposition: the biological fate of chemicals. 1989 Nov; 17(6):590-4. doi: NULL. [PMID: 2575492]