navuridine

Names

[ Name ]:
navuridine

[Synonym ]:
AzddU
3'-Azido-2',3'-dideoxyuridine
Uridine, 3'-azido-2',3'-dideoxy-
2',3'-Dideoxy-3'-azidouridine
3'-Azido-2',3'-dideoxy-D-uridine
navuridine
3'-Az-ddU
CS-87

Biological Activity

[Description]:

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].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[Target]

HIV

[In Vitro]

3'-Azido-2',3'-dideoxyuridine 抑制感染 HIV-1 的 PBMC 中的 HIV 复制，中位有效浓度为 0.18-0.46 μM[2]。 3'-Azido-2',3'-dideoxyuridine 抑制人类 T 细胞系 MT-4 和 ATH8 中 HIV 介导的细胞病变效应，中位有效浓度为 0.4 µM[3]。< br/>3'-Azido-2',3'-dideoxyuridine 依次被细胞激酶磷酸化为单磷酸、二磷酸和三磷酸代谢物[3]。

[In Vivo]

3′-Azido-2′,3′-dideoxyuridine (25-100 mg/kg, 静脉注射或者灌胃，一次)具有良好的药代动力学特征[3]。 Pharmacokinetic Parameters of 3′-Azido-2′,3′-dideoxyuridine in male Sprague-Dawley rats[3]. IV (25 mg/kg) IV (100 mg/kg) PO (25 mg/kg) PO (100 mg/kg) Cmax (μg/mL) 9.2±1.9 41±15 Tmax (h) 0.38±0.13 0.63±0.22 AUC (μg/mL∗h) 19±1.2 156±7.0 12±0.54 70±13 CLT (L/h/kg) 1.4±0.2 0.70±0.09 CLR (L/h/kg) 0.90±0.27 0.43±0.12 t1/2 (h) 0.5±0.0 0.68±0.1 1.0±0.3 1.1±0.4 Vss (L/kg) 0.78±0.26 0.34±0.11 F (%) 60 46 Animal Model: Adult male Sprague-Dawley rats (300-400 g)[3] Dosage: 25, 100 mg/kg Administration: Intravenous bolus injection or oral gavage (Pharmacokinetic Analysis) Result: The oral bioavailability estimates of 3′-Azido-2′,3′-dideoxyuridine at doses of 25 and 100 mg/kg averaged 53%.

[References]

[1]. Zhu Z, et al. Cellular metabolism of 3'-azido-2',3'-dideoxyuridine with formation of 5'-O-diphosphohexose derivatives by previously unrecognized metabolic pathways for 2'-deoxyuridine analogs. Mol Pharmacol. 1990 Dec;38(6):929-38.

[2]. Chu CK, et al. Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells. J Med Chem. 1989 Mar;32(3):612-7.

[3]. Kong L, et al. Pharmacokinetic evaluation of 3'-azido-2', 3'-dideoxyuridine-5'-O-valinate-hydrochloride as a prodrug of the anti-HIV nucleoside 3'-azido-2', 3'-dideoxyuridine. Antivir Chem Chemother. 2003 Sep;14(5):263-70.

Chemical & Physical Properties

[ Density]:
1.357 g/cm

[ Melting Point ]:
161-163ºC

[ Molecular Formula ]:
C₉H₁₁N₅O₄

[ Molecular Weight ]:
253.215

[ Exact Mass ]:
253.081100

[ PSA ]:
134.07000

[ LogP ]:
-1.12

[ Storage condition ]:
−20°C

Safety Information

[ Hazard Codes ]:
Xn

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%