3′-Azido-2′,3′-dideoxyuridine

• CAT Number: I008247
• CAS Number: 84472-85-5
• Molecular Formula: C9H11N5O4
• Molecular Weight: 253.21
• Purity: ≥95%
• Synonyms: 1-[(2R,4R,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 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)/t5-,6-,8-/m1/s1
• InChIKey: ZSNNBSPEFVIUDS-ATRFCDNQSA-N
• SMILES: C1C(C(OC1N2C=CC(=O)NC2=O)CO)N=[N+]=[N-]

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.
3′-Azido-2′,3′-dideoxyuridine inhibits HIV replication in PBMC infected with HIV-1, with a median effective concentration of 0.18-0.46 μM[2].
3′-Azido-2′,3′-dideoxyuridine inhibits HIV-mediated cytopathic effects in the human T-cell lines MT-4 and ATH8, with the median effective of 0.4 µM[3].
3′-Azido-2′,3′-dideoxyuridine is sequentially phosphorylated to its mono-, di-, and triphosphate metabolites by cellular kinases[3].
3′-Azido-2′,3′-dideoxyuridine (25-100 mg/kg, IV or PO, once) shows good pharmacokinetic profiles[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.

Reference

[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.
 [Content Brief]

[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.
 [Content Brief]

[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.
 [Content Brief]