Zidovudine

Category	Human immunodeficiency Virus (HIV)
CAS	30516-87-1
Description	Zidovudine is a nucleoside reverse transcriptase inhibitor that, following triphosphorylation by thymidine kinase, potently blocks replication of HIV (EC50 = 3 nM) with low cytotoxicity (CC50 > 5 μM). It is commonly used in combination therapy to slow the replication of HIV in vivo.

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Product Information

Synonyms	3'-Azido-3-deoxythymidine; AZT; BWA509U; BWA 509U; BWA-509U; ZDV; Azidothymidine; Retrovir; Timazid; NSC 602670; 3'-Azido-2',3'-dideoxythymidine; 1-(3-Azido-2,3-dideoxy-β-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione; 1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidin-2,4(1H,3H)-dione; 1-(3-Azido-2,3-dideoxy-β-D-ribofuranosyl)thymine
IUPAC Name	1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Molecular Weight	267.24
Molecular Formula	C10H13N5O4
Canonical 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
InChIKey	HBOMLICNUCNMMY-XLPZGREQSA-N
Melting Point	113-115°C
Purity	≥95%
Solubility	Soluble in DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
Appearance	White Crystalline Powder
Application	Anti-hiv agents; antimetabolites; antimetabolites, Antineoplastic; reverse transcriptase inhibitors
Storage	Store at 2-8°C
Animal Admin	Mice C57BL/6J (wild-type), Nlrp3-/-, and P2rx7-/- mice are used. The NRTIs 3TC, AZT, and ABC or the P2X7 antagonist A438079 hydrochloride are dissolved in PBS. For CNV, each group of mice is injected once with 1 μL of NRTIs (3TC, 125 ng/μL; ABC, 183 ng/μL; AZT, 146 ng/μL), 1 μL of A438079 hydrochloride (3, 30, or 300 ng/μL), or the same volume of vehicle (PBS) into the vitreous humor using a 33-gauge needle immediately after laser injury. Another group of mice is injected with 3TC (125 ng) in combination with an anti-mouse VEGF polyclonal antibody (10 ng).
Complexity	484
Exact Mass	267.09675391
Index Of Refraction	47 ° (C=1, H2O)
In Vitro	Zidovudine inhibits SVG, Primary human fetal astrocytes (PFA), peripheral blood mononuclear cells (PBMC), and monocyte-derived macrophages (MDM) with EC50 of 17, 1311, 8, and 5 nM, respectively. Zidovudine inhibits SVG, PFA, PBMC, and MDM with EC90 of 0.205 μM, 44.157 μM, 0.481 μM, and 0.219 μM, respectively.
In Vivo	Intravitrous injection of the NRTIs Lamivudine (3TC), Zidovudine (AZT), or Abacavir (ABC) suppresses the laser-induced choroidal neovascularization (CNV) in wild-type mice compared to PBS vehicle. The mean level of VEGF-A in the RPE/choroid, which peaks on day 3 after laser injury, is significantly reduced in 3TC-, AZT- and ABC-treated eyes compared with control eyes in wild-type mice, but not inP2rx7-/- mice.
PSA	134.07000
Target	HIV-1; CRISPR/Cas9
XLogP3-AA	0