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    InvivoChem Cat #: V2635
    CAS #: 198904-31-3 Purity ≥98%

    Description: Atazanavir (also called Latazanavir, Zrivada, Reyataz, BMS-232632) is an azapeptide and HIV-protease inhibitor that is used in the treatment of HIV infections and AIDS in combination with other anti-HIV agents. Atazanavir acts by inhibiting HIV protease with Ki of 2.66 nM in a cell-free assay. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus. Atazanavir is distinguished from other PIs in that it can be given once-daily and has lesser effects on the patient's lipid profile. Like other protease inhibitors, it is used only in combination with other HIV medications. 

    References: Antimicrob Agents Chemother. 2000 Aug;44(8):2093-9; Cancer Res. 2007 Nov 15;67(22):10920-8.

    Related CAS#: 1192224-24-0 (Atazanavir metabolite); 229975-97-7 (sulfate) 

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    Molecular Weight (MW)704.86
    CAS No.198904-31-3 (free base); 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 100 mg/mL (141.9 mM)
    Water: <1 mg/mL
    Ethanol: 32 mg/mL (45.4 mM)

    Latazanavir, Zrivada, Reyataz, BMS-232632; BMS232632; BMS 232632; Atazanavir;

    Chemical Name: methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate 

    Exact Mass: 704.38975 

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    In Vitro

    In vitro activity: Atazanavir inhibits the proteolytic cleavage of the viral gag precursor p55 polyprotein with IC50 of ~47 nM in virus-infected H9 cells. Atazanavir exhibits potent antiviral activity with EC50 of 3.89 nM in RF/MT-2 strains. Atazanavir is shown to be an inhibitor of bilirubin glucuronidation with IC50 of 2.4 μM. Atazanavir inhibits recombinant UGT1A1 with Ki of 1.9 μM. Atazanavir inhibits cell growth in U251, T98G, and LN229 glioblastoma cell lines, with strikingly increased GRP78 and CHOP protein levels. Atazanavir causes a prominent increase of polyubiquitinated proteins of various different sizes in U251 glioblastoma cells. Atazanavir also inhibits human 20S proteasome with IC50 of 26 μM. Atazanavir (30 μM) changes the magnitudes of ER stress and UPR gene expression in HepG2 cells. Atazanavir (30 mM) causes a 2.5-fold increase in immunoreactive P-gp expression with decreased intracellular Rh123 in LS180V cells.

    Kinase Assay: To determine the inhibition constants (Ki) for each Prt inhibitor, purified HIV-1 RF wild-type Prt (2.5 nM) is incubated at 37 ℃ with 1 μM to 15 μM fluorogenic substrate in reaction buffer (1 M NaCl, 1 mM EDTA, 0.1 M sodium acetate [pH 5.5], 0.1% polyethylene glycol 8000) in the presence or absence of Atazanavir. Cleavage of the substrate is quantified by measuring an increase in fluorescent emission at 490 nM after excitation at 340 nM using a Cytofluor 4000. Reactions are carried out using 1.36 μM, 1.66 μM, 2.1 μM, 3.0 μM, 5.0 μM, or 15 μM substrate in the presence of five concentrations of Atazanavir (1.25 nM to 25 nM). Substrate cleavage is monitored at 5-min intervals for 30 min. Cleavage rates are then determined for each sample at early time points in the reaction, and Ki values are determined from the slopes of the resulting Michaelis-Menten plots. 

    Cell Assay: To determine cytotoxicity, host cells are incubated in the presence of serially diluted Atazanavir for 6 days and cell viability is quantitated using an XTT[2,3-bis(2-methoxy-4-nitro-5-sulfophenyl-2H-tetrazolium-5-carboxanilide] assay to calculate the 50% cytotoxic concentrations (CC50s). To assess the effect of human serum proteins on antiviral activity, the 10% fetal calf serum normally used for assays is replaced with 40% adult human serum or 1 mg of α1-acid glycoprotein/mL.

    In VivoAtazanavir has excellent oral bioavailability in the range of 60-70% 
    Animal modelThe WT mice (FVB/NTac strain), TKO mice (FVB/N7 strain)
    Formulation & DosageDissolved in a mixture of ethanol, polyethylene glycol 200, and 5% glucose (2:6:2); 10 mg/kg; i.v.  

    Antimicrob Agents Chemother. 2000 Aug;44(8):2093-9; Cancer Res. 2007 Nov 15;67(22):10920-8; Antimicrob Agents Chemother. 2014;58(3):1713-22

    These protocols are for reference only. InvivoChem does not independently validate these methods.





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