Atazanavir Sulfate

Category	Human immunodeficiency Virus (HIV)
CAS	229975-97-7
Description	Atazanavir is a HIV protease inhibitor with Ki of 2.66 nM. It is an antiretroviral drug of the protease inhibitor (PI) class. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus.

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Product Information

Synonyms	BMS-232632; BMS 232632; BMS232632; Reyataz
IUPAC 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;sulfuric acid
Molecular Weight	802.93
Molecular Formula	C38H52N6O7.H2SO4
Canonical SMILES	CC(C)(C)C(C(=O)NC(CC1=CC=CC=C1)C(CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)C(C(C)(C)C)NC(=O)OC)O)NC(=O)OC.OS(=O)(=O)O
InChI	InChI=1S/C38H52N6O7.H2O4S/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28;1-5(2,3)4/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47);(H2,1,2,3,4)/t29-,30-,31+,32+;/m0./s1
InChIKey	DQSGVVGOPRWTKI-QVFAWCHISA-N
Boiling Point	995.5°C at 760 mmHg
Melting Point	195.0°, or acetone; mp 198-199° (dec)
Flash Point	555.8°C
Purity	>98%
Density	1.164g/cm3
Solubility	In Vitro: DMSO : 166 mg/mL(206.74 mM;Need ultrasonic and warming) H2O : < 0.1 mg/mL(insoluble) In Vivo: 1.Add each solvent one by one:10% DMSO >> 40%PEG300 >> 5%Tween-80 >> 45% saline Solubility: ≥ 2.5 mg/mL (3.11 mM); Clear solution 2.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline) Solubility: ≥ 2.5 mg/mL (3.11 mM); Clear solution 3.Add each solvent one by one:10% DMSO >> 90%corn oil Solubility: ≥ 2.5 mg/mL (3.11 mM); Clear solution 4.Add each solvent one by one:5% DMSO >> 40%PEG300 >> 5%Tween-80 >> 50% saline Solubility: ≥ 2.5 mg/mL (3.11 mM); Clear solution 5.Add each solvent one by one:5% DMSO >> 95% (20%SBE-β-CDin saline) Solubility: ≥ 2.5 mg/mL (3.11 mM); Clear solution
Appearance	White to light yellow (Solid)
Application	HIV Protease Inhibitors
Storage	4°C, sealed storage, away from moisture * In solvent : -80°C, 6 months -20°C, 1 month (sealed storage, away from moisture)
Complexity	1190
Exact Mass	802.357117
In Vitro	Atazanavir acts on virus-infected H9 cells and inhibits the proteolytic lysis of the viral gag precursor p55 polymerization protein, with an IC50 of ~47 nM. Atazanavir acts on the RF/MT-2 strain and has potent antiviral activity with an EC50 of 3.89 nM. Atazanavir is also an inhibitor of Bilirubin glucuronidation with an IC50 of 2.4 μM. Atazanavir inhibits recombinant UGT1A1 with a Ki of 1.9 μM. Atazanavir inhibits cell growth in U251, T98G, and LN229 glioblastoma cell lines, dramatically increasing GRP78 and CHOP protein levels. Atazanavir acts on U251 glioma cells, significantly increasing a variety of different sizes of polyubiquitinated proteins. Atazanavir also inhibits human 20S proteasome proteasomes with an IC50 of 26 μM. Atazanavir (30 μM) acts on HepG2 cells to alter the amplitude of endoplasmic reticulum stress and UPR gene expression. Atazanavir (30 mM) acts on LS180V cells, with a 2.5-fold increase in P-gp expression in the immune response and a decrease in intracellular Rh123.
PSA	254.20000
Target	HIV; HIV Protease; SARS-CoV; Cytochrome P450; P-glycoprotein
Vapor Pressure	0mmHg at 25°C