Amprenavir

Category	HIV Protease
CAS	161814-49-9
Description	Amprenavir promotes the specific interactions between the nuclear receptor pregnane X receptor (PXR) and the coactivators SRC-1 and PBP.

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Product Information

Synonyms	VX-478; VX 478; VX478; Amprenavir; Agenerase; Prozei.
IUPAC Name	[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
Molecular Weight	505.63
Molecular Formula	C25H35N3O6S
Canonical SMILES	CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
InChI	InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
InChIKey	YMARZQAQMVYCKC-OEMFJLHTSA-N
Boiling Point	722.5±70.0 °C at 760 mmHg
Melting Point	72-74ºC
Flash Point	390.8±35.7 °C
Purity	>98%
Density	1.3±0.1 g/cm3
Solubility	In Vitro: DMSO : ≥ 100 mg/mL(197.77 mM) In Vivo: 1.Add each solvent one by one:10% DMSO >>40%PEG300 >>5%Tween-80 >>45% saline Solubility: ≥ 2.5 mg/mL (4.94 mM); Clear solution 2.Add each solvent one by one:10% DMSO >>90% (20%SBE-β-CDin saline) Solubility: ≥ 2.5 mg/mL (4.94 mM); Clear solution 3.Add each solvent one by one:10% DMSO >>90%corn oil Solubility: ≥ 2.5 mg/mL (4.94 mM); Clear solution
Appearance	Solid powder
Application	Amprenavir is indicated in combination with other antiretroviral agents in the treatment of hiv-1 infection
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Complexity	745
Exact Mass	505.224670
Index Of Refraction	1.602
In Vitro	Amprenavir has an enzyme inhibition constant (Ki = 0.6 nM) that falls within the Ki range of the other protease inhibitors. Amprenavir's in vitro 50% inhibitory concentration (IC50) against wild-type clinical HIV isolates is 14.6 +/- 12.5 ng/mL (mean +/- SD) . It also had direct inhibitory effects on invasion of Huh-7 hepatocarcinoma cell lines, inhibiting MMP proteolytic activation.
In Vivo	Amprenavir was able to promote regression of hepatocarcinoma growth in vivo by anti-angiogenetic and overall anti-tumor activities, independently by PI3K/AKT related pathways that at today is one of the more suggestive hypothesis to explain the anti-tumor effects of the different protease inhibitors. It efficiently activated PXR and induced PXR target gene expression in vitro and in vivo.
PSA	139.57000
Target	HIV; HIV Protease; SARS-CoV
Vapor Pressure	0.0±2.5 mmHg at 25°C
XLogP3-AA	2.9