Name | AMPRENAVIR |
Synonyms | 141W94 PROZEI KVX-478 AGENERASE AMPRENAVIR Angenerase 141W94, KVX-478, Agenerase, Prozei, tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate Carbamic acid, (1S,2R)-3-(4-aminophenyl)sulfonyl(2-methylpropyl)amino-2-hydroxy-1-(phenylmethyl)propyl-, (3S)-tetrahydro-3-furanyl ester |
CAS | 161814-49-9 |
EINECS | 827-179-5 |
InChI | InChI=1/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 |
Molecular Formula | C25H35N3O6S |
Molar Mass | 505.63 |
Density | 1.30±0.1 g/cm3(Predicted) |
Melting Point | 72-74°C |
Solubility | DMSO: soluble20mg/mL, clear |
Appearance | off-white to pale yellow |
Color | white to beige |
pKa | 11.54±0.46(Predicted) |
Storage Condition | -20°C |
Refractive Index | 1.61 |
In vitro study | Amprenavir promotes the specific interaction between the nuclear receptor pregnane X receptor (PXR) and the coactivators SRC-1 and PBP. Amprenavir incorporated into the complex high-resolution crystal structure of human PXR with sr12813. Amprenavir occupies all four binding bodies, and its hydroxyl group forms a hydrogen bond with Ser247, which is located in the linking region of PXR and contributes to the optimal orientation of the drug in the body. Amprenavir with XR activates a residue on the αaf surface of functional -2(AF-2), Phe429, which may stabilize the active AF-2 conformational receptor, and contributes to amprenavir's direct exposure to PXR agonist activity. In HepaRG cells and LS180 cells, Amprenavir induced the target gene of bona fide PXR, involved in the first phase (CYP3A4), second phase (UGT1A1) and third phase (MDR1) metabolism. |
In vivo study | Amprenavir increased the atherosclerotic LDL cholesterol fraction in wild-type mice, but not in PXR-/-mice. In the intestine of wild-type mice but not in PXR-/-mice, Amprenavir stimulated the expression of known PXR target genes, including CYP3A11, glutathione transferase A1, and MDR1a. Amprenavir-mediated PXR activation stimulates the expression of LiPF and LIPA in the intestine of wild-type mice but not in PXR-/-mice, indicates that intestinal PXR may play a role in mediating mammalian feed lipolysis and absorption. |
UN IDs | 3077 |
WGK Germany | 3 |
HS Code | 29350090 |