A8201-5mg | Amprenavir (agenerase) [161814-49-9] Clinisciences

Background

Amprenavir (agenerase), an N,N-disubstituted hydroxyethylamino sulfonamide, is a novel inhibitor of human immunodeficiency virus type 1 (HIV-1) protease that potently inhibits the activity of HIV-1 protease with a value of 50% inhibition concentration IC₅₀ of 0.6 nM and also weakly inhibits HIV-2 protease with IC₅₀value of 19 nM. Amprenavir binds to the catalytic aspartate residues of the HIV-1 protease and hence inhibits the processing of the gag and gag-pol polyprotein precursors, which cleave to yield structural proteins and replication enzymes of HIV, resulting in immature and noninfectious viral particles. Amprenavir has been effectively used for the treatment of HIV disease in patients with primary HIV infection.

Reference

Fung HB, Kirschenbaum HL, Hameed R. Amprenavir: a new human immunodeficiency virus type 1 protease inhibitor. Clin Ther. 2000 May;22(5):549-72.

Chemical Properties

Physical Appearance	A solid
Storage	Store at -20°C
M.Wt	505.63
Cas No.	161814-49-9
Formula	C₂₅H₃₅N₃O₆S
Solubility	insoluble in H2O; ≥14.85 mg/mL in EtOH; ≥25 mg/mL in EtOH with ultrasonic
Chemical Name	[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
SDF	Download SDF
Canonical SMILES	CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)O)S(=O)(=O)C3=CC=C(C=C3)N
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:
Cell lines	HepaRG hepatoma cells and LS180 intestinal cells
Preparation method	The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20 °C for several months.
Reaction Conditions	10 μM; 24 hrs
Applications	Amprenavir induced PXR target gene expression in both HepaRG hepatoma cells and LS180 intestinal cells.
Animal experiment [1]:
Animal models	WT and PXR-/- mice
Dosage form	10 mg/kg; p.o.; for 1 week
Applications	In the intestine of WT mice, Amprenavir-mediated PXR activation stimulated the expression of both LipF and LipA.
Other notes	Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.
References: [1]. Helsley RN, Sui Y, Ai N, Park SH, Welsh WJ, Zhou C. Pregnane X receptor mediates dyslipidemia induced by the HIV protease inhibitor amprenavir in mice. Mol Pharmacol. 2013 Jun;83(6):1190-9.