(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 583
• Molecular Formular: C25H35N3O6S
• Molecular Mass: 505.6269
• Monoisotopic Mass: 505.22465686
• SMILES: S(=O)(=O)(N(C[C@@H](O)[C@@H](NC(=O)O[C@H]1CCOC1)Cc1ccccc1)CC(C)C)c1ccc(N)cc1
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]1CCOC1)O)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate; amprenavir
• Brand Name: Agenerase; Prozei; Vertex
• Synonyms: AMP; AMV; APV; VX-478; Amprenavir; N-[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic Acid (3S)-Tetrahydro-3-furanyl Ester; 141W94; KVX-478; Agenerase; Prozei

Database IDs

• CAS Number: 161814-49-9
• MDL Number: MFCD00934214
• PubChem SID: 46507537; 160964046
• PubChem CID: 65016

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.614255
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.4266205
• LogD (pH = 7.4): 2.4269483
• Log P: 2.4269526
• Molar Refractivity: 134.0815 cm^3
• Polarizability: 52.798065 Å^3
• Polar Surface Area: 131.19 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.85
• LOG S: -4.01
• Solubility (Water): 4.91e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White to Beige Solid
• Melting Point: 72-74°C

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00701

• Drug Groups: approved
• Description: Amprenavir is a protease inhibitor used to treat HIV infection.
• Indication: For the treatment of HIV-1 infection in combination with other antiretroviral agents.
• Pharmacology: Amprenavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Amprenavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Hepatic. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system. The 2 major metabolites result from oxidation of the tetrahydrofuran and aniline moieties. Glucuronide conjugates of oxidized metabolites have been identified as minor metabolites in urine and feces.
• Absorption: Rapidly absorbed after oral administration in HIV-1-infected patients with a time to peak concentration (T_max) typically between 1 and 2 hours after a single oral dose. The absolute oral bioavailability of amprenavir in humans has not been established.
• Half Life: 7.1-10.6 hours
• Protein Binding: Very high (90%). Amprenavir has the highest affinity for alpha(1)-acid glycoprotein.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A634400

A selective HIV protease inhibitor. An analogue of Ritonavir.

REFERENCES

• Adkins, J.C., et al.: Drugs, 55, 837 (1998)