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Merck
CN

SML0685

Amprenavir

≥98% (HPLC), HIV Protease Inhibitor, powder

Synonym(s):

N-[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid (3S)-tetrahydro-3-furanyl ester, VX-478

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About This Item

Empirical Formula (Hill Notation):
C25H35N3O6S
CAS Number:
161814-49-9
Molecular Weight:
505.63
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

Amprenavir, ≥98% (HPLC)

SMILES string

[S](=O)(=O)(N(C[C@@H](O)[C@@H](NC(=O)O[C@@H]3COCC3)Cc2ccccc2)CC(C)C)c1ccc(cc1)N

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

InChI key

YMARZQAQMVYCKC-OEMFJLHTSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +8 to +12°, c = 0.5 in methanol

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Amprenavir is an antiretroviral HIV Protease Inhibitor.
Amprenavir is an antiretroviral HIV Protease Inhibitor. It is the active metabolite of fosamprenavir.
Protease inhibition results in inactive and immature virus.

General description

Amprenavir is a second-generation drug derived from hydroxyethylamine sulfonamide.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000370706
0000370709
0000370709
0000370706
0000231294

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S Noble et al.
Drugs, 60(6), 1383-1410 (2001-01-11)
The virological/immunological efficacy of amprenavir-containing combination regimens has been evaluated in a small number of clinical trials in patients with HIV infection. Amprenavir plus 2 nucleoside reverse transcriptase inhibitors (NRTIs) was more effective than 2 NRTIs (in treatment-naive patients) or
Role of P-glycoprotein on the CNS disposition of amprenavir (141W94), an HIV protease inhibitor.
Polli J W, et al.
Pharmaceutical Research, 16(8), 1206-1212 (1999)
Jenna A Rhoades et al.
Pharmaceutical research, 29(4), 972-982 (2011-12-14)
To predict and determine whether the protease inhibitors (PIs) nelfinavir, amprenavir, atazanavir, ritonavir, and saquinavir could serve as metabolic inhibitors of the human CES1 (hCES1) using both molecular modeling techniques and in vitro inhibition assays. Initially, a molecular modeling approach
Maya Okamura et al.
Cells, 9(10) (2020-10-21)
Pregnane X receptor (PXR) is a liver-enriched xenobiotic-responsive transcription factor. Although recent studies suggest that PXR shows anti-inflammatory effects by suppressing nuclear factor kappa B (NF-κB), the detailed mechanism remains unclear. In this study, we aimed to elucidate this mechanism.
Satoko Matsunaga et al.
Journal of proteomics, 75(15), 4863-4873 (2012-06-13)
Xenotropic murine leukemia virus-related virus (XMRV) is a virus generated under artificial conditions by the recombination of 2 murine leukemia virus (MLV) proviruses, PreXMRV-1 and PreXMRV-2, during the in vivo passage of human prostate cancer cells in athymic nude mice.
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