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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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Georgios Leonis et al.
Journal of chemical information and modeling, 53(8), 2141-2153 (2013-07-10)
The emergence of HIV-1 drug-resistant mutations is the major problem against AIDS treatment. We employed molecular dynamics (MD) calculations and free energy (MM-PBSA and thermodynamic integration) analyses on wild-type (WT) and mutated HIV-1 protease (HIV-1 PR) complexes with darunavir, amprenavir
Irene T Weber et al.
Journal of medicinal chemistry, 56(13), 5631-5635 (2013-06-19)
HIV-1 protease is an important target for the development of antiviral inhibitors to treat AIDS. A room-temperature joint X-ray/neutron structure of the protease in complex with clinical drug amprenavir has been determined at 2.0 Å resolution. The structure provides direct
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)
Mary Beth Wire et al.
Clinical pharmacokinetics, 45(2), 137-168 (2006-02-21)
Fosamprenavir is one of the most recently approved HIV-1 protease inhibitors (PIs) and offers reductions in pill number and pill size, and omits the need for food and fluid requirements associated with the earlier-approved HIV-1 PIs. Three fosamprenavir dosage regimens
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