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SML0685

Sigma-Aldrich

Amprenavir

≥98% (HPLC)

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

Quality Level

100

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

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

General description

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

Biochem/physiol Actions

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

Storage Class Code

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
0000370709
0000370706
0000370709
0000370706
0000268276

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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
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
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)
Mélanie Prague et al.
Computer methods and programs in biomedicine, 111(2), 447-458 (2013-06-15)
Models based on ordinary differential equations (ODE) are widespread tools for describing dynamical systems. In biomedical sciences, data from each subject can be sparse making difficult to precisely estimate individual parameters by standard non-linear regression but information can often be
Cédric Arvieux et al.
Drugs, 65(5), 633-659 (2005-03-08)
Amprenavir is an HIV-1 protease inhibitor, the first in vitro activity studies of which were published in 1995. During in vivo development, it became clear that the pharmacokinetics of the drug would result in patients taking a large number of
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