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Key Documents

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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)
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