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SML0685

Amprenavir

Name: Amprenavir
Brand: SIGMA

≥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

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Properties

Product Name

Amprenavir, ≥98% (HPLC)

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

Description

General description

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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A contribution to the drug resistance mechanism of darunavir, amprenavir, indinavir, and saquinavir complexes with HIV-1 protease due to flap mutation I50V: a systematic MM-PBSA and thermodynamic integration study.

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

Joint X-ray/neutron crystallographic study of HIV-1 protease with clinical inhibitor amprenavir: insights for drug design.

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

Energetic basis for drug resistance of HIV-1 protease mutants against amprenavir.

Parimal Kar et al.

Journal of computer-aided molecular design, 26(2), 215-232 (2012-02-22)

Amprenavir (APV) is a high affinity (0.15 nM) HIV-1 protease (PR) inhibitor. However, the affinities of the drug resistant protease variants V32I, I50V, I54V, I54M, I84V and L90M to amprenavir are decreased 3 to 30-fold compared to the wild-type. In

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