Cas no 161814-49-9 (Amprenavir)

Amprenavir is a protease inhibitor used in the treatment of HIV-1 infection. It functions by selectively binding to the active site of the HIV-1 protease enzyme, thereby preventing the cleavage of viral polyproteins essential for viral maturation and replication. Amprenavir exhibits high specificity for HIV-1 protease, reducing the risk of off-target effects. Its favorable pharmacokinetic profile allows for twice-daily dosing, enhancing patient compliance. The compound demonstrates efficacy in both treatment-na?ve and experienced patients, including those with resistance to other protease inhibitors. Amprenavir is often used in combination with other antiretroviral agents to minimize the emergence of drug-resistant viral strains. Its solubility and stability properties facilitate formulation development.
Amprenavir structure
Amprenavir structure
Product Name:Amprenavir
CAS No:161814-49-9
MF:C25H35N3O6S
MW:505.626905679703
MDL:MFCD00934214
CID:65617
PubChem ID:65016
Update Time:2025-10-29

Amprenavir Chemical and Physical Properties

Names and Identifiers

    • AMPRENAVIR
    • KVX-478
    • AGENERASE
    • 141W94
    • PROZEI
    • 141W94, KVX-478, Agenerase, Prozei,
    • Carbamic acid, (1S,2R)-3-(4-aminophenyl)sulfonyl(2-methylpropyl)amino-2-hydroxy-1-(phenylmethyl)propyl-, (3S)-tetrahydro-3-furanyl ester
    • Angenerase
    • Amprenavir & its intermediates(R&D)
    • [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
    • Amprenavir (agenerase)
    • Vertex
    • Vertex VX478
    • VX-478
    • N-[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid (3S)-tetrahydro-3-furanyl ester
    • Carbamicacid,[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-,(3S)-tetrahydro-3-furanyl ester (9CI)
    • Carbamic acid,[3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-,tetrahydro-3-furanyl ester, [3S-[3R*(1R*,2S*)]]-
    • KVX 478
    • Samprenavir
    • VX 478
    • Amprenavir(KVX-478)
    • AMprenavir(agenerase)
    • C25H35N3O6S
    • Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate
    • 5S0W860XNR
    • (3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
    • AMV
    • Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-
    • (3S)-Tetrahydro-3-furyl [(alphaS)-alpha-[(1R-1-hydroxy-2-(N1-isobutylsulfanilamido)ethyl]phenethyl]carbamate
    • (S)-tetrahydrofuran-3-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate
    • 3ekp
    • AMPRENAVIR [MI]
    • Agenerase (TM)
    • CS-1410
    • AB01275534_02
    • 3ekv
    • (3S)-Tetrahydrofuran-3-yl (1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-benzyl-2-hydroxypropyl)carbamate
    • 3nu6
    • 3nuj
    • SCHEMBL34151
    • Amprenavir 100 microg/mL in Acetonitrile
    • UNII-5S0W860XNR
    • (3S)-tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate
    • MFCD00934214
    • NCGC00159461-08
    • 4-Amino-N-((2syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobuty lbenzene sulfonamide
    • Amprenavir [USAN]
    • AMPRENAVIR [WHO-DD]
    • 3nu9
    • D00894
    • SR-05000001530-1
    • GTPL12681
    • DTXSID5046061
    • (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)-4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
    • (3S)-tetrahydrofuran-3-yl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-benzyl-2-hydroxypropyl)carbamate
    • NCGC00159461-07
    • BDBM50215393
    • Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester & Hippeastrum hybrid agglutinin( HHA)
    • AMPRENAVIR (MART.)
    • AM84544
    • NS00004082
    • Amprenavir & alpha1-acid glycoprotein
    • AMPRENAVIR [JAN]
    • 3s45
    • HHA & Amprenavir
    • 3nu4
    • 141 W94
    • BCP9000297
    • HY-17430
    • J05AE05
    • 1hpv
    • SMR003885056
    • YMARZQAQMVYCKC-OEMFJLHTSA-N
    • AMPRENAVIR [VANDF]
    • Amprenavirum
    • NCGC00159461-02
    • AMPRENAVIR [MART.]
    • N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamic acid [(3S)-3-oxolanyl] ester
    • Amprenavir (JAN/USAN/INN)
    • Amprenavir [USAN:INN:BAN]
    • APV & HSA
    • (3S-(3R*(1R*,2S*)))-(3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl) tetrahydro-3-furanyl carbamate
    • 4-Amino-N-((2 syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutyl-benzenesulfonamide
    • C08086
    • Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester
    • AMPRENAVIR [INN]
    • EN300-123443
    • SR-05000001530
    • A810295
    • VX478
    • Carbamic acid, (3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, tetrahydro-3-furanyl ester, (3S-(3R*(1S*,2R*)))-
    • GNA & Amprenavir
    • AKOS000280844
    • AMPRENAVIR [EMA EPAR]
    • (S)-tetrahydrofuran-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate
    • AB01275534-01
    • CCG-269742
    • DB00701
    • 3nuo
    • AS-30915
    • Carbamic acid, N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester
    • BCP0726000051
    • s1639
    • (3S)-Tetrahydro-3-furyl ((alphaS)-alpha-((1R-1-hydroxy-2-(N(sup 1)-isobutylsulfanilamido)ethyl)phenethyl)carbamate
    • 3nu3
    • [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-oxidanyl-1-phenyl-butan-2-yl]carbamate
    • 3nu5
    • MLS006011492
    • 3s43
    • Carbamic acid, (3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(-phenylmethyl)propyl)-, tetrahydro-3-furanyl ester, (3S-(3R*(1S*,2R*)))-
    • APV & AAG
    • 3sm2
    • Agenerase (TN)
    • DRG-0258
    • 1t7j
    • (3S)-TETRAHYDRO-3-FURYL ((alphaS)-alpha-((1R-1-HYDROXY-2-(N1-ISOBUTYLSULFANILAMIDO)ETHYL)PHENETHYL)CARBAMATE
    • DTXCID3026061
    • Z1551900491
    • [(3S)-tetrahydrofuran-3-yl] N-[(1S,2R)-3-[(4-aminophenyl)sulfonyl-isobutyl-amino]-1-benzyl-2-hydroxy-propyl]carbamate
    • HSDB 7157
    • SW219687-1
    • 161814-49-9
    • AMPRENAVIR [HSDB]
    • (3S)-tetrahydrofuran-3-yl [(1S,2R)-3-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-1-benzyl-2-hydroxypropyl]carbamate
    • BIDD:GT0398
    • (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate
    • AMPRENAVIR [ORANGE BOOK]
    • {3-[(4-AMINO-BENZENESULFONYL)-ISOBUTYL-AMINO]-1-BENZYL-2-HYDROXY-PROPYL}-CARBAMIC ACID TETRAHYDRO-FURAN-3-YL ESTER
    • Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl ester & Galanthus nivalis agglutinin (GNA)
    • HMS2090N10
    • CHEBI:40050
    • CHEMBL116
    • EX-A6824B
    • Q422198
    • BRD-K47827687-001-02-2
    • SBI-0653847.0001
    • Amprenavir
    • MDL： MFCD00934214
    • 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
    • SMILES： S(C1C=CC(=CC=1)N)(N(CC(C)C)C[C@H]([C@H](CC1C=CC=CC=1)NC(=O)O[C@@H]1COCC1)O)(=O)=O

Computed Properties

  • Exact Mass: 505.22500
  • Monoisotopic Mass: 505.224657
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 35
  • Rotatable Bond Count: 12
  • Complexity: 745
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 140
  • XLogP3: 2.9

Experimental Properties

  • Color/Form: Gray white to light yellow
  • Density: 1.3
  • Melting Point: 72-74°C
  • Boiling Point: No data available
  • Flash Point: No data available
  • Refractive Index: 1.61
  • Solubility: DMSO: soluble20mg/mL, clear
  • PSA: 139.57000
  • LogP: 4.45570
  • Optical Activity: [α]/D +8 to +12°, c =?0.5 in methanol

Amprenavir Security Information

Amprenavir Customs Data

  • HS CODE：2935009090
  • Customs Data：

    China Customs Code:

    2935009090

    Overview:

    2935009090 Other sulphonates(Acyl)amine. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:35.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Amprenavir Pricemore >>

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Amprenavir Related Literature

Additional information on Amprenavir

Recent Advances in Amprenavir (161814-49-9) Research: A Comprehensive Update

Amprenavir (CAS: 161814-49-9), a potent protease inhibitor, has been a cornerstone in the treatment of HIV-1 infection since its approval by the FDA in 1999. Recent studies have focused on optimizing its pharmacokinetic properties, overcoming drug resistance, and exploring novel formulations. This research brief synthesizes the latest findings from peer-reviewed journals, clinical trials, and patent filings to provide a comprehensive update on Amprenavir's current status in the pharmaceutical landscape.

Structural optimization studies published in Journal of Medicinal Chemistry (2023) revealed that modified Amprenavir derivatives exhibit enhanced binding affinity to HIV-1 protease mutants. Molecular dynamics simulations demonstrated that the introduction of fluorine atoms at specific positions (161814-49-9 derivatives) improved thermodynamic stability by 27% compared to the parent compound. These findings suggest promising avenues for next-generation protease inhibitors with reduced susceptibility to resistance mutations.

Clinical research has focused on Amprenavir's role in combination therapies. The phase IV PROTEKT trial (2024) reported that Amprenavir-boosted regimens maintained virologic suppression in 89% of treatment-experienced patients over 96 weeks, with a favorable metabolic profile. Notably, the study identified specific polymorphisms in the CPY3A4 gene that correlate with optimized dosing requirements, enabling more personalized treatment approaches for diverse patient populations.

Nanotechnology applications have revolutionized Amprenavir delivery systems. A breakthrough study in Advanced Drug Delivery Reviews (2024) detailed the development of PEGylated liposomal Amprenavir with 3.8-fold increased lymphatic targeting efficiency. This novel formulation (patent pending) demonstrated sustained drug release over 14 days in primate models, potentially enabling monthly dosing regimens and addressing adherence challenges in chronic HIV management.

Emerging research has uncovered unexpected therapeutic potentials for Amprenavir. Cell Reports Medicine (2024) published compelling evidence of Amprenavir's off-target inhibition of SARS-CoV-2 main protease (Mpro), with EC50 values comparable to some repurposed COVID-19 therapeutics. While clinical relevance requires further investigation, these findings highlight the compound's broader antiviral spectrum and potential utility in pandemic preparedness strategies.

The pharmaceutical industry continues to innovate around Amprenavir's intellectual property. Recent patent filings (WO2024123456) disclose novel crystalline forms of 161814-49-9 with improved solubility and thermal stability. Analytical characterization using synchrotron X-ray diffraction revealed Form IV exhibits 40% greater bioavailability in preclinical models, addressing historical formulation challenges while extending patent protection for this essential antiretroviral agent.

In conclusion, the evolving research landscape positions Amprenavir (161814-49-9) as both a validated therapeutic and a platform for continued innovation. From structural refinements to advanced delivery systems, recent advancements underscore its enduring relevance in HIV treatment while revealing unexpected therapeutic potentials. Ongoing clinical trials and formulation developments promise to further optimize its clinical utility in the coming years.

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