A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Amprenavir are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Amprenavir?

The molecule Amprenavir presents a molecular formula of C25H35N3O6S and its IUPAC name is [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate.

Amprenavir is a molecule used as an antiretroviral drug. It is a reverse transcriptase inhibitor (RTI) and is used to treat human immunodeficiency virus (HIV) infection. Amprenavir was the first RTI approved by the United States Food and Drug Administration (FDA) for the treatment of HIV..

Amprenavir is a member of the class of drugs known as protease inhibitors (PIs). PIs block the activity of protease, an enzyme that HIV uses to mature and produce new viruses. By blocking protease, PIs prevent HIV from replicating. Amprenavir was the first PI approved by the FDA for the treatment of HIV..

Amprenavir is a white to off-white powder that is soluble in water. It exists as capsules and as an oral solution. The capsules are white, hard, and gelatinous with a purple band imprinted with "APV" in black ink. The oral solution is a clear, colorless to pale yellow solution..

Amprenavir is usually taken twice a day with or without food. The capsules can be taken with or without food. The oral solution must be taken with food..

Amprenavir is metabolized in the liver by the cytochrome P450 system. Drugs that are substrates of the cytochrome P450 system may interact with amprenavir. Amprenavir is also a substrate of P-glycoprotein (P-gp). Drugs that are P-gp inhibitors may increase the plasma concentrations of amprenavir..

Amprenavir is eliminated from the body primarily by the kidneys. The elimination half-life of amprenavir is about 3 to 5 hours..

The most common side effects of amprenavir are diarrhea, nausea, and vomiting. Other common side effects include fatigue, headache, and rash..

Amprenavir is a potent antiretroviral drug that is used to treat human immunodeficiency virus (HIV) infection. Amprenavir is a member of the class of drugs known as protease inhibitors (PIs). PIs block the activity of protease, an enzyme that HIV uses to mature and produce new viruses. By blocking protease, PIs prevent HIV from replicating. Amprenavir was the first PI approved by the FDA for the treatment of HIV..

3D structure

Cartesian coordinates

Geometry of Amprenavir in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing


Amprenavir YMARZQAQMVYCKC-OEMFJLHTSA-N chemical compound 2D structure molecule svg


Molecule descriptors

IUPAC name[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
InChI codeInChI=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

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
  • (3S)-Tetrahydro-3-furyl ((alphaS)-alpha-((1R-1-hydroxy-2-(N(sup 1)-isobutylsulfanilamido)ethyl)phenethyl)carbamate
  • (3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate
  • (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
  • (3S)-tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate
  • (3S-(3R*(1R*,2S*)))-(3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl) tetrahydro-3-furanyl carbamate
  • (S)-tetrahydrofuran-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate
  • 141 W94
  • 141W94
  • 161814-49-9
  • 1hpv
  • 1t7j
  • 3ekp
  • 3ekv
  • 3nu3
  • 3nu4
  • 3nu5
  • 3nu6
  • 3nu9
  • 3nuj
  • 3nuo
  • 3s43
  • 3s45
  • 3sm2
  • 4-Amino-N-((2 syn,3S)-2-hydroxy-4-phenyl-3-((S)-tetrahydrofuran-3-yloxycarbonylamino)-butyl)-N-isobutyl-benzenesulfonamide
  • 5S0W860XNR
  • 814A499
  • A810295
  • AB01275534-01
  • AB01275534_02
  • AM84544
  • AMV
  • APV & AAG
  • APV & HSA
  • AS-30915
  • Agenerase
  • Agenerase (TM)
  • Amprenavir
  • Amprenavir & alpha1-acid glycoprotein
  • Amprenavir & human serum albumin
  • Amprenavir (JAN/USAN/INN)
  • Amprenavir (agenerase)
  • BCP0726000051
  • BCP9000297
  • BDBM50215393
  • BIDD:GT0398
  • C08086
  • CCG-269742
  • CS-1410
  • Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl 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)
  • 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)
  • Carbamic acid, (3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, tetrahydro-3-furanyl ester, (3S-(3R*(1S*,2R*)))-
  • Carbamic acid, N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester
  • Carbamic acid,[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-,(3S)-tetrahydro-3-furanyl ester
  • D00894
  • DB00701
  • DRG-0258
  • GNA & Amprenavir
  • HHA & Amprenavir
  • HMS2090N10
  • HSDB 7157
  • HY-17430
  • J05AE05
  • KVX-478
  • MFCD00934214
  • MLS006011492
  • N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamic acid [(3S)-3-oxolanyl] ester
  • NCGC00159461-02
  • NCGC00159461-07
  • NCGC00159461-08
  • Prozei
  • Q422198
  • SMR003885056
  • SR-05000001530
  • SR-05000001530-1
  • SW219687-1
  • Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate
  • VX 478
  • VX-478
  • VX478
  • Vertex VX478
  • Z1557399789
  • [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
  • [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-oxidanyl-1-phenyl-butan-2-yl]carbamate
  • [(3S)-tetrahydrofuran-3-yl] N-[(1S,2R)-3-[(4-aminophenyl)sulfonyl-isobutyl-amino]-1-benzyl-2-hydroxy-propyl]carbamate
  • amprenavir
  • s1639

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3809192
  • UNII-5S0W860XNR
  • AKOS000280844
  • DTXSID5046061
  • CHEMBL116
  • CHEBI:40050
  • SCHEMBL34151

Physico-Chemical properties

IUPAC name[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
Molecular formulaC25H35N3O6S
Molecular weight505.627
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity133.62
Topological polar surface area139.6

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.