Amprenavir (CHEM002251)

Record Information
Version1.0
Creation Date2009-07-21 20:27:27 UTC
Update Date2026-05-14 16:46:28 UTC
Accession NumberCHEM002251
Identification
Common NameAmprenavir
ClassSmall Molecule
Description
Amprenavir is only found in individuals that have used or taken this drug. It is a protease inhibitor used to treat HIV infection.Amprenavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anti-HIV Agent
  • Antibiotic, Antitubercular
  • Drug
  • Ester
  • Ether
  • HIV Protease Inhibitor
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamateChEBI
AgeneraseChEBI
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acidGenerator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamateGenerator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acidGenerator
AMPHMDB
AMVHMDB
VX-478HMDB
GlaxoSmithKline brand OF amprenavirHMDB
Vertex VX478HMDB
Glaxo wellcome brand OF amprenavirHMDB
Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamateHMDB
Chemical FormulaC25H35N3O6S
Average Molecular Mass505.627 g/mol
Monoisotopic Mass505.225 g/mol
CAS Registry Number161814-49-9
IUPAC Name(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
Traditional Nameamprenavir
SMILESCC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1
InChI IdentifierInChI=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 KeyYMARZQAQMVYCKC-OEMFJLHTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Phenylbutylamine
  • Amphetamine or derivatives
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Carbamic acid ester
  • Tetrahydrofuran
  • Sulfonyl
  • Carbonic acid derivative
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility4.91e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP1.85ALOGPS
logP2.43ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.19 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity134.08 m³·mol⁻¹ChemAxon
Polarizability53.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureRapidly absorbed after oral administration in HIV-1-infected patients with a time to peak concentration (Tmax) typically between 1 and 2 hours after a single oral dose. The absolute oral bioavailability of amprenavir in humans has not been established.
Mechanism of ToxicityAmprenavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
MetabolismHepatic. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system. The 2 major metabolites result from oxidation of the tetrahydrofuran and aniline moieties. Glucuronide conjugates of oxidized metabolites have been identified as minor metabolites in urine and feces. Half Life: 7.1-10.6 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of HIV-1 infection in combination with other antiretroviral agents.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentIf overdosage occurs, the patient should be monitored for evidence of toxicity and standard supportive treatment applied as necessary. (2)
Concentrations
Not Available
External Links
DrugBank IDDB00701
HMDB IDHMDB0014839
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB ID478
Wikipedia LinkAmprenavir
Chemspider ID58532
ChEBI ID40050
PubChem Compound ID65016
Kegg Compound IDC08086
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSNot Available
General References