Fosamprenavir calcium (CHEM019243)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:56:34 UTC
Update Date2016-11-09 01:15:57 UTC
Accession NumberCHEM019243
Identification
Common NameFosamprenavir calcium
ClassSmall Molecule
DescriptionFosamprenavir (marketed by ViiV Healthcare as the calcium salt under the trade names Lexiva in the U.S. and Telzir in Europe) is a drug for the treatment of HIV infections. It is a pro-drug of the protease inhibitor and antiretroviral drug amprenavir. The FDA approved it October 20, 2003, while the EMA approved it on July 12, 2004. The human body metabolizes fosamprenavir in order to form amprenavir, which is the active ingredient. That metabolization increases the duration that amprenavir is available, making fosamprenavir a slow-release version of amprenavir and thus reducing the number of pills required versus standard amprenavir. A head-to-head study with lopinavir showed the two drugs to have comparable potency, but patients on fosamprenavir tended to have a higher serum cholesterol. Fosamprenavir's main advantage over lopinavir is that it is cheaper.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LexivaKegg
TelzirKegg
(3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)carbamic acid C-(tetrahydro-3-furanyl) esterMeSH
VX175 CPDMeSH
Fos-amprenavirMeSH
FosamprenavirMeSH
GW908 CPDMeSH
Calcium;[(2R,3S)-1-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphoric acidGenerator
Calcium;[(2R,3S)-1-[(4-aminophenyl)sulphonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphateGenerator
Calcium;[(2R,3S)-1-[(4-aminophenyl)sulphonyl-(2-methylpropyl)amino]-3-[[(3S)-oxolan-3-yl]oxycarbonylamino]-4-phenylbutan-2-yl] phosphoric acidGenerator
Fosamprenavir calciumMeSH
Calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidic acidGenerator
Calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulphonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidateGenerator
Calcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulphonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidic acidGenerator
Chemical FormulaC25H34CaN3O9PS
Average Molecular Mass623.670 g/mol
Monoisotopic Mass623.138 g/mol
CAS Registry Number226700-81-8
IUPAC Namecalcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidate
Traditional Namecalcium N-[(2S,3R)-3-(hydrogen phosphonatooxy)-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]-1-[(3S)-oxolan-3-yloxy]methanecarboximidate
SMILES[Ca++].[H][C@](CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1)(OP(O)([O-])=O)[C@]([H])(CC1=CC=CC=C1)N=C([O-])O[C@@]1([H])CCOC1
InChI IdentifierInChI=1S/C25H36N3O9PS.Ca/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21;/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32);/q;+2/p-2/t21-,23-,24+;/m0./s1
InChI KeyPMDQGYMGQKTCSX-HQROKSDRSA-L
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
  • Phosphoethanolamine
  • Aniline or substituted anilines
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Organosulfonic acid amide
  • Alkyl phosphate
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Carbamic acid ester
  • Tetrahydrofuran
  • Sulfonyl
  • Carbonic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Ether
  • Organic calcium salt
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Organic zwitterion
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.072 g/LALOGPS
logP2.68ALOGPS
logP2.65ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)1.36ChemAxon
pKa (Strongest Basic)2.43ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area186.87 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity155.17 m³·mol⁻¹ChemAxon
Polarizability56.69 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-95a294b3c9beee05048dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000009000-95a294b3c9beee05048dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0000009000-95a294b3c9beee05048dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-f67ad6df1b5fddfff332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000009000-f67ad6df1b5fddfff332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000009000-f67ad6df1b5fddfff332Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001228
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFosamprenavir
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131535
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available