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CHEBI:82941 - fosamprenavir

ChEBI IDCHEBI:82941
ChEBI Namefosamprenavir
Stars
DefinitionA sulfonamide with a structure based on that of sulfanilamide substituted on the sulfonamide nitrogen by a (2R,3S)-4-phenyl-2-(phosphonooxy)-3-({[(3S)-tetrahydrofuran-3-yloxy]carbonyl}amino)butyl group. It is a pro-drug of the HIV protease inhibitor and antiretroviral drug amprenavir.
Last Modified22 February 2017
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC25H36N3O9PS
Net Charge0
Average Mass585.616
Monoisotopic Mass585.19099
SMILESCC(C)CN(C[C@@H](OP(=O)(O)O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)c1ccc(N)cc1
InChIInChI=1S/C25H36N3O9PS/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)/t21-,23-,24+/m0/s1
InChIKeyMLBVMOWEQCZNCC-OEMFJLHTSA-N
Wikipedia
Roles Classification
Application:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
fosamprenavir (CHEBI:82941) has functional parent sulfanilamide (CHEBI:45373)
fosamprenavir (CHEBI:82941) has role prodrug (CHEBI:50266)
fosamprenavir (CHEBI:82941) is a sulfonamide (CHEBI:35358)
IUPAC Name 
(3S)-tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate
INN  Source
fosamprenavirChemIDplus
Synonym  Source
FOS-APVChemIDplus
Manual XrefsDatabases
FosamprenavirWikipedia
D02497KEGG DRUG
DB01319DrugBank
HMDB0015416HMDB
1240DrugCentral
Registry NumbersSources
Reaxys:9824450Reaxys
CAS:226700-79-4ChemIDplus
Citations