CHEBI:82941 - fosamprenavir

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ChEBI Name fosamprenavir
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H36N3O9PS
Net Charge 0
Average Mass 585.60700
Monoisotopic Mass 585.19099
InChI InChI=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
SMILES CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)c1ccc(N)cc1
Roles Classification
Application(s): 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.
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ChEBI Ontology
Outgoing 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)
(3S)-tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-1-phenyl-3-(phosphonooxy)butan-2-yl]carbamate
INN Source
fosamprenavir ChemIDplus
Synonym Source
FOS-APV ChemIDplus
Manual Xrefs Databases
1240 DrugCentral
DB01319 DrugBank
Fosamprenavir Wikipedia
HMDB0015416 HMDB
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Registry Numbers Types Sources
226700-79-4 CAS Registry Number ChemIDplus
9824450 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16890834 PubMed citation Europe PMC
22100576 PubMed citation Europe PMC
23314414 PubMed citation Europe PMC
23811744 PubMed citation Europe PMC
24741696 PubMed citation Europe PMC
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Last Modified
22 February 2017