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CHEBI:367163 - darunavir

ChEBI IDCHEBI:367163
ChEBI Namedarunavir
Stars
DefinitionAn N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.
Secondary ChEBI IDsCHEBI:39487, CHEBI:589942
Last Modified22 February 2017
DownloadsMolfile
FormulaC27H37N3O7S
Net Charge0
Average Mass547.674
Monoisotopic Mass547.23522
SMILES[H][C@]12OCC[C@@]1([H])[C@@H](OC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CN(CC(C)C)S(=O)(=O)c1ccc(N)cc1)CO2
InChIInChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
InChIKeyCJBJHOAVZSMMDJ-HEXNFIEUSA-N
Wikipedia
Roles Classification
Biological Roles:
HIV protease inhibitor  An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
Application:
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
ChEBI Ontology
Outgoing Relation(s)
darunavir (CHEBI:367163) has role antiviral drug (CHEBI:36044)
darunavir (CHEBI:367163) has role HIV protease inhibitor (CHEBI:35660)
darunavir (CHEBI:367163) is a carbamate ester (CHEBI:23003)
darunavir (CHEBI:367163) is a furofuran (CHEBI:47790)
darunavir (CHEBI:367163) is a sulfonamide (CHEBI:35358)
Incoming Relation(s)
Prezcobix (CHEBI:90928) has part darunavir (CHEBI:367163)
IUPAC Name 
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate
INNs  Source
darunavirumChemIDplus
darunavirChemIDplus
Synonyms  Source
(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATEPDBeChem
(3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamateChEMBL
TMC114ChEMBL
{(1S,2R)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) esterChEMBL
(3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamateChEMBL
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) esterChEMBL
Manual XrefsDatabases
017PDBeChem
D03656KEGG DRUG
DB01264DrugBank
DarunavirWikipedia
4143DrugCentral
Registry NumbersSources
Reaxys:7960555Reaxys
CAS:206361-99-1KEGG DRUG
CAS:206361-99-1ChemIDplus
Citations