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CHEBI:367163 - darunavir

Default Structure
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
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
antiviral agent  A substance that destroys or inhibits replication of viruses.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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.
Applications:
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
ChEBI Ontology
Outgoing Relation(s)
darunavir (CHEBI:367163) has role anti-HIV agent (CHEBI:64946)
darunavir (CHEBI:367163) has role antifungal agent (CHEBI:35718)
darunavir (CHEBI:367163) has role antiinfective agent (CHEBI:35441)
darunavir (CHEBI:367163) has role antiviral agent (CHEBI:22587)
darunavir (CHEBI:367163) has role antiviral drug (CHEBI:36044)
darunavir (CHEBI:367163) has role HIV protease inhibitor (CHEBI:35660)
darunavir (CHEBI:367163) has role insulin-sensitizing drug (CHEBI:50864)
darunavir (CHEBI:367163) is a benzenes (CHEBI:22712)
darunavir (CHEBI:367163) is a carbamate ester (CHEBI:23003)
darunavir (CHEBI:367163) is a furofuran (CHEBI:47790)
darunavir (CHEBI:367163) is a organic amino compound (CHEBI:50047)
darunavir (CHEBI:367163) is a organic molecular entity (CHEBI:50860)
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
darunavirChemIDplus
darunavirumChemIDplus
Synonyms  Source
{(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)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N1-isobutylsulfanilamido)propyl)carbamateChemIDplus
(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
(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
(-)-darunavirChEMBL
Brand Names  Source
Darunavir component of prezcobixChEMBL
Darunavir component of symtuzaChEMBL
Darunavir krkaChEMBL
Darunavir krka d.d.ChEMBL
Darunavir viatris (previously darunavir mylan)ChEMBL
Manual XrefsDatabases
017PDBeChem
4143DrugCentral
D03656KEGG DRUG
DarunavirWikipedia
DB01264DrugBank
Registry NumbersSources
Reaxys:7960555Reaxys
CAS:206361-99-1KEGG DRUG
CAS:206361-99-1ChemIDplus
Citations