CHEBI:367163 - darunavir

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ChEBI Name darunavir
ChEBI ID CHEBI:367163
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39487, CHEBI:589942
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Formula C27H37N3O7S
Net Charge 0
Average Mass 547.66400
Monoisotopic Mass 547.235
InChI InChI=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
InChIKey CJBJHOAVZSMMDJ-HEXNFIEUSA-N
SMILES [H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](Cc1ccccc1)[C@H](O)CN(CC(C)C)S(=O)(=O)c1ccc(N)cc1
Roles Classification
Biological Role(s): 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(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
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ChEBI Ontology
Outgoing 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 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 Sources
darunavir ChemIDplus
darunavirum ChemIDplus
Synonyms Sources
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N1-isobutylsulfanilamido)propyl)carbamate ChemIDplus
(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE PDBeChem
(3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate ChEMBL
(3R,3aS,6aR)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate ChEMBL
[(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) ester ChEMBL
Darunavir ChEMBL
N-((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamide ChemIDplus
TMC114 ChEMBL
{(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) ester ChEMBL
Manual Xrefs Databases
017 PDBeChem
4143 DrugCentral
D03656 KEGG DRUG
Darunavir Wikipedia
DB01264 DrugBank
View more database links
Registry Numbers Types Sources
206361-99-1 CAS Registry Number ChemIDplus
206361-99-1 CAS Registry Number KEGG DRUG
7960555 Reaxys Registry Number Reaxys
7960555 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
15771427 PubMed citation ChEMBL
16480273 PubMed citation ChEMBL
25017682 PubMed citation Europe PMC
Last Modified
22 February 2017