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darunavir

CHEBI: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.

Chemical Information

Molecular Formula
C27H37N3O7S
Molecular Mass
547.66400
Charge
0
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
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

Alternative Names

  • (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
  • (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamate
  • (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE
  • (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
  • (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
  • [(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
  • {(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
  • darunavir
  • Darunavir
  • darunavirum
  • 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
  • TMC114

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

core#notation
CHEBI:367163
oboInOwl#hasDbXref
Wikipedia:Darunavir
DRON_00010000
460132

Additional References

Wikipedia:Darunavir

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT
listing_expiration_date
20241231
route
ORAL
dosage_form
POWDER
marketing_start_date
20130420
labeler_name
JANSSEN ORTHO LLC
spl_id
0bfdfac4-aec7-0e33-e063-6394a90a925d
package_ndc
50370-0037-1
application_number
NDA021976
package_marketing_start_date
20-APR-13
package_description
60 kg in 1 DRUM (50370-0037-1)
rxcui
1600710
active_ingredient_strength
1 kg/kg
nui
N0000175889
manufacturer_name
Cipla USA Inc.
active_ingredient_name
DARUNAVIR DIHYDRATE
unii
YO603Y8113
spl_set_id
814301f9-c990-46a5-b481-2879a521a16f
upc
0359676563013
core#notation
CHEBI:367163
pharm_class_moa
HIV Protease Inhibitors [MoA]
pharm_class
Protease Inhibitor [EPC]
pharm_class_epc
Protease Inhibitor [EPC]
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
oboInOwl#hasOBONamespace
chebi_ontology
oboInOwl#hasDbXref
Wikipedia:Darunavir
DRON_00010000
460132
oboInOwl#id
CHEBI:367163
oboInOwl#hasAlternativeId
CHEBI:589942
generic_name
Darunavir Hydrate
brand_name
PREZISTA
brand_name_base
PREZISTA
product_ndc
50370-0037
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_35660
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect22215
owl#annotatedSource
t204243
owl#someValuesFrom
t3318203