darunavir   Click here for help

GtoPdb Ligand ID: 11243

Abbreviated name: DRV
Synonyms: Prezista® | TMC114 | UIC-94017
Approved drug PDB Ligand
darunavir is an approved drug (FDA (2006), EMA (2007))
Compound class: Synthetic organic
Comment: Darunavir is a second-generation human immunodeficiency virus 1 (HIV-1) protease inhibitor (PI) [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 148.8
Molecular weight 547.24
XLogP 2.28
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@@H]2[C@H]1CCO2)O)C
Isomeric SMILES CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@@H]2[C@H]1CCO2)O)C
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
InChI Key CJBJHOAVZSMMDJ-HEXNFIEUSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2006), EMA (2007))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
[(3R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofuro[5,4-b]furan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
8305 darunavir
Synonyms Click here for help
Prezista® | TMC114 | UIC-94017
Database Links Click here for help
CAS Registry No. 206361-99-1 (source: Scifinder)
ChEBI CHEBI:367163
ChEMBL Ligand CHEMBL1323
DrugBank Ligand DB01264
DrugCentral Ligand 4143
GtoPdb PubChem SID 434122303
PubChem CID 213039
RCSB PDB Ligand 017
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Wikipedia Darunavir