darunavir   

GtoPdb Ligand ID: 11243

Abbreviated name: DRV
Synonyms: Prezista® | TMC114 | UIC-94017
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
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
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
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
[(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
INN number INN
8305 darunavir
Synonyms
Prezista® | TMC114 | UIC-94017
Database Links
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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Search UniChem for chemical match using the InChIKey CJBJHOAVZSMMDJ-HEXNFIEUSA-N
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Wikipedia Darunavir