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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View more information in the IUPHAR Pharmacology Education Project: darunavir

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2006), EMA (2007))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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
Specialist databases
Reactome Reaction Reactome logo R-HSA-9697043
Other databases
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
Search Google for chemical match using the InChIKey CJBJHOAVZSMMDJ-HEXNFIEUSA-N
Search Google for chemicals with the same backbone CJBJHOAVZSMMDJ
Search PubMed clinical trials darunavir
Search PubMed titles darunavir
Search PubMed titles/abstracts darunavir
UniChem Compound Search for chemical match using the InChIKey CJBJHOAVZSMMDJ-HEXNFIEUSA-N
UniChem Connectivity Search for chemical match using the InChIKey CJBJHOAVZSMMDJ-HEXNFIEUSA-N
Wikipedia Darunavir