lopinavir   Click here for help

GtoPdb Ligand ID: 11504

Synonyms: A-157378-0 | A-1573780 | ABT-378 | ABT378 | Aluviran® | Kaletra® (LPV+RTV)
Approved drug PDB Ligand
lopinavir is an approved drug (FDA (2000), EMA (2001))
Compound class: Synthetic organic
Comment: Lopinavir is an antiretroviral protease inhibitor. It has subsequently been discovered to exhibit antiviral activity against human papilloma virus (HPV), and to inhibit MERS-CoV replication in vitro [3]. Antiviral activity against SARS-CoV-2 has been explored [1], however lopinavir/ritonavir therapy provided no benefit in hospitalised COVID-19 patients [2].
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 8
Hydrogen bond donors 4
Rotatable bonds 17
Topological polar surface area 120
Molecular weight 628.36
XLogP 4.84
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 O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)[C@@H](N1CCCNC1=O)C(C)C)O)Cc1ccccc1)COc1c(C)cccc1C
Isomeric SMILES O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)[C@@H](N1CCCNC1=O)C(C)C)O)Cc1ccccc1)COc1c(C)cccc1C
InChI InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1
InChI Key KJHKTHWMRKYKJE-SUGCFTRWSA-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 (2000), EMA (2001))
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.
Prodrug His-Leu-lopinavir
IUPAC Name Click here for help
(2S)-N-[(2S,4S,5S)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
International Nonproprietary Names Click here for help
INN number INN
7798 lopinavir
Synonyms Click here for help
A-157378-0 | A-1573780 | ABT-378 | ABT378 | Aluviran® | Kaletra® (LPV+RTV)
Database Links Click here for help
BindingDB Ligand 50180655
CAS Registry No. 192725-17-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL729
DrugBank Ligand DB01601
GtoPdb PubChem SID 441604876
PubChem CID 92727
RCSB PDB Ligand AB1
Search Google for chemical match using the InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N
Search Google for chemicals with the same backbone KJHKTHWMRKYKJE
Search PubMed clinical trials lopinavir
Search PubMed titles lopinavir
Search PubMed titles/abstracts lopinavir
UniChem Compound Search for chemical match using the InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N
UniChem Connectivity Search for chemical match using the InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N