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].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2000), EMA (2001))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). 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
Search UniChem for chemical match using the InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N
Search UniChem for chemicals with the same backbone KJHKTHWMRKYKJE