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].
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2D Structure
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Physico-chemical Properties
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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
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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
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
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)
DrugBank Ligand DB01601
GtoPdb PubChem SID 441604876
PubChem CID 92727
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UniChem Compound Search for chemical match using the InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N
UniChem Connectivity Search for chemical match using the InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N