CHEBI:31781 - lopinavir

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ChEBI Name lopinavir
ChEBI ID CHEBI:31781
Definition A dicarboxylic acid amide in which a parent structure of amphetamine is substituted on nitrogen by a (2,6-dimethylphenoxy)acetyl group and on the carbon alpha to nitrogen by a (1S,3S)-1-hydroxy-3-{[(2S)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoyl]amino}-4-phenylbutyl group. An antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C37H48N4O5
Net Charge 0
Average Mass 628.80080
Monoisotopic Mass 628.362
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
InChIKey KJHKTHWMRKYKJE-SUGCFTRWSA-N
SMILES CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](Cc1ccccc1)NC(=O)COc1c(C)cccc1C)Cc1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
HIV protease inhibitor
An inhibitor of HIV protease, an enzyme required for production of proteins needed for viral assembly.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
(via amphetamines )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lopinavir (CHEBI:31781) has role antiviral drug (CHEBI:36044)
lopinavir (CHEBI:31781) has role HIV protease inhibitor (CHEBI:35660)
lopinavir (CHEBI:31781) is a amphetamines (CHEBI:35338)
lopinavir (CHEBI:31781) is a dicarboxylic acid diamide (CHEBI:35779)
IUPAC Name
(2S)-N-[(2S,4S,5S)-5-{[(2,6-dimethylphenoxy)acetyl]amino}-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide
Synonym Source
Lopinavir KEGG COMPOUND
Manual Xrefs Databases
1601 DrugCentral
AB1 PDBeChem
C12871 KEGG COMPOUND
D01425 KEGG DRUG
DB01601 DrugBank
HMDB0015539 HMDB
LSM-6027 LINCS
View more database links
Registry Numbers Types Sources
192725-17-0 CAS Registry Number ChemIDplus
9309881 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
24014186 PubMed citation Europe PMC
24518130 PubMed citation Europe PMC
24566184 PubMed citation Europe PMC
24805184 PubMed citation Europe PMC
24906762 PubMed citation Europe PMC
24958908 PubMed citation Europe PMC
25120613 PubMed citation Europe PMC
Last Modified
22 February 2017