Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0976)
Drug Name
Lopinavir
Synonyms
Lopinavir; Lopinavir (ABT-378); RS-346; Aluviran; Kaletra; Koletra; (alphaS)-Tetrahydro-N-((alphaS)-alpha-((2S,3S)-2-hydroxy-4-phenyl-3-(2-(2,6-xylyloxy)acetamido)butyl)phenethyl)-alpha-isopropyl-2-oxo-1(2H)-pyrimidineacetamide; 192725-17-0; 2494G1JF75; A 157378; A 157378.0; A-157378-0; A-157378.0; ABT 378; ABT-378; CHEBI:31781; DSSTox_RID_81630; LPV; N-{1-BENZYL-4-[2-(2,6-DIMETHYL-PHENOXY)-ACETYLAMINO]-3-HYDROXY-5-PHENYL-PENTYL}-3-METHYL-2-(2-OXO-TETRAHYDRO-PYRIMIDIN-1-YL)-BUTYRAMIDE; NCGC00164576-02; UNII-2494G1JF75
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 628.8 Topological Polar Surface Area 120
Heavy Atom Count 46 Rotatable Bond Count 15
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
92727
PubChem SID
583260 ; 615079 ; 826916 ; 841952 ; 7848488 ; 7885634 ; 7979791 ; 10225535 ; 11108093 ; 11528784 ; 14912304 ; 14912305 ; 26737285 ; 26757998 ; 44423527 ; 46392556 ; 46508588 ; 49853992 ; 50086984 ; 50096471 ; 50096475 ; 50111692 ; 53812811 ; 53812974 ; 56310583 ; 57335304 ; 76999753 ; 87557375 ; 87557376 ; 99437252 ; 103198077 ; 104178992 ; 104408196 ; 123080504 ; 124757206 ; 124893167 ; 125164010 ; 126522368 ; 126655919 ; 126665841 ; 127310211 ; 127310212 ; 127310213 ; 127338643 ; 127338644 ; 127338645 ; 134337997 ; 135051036 ; 136283935 ; 136367896
ChEBI ID
CHEBI:31781
CAS Number
192725-17-0
TTD Drug ID
D0U5GB
Formula
C37H48N4O5
Canonical SMILES
CC1=C(C(=CC=C1)C)OCC(=O)NC(CC2=CC=CC=C2)C(CC(CC3=CC=CC=C3)NC(=O)C(C(C)C)N4CCCNC4=O)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Lopinavir Metabolite M-2 DM006421 N. A. Oxidation - Oxidationn 1 [3]
Lopinavir Metabolite M-3/M-4 DM006419
46782075
Oxidation - Oxidationn 1 [2]
Lopinavir Metabolite M-1 DM006420
486506
Other reaction - Ketone formation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006898 Lopinavir Lopinavir Metabolite M-3/M-4 Oxidation - Oxidationn CYP3A4 [2]
MR006900 Lopinavir Lopinavir Metabolite M-2 Oxidation - Oxidationn Unclear [3]
MR006899 Lopinavir Metabolite M-3/M-4 Lopinavir Metabolite M-1 Other reaction - Ketone formation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Lopinavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Synthesis and antiviral activities of the major metabolites of the HIV protease inhibitor ABT-378 (Lopinavir). Bioorg Med Chem Lett. 2001 Jun 4;11(11):1351-3.
3 In vitro metabolism of the HIV-1 protease inhibitor ABT-378: species comparison and metabolite identification

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