Compound: Lopinavir
SMILES: O=C1N([C@H](C(=O)N[C@@H](Cc2ccccc2)C[C@H](O)[C@@H](NC(=O)COc3c(cccc3C)C)Cc4ccccc4)C(C)C)CCCN1
InChIKey: KJHKTHWMRKYKJE-SUGCFTRWSA-N
Synonyms: Lopinavir, 192725-17-0, ABT-378, Aluviran, Koletra, A 157378.0, A-157378.0, Lopinavirum, CHEBI:31781, A-157378-0, ABT378, DTXSID8046456, Lopinavir, (s-(2s,4s,5s))-, (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, 2494G1JF75, DTXCID6026456, (1S-(1R*(R*),3R*,4R*))-N-(4-(((2,6-Dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide, (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, 1(2H)-Pyrimidineacetamide, N-((1S,3S,4S)-4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahyrdo-alpha-1-methylethyl)-2-oxo-, (alphaS)-, (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, (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, N-(4-(((2,6-dimethylphenoxy)acetyl)amino)-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl)tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pydrimidineacetamide, RefChem:5960, ABT-378/r, A157378.0, J05AE06, ABT 378, (S)-N-((2S,4S,5S)-5-(2-(2,6-dimethylphenoxy)acetamido)-4-hydroxy-1,6-diphenylhexan-2-yl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide, RS-346, LPV, (alphaS)-N-[(1S,3S,4S)-4-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide, (2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide, A 157378, MFCD22628840, 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, C37H48N4O5, (2S)-N-[(1S,3S,4S)-1-benzyl-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-pentyl]-3-methyl-2-(2-oxohexahydropyrimidin-1-yl)butanamide, SMR002529581, CAS-192725-17-0, MFCD22373646, Lopinavir-, Lopinavir?, Lopinavir RS, Lopinavir CRS, UNII-2494G1JF75, HSDB 8138, 1mui, 2qhc, 2rkf, 2rkg, 3ogq, Lopinavir [USAN:USP:INN:BAN], AIDS032937, (2S)-N-((1S,3S,4S)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl)-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide, (2S)-N-[(1S,3S,4S)-1-benzyl-4-{[(2,6-dimethylphenoxy)acetyl]amino}-3-hydroxy-5-phenylpentyl]-3-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanamide, (2S)-N-{(2S,4S,5S)-5-[2-(2,6-Dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide, Lopinavir & PLGA, Lopinavir (Standard), Kaletra (LPV+RTV), 2o4s, 2q5k, 4l1a, LOPINAVIR [INN], LOPINAVIR [JAN], LOPINAVIR [MI], LOPINAVIR [USAN], LOPINAVIR [VANDF], Lopinavir (ABT-378), CHEMBL729, Epitope ID:231715, LOPINAVIR [MART.], LPV & AAG, LOPINAVIR [USP-RS], LOPINAVIR [WHO-DD], LOPINAVIR [WHO-IP], Lopinavir (JAN/USP/INN), SCHEMBL21775, LOPINAVIR [EMA EPAR], MLS003915624, MLS004774152, MLS006011206, ABT-378; LOPINAVIR, Lopinavir - Bio-X trade mark, orb1307985, LOPINAVIR [ORANGE BOOK], LOPINAVIR [EP MONOGRAPH], GTPL11504, LOPINAVIR [USP MONOGRAPH], KALETRA COMPONENT LOPINAVIR, KJHKTHWMRKYKJE-SUGCFTRWSA-N, GLXC-02734, LOPINAVIRUM [WHO-IP LATIN], EX-A4008, MSK10437, Tox21_112204, BDBM50180655, EBC-06069, HB7108, HY-14588R, Lopinavir & alpha1-acid glycoprotein, Lopinavir for system suitability CRS, s1380, Lopinavir for peak identification CRS, AKOS025243115, Tox21_112204_1, CCG-270285, CS-2077, DB01601, FL16558, KS-1436, Lopinavir 100 microg/mL in Acetonitrile, NCGC00164576-01, NCGC00164576-03, NCGC00164576-04, BL164636, HY-14588, SY073885, L0377, NS00008581, SW219767-1, D01425, SBI-0654097.0001, AB01274785-01, AB01274785_02, EN300-7402887, Q422585, SR-01000931910, SR-01000931910-2, A-1573780, BRD-K99451608-001-02-4, BRD-K99451608-001-07-3, Z2235801862, Lopinavir Working Standard (Secondary Reference Standard), (?-S)-N-[(1S,3S,4S)-4-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-?-(1-methylethyl)-, (|_S)-N-[(1S,3S,4S)-4-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-|_-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide, (|AS)-N-[(1S,3S,4S)-4-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-|A-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide, (1S-(1R*(R*),3R*,4R*))-N-(4-(((2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL)TETRAHYDRO-.ALPHA.-(1-METHYLETHYL)-2-OXO-1(2H)-PYRIMIDINEACETAMIDE, (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, 1(2H)-Pyrimidineacetamide, N-[(1S,3S,4S)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-.alpha.-(1-methylethyl)-2-oxo-, (aS)-, 1(2H)-Pyrimidineacetamide, N-[(1S,3S,4S)-4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, (alphaS)- (9CI), 1(2H)-pyrimidineacetamide, N-[(1S,3S,4S)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, (alphaS)-, 1(2H)-Pyrimidineacetamide, N-[4-[[(2,6-dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-alpha-(1-methylethyl)-2-oxo-, [1S-[1R*(R*),3R*,4R*]]-
Theoretical properties:
molecular_formula: C37H48N4O5
molecular_weight: 628.8 g/mol
exact_mass: 628.36247064 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 15
heavy_atom_count: 46
topological_polar_surface_area: 120 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless solid from ethyl acetone
color: Colorless solid from ethyl acetone
melting_point: 124-127 °C
solubility: Practically insoluble
Descriptions:
pubchem: Lopinavir is a dicarboxylic acid diamide that is 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-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. It has a role as an anticoronaviral agent, a HIV protease inhibitor and an antiviral drug. It is a member of amphetamines and a dicarboxylic acid diamide.
chebi: A dicarboxylic acid diamide that is amphetamine is substituted on nitrogen by a (2,6-dimethylphenoxy)acetyl group and on the carbon α- to nitrogen by a (1<i>S</i>,3<i>S</i>)-1-hydroxy-3-{[(2<i>S</i>)-3-methyl-2-(2-oxotetrahydropyrimidin-1-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.
chembl: LOPINAVIR is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Lopinavir is an antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir (lopinavir/ritonavir).
It was patented in 1995 and approved for medical use in 2000. Considered now as second-line therapy in the West, it is still prescribed in LMIC, especially among children living with HIV. Lopinavir and ritonavir can be taken as a tablet or an oral solution, a preferred option in children. In the early stages of COVID-19 pandemics, lopinavir was repurposed against the SARS-CoV-2 virus in the hope of disturbing its protease activity.