LOPINAVIR

Search structure
Synonyms:
Status: Approved (2000)
Entry Type: Small molecule
Molecule Category: Parent
UNII: 2494G1JF75

Structure
InChI Key KJHKTHWMRKYKJE-SUGCFTRWSA-N
Smile Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)C[C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)N1CCCNC1=O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C37H48N4O5
Molecular Weight 628.81
AlogP 4.33
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 15.0
Polar Surface Area 120.0
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 46.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Human immunodeficiency virus type 1 protease inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - 410-1000 -
Enzyme Protease Aspartic protease Aspartic protease AA clan Aspartic protease A2A subfamily
- 25 0.1 0.0013-6.1 93-93
Enzyme Protease Cysteine protease Cysteine protease PAC clan Cysteine protease C3A subfamily
1160 2.5-25 0.0013-1.1 0.005-1.4 -
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M48A subfamily
- 18400 - - -
Enzyme Transferase
- 9120 - - 1.914-33
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - 0.69-18.98
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 8511.38 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 84.6
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 1700-10300 - - 50
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 21000 - - -
Transporter Primary active transporter ATP-binding cassette ABCG subfamily
- 7600 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 4 D015658 ClinicalTrials
Coronavirus Infections 3 D018352 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Pneumonia 3 D011014 ClinicalTrials
Coronavirus Infections 3 D018352 ClinicalTrials
Influenza, Human 3 D007251 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Pregnancy 2 D011247 ClinicalTrials
Infections 2 D007239 ClinicalTrials
Tuberculosis 1 D014376 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Insulin Resistance 1 D007333 ClinicalTrials
Respiratory Distress Syndrome 1 D012128 ClinicalTrials
Anus Neoplasms 1 D001005 ClinicalTrials

Related Entries

Scaffolds

Mixture
Mixture

Cross References

Resources Reference
CAS NUMBER 192725-17-0
ChEBI 31781
ChEMBL CHEMBL729
DrugBank DB01601
DrugCentral 1601
EPA CompTox DTXSID8046456
FDA SRS 2494G1JF75
Human Metabolome Database HMDB15539
KEGG C12871
PDB AB1
PharmGKB PA450264
PubChem 92727
SureChEMBL SCHEMBL21775
ZINC ZINC000003951740
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