(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

• ChemBase ID: 1378
• Molecular Formular: C37H48N4O5
• Molecular Mass: 628.80082
• Monoisotopic Mass: 628.36247066
• SMILES: O[C@@H](C[C@@H](NC(=O)[C@@H](N1CCCNC1=O)C(C)C)Cc1ccccc1)[C@@H](NC(=O)COc1c(cccc1C)C)Cc1ccccc1
• 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
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: lopinavir
• Brand Name: Aluviran; Koletra
• Synonyms: (αS)-N-[(1S,3S,4S)-4-[[2-(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetamide; A 157378.0; ABT 378; Aluviran; Koletra; ABT-378; LPV; Lopinavir

Database IDs

• CAS Number: 192725-17-0
• MDL Number: MFCD22373646
• PubChem SID: 46508588; 160964838
• PubChem CID: 92727

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.3924265
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 4.687642
• LogD (pH = 7.4): 4.6876416
• Log P: 4.687642
• Molar Refractivity: 179.3637 cm^3
• Polarizability: 69.683624 Å^3
• Polar Surface Area: 120.0 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.91
• LOG S: -5.51
• Solubility (Water): 1.92e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: White Crystalline Solid
• Melting Point: 124-127°C

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

Pharmacology Properties

• Target: protease

Product Information

• Purity: 95%; 98%
• Salt Data: Free Base

DETAILS

DrugBank - DB01601

• Drug Groups: approved
• Description: Lopinavir (ABT-378) is an antiretroviral of the protease inhibitor class. It is marketed by Abbott as Kaletra, a co-formulation with a sub-therapeutic dose of ritonavir, as a component of combination therapy to treat HIV/AIDS.
• Indication: Indicated in combination with other antiretroviral agents for the treatment of HIV-infection.
• Pharmacology: Lopinavir is an antiretroviral of the protease inhibitor class. Inhibiting HIV-1 protease (responsible for protein cleavage), results in selectively inhibiting the cleavage of HIV gag and gag-pol polyproteins, thereby preventing viral maturation.
• Toxicity: Although human experience of acute overdosage with lopinavir is limited, accidental ingestion of the product by a young child could result in significant alcohol-related toxicity and could approach the potential lethal dose of alcohol.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Hepatic. Lopinavir is extensively metabolized by the hepatic cytochrome P450 system, almost exclusively by the CYP3A isozyme.
• Absorption: Administered alone, lopinavir has insufficient bioavailability; however, like several HIV protease inhibitors, its blood levels are greatly increased by low doses of ritonavir, a potent inhibitor of cytochrome P450 3A4.
• Protein Binding: Lopinavir is highly bound to plasma proteins (98-99%).
• External Links: Wikipedia; RxList; PDRhealth

Selleck Chemicals - S1380

Research Area: Infection
Biological Activity:
Lopinavir (ABT-378) is an antiretroviral of the protease inhibitor class. As a component of combination therapy to treat HIV/AIDS. Inhibition of HIV-1 protease prevents cleavage of the viral polyprotein precursor and results in the release of immature, noninfectious virions. [1]

Toronto Research Chemicals - L469480

A selective HIV protease inhibitor. An analogue of Ritonavir. Antiviral.

REFERENCES

• http://www.rxlist.com/kaletra-capsules-drug.htm
• Sham, H.L., et al.: Antimicrob. Ag. Chemother., 42, 3218 (1998)
• Kumar, G.N., et al.: Drug Metab. Dispos., 27, 86 (1998)
• Murphy, R.L., et al.: Antiviral Ther., 4, Suppl. 3, 85 (1999)