U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H48N4O5
Molecular Weight 628.8008
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOPINAVIR

SMILES

CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC2=CC=CC=C2)NC(=O)COC3=C(C)C=CC=C3C)CC4=CC=CC=C4

InChI

InChIKey=KJHKTHWMRKYKJE-SUGCFTRWSA-N
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

HIDE SMILES / InChI

Molecular Formula C37H48N4O5
Molecular Weight 628.8008
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Lopinavir (ABT-378) is an antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir, under the trade names Kaletra.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.3 pM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Principles and practice of HIV-protease inhibitor pharmacoenhancement.
2001 Apr
Combination of protease inhibitors for the treatment of HIV-1-infected patients: a review of pharmacokinetics and clinical experience.
2001 Dec
Therapeutic drug monitoring of HIV protease inhibitors using high-performance liquid chromatography with ultraviolet or photodiode array detection.
2001 Dec
Ototoxicity may be associated with protease inhibitor therapy.
2001 Dec 15
New drug approvals in 2000.
2001 Jul-Aug
Antiretroviral approved for use in infants.
2001 Jun 15
Resistant to everything.
2001 May
Lopinavir-Ritonavir: a new protease inhibitor.
2001 Nov
DPC 681 and DPC 684: potent, selective inhibitors of human immunodeficiency virus protease active against clinically relevant mutant variants.
2001 Nov
New developments in anti-HIV chemotherapy.
2001 Nov
Pharmacokinetics of amprenavir and lopinavir in combination with nevirapine in highly pretreated HIV-infected patients.
2001 Nov 23
What's new: newly approved drugs for children.
2001 Oct
Anti-HIV agents. Lopinavir--results after one year.
2001 Winter
Simultaneous determination of the six HIV protease inhibitors (amprenavir, indinavir, lopinavir, nelfinavir, ritonavir, and saquinavir) plus M8 nelfinavir metabolite and the nonnucleoside reverse transcription inhibitor efavirenz in human plasma by solid-phase extraction and column liquid chromatography.
2002 Apr
Absence of opioid withdrawal symptoms in patients receiving methadone and the protease inhibitor lopinavir-ritonavir.
2002 Apr 15
Simultaneous quantitative assay of six HIV protease inhibitors, one metabolite, and two non-nucleoside reverse transcriptase inhibitors in human plasma by isocratic reversed-phase liquid chromatography.
2002 Aug
X-ray crystallographic structure of ABT-378 (lopinavir) bound to HIV-1 protease.
2002 Aug
Gateways to clinical trials.
2002 Dec
Comparison of the efficacy, safety and predictive value of HIV genotyping using distinct ritonavir-boosted protease inhibitors.
2002 Dec
Efficacy of highly active antiretroviral therapy in HIV-1 infected children.
2002 Feb
Unfavourable interaction of amprenavir and lopinavir in combination with ritonavir?
2002 Jan 25
Differences in the detection of three HIV-1 protease inhibitors in non-blood compartments: clinical correlations.
2002 Jan-Feb
In vitro antiviral interaction of lopinavir with other protease inhibitors.
2002 Jul
Determination of lopinavir and nevirapine by high-performance liquid chromatography after solid-phase extraction: application for the assessment of their transplacental passage at delivery.
2002 Jul 15
New developments in anti-HIV chemotherapy.
2002 Jul 18
Kaletra (lopinavir/ritonavir).
2002 Jul-Aug
High-performance liquid chromatographic method for the simultaneous determination of the six HIV-protease inhibitors and two non-nucleoside reverse transcriptase inhibitors in human plasma.
2002 Jun
Lopinavir-ritonavir versus nelfinavir for the initial treatment of HIV infection.
2002 Jun 27
Increasing choices for HIV therapy.
2002 Jun 27
Efavirenz-induced skin eruption and successful desensitization.
2002 Mar
Delavirdine increases drug exposure of ritonavir-boosted protease inhibitors.
2002 Mar 29
Drug interaction between amprenavir and lopinavir/ritonavir in salvage therapy.
2002 Mar 29
Amprenavir-resistant HIV-1 exhibits lopinavir cross-resistance and reduced replication capacity.
2002 May 3
Select HIV protease inhibitors alter bone and fat metabolism ex vivo.
2002 May 31
Encouraging resistance data for Kaletra (lopinavir/ritonavir).
2002 May-Jun
New anti-HIV agents and targets.
2002 Nov
Epoxyalcohol route to hydroxyethylene dipeptide isosteres. Stereodivergent synthesis of the diamino alcohol core of ritonavir and its C-2 epimer.
2002 Nov 29
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir].
2002 Oct
Genotypic and phenotypic cross-resistance patterns to lopinavir and amprenavir in protease inhibitor-experienced patients with HIV viremia.
2002 Sep 20
Lopinavir/ritonavir: a review of its use in the management of HIV infection.
2003
HIV-1 RNA levels, resistance, and drug diffusion in semen versus blood in patients receiving a lopinavir-containing regimen.
2003 Apr 1
Phase II clinical trials of Kaletra.
2003 Apr 11
Brief report: efficacy and treatment-limiting toxicity with the concurrent use of lopinavir/ritonavir and a third protease inhibitor in treatment-experienced HIV-infected patients.
2003 Apr 15
Determination of protease inhibitors using liquid chromatography-tandem mass spectrometry.
2003 Apr 25
Rapid quantification of HIV protease inhibitors in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2003 Feb
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography.
2003 Feb 5
Immunovirological outcomes in 70 HIV-1-infected patients who switched to lopinavir/ritonavir after failing at least one protease inhibitor-containing regimen: a retrospective cohort study.
2003 Jan
Lopinavir/ritonavir absorption in a gastrectomized patient.
2003 Jan 3
Determining the relative efficacy of highly active antiretroviral therapy.
2003 Mar 15
Small dense LDL and atherogenic lipid profile in HIV-positive adults: influence of lopinavir/ritonavir-containing regimen.
2003 Mar 28
Patents

Sample Use Guides

In Vivo Use Guide
Kaletra (combination of lopinavir and ritonavir) capsules and oral solution should be adminstered orally with food. Dosage for therapy-naïve adult patients KALETRA 400/100 mg (3 capsules or 5.0 mL) twice-daily taken with food or KALETRA 800/200 mg (6 capsules or 10 mL) once-daily taken with food. For therapy-experienced patients KALETRA 400/100 mg (3 capsules or 5.0 mL) twice-daily taken with food.
Route of Administration: Oral
In Vitro Use Guide
MT4 cells and wild-type virus stocks were obtained through the AIDS Research and Reference Reagent Program, AIDS Program, National Institute of Allergy and Infectious Diseases. For drug susceptibility assays, viruses were propagated in CEM cells and titers were determined in MT4 cells. Inhibition of viral replication and compound cytotoxicity were determined in parallel in MT4 cells by a standard colorimetric assay. The EC50s of lopinavir in the absence and presence of 50% human serum were 17 ± 4 and 102 ± 44 nM, respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:48:23 UTC 2019
Edited
by admin
on Mon Oct 21 19:48:23 UTC 2019
Record UNII
2494G1JF75
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOPINAVIR
EMA EPAR   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
LOPINAVIR, (S-(2S,4S,5S))-
Common Name English
LOPINAVIR [WHO-DD]
Common Name English
KOLETRA
Common Name English
LOPINAVIR COMPONENT OF KALETRA
Common Name English
(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
Systematic Name English
ALUVIRAN
Common Name English
A-157378.0
Code English
LOPINAVIR [INN]
Common Name English
LOPINAVIR [ORANGE BOOK]
Common Name English
A-157378-0
Code English
LOPINAVIR [WHO-IP]
Common Name English
LOPINAVIR [EMA EPAR]
Common Name English
(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
Common Name English
KALETRA COMPONENT LOPINAVIR
Common Name English
LOPINAVIR [MI]
Common Name English
LOPINAVIR [VANDF]
Common Name English
LOPINAVIR [USAN]
Common Name English
ABT-378
Code English
LOPINAVIR [USP-RS]
Common Name English
(.ALPHA.S)-TETRAHYDRO-N-((.ALPHA.S)-.ALPHA.-((2S,3S)-2-HYDROXY-4-PHENYL-3-(2-(2,6-XYLYLOXY)ACETAMIDO)BUTYL)PHENETHYL)-.ALPHA.-ISOPROPYL-2-OXO-1(2H)-PYRIMIDINEACETAMIDE
Common Name English
LOPINAVIR [MART.]
Common Name English
LOPINAVIRUM [WHO-IP LATIN]
Common Name English
LOPINAVIR [JAN]
Common Name English
LOPINAVIR-
Common Name English
Classification Tree Code System Code
WHO-ATC J05AE06
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
WHO-ATC J05AR10
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
LIVERTOX 568
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
NDF-RT N0000000246
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
EMA ASSESSMENT REPORTS LOPINAVIR (AUHTORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
WHO-VATC QJ05AR10
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LPV/R)
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
EMA ASSESSMENT REPORTS KALETRA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
NDF-RT N0000175889
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
NCI_THESAURUS C97366
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
Code System Code Type Description
INN
7798
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
EVMPD
SUB02970MIG
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LOPINAVIR
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY Description: A white or almost white powder.Solubility: Freely soluble in methanol and dichloromethane, practically insoluble in water.Category: Antiretroviral (Protease Inhibitor).Storage: Lopinavir should be kept in a tightly closed container, protected from light.Additional information: Lopinavir is hygroscopic and is usually obtained in a hydrated form ; it may exhibit polymorphism.Definition: Lopinavir contains not less than 98.5% and not more than 101.5% of lopinavir (C37H48N4O5), calculated with reference to the anhydrous substance.
NDF-RT
N0000185503
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
HSDB
192725-17-0
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
DRUG BANK
DB01601
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
RXCUI
195088
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY RxNorm
EPA CompTox
192725-17-0
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
NDF-RT
N0000190114
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
CAS
192725-17-0
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
MERCK INDEX
M6900
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C2095
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
MESH
D061466
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
ChEMBL
CHEMBL729
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
NDF-RT
N0000190107
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
WIKIPEDIA
LOPINAVIR
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
LactMed
192725-17-0
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
PUBCHEM
92727
Created by admin on Mon Oct 21 19:48:23 UTC 2019 , Edited by admin on Mon Oct 21 19:48:23 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
MAJOR
METABOLITE -> PARENT
LOPINAVIR Impurity C. Amount not specified.
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
LOPINAVIR Impurity H. Amount not specified.
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
LOPINAVIR Impurity A. Amount not specified.
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
LOPINAVIR Impurity B. Amount not specified.
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
LOPINAVIR Impurity I. Amount not specified.
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY