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 No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021226s030lbl.pdf

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.3 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KALETRA

Approved Use

KALETRA (lopinavir/ritonavir) is a co-formulation of lopinavir and ritonavir. Lopinavir is an inhibitor of the HIV protease. As co-formulated in KALETRA, ritonavir inhibits the CYP3Amediated metabolism of lopinavir, thereby providing increased plasma levels of lopinavir/ KALETRA is indicated in combination with other antiretroviral agents for the treatment of HIV-infection

Launch Date

9.6897597E11
Primary
LOPIMUNE

Approved Use

LOPIMUNE (lopinavir/ritonavir) is a co-formulation of lopinavir and ritonavir. Lopinavir is an inhibitor of the HIV protease. As co-formulated in LOPIMUNE, ritonavir inhibits the CYP3Amediated metabolism of lopinavir, thereby providing increased plasma levels of lopinavir/ LOPIMUNEis indicated in combination with other antiretroviral agents for the treatment of HIV-infection
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6539 ng/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.8 μg/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
11.8 μg/mL
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
60328 ng × h/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
92.6 μg × h/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
154.1 μg × h/mL
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.4 h
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1.5%
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
PubMed

PubMed

TitleDatePubMed
Inflammatory oedema of the legs: a new side-effect of lopinavir.
2001 Apr 13
Antiviral drugs: current state of the art.
2001 Aug
Ototoxicity may be associated with protease inhibitor therapy.
2001 Dec 15
Trifluoromethyl-containing 3-alkoxymethyl- and 3-aryloxymethyl-2-pyridinones are potent inhibitors of HIV-1 non-nucleoside reverse transcriptase.
2001 Feb 12
ABT-378/ritonavir plus stavudine and lamivudine for the treatment of antiretroviral-naive adults with HIV-1 infection: 48-week results.
2001 Jan 5
Lopinavir/ritonavir: a protease inhibitor combination.
2001 Jan 8
Combination drug approved to treat HIV.
2001 Jan-Feb
New drug approvals in 2000.
2001 Jul-Aug
Kaletra: applying advances in pharmacokinetics to treating HIV.
2001 Winter
Synthesis and structure-activity relationships of a novel series of HIV-1 protease inhibitors encompassing ABT-378 (Lopinavir).
2002 Apr 22
Treatment with lopinavir/ritonavir in heavily pretreated subjects failing multiple antiretroviral regimens in clinical practice.
2002 Aug 15
Serious bradyarrhythmia that was possibly induced by lopinavir-ritonavir in 2 patients with acquired immunodeficiency syndrome.
2002 Aug 15
Simultaneous determination of indinavir, ritonavir and lopinavir (ABT 378) in human plasma by high-performance liquid chromatography.
2002 Aug 5
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
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
Lopinavir-ritonavir versus nelfinavir for the initial treatment of HIV infection.
2002 Jun 27
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
[When nucleoside analogs cannot be tolerated. HIV therapy with booster].
2002 May 9
New anti-HIV agents and targets.
2002 Nov
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir].
2002 Oct
Lopinavir/ritonavir: a review of its use in the management of HIV infection.
2003
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
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography.
2003 Feb 5
Determining the relative efficacy of highly active antiretroviral therapy.
2003 Mar 15
Patents

Sample Use Guides

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 Fri Dec 15 15:39:15 UTC 2023
Edited
by admin
on Fri Dec 15 15:39:15 UTC 2023
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
KOLETRA
Common Name English
Lopinavir [WHO-DD]
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 [USP MONOGRAPH]
Common Name 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
(αS)-Tetrahydro-N-[(αS)-α-[(2S,3S)-2-hydroxy-4-phenyl-3-[2-(2,6-xylyloxy)acetamido]butyl]phenethyl]-α-isopropyl-2-oxo-1(2H)-pyrimidineacetamide
Common Name English
LOPINAVIR [MART.]
Common Name English
LOPINAVIRUM [WHO-IP LATIN]
Common Name English
LOPINAVIR [EP MONOGRAPH]
Common Name English
LOPINAVIR [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AE06
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
WHO-ATC J05AR10
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
LIVERTOX NBK547961
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
NDF-RT N0000000246
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
EMA ASSESSMENT REPORTS LOPINAVIR (AUHTORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
WHO-VATC QJ05AR10
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.2.3 (LPV/R)
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
EMA ASSESSMENT REPORTS KALETRA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
NDF-RT N0000175889
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
NCI_THESAURUS C97366
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
Code System Code Type Description
SMS_ID
100000089405
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
INN
7798
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
EVMPD
SUB02970MIG
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
DRUG CENTRAL
1601
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
LOPINAVIR
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
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 Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY P-Glycoprotein Inhibitors [MoA]
HSDB
8138
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
CHEBI
31781
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
DRUG BANK
DB01601
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
RXCUI
195088
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8046456
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
NDF-RT
N0000190114
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
FDA UNII
2494G1JF75
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
LACTMED
Lopinavir
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
CAS
192725-17-0
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
MERCK INDEX
m6900
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C2095
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
RS_ITEM_NUM
1370101
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
MESH
D061466
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
ChEMBL
CHEMBL729
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
NDF-RT
N0000190107
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
WIKIPEDIA
LOPINAVIR
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
USAN
KK-30
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
DAILYMED
2494G1JF75
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
PUBCHEM
92727
Created by admin on Fri Dec 15 15:39:15 UTC 2023 , Edited by admin on Fri Dec 15 15:39:15 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
TRANSPORTER -> SUBSTRATE
TARGET ORGANISM->INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
SOLVATE->ANHYDROUS
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
MAJOR
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
LOPINAVIR Impurity G. Amount not specified.
IMPURITY -> PARENT
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
LOPINAVIR Impurity D. Amount not specified.
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
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