LOPINAVIR

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9835517
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 protease 36 Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9835517	Inhibitor 8504		1.3 pM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV infection 21 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021226s030lbl.pdf	Primary		Approved 8583	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 2000
HPV positive with high grade squamous intraepithelial lesions 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26824902	Primary		Phase II 1147	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

C_max

Value	Dose	Co-administered	Analyte	Population
6539 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24632753	400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021251s052_021906s046lbl.pdf	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
9.8 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021251s052_021906s046lbl.pdf	400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
60328 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24632753	400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
154.1 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021251s052_021906s046lbl.pdf	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
92.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021251s052_021906s046lbl.pdf	400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24632753	400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021251s052_021906s046lbl.pdf	400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: RITONAVIR	RITONAVIR	LOPINAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31781	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31781
eMolecules	6719306	https://www.emolecules.com/cgi-bin/more?vid=6719306
MolPort	MolPort-003-848-410	https://www.molport.com/shop/molecule-link/MolPort-003-848-410
Selleck Chemicals	Lopinavir	http://www.selleckchem.com/products/Lopinavir.html
ZINC	ZINC000003951740	http://zinc15.docking.org/substances/ZINC000003951740

PubMed

Title	Date	PubMed
Determination of protease inhibitors using liquid chromatography-tandem mass spectrometry.	2003-04-25	12650761
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.	2003-04-15	12679700
Phase II clinical trials of Kaletra.	2003-04-11	12660556
HIV-1 RNA levels, resistance, and drug diffusion in semen versus blood in patients receiving a lopinavir-containing regimen.	2003-04-01	12640207
The safety and tolerability of switching from a non-failing antiretroviral regimen to lopinavir.	2003-04	12643876
Small dense LDL and atherogenic lipid profile in HIV-positive adults: influence of lopinavir/ritonavir-containing regimen.	2003-03-28	12646808
Determining the relative efficacy of highly active antiretroviral therapy.	2003-03-15	12660935
Evaluation of antiretroviral drug measurements by an interlaboratory quality control program.	2003-03-01	12626888
Forty-eight-week evaluation of lopinavir/ritonavir, a new protease inhibitor, in human immunodeficiency virus-infected children.	2003-03	12634581
Protease inhibitor shown to hold HIV at undetectable levels.	2003-02-15	12585228
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography.	2003-02-05	12505781
The efficacy of lopinavir in individuals experiencing protease inhibitor failure.	2003-02-01	12571536
Effect of therapeutic drug monitoring on outcome in antiretroviral experienced HIV-infected individuals.	2003-02	12600653
Rapid quantification of HIV protease inhibitors in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2003-02	12577282
Simultaneous quantitative determination of the HIV protease inhibitors indinavir, amprenavir, ritonavir, lopinavir, saquinavir, nelfinavir and the nelfinavir active metabolite M8 in plasma by liquid chromatography.	2003-01-15	12482492
Lopinavir/ritonavir absorption in a gastrectomized patient.	2003-01-03	12478084
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.	2003-01	12493805
Lopinavir/ritonavir: a review of its use in the management of HIV infection.	2003	12662125
Gateways to clinical trials.	2002-12	12616965
Comparison of the efficacy, safety and predictive value of HIV genotyping using distinct ritonavir-boosted protease inhibitors.	2002-12	12458138
Epoxyalcohol route to hydroxyethylene dipeptide isosteres. Stereodivergent synthesis of the diamino alcohol core of ritonavir and its C-2 epimer.	2002-11-29	12444650
Remission of HIV-associated myelopathy after initiation of lopinavir in a patient with extensive previous exposure to highly active antiretroviral therapy.	2002-11-22	12441823
Novel lopinavir analogues incorporating non-Aromatic P-1 side chains--synthesis and structure--activity relationships.	2002-11-04	12372511
New anti-HIV agents and targets.	2002-11	12369088
Clinical use of lopinavir/ritonavir in a salvage therapy setting: pharmacokinetics and pharmacodynamics.	2002-10-18	12370509
Gateways to clinical trials.	2002-10	12500432
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir].	2002-10	12372245
Genotypic and phenotypic cross-resistance patterns to lopinavir and amprenavir in protease inhibitor-experienced patients with HIV viremia.	2002-09-20	12396453
Pharmacokinetic interaction between lopinavir/r and amprenavir in salvage therapy.	2002-09-01	12352158
Analysis of the virological response with respect to baseline viral phenotype and genotype in protease inhibitor-experienced HIV-1-infected patients receiving lopinavir/ritonavir therapy.	2002-09	12487383
Salvage treatment with lopinavir/ritonavir (Kaletra) in HIV-infected patients failing all current antiretroviral drug families.	2002-08-21	12187504
[Plasmatic dosage of antiretroviral drugs by high performance liquid chromathography ].	2002-08-21	12185966
Limited penetration of lopinavir into seminal plasma of HIV-1-infected men.	2002-08-16	12172099
Treatment with lopinavir/ritonavir in heavily pretreated subjects failing multiple antiretroviral regimens in clinical practice.	2002-08-15	12154345
Serious bradyarrhythmia that was possibly induced by lopinavir-ritonavir in 2 patients with acquired immunodeficiency syndrome.	2002-08-15	12145735
Simultaneous determination of indinavir, ritonavir and lopinavir (ABT 378) in human plasma by high-performance liquid chromatography.	2002-08-05	12113989
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.	2002-08	12142642
X-ray crystallographic structure of ABT-378 (lopinavir) bound to HIV-1 protease.	2002-08	12057670
New developments in anti-HIV chemotherapy.	2002-07-18	12084468
Determination of lopinavir and nevirapine by high-performance liquid chromatography after solid-phase extraction: application for the assessment of their transplacental passage at delivery.	2002-07-15	12076682
In vitro antiviral interaction of lopinavir with other protease inhibitors.	2002-07	12069982
Kaletra (lopinavir/ritonavir).	2002-06-28	12086554
Lopinavir-ritonavir versus nelfinavir for the initial treatment of HIV infection.	2002-06-27	12087139
Increasing choices for HIV therapy.	2002-06-27	12087136
Delavirdine in rescue regimens.	2002-06-18	12064317
Encouraging resistance data for Kaletra (lopinavir/ritonavir).	2002-06-18	12064017
[When nucleoside analogs cannot be tolerated. HIV therapy with booster].	2002-05-09	12116561
[After 3 years no resistance development. Protease inhibitor with staying power].	2002-04-09	12043076
New drugs.	2001-01	12184254
Anti-HIV agents. Lopinavir--results after one year.	2001	12132436

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 Mar 31 18:04:20 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:20 GMT 2025`
Record UNII	2494G1JF75
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOPINAVIR

Official Name

English

KALETRA COMPONENT LOPINAVIR

Preferred Name

English

LOPINAVIR, (S-(2S,4S,5S))-

Common Name

English

KOLETRA

Common Name

English

Lopinavir [WHO-DD]

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

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

(?S)-Tetrahydro-N-[(?S)-?-[(2S,3S)-2-hydroxy-4-phenyl-3-[2-(2,6-xylyloxy)acetamido]butyl]phenethyl]-?-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