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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H48N4O5.H2O
Molecular Weight 646.8161
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOPINAVIR MONOHYDRATE

SMILES

O.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=XLJJEFLRMQZJDB-YIUCRBITSA-N
InChI=1S/C37H48N4O5.H2O/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);1H2/t30-,31-,32-,34-;/m0./s1

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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.

CNS Activity

Originator

Approval Year

2000
172
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.3 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Determination of protease inhibitors using liquid chromatography-tandem mass spectrometry.
2003-04-25
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
Phase II clinical trials of Kaletra.
2003-04-11
HIV-1 RNA levels, resistance, and drug diffusion in semen versus blood in patients receiving a lopinavir-containing regimen.
2003-04-01
The safety and tolerability of switching from a non-failing antiretroviral regimen to lopinavir.
2003-04
Small dense LDL and atherogenic lipid profile in HIV-positive adults: influence of lopinavir/ritonavir-containing regimen.
2003-03-28
Determining the relative efficacy of highly active antiretroviral therapy.
2003-03-15
Evaluation of antiretroviral drug measurements by an interlaboratory quality control program.
2003-03-01
Forty-eight-week evaluation of lopinavir/ritonavir, a new protease inhibitor, in human immunodeficiency virus-infected children.
2003-03
Protease inhibitor shown to hold HIV at undetectable levels.
2003-02-15
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography.
2003-02-05
The efficacy of lopinavir in individuals experiencing protease inhibitor failure.
2003-02-01
Effect of therapeutic drug monitoring on outcome in antiretroviral experienced HIV-infected individuals.
2003-02
Rapid quantification of HIV protease inhibitors in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2003-02
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
Lopinavir/ritonavir absorption in a gastrectomized patient.
2003-01-03
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
Lopinavir/ritonavir: a review of its use in the management of HIV infection.
2003
Gateways to clinical trials.
2002-12
Comparison of the efficacy, safety and predictive value of HIV genotyping using distinct ritonavir-boosted protease inhibitors.
2002-12
Epoxyalcohol route to hydroxyethylene dipeptide isosteres. Stereodivergent synthesis of the diamino alcohol core of ritonavir and its C-2 epimer.
2002-11-29
Remission of HIV-associated myelopathy after initiation of lopinavir in a patient with extensive previous exposure to highly active antiretroviral therapy.
2002-11-22
Novel lopinavir analogues incorporating non-Aromatic P-1 side chains--synthesis and structure--activity relationships.
2002-11-04
New anti-HIV agents and targets.
2002-11
Clinical use of lopinavir/ritonavir in a salvage therapy setting: pharmacokinetics and pharmacodynamics.
2002-10-18
Gateways to clinical trials.
2002-10
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir].
2002-10
Genotypic and phenotypic cross-resistance patterns to lopinavir and amprenavir in protease inhibitor-experienced patients with HIV viremia.
2002-09-20
Pharmacokinetic interaction between lopinavir/r and amprenavir in salvage therapy.
2002-09-01
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
Salvage treatment with lopinavir/ritonavir (Kaletra) in HIV-infected patients failing all current antiretroviral drug families.
2002-08-21
[Plasmatic dosage of antiretroviral drugs by high performance liquid chromathography ].
2002-08-21
Limited penetration of lopinavir into seminal plasma of HIV-1-infected men.
2002-08-16
Treatment with lopinavir/ritonavir in heavily pretreated subjects failing multiple antiretroviral regimens in clinical practice.
2002-08-15
Serious bradyarrhythmia that was possibly induced by lopinavir-ritonavir in 2 patients with acquired immunodeficiency syndrome.
2002-08-15
Simultaneous determination of indinavir, ritonavir and lopinavir (ABT 378) in human plasma by high-performance liquid chromatography.
2002-08-05
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
X-ray crystallographic structure of ABT-378 (lopinavir) bound to HIV-1 protease.
2002-08
New developments in anti-HIV chemotherapy.
2002-07-18
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
In vitro antiviral interaction of lopinavir with other protease inhibitors.
2002-07
Kaletra (lopinavir/ritonavir).
2002-06-28
Lopinavir-ritonavir versus nelfinavir for the initial treatment of HIV infection.
2002-06-27
Increasing choices for HIV therapy.
2002-06-27
Delavirdine in rescue regimens.
2002-06-18
Encouraging resistance data for Kaletra (lopinavir/ritonavir).
2002-06-18
[When nucleoside analogs cannot be tolerated. HIV therapy with booster].
2002-05-09
[After 3 years no resistance development. Protease inhibitor with staying power].
2002-04-09
New drugs.
2001-01
Anti-HIV agents. Lopinavir--results after one year.
2001
Patents

Patents

JP2007536237A
19
JP2011508748A
30

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 Wed Apr 02 06:13:32 GMT 2025
Edited
by admin
on Wed Apr 02 06:13:32 GMT 2025
Record UNII
JK38KEB9D9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOPINAVIR HYDRATE
Preferred Name English
LOPINAVIR MONOHYDRATE
Common Name English
1(2H)-PYRIMIDINEACETAMIDE, N-((1S,3S,4S)-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL)TETRAHYDRO-.ALPHA.-(1-METHYLETHYL)-2-OXO-, HYDRATE (1:1), (.ALPHA.S)-
Systematic Name English
Code System Code Type Description
FDA UNII
JK38KEB9D9
Created by admin on Wed Apr 02 06:13:32 GMT 2025 , Edited by admin on Wed Apr 02 06:13:32 GMT 2025
PRIMARY
PUBCHEM
66766312
Created by admin on Wed Apr 02 06:13:32 GMT 2025 , Edited by admin on Wed Apr 02 06:13:32 GMT 2025
PRIMARY
CAS
1239071-09-0
Created by admin on Wed Apr 02 06:13:32 GMT 2025 , Edited by admin on Wed Apr 02 06:13:32 GMT 2025
PRIMARY
Related Record Type Details
Structure of LOPINAVIR
ANHYDROUS->SOLVATE
NIH
NCATS
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