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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/9835517Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021226s030lbl.pdf
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 |
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Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9835517 |
1.3 pM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | KALETRA Approved UseKALETRA (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 Date9.6897597E11 |
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Primary | LOPIMUNE Approved UseLOPIMUNE (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
Value | Dose | Co-administered | Analyte | Population |
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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 |
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
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 |
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
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 |
LOPINAVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
Therapeutic drug monitoring of HIV protease inhibitors using high-performance liquid chromatography with ultraviolet or photodiode array detection. | 2001 Dec |
|
Lopinavir/ritonavir: a protease inhibitor combination. | 2001 Jan 8 |
|
DPC 681 and DPC 684: potent, selective inhibitors of human immunodeficiency virus protease active against clinically relevant mutant variants. | 2001 Nov |
|
Serious bradyarrhythmia that was possibly induced by lopinavir-ritonavir in 2 patients with acquired immunodeficiency syndrome. | 2002 Aug 15 |
|
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 |
|
New developments in anti-HIV chemotherapy. | 2002 Jul 18 |
|
Lopinavir/ritonavir (ABT-378/r). | 2002 Mar |
|
Safety and antiviral activity at 48 weeks of lopinavir/ritonavir plus nevirapine and 2 nucleoside reverse-transcriptase inhibitors in human immunodeficiency virus type 1-infected protease inhibitor-experienced patients. | 2002 Mar 1 |
|
Delavirdine increases drug exposure of ritonavir-boosted protease inhibitors. | 2002 Mar 29 |
|
[When nucleoside analogs cannot be tolerated. HIV therapy with booster]. | 2002 May 9 |
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Delavirdine in rescue regimens. | 2002 May-Jun |
|
New anti-HIV agents and targets. | 2002 Nov |
|
Pharmacokinetic interaction between lopinavir/r and amprenavir in salvage therapy. | 2002 Sep 1 |
|
Lopinavir/ritonavir: a review of its use in the management of HIV infection. | 2003 |
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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 |
|
Effect of therapeutic drug monitoring on outcome in antiretroviral experienced HIV-infected individuals. | 2003 Feb |
|
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography. | 2003 Feb 5 |
|
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 Jan 15 |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9835517
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.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
J05AE06
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WHO-ATC |
J05AR10
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LIVERTOX |
NBK547961
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NDF-RT |
N0000000246
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EMA ASSESSMENT REPORTS |
LOPINAVIR (AUHTORIZED: HIV INFECTIONS)
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WHO-VATC |
QJ05AR10
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WHO-ESSENTIAL MEDICINES LIST |
6.4.2.3 (LPV/R)
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EMA ASSESSMENT REPORTS |
KALETRA (AUTHORIZED: HIV INFECTIONS)
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NDF-RT |
N0000175889
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NCI_THESAURUS |
C97366
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100000089405
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7798
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SUB02970MIG
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1601
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LOPINAVIR
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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. | ||
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N0000185503
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PRIMARY | P-Glycoprotein Inhibitors [MoA] | ||
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8138
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31781
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DB01601
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195088
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DTXSID8046456
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N0000190114
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PRIMARY | Cytochrome P450 3A Inhibitors [MoA] | ||
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2494G1JF75
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Lopinavir
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192725-17-0
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m6900
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PRIMARY | Merck Index | ||
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C2095
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1370101
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D061466
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CHEMBL729
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N0000190107
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PRIMARY | Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA] | ||
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LOPINAVIR
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KK-30
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2494G1JF75
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92727
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ACTIVE MOIETY
METABOLITE (PARENT)