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
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
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 |
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 |
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 |
---|---|---|---|
Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9835517 |
1.3 pM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
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 Date2000 |
|||
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 |
---|---|---|---|---|
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 |
---|---|---|
Ototoxicity may be associated with protease inhibitor therapy. | 2001 Dec 15 |
|
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. | 2001 Mar-Apr |
|
Resistant to everything. | 2001 May |
|
The importance of sequencing in treatment options. | 2001 May-Jun |
|
DPC 681 and DPC 684: potent, selective inhibitors of human immunodeficiency virus protease active against clinically relevant mutant variants. | 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 |
|
Kaletra: applying advances in pharmacokinetics to treating HIV. | 2001 Winter |
|
[After 3 years no resistance development. Protease inhibitor with staying power]. | 2002 Apr 9 |
|
X-ray crystallographic structure of ABT-378 (lopinavir) bound to HIV-1 protease. | 2002 Aug |
|
Limited penetration of lopinavir into seminal plasma of HIV-1-infected men. | 2002 Aug 16 |
|
Efficacy of highly active antiretroviral therapy in HIV-1 infected children. | 2002 Feb |
|
Drug resistance test shows encouraging results. | 2002 Feb |
|
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 |
|
Delavirdine in rescue regimens. | 2002 May-Jun |
|
Encouraging resistance data for Kaletra (lopinavir/ritonavir). | 2002 May-Jun |
|
Gateways to clinical trials. | 2002 Oct |
|
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir]. | 2002 Oct |
|
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 Sep |
|
Genotypic and phenotypic cross-resistance patterns to lopinavir and amprenavir in protease inhibitor-experienced patients with HIV viremia. | 2002 Sep 20 |
|
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 |
|
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 |
|
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 |
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.
Substance Class |
Chemical
Created
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Record UNII |
JK38KEB9D9
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Record Status |
Validated (UNII)
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Record Version |
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ANHYDROUS->SOLVATE |
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