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
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 |
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 |
---|---|---|
New drugs. | 2001 Jan |
|
New drug approvals in 2000. | 2001 Jul-Aug |
|
Anti-HIV agents. Lopinavir--results after one year. | 2001 Winter |
|
Simultaneous determination of the six HIV protease inhibitors (amprenavir, indinavir, lopinavir, nelfinavir, ritonavir, and saquinavir) plus M8 nelfinavir metabolite and the nonnucleoside reverse transcription inhibitor efavirenz in human plasma by solid-phase extraction and column liquid chromatography. | 2002 Apr |
|
[After 3 years no resistance development. Protease inhibitor with staying power]. | 2002 Apr 9 |
|
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 Aug |
|
X-ray crystallographic structure of ABT-378 (lopinavir) bound to HIV-1 protease. | 2002 Aug |
|
Simultaneous determination of indinavir, ritonavir and lopinavir (ABT 378) in human plasma by high-performance liquid chromatography. | 2002 Aug 5 |
|
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 |
|
In vitro antiviral interaction of lopinavir with other protease inhibitors. | 2002 Jul |
|
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 |
|
Salvage treatment with lopinavir/ritonavir (Kaletra) in HIV-infected patients failing all current antiretroviral drug families. | 2002 Jul-Aug |
|
Kaletra (lopinavir/ritonavir). | 2002 Jul-Aug |
|
High-performance liquid chromatographic method for the simultaneous determination of the six HIV-protease inhibitors and two non-nucleoside reverse transcriptase inhibitors in human plasma. | 2002 Jun |
|
Lopinavir-ritonavir versus nelfinavir for the initial treatment of HIV infection. | 2002 Jun 27 |
|
Increasing choices for HIV therapy. | 2002 Jun 27 |
|
Efavirenz-induced skin eruption and successful desensitization. | 2002 Mar |
|
[Plasmatic dosage of antiretroviral drugs by high performance liquid chromathography ]. | 2002 Mar-Apr |
|
[When nucleoside analogs cannot be tolerated. HIV therapy with booster]. | 2002 May 9 |
|
Delavirdine in rescue regimens. | 2002 May-Jun |
|
Encouraging resistance data for Kaletra (lopinavir/ritonavir). | 2002 May-Jun |
|
Remission of HIV-associated myelopathy after initiation of lopinavir in a patient with extensive previous exposure to highly active antiretroviral therapy. | 2002 Nov 22 |
|
Epoxyalcohol route to hydroxyethylene dipeptide isosteres. Stereodivergent synthesis of the diamino alcohol core of ritonavir and its C-2 epimer. | 2002 Nov 29 |
|
Novel lopinavir analogues incorporating non-Aromatic P-1 side chains--synthesis and structure--activity relationships. | 2002 Nov 4 |
|
Gateways to clinical trials. | 2002 Oct |
|
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir]. | 2002 Oct |
|
Clinical use of lopinavir/ritonavir in a salvage therapy setting: pharmacokinetics and pharmacodynamics. | 2002 Oct 18 |
|
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 |
|
Pharmacokinetic interaction between lopinavir/r and amprenavir in salvage therapy. | 2002 Sep 1 |
|
Genotypic and phenotypic cross-resistance patterns to lopinavir and amprenavir in protease inhibitor-experienced patients with HIV viremia. | 2002 Sep 20 |
|
Lopinavir/ritonavir: a review of its use in the management of HIV infection. | 2003 |
|
The safety and tolerability of switching from a non-failing antiretroviral regimen to lopinavir. | 2003 Apr |
|
HIV-1 RNA levels, resistance, and drug diffusion in semen versus blood in patients receiving a lopinavir-containing regimen. | 2003 Apr 1 |
|
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 |
|
Determination of protease inhibitors using liquid chromatography-tandem mass spectrometry. | 2003 Apr 25 |
|
Effect of therapeutic drug monitoring on outcome in antiretroviral experienced HIV-infected individuals. | 2003 Feb |
|
Rapid quantification of HIV protease inhibitors in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. | 2003 Feb |
|
The efficacy of lopinavir in individuals experiencing protease inhibitor failure. | 2003 Feb 1 |
|
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography. | 2003 Feb 5 |
|
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 |
|
Lopinavir/ritonavir absorption in a gastrectomized patient. | 2003 Jan 3 |
|
Protease inhibitor shown to hold HIV at undetectable levels. | 2003 Jan-Feb |
|
Forty-eight-week evaluation of lopinavir/ritonavir, a new protease inhibitor, in human immunodeficiency virus-infected children. | 2003 Mar |
|
Evaluation of antiretroviral drug measurements by an interlaboratory quality control program. | 2003 Mar 1 |
|
Determining the relative efficacy of highly active antiretroviral therapy. | 2003 Mar 15 |
|
Small dense LDL and atherogenic lipid profile in HIV-positive adults: influence of lopinavir/ritonavir-containing regimen. | 2003 Mar 28 |
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
by
admin
on
Edited
Fri Dec 15 15:39:15 GMT 2023
by
admin
on
Fri Dec 15 15:39:15 GMT 2023
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Record UNII |
2494G1JF75
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Record Status |
Validated (UNII)
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Record Version |
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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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Code System | Code | Type | Description | ||
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100000089405
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PRIMARY | |||
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7798
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PRIMARY | |||
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SUB02970MIG
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PRIMARY | |||
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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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PRIMARY | |||
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Lopinavir
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192725-17-0
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PRIMARY | |||
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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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PRIMARY | |||
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92727
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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TRANSPORTER -> SUBSTRATE | |||
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TARGET ORGANISM->INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SOLVATE->ANHYDROUS |
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TARGET -> INHIBITOR |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
MAJOR
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||
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METABOLITE -> PARENT |
LOPINAVIR Impurity C.
Amount not specified.
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
LOPINAVIR Impurity H.
Amount not specified.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
LOPINAVIR Impurity G.
Amount not specified.
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IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
LOPINAVIR Impurity D.
Amount not specified.
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
LOPINAVIR Impurity A.
Amount not specified.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
LOPINAVIR Impurity B.
Amount not specified.
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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||
|
IMPURITY -> PARENT |
Procedure 2
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
LOPINAVIR Impurity I.
Amount not specified.
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IMPURITY -> PARENT |
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||
|
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
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||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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