Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C32H45N3O4S |
| Molecular Weight | 567.782 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCCC[C@]1([H])CN(C[C@@H](O)[C@H](CSC3=CC=CC=C3)NC(=O)C4=C(C)C(O)=CC=C4)[C@@H](C2)C(=O)NC(C)(C)C
InChI
InChIKey=QAGYKUNXZHXKMR-HKWSIXNMSA-N
InChI=1S/C32H45N3O4S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39)/t22-,23+,26-,27-,29+/m0/s1
| Molecular Formula | C32H45N3O4S |
| Molecular Weight | 567.782 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00220Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020778s035,020779s056,021503s017lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00220
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020778s035,020779s056,021503s017lbl.pdf
Nelfinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Nelfinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs. Nelfinavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles. Nelfinavir is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. Nelfinavir is marketed under the brand name Viracept.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL378 |
12.0 nM [IC50] | ||
Target ID: CHEMBL1293287 |
100.0 µM [IC50] | ||
Target ID: CHEMBL368 |
7.3 µM [IC50] | ||
Target ID: CHEMBL395 |
5.1 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | VIRACEPT Approved UseVIRACEPT in combination with other antiretroviral agents is indicated for the treatment of HIV infection. Launch Date1997 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.7 mg/L |
1250 mg 2 times / day steady-state, oral dose: 1250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3 mg/L |
750 mg 3 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4 mg/L |
1250 mg 2 times / day multiple, oral dose: 1250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.3 mg × h/L |
1250 mg 2 times / day steady-state, oral dose: 1250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
43.6 mg × h/L |
750 mg 3 times / day multiple, oral dose: 750 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
52.8 mg × h/L |
1250 mg 2 times / day multiple, oral dose: 1250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.8 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
3.4 h |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
NELFINAVIR MESYLATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2% |
unknown, unknown |
NELFINAVIR MESYLATE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 25-77 years) n = 15 Health Status: unhealthy Condition: Adenoid Cystic Carcinoma Age Group: 52 years (range: 25-77 years) Sex: M+F Population Size: 15 Sources: |
Disc. AE: Hyponatremia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Hyponatremia (grade 4, 1 patient) Sources: Thrombocytopenia (grade 3, 1 patient) Dizziness (grade 3, 1 patient) Elevated liver enzymes (grade 3, 2 patients) |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
Disc. AE: Esophagitis, Nausea... Other AEs: Leukopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Esophagitis (grade 3, 1 patient) Other AEs:Nausea (grade 3, 1 patient) Fatigue (grade 3, 1 patient) Leukopenia (grade 3, 2 patients) Sources: Thrombocytopenia (grade 3, 2 patients) Dyspnea (grade 3, 1 patient) |
650 mg 2 times / day steady, oral Dose: 650 mg, 2 times / day Route: oral Route: steady Dose: 650 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 5 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 5 Sources: |
Other AEs: Thrombocytopenia... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dizziness | grade 3, 1 patient Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 25-77 years) n = 15 Health Status: unhealthy Condition: Adenoid Cystic Carcinoma Age Group: 52 years (range: 25-77 years) Sex: M+F Population Size: 15 Sources: |
| Thrombocytopenia | grade 3, 1 patient Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 25-77 years) n = 15 Health Status: unhealthy Condition: Adenoid Cystic Carcinoma Age Group: 52 years (range: 25-77 years) Sex: M+F Population Size: 15 Sources: |
| Elevated liver enzymes | grade 3, 2 patients Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 25-77 years) n = 15 Health Status: unhealthy Condition: Adenoid Cystic Carcinoma Age Group: 52 years (range: 25-77 years) Sex: M+F Population Size: 15 Sources: |
| Hyponatremia | grade 4, 1 patient Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 52 years (range: 25-77 years) n = 15 Health Status: unhealthy Condition: Adenoid Cystic Carcinoma Age Group: 52 years (range: 25-77 years) Sex: M+F Population Size: 15 Sources: |
| Dyspnea | grade 3, 1 patient | 1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
| Esophagitis | grade 3, 1 patient Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
| Fatigue | grade 3, 1 patient Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
| Nausea | grade 3, 1 patient Disc. AE |
1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
| Leukopenia | grade 3, 2 patients | 1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
| Thrombocytopenia | grade 3, 2 patients | 1250 mg 2 times / day steady, oral MTD Dose: 1250 mg, 2 times / day Route: oral Route: steady Dose: 1250 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 8 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 8 Sources: |
| Thrombocytopenia | grade 4, 1 patient | 650 mg 2 times / day steady, oral Dose: 650 mg, 2 times / day Route: oral Route: steady Dose: 650 mg, 2 times / day Sources: |
unhealthy, 59 years (range: 54–75 years) n = 5 Health Status: unhealthy Condition: Unresectable Stage IIIA/IIIB Non-small Cell Lung Cancer Age Group: 59 years (range: 54–75 years) Sex: M+F Population Size: 5 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| International Congress on Chemotherapy. | 1995 Sep |
|
| Viracept and irregular heartbeat warning. | 1999 Oct |
|
| Saquinavir soft gelatin capsule: a comparative safety review. | 2001 |
|
| Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors. | 2001 Apr |
|
| Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport. | 2001 Apr 13 |
|
| Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography. | 2001 Apr 13 |
|
| Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology. | 2001 Apr 15 |
|
| Lack of association between pregnancy and selected gastrointestinal adverse events among women prescribed nelfinavir. | 2001 Apr 15 |
|
| High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire. | 2001 Apr 15 |
|
| A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir. | 2001 Apr 15 |
|
| Lipid abnormalities in a healthcare worker receiving HIV prophylaxis. | 2001 Aug |
|
| Nelfinavir plasma levels under twice-daily and three-times-daily regimens: high interpatient and low intrapatient variability. | 2001 Aug |
|
| Antiretrovirals: simultaneous determination of five protease inhibitors and three nonnucleoside transcriptase inhibitors in human plasma by a rapid high-performance liquid chromatography--mass spectrometry assay. | 2001 Aug |
|
| Antiviral drugs: current state of the art. | 2001 Aug |
|
| Comparison of virologic, immunologic, and clinical response to five different initial protease inhibitor-containing and nevirapine-containing regimens. | 2001 Aug 1 |
|
| HIV-protease inhibitors contribute to P-glycoprotein efflux function defect in peripheral blood lymphocytes from HIV-positive patients receiving HAART. | 2001 Aug 1 |
|
| Antiapoptotic mechanism of HIV protease inhibitors: preventing mitochondrial transmembrane potential loss. | 2001 Aug 15 |
|
| Antiretroviral therapy for previously treated patients. | 2001 Aug 9 |
|
| Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection. | 2001 Aug 9 |
|
| [Resistance to protease inhibitors]. | 2001 Feb |
|
| Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases. | 2001 Jan-Feb |
|
| New developments in anti-HIV chemotherapy. | 2001 Jan-Feb |
|
| Combination therapy with saquinavir soft gelatin capsules in children with human immunodeficiency virus infection. | 2001 Jul |
|
| CMVR diagnoses and progression of CD4 cell counts and HIV viral load measurements in HIV patients on HAART. | 2001 Jul |
|
| Capillary electrophoretic separation of protease inhibitors used in human immunodeficiency virus therapy. | 2001 Jul 13 |
|
| High-performance liquid chromatographic assay to determine the plasma levels of HIV-protease inhibitors (amprenavir, indinavir, nelfinavir, ritonavir and saquinavir) and the non-nucleoside reverse transcriptase inhibitor (nevirapine) after liquid-liquid extraction. | 2001 Jul 15 |
|
| Stable or increasing bone mineral density in HIV-infected patients treated with nelfinavir or indinavir. | 2001 Jul 6 |
|
| AVANTI 3: a randomized, double-blind trial to compare the efficacy and safety of lamivudine plus zidovudine versus lamivudine plus zidovudine plus nelfinavir in HIV-1-infected antiretroviral-naive patients. | 2001 Jun |
|
| Antiretroviral activity and safety of abacavir in combination with selected HIV-1 protease inhibitors in therapy-naive HIV-1-infected adults. | 2001 Jun |
|
| The effects of antiretroviral protease inhibitors on serum lipid levels in HIV-infected patients. | 2001 Jun |
|
| Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease. | 2001 Jun |
|
| The HIV protease inhibitor nelfinavir induces insulin resistance and increases basal lipolysis in 3T3-L1 adipocytes. | 2001 Jun |
|
| Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART. | 2001 Jun |
|
| The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study. | 2001 Jun 1 |
|
| Design and synthesis of a conformationally restricted trans peptide isostere based on the bioactive conformations of saquinavir and nelfinavir. | 2001 Jun 1 |
|
| Simultaneous determination of the HIV-protease inhibitors indinavir, amprenavir, ritonavir, saquinavir and nelfinavir in human plasma by reversed-phase high-performance liquid chromatography. | 2001 Jun 15 |
|
| The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design. | 2001 Jun 15 |
|
| Analysis of human immunodeficiency virus type 1 drug resistance in children receiving nucleoside analogue reverse-transcriptase inhibitors plus nevirapine, nelfinavir, or ritonavir (Pediatric AIDS Clinical Trials Group 377). | 2001 Jun 15 |
|
| Predictors of virological response in HIV-infected patients to salvage antiretroviral therapy that includes nelfinavir. | 2001 Mar |
|
| Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine. | 2001 May |
|
| Ergotism related to interaction between nelfinavir and ergotamine. | 2001 May |
|
| Nelfinavir desensitization. | 2001 May |
|
| Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy. | 2001 May 25 |
|
| Editorial comment on Analysis of variation in plasma concentrations of nelfinavir and its active metabolite M8 in HIV-positive patients. | 2001 May 25 |
|
| Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment. | 2001 May 25 |
|
| Analysis of variation in plasma concentrations of nelfinavir and its active metabolite M8 in HIV-positive patients. | 2001 May 25 |
|
| Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography. | 2001 May 5 |
|
| Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro. | 2001 Sep |
|
| Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5. | 2001 Sep 14 |
|
| Peptide mimetic HIV protease inhibitors are ligands for the orphan receptor SXR. | 2001 Sep 7 |
Sample Use Guides
The recommended dose is 1250 mg (five 250 mg tablets or two 625 mg tablets) twice daily or 750 mg (three 250 mg tablets) three times daily. VIRACEPT should be taken with a meal. Patients unable to swallow the 250 or 625 mg tablets may dissolve the tablets in a small amount of water. Once dissolved, patients should mix the cloudy liquid well, and consume it immediately.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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on
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Sat Dec 16 16:26:02 GMT 2023
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| Record UNII |
HO3OGH5D7I
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English | ||
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Code | English | ||
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Common Name | English |
| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
554316
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NDF-RT |
N0000175889
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WHO-ATC |
J05AE04
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NCI_THESAURUS |
C97366
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WHO-VATC |
QJ05AE04
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LIVERTOX |
NBK548311
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NDF-RT |
N0000000246
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| Code System | Code | Type | Description | ||
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SUB09186MIG
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PRIMARY | |||
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64143
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PRIMARY | |||
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159989-64-7
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PRIMARY | |||
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HO3OGH5D7I
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PRIMARY | |||
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m7798
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PRIMARY | Merck Index | ||
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100000085450
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PRIMARY | |||
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Nelfinavir
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PRIMARY | |||
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D019888
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PRIMARY | |||
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NELFINAVIR
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HO3OGH5D7I
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PRIMARY | |||
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C29285
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747167
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134527
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1893
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7496
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CHEMBL584
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DB00220
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DTXSID5035080
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PRIMARY | |||
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7494
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
FECAL
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TARGET ORGANISM->INHIBITOR |
Other
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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EXCRETED UNCHANGED |
Only 1-2% of the dose was recovered in urine, of which unchanged nelfinavir was the major component.
URINE
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METABOLIC ENZYME -> SUBSTRATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE -> PARENT |
PLASMA
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METABOLITE ACTIVE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Biological Half-life | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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