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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17591677
Curator's Comment: Nelfinavir has poor penetration into the macaque's brain and CSF, and P-gp inhibition at the BBB by zosuquidar enhanced the distribution of nelfinavir into the brain by 146-fold.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21256008 |
12.0 nM [IC50] | ||
Target ID: CHEMBL1293287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17026490 |
100.0 µM [IC50] | ||
Target ID: CHEMBL368 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25464510 |
7.3 µM [IC50] | ||
Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22759761 |
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 Date8.5821122E11 |
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 |
|
An open-label randomized trial to evaluate different therapeutic strategies of combination therapy in HIV-1 infection: design, rationale, and methods of the initio trial. | 2001 Apr |
|
Circulating metabolites of the human immunodeficiency virus protease inhibitor nelfinavir in humans: structural identification, levels in plasma, and antiviral activities. | 2001 Apr |
|
Performance of a quadruple combination including nelfinavir plus efavirenz in naive subjects with high baseline viral load and in patients failing protease inhibitor-containing regimens. | 2001 Apr 1 |
|
Resolution of chronic parvovirus b19-induced anemia, by use of highly active antiretroviral therapy, in a patient with acquired immunodeficiency syndrome. | 2001 Apr 1 |
|
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 |
|
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 |
|
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 |
|
Pharmacology and clinical experience with saquinavir. | 2001 Feb |
|
Failure of postexposure prophylaxis after sexual exposure to HIV. | 2001 Feb 16 |
|
An argument for routine therapeutic drug monitoring of HIV-1 protease inhibitors during pregnancy. | 2001 Feb 16 |
|
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 |
|
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 |
|
The effects of antiretroviral protease inhibitors on serum lipid levels in HIV-infected patients. | 2001 Jun |
|
The HIV protease inhibitor nelfinavir induces insulin resistance and increases basal lipolysis in 3T3-L1 adipocytes. | 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 |
|
Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection. | 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 |
|
Phase III trials for new PI. | 2001 Mar |
|
Severe bleeding complications in HIV-positive haemophiliac patients treated with protease inhibitors. | 2001 Mar 26 |
|
Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors. | 2001 Mar 30 |
|
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine. | 2001 May |
|
Secreted aspartic proteases of Candida albicans, Candida tropicalis, Candida parapsilosis and Candida lusitaniae. Inhibition with peptidomimetic inhibitors. | 2001 May |
|
Tolerability of postexposure prophylaxis with zidovudine, lamivudine, and nelfinavir for human immunodeficiency virus infection. | 2001 May 15 |
|
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy. | 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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23454896
Nelfinavir inhibited intracellular proteasome activity in situ at drug concentrations <40 uM in human primary myeloma cells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 21:55:22 UTC 2023
by
admin
on
Thu Jul 06 21:55:22 UTC 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
Created by
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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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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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PRIMARY | |||
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DB00220
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DTXSID5035080
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PRIMARY | |||
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7494
Created by
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PRIMARY |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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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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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 | |||
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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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 |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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