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
CC1=C(C=CC=C1O)C(=O)N[C@@H](CSC2=CC=CC=C2)[C@H](O)CN3C[C@H]4CCCC[C@H]4C[C@H]3C(=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 Date1997 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
4.7 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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
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) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Unexplained thrombosis in HIV-infected patients receiving protease inhibitors: report of seven cases. | 1999 Dec |
|
A generalized seizure following initiation of nelfinavir in a patient with human immunodeficiency virus type 1 infection, suspected due to interaction between nelfinavir and phenytoin. | 1999 Mar |
|
Inhibition of human immunodeficiency virus type 1 replication in acutely and chronically infected cells by EM2487, a novel substance produced by a Streptomyces species. | 1999 Oct |
|
Inhibition of HIV-1 protease by a boron-modified polypeptide. | 2000 Oct 1 |
|
In vitro inhibition of HIV-1 by Met-SDF-1beta alone or in combination with antiretroviral drugs. | 2000 Sep |
|
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography. | 2001 Apr 13 |
|
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 |
|
Sensitive and rapid method for the simultaneous quantification of the HIV-protease inhibitors indinavir, nelfinavir, ritonavir, and saquinavir in human plasma by reversed-phase liquid chromatography. | 2001 Feb |
|
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 |
|
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 |
|
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy. | 2001 May 25 |
|
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 |
|
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
Wed Apr 02 07:50:12 GMT 2025
by
admin
on
Wed Apr 02 07:50:12 GMT 2025
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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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Preferred Name | English | ||
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Official 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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SUB09186MIG
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64143
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159989-64-7
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HO3OGH5D7I
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m7798
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100000085450
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Nelfinavir
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D019888
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NELFINAVIR
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HO3OGH5D7I
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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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7494
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> 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 -> SUBSTRATE | |||
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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 | ||
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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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