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 |
|---|---|---|
| Non-active site changes elicit broad-based cross-resistance of the HIV-1 protease to inhibitors. | 1999 Aug 20 |
|
| 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 |
|
| Design and fast synthesis of C-terminal duplicated potent C(2)-symmetric P1/P1'-modified HIV-1 protease inhibitors. | 1999 Sep 23 |
|
| Didanosine-induced hepatitis. | 2000 Aug |
|
| Structural and kinetic analyses of the protease from an amprenavir-resistant human immunodeficiency virus type 1 mutant rendered resistant to saquinavir and resensitized to amprenavir. | 2000 Aug |
|
| BMS-232632, a highly potent human immunodeficiency virus protease inhibitor that can be used in combination with other available antiretroviral agents. | 2000 Aug |
|
| Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins. | 2000 Dec |
|
| A randomized, comparative study of lamivudine plus stavudine, with indinavir or nelfinavir, in treatment-experienced HIV-infected patients. | 2000 Jan 28 |
|
| In vitro activity of human immunodeficiency virus protease inhibitors against Pneumocystis carinii. | 2000 May |
|
| A mutation in human immunodeficiency virus type 1 protease, N88S, that causes in vitro hypersensitivity to amprenavir. | 2000 May |
|
| 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 |
|
| In vitro resistance profile of the human immunodeficiency virus type 1 protease inhibitor BMS-232632. | 2000 Sep |
|
| Tipranavir inhibits broadly protease inhibitor-resistant HIV-1 clinical samples. | 2000 Sep 8 |
|
| Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology. | 2001 Apr 15 |
|
| Antiapoptotic mechanism of HIV protease inhibitors: preventing mitochondrial transmembrane potential loss. | 2001 Aug 15 |
|
| Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion. | 2001 Feb |
|
| Failure of postexposure prophylaxis after sexual exposure to HIV. | 2001 Feb 16 |
|
| 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 |
|
| Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART. | 2001 Jun |
|
| 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 |
|
| Predictors of virological response in HIV-infected patients to salvage antiretroviral therapy that includes nelfinavir. | 2001 Mar |
|
| Lack of removal of nelfinavir during a haemodialysis session in an HIV-1 infected patient with hepatic and renal insufficiency. | 2001 Mar |
|
| Ergotism related to interaction between nelfinavir and ergotamine. | 2001 May |
|
| Induction of P-glycoprotein and cytochrome P450 3A by HIV protease inhibitors. | 2001 May |
|
| P1/P1' modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays. | 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 |
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
by
admin
on
Edited
Sat Dec 16 16:26:02 GMT 2023
by
admin
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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 |
| 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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PRIMARY | |||
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64143
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PRIMARY | |||
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159989-64-7
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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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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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PRIMARY | RxNorm | ||
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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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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 | |||
|
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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