U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C32H45N3O4S
Molecular Weight 567.7847
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NELFINAVIR

SMILES

Cc1c(cccc1O)C(=N[C@@]([H])(CSc2ccccc2)[C@@]([H])(CN3C[C@@]4([H])CCCC[C@@]4([H])C[C@@]3([H])C(=NC(C)(C)C)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C32H45N3O4S
Molecular Weight 567.7847
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: 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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
12 nM [IC50]
100 µM [IC50]
7.29999999999999982 µM [IC50]
5.09999999999999964 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIRACEPT

Approved Use

VIRACEPT in combination with other antiretroviral agents is indicated for the treatment of HIV infection.

Launch Date

858211200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown, unknown
NELFINAVIR MESYLATE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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)
Thrombocytopenia (grade 3, 1 patient)
Dizziness (grade 3, 1 patient)
Elevated liver enzymes (grade 3, 2 patients)
Sources:
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)
Nausea (grade 3, 1 patient)
Fatigue (grade 3, 1 patient)
Other AEs:
Leukopenia (grade 3, 2 patients)
Thrombocytopenia (grade 3, 2 patients)
Dyspnea (grade 3, 1 patient)
Sources:
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...
Other AEs:
Thrombocytopenia (grade 4, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
International Congress on Chemotherapy.
1995 Sep
Design and fast synthesis of C-terminal duplicated potent C(2)-symmetric P1/P1'-modified HIV-1 protease inhibitors.
1999 Sep 23
Small molecule inhibitor of HIV-1 nuclear import suppresses HIV-1 replication in human lymphoid tissue ex vivo: a potential addition to current anti-HIV drug repertoire.
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
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.
2000 Dec
In vitro activity of human immunodeficiency virus protease inhibitors against Pneumocystis carinii.
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
Anti-toxoplasma activities of antiretroviral drugs and interactions with pyrimethamine and sulfadiazine in vitro.
2000 Sep
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.
2001 Apr
Gynecomastia associated with highly active antiretroviral therapy.
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
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
Antiviral drugs: current state of the art.
2001 Aug
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
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
Genetic analysis of hiv type 1 strains in bujumbura (burundi): predominance of subtype c variant.
2001 Feb 10
Failure of postexposure prophylaxis after sexual exposure to HIV.
2001 Feb 16
Reasons for modification and discontinuation of antiretrovirals: results from a single treatment centre.
2001 Jan 26
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
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
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
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
Lack of removal of nelfinavir during a haemodialysis session in an HIV-1 infected patient with hepatic and renal insufficiency.
2001 Mar
Feasibility of postexposure prophylaxis (PEP) against human immunodeficiency virus infection after sexual or injection drug use exposure: the San Francisco PEP Study.
2001 Mar 1
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine.
2001 May
Nelfinavir desensitization.
2001 May
Secreted aspartic proteases of Candida albicans, Candida tropicalis, Candida parapsilosis and Candida lusitaniae. Inhibition with peptidomimetic inhibitors.
2001 May
P1/P1' modified HIV protease inhibitors as tools in two new sensitive surface plasmon resonance biosensor screening assays.
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
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
Patents

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
Nelfinavir inhibited intracellular proteasome activity in situ at drug concentrations <40 uM in human primary myeloma cells.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:57:53 UTC 2021
Edited
by admin
on Fri Jun 25 21:57:53 UTC 2021
Record UNII
HO3OGH5D7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NELFINAVIR
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NELFINAVIR [EMA EPAR]
Common Name English
NELFINAVIR [INN]
Common Name English
NELFINAVIR [MI]
Common Name English
NSC-747167
Code English
NELFINAVIR [WHO-DD]
Common Name English
NELFINAVIR [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175889
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
WHO-ATC J05AE04
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
NCI_THESAURUS C97366
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
WHO-VATC QJ05AE04
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
FDA ORPHAN DRUG 554316
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
LIVERTOX 675
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
NDF-RT N0000000246
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
Code System Code Type Description
EVMPD
SUB09186MIG
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
PUBCHEM
64143
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
CAS
159989-64-7
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
FDA UNII
HO3OGH5D7I
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
MERCK INDEX
M7798
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY Merck Index
LACTMED
Nelfinavir
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
MESH
D019888
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
WIKIPEDIA
NELFINAVIR
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
NCI_THESAURUS
C29285
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
RXCUI
134527
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
1893
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL584
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
DRUG BANK
DB00220
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
EPA CompTox
159989-64-7
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
INN
7494
Created by admin on Fri Jun 25 21:57:53 UTC 2021 , Edited by admin on Fri Jun 25 21:57:53 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
FECAL
TARGET ORGANISM->INHIBITOR
Other
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
EXCRETED UNCHANGED
Only 1-2% of the dose was recovered in urine, of which unchanged nelfinavir was the major component.
URINE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC