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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
Structure of NELFINAVIR

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

HIDE SMILES / InChI

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

Description
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

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
12.0 nM [IC50]
100.0 µM [IC50]
7.3 µM [IC50]
5.1 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

1997
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

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
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
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 Wed Apr 02 07:50:12 GMT 2025
Edited
by admin
on Wed Apr 02 07:50:12 GMT 2025
Record UNII
HO3OGH5D7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NELFINAVIR [EMA EPAR]
Preferred Name English
NELFINAVIR
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
nelfinavir [INN]
Common Name English
Nelfinavir [WHO-DD]
Common Name English
NELFINAVIR [MI]
Common Name English
NSC-747167
Code English
NELFINAVIR [VANDF]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 554316
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
NDF-RT N0000175889
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
WHO-ATC J05AE04
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
NCI_THESAURUS C97366
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
WHO-VATC QJ05AE04
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
LIVERTOX NBK548311
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
NDF-RT N0000000246
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
Code System Code Type Description
EVMPD
SUB09186MIG
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
PUBCHEM
64143
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
CAS
159989-64-7
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
FDA UNII
HO3OGH5D7I
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
MERCK INDEX
m7798
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY Merck Index
SMS_ID
100000085450
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
LACTMED
Nelfinavir
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
MESH
D019888
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
WIKIPEDIA
NELFINAVIR
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
DAILYMED
HO3OGH5D7I
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
NCI_THESAURUS
C29285
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
NSC
747167
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
RXCUI
134527
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
1893
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
CHEBI
7496
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL584
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
DRUG BANK
DB00220
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID5035080
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
INN
7494
Created by admin on Wed Apr 02 07:50:13 GMT 2025 , Edited by admin on Wed Apr 02 07:50:13 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
FECAL
TARGET ORGANISM->INHIBITOR
Other
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
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