NELFINAVIR

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 Search

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
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Human immunodeficiency virus 1 34 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21256008	Inhibitor 8504	12.0 nM [IC50]
Insulin-degrading enzyme 2 Target ID: CHEMBL1293287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17026490	Inhibitor 8504	100.0 µM [IC50]
Trypanosoma cruzi 12 Target ID: CHEMBL368 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25464510	Inhibitor 8504	7.3 µM [IC50]
HepG2 16 Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22759761	Inhibitor 8504	5.1 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV infection 21 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020778s035,020779s056,021503s017lbl.pdf	Primary		Approved 8583	VIRACEPT Approved Use VIRACEPT in combination with other antiretroviral agents is indicated for the treatment of HIV infection. Launch Date 1997

C_max

Value	Dose	Analyte	Population
4 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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	Analyte	Population
52.8 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.8 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10200859	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/10200859	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020778s041,020779s062,021503s024lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/24596143	unhealthy, 52 years (range: 25-77 years) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24596143	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: https://pubmed.ncbi.nlm.nih.gov/24596143
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919	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: https://pubmed.ncbi.nlm.nih.gov/22425919
650 mg 2 times / day steady, oral Dose: 650 mg, 2 times / day Route: oral Route: steady Dose: 650 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919	Other AEs: Thrombocytopenia... Other AEs: Thrombocytopenia (grade 4, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/22425919

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: https://pubmed.ncbi.nlm.nih.gov/24596143	unhealthy, 52 years (range: 25-77 years) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24596143
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: https://pubmed.ncbi.nlm.nih.gov/24596143	unhealthy, 52 years (range: 25-77 years) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24596143
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: https://pubmed.ncbi.nlm.nih.gov/24596143	unhealthy, 52 years (range: 25-77 years) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24596143
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: https://pubmed.ncbi.nlm.nih.gov/24596143	unhealthy, 52 years (range: 25-77 years) Health Status: unhealthy Age Group: 52 years (range: 25-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/24596143
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919
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: https://pubmed.ncbi.nlm.nih.gov/22425919	unhealthy, 59 years (range: 54–75 years) Health Status: unhealthy Age Group: 59 years (range: 54–75 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22425919

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7496	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7496
ChemicalBook	CB8213806	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8213806
MolPort	MolPort-000-883-833	https://www.molport.com/shop/molecule-link/MolPort-000-883-833
ZINC	ZINC000003833846	http://zinc15.docking.org/substances/ZINC000003833846

PubMed

Title	Date	PubMed
Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5.	2001-09-14	11454872
Peptide mimetic HIV protease inhibitors are ligands for the orphan receptor SXR.	2001-09-07	11466304
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.	2001-09	11448730
Antiapoptotic mechanism of HIV protease inhibitors: preventing mitochondrial transmembrane potential loss.	2001-08-15	11493454
Antiretroviral therapy for previously treated patients.	2001-08-09	11496858
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection.	2001-08-09	11496850
Eruptive cheilitis: a new adverse effect in reactive HIV-positive patients subjected to high activity antiretroviral therapy (HAART). Presentation of six clinical cases.	2001-08-08	11488127
Comparison of virologic, immunologic, and clinical response to five different initial protease inhibitor-containing and nevirapine-containing regimens.	2001-08-01	11468423
HIV-protease inhibitors contribute to P-glycoprotein efflux function defect in peripheral blood lymphocytes from HIV-positive patients receiving HAART.	2001-08-01	11468419
Lipid abnormalities in a healthcare worker receiving HIV prophylaxis.	2001-08	11487394
Nelfinavir plasma levels under twice-daily and three-times-daily regimens: high interpatient and low intrapatient variability.	2001-08	11477322
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.	2001-08	11477320
Antiviral drugs: current state of the art.	2001-08	11418355
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.	2001-07-15	11486821
Capillary electrophoretic separation of protease inhibitors used in human immunodeficiency virus therapy.	2001-07-13	11486877
Stable or increasing bone mineral density in HIV-infected patients treated with nelfinavir or indinavir.	2001-07-06	11426072
Combination therapy with saquinavir soft gelatin capsules in children with human immunodeficiency virus infection.	2001-07	11465838
CMVR diagnoses and progression of CD4 cell counts and HIV viral load measurements in HIV patients on HAART.	2001-07	11423459
Simultaneous determination of the HIV-protease inhibitors indinavir, amprenavir, ritonavir, saquinavir and nelfinavir in human plasma by reversed-phase high-performance liquid chromatography.	2001-06-15	11417878
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design.	2001-06-15	11396919
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).	2001-06-15	11372025
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.	2001-06-01	11404533
Design and synthesis of a conformationally restricted trans peptide isostere based on the bioactive conformations of saquinavir and nelfinavir.	2001-06-01	11374993
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.	2001-06	11491417
Antiretroviral activity and safety of abacavir in combination with selected HIV-1 protease inhibitors in therapy-naive HIV-1-infected adults.	2001-06	11491415
The effects of antiretroviral protease inhibitors on serum lipid levels in HIV-infected patients.	2001-06	11424549
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001-06	11397623
The HIV protease inhibitor nelfinavir induces insulin resistance and increases basal lipolysis in 3T3-L1 adipocytes.	2001-06	11375344
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.	2001-06	11368826
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.	2001-05-25	11399999
Editorial comment on Analysis of variation in plasma concentrations of nelfinavir and its active metabolite M8 in HIV-positive patients.	2001-05-25	11399989
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment.	2001-05-25	11399984
Analysis of variation in plasma concentrations of nelfinavir and its active metabolite M8 in HIV-positive patients.	2001-05-25	11399981
New developments in anti-HIV chemotherapy.	2001-05-12	11347962
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography.	2001-05-05	11393736
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine.	2001-05	11377177
Ergotism related to interaction between nelfinavir and ergotamine.	2001-05	11347624
Nelfinavir desensitization.	2001-05	11346060
Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology.	2001-04-15	11401294
Lack of association between pregnancy and selected gastrointestinal adverse events among women prescribed nelfinavir.	2001-04-15	11391176
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001-04-15	11391173
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir.	2001-04-15	11391165
Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport.	2001-04-13	11371681
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.	2001-04-13	11355843
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.	2001-04	11359661
Predictors of virological response in HIV-infected patients to salvage antiretroviral therapy that includes nelfinavir.	2001-03	11417761
[Resistance to protease inhibitors].	2001-02	11428058
Saquinavir soft gelatin capsule: a comparative safety review.	2001	11347724
Viracept and irregular heartbeat warning.	1999-10	11366874
International Congress on Chemotherapy.	1995-09	11362904

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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Name

Type

Language

NELFINAVIR [EMA EPAR]

Preferred Name

English

NELFINAVIR

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