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
Unexplained thrombosis in HIV-infected patients receiving protease inhibitors: report of seven cases.	1999 Dec	10625032
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	10337948
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	10508005
Inhibition of HIV-1 protease by a boron-modified polypeptide.	2000 Oct 1	10974201
In vitro inhibition of HIV-1 by Met-SDF-1beta alone or in combination with antiretroviral drugs.	2000 Sep	11075940
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.	2001 Apr 13	11355843
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	11477320
Antiviral drugs: current state of the art.	2001 Aug	11418355
Comparison of virologic, immunologic, and clinical response to five different initial protease inhibitor-containing and nevirapine-containing regimens.	2001 Aug 1	11468423
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	11206045
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	11417878
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	11372025
Predictors of virological response in HIV-infected patients to salvage antiretroviral therapy that includes nelfinavir.	2001 Mar	11417761
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine.	2001 May	11377177
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.	2001 May 25	11399999
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	11448730
Peptide mimetic HIV protease inhibitors are ligands for the orphan receptor SXR.	2001 Sep 7	11466304

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