NELFINAVIR MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H45N3O4S.CH4O3S
Molecular Weight	663.888
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.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=NQHXCOAXSHGTIA-SKXNDZRYSA-N

InChI=1S/C32H45N3O4S.CH4O3S/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;1-5(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);1H3,(H,2,3,4)/t22-,23+,26-,27-,29+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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	10906218
A mutation in human immunodeficiency virus type 1 protease, N88S, that causes in vitro hypersensitivity to amprenavir.	2000 May	10756056
In vitro inhibition of HIV-1 by Met-SDF-1beta alone or in combination with antiretroviral drugs.	2000 Sep	11075940
Anti-toxoplasma activities of antiretroviral drugs and interactions with pyrimethamine and sulfadiazine in vitro.	2000 Sep	10952623
Analysis of HIV-1 mutation patterns in patients failing antiretroviral therapy.	2001	11170234
An open-label randomized trial to evaluate different therapeutic strategies of combination therapy in HIV-1 infection: design, rationale, and methods of the initio trial.	2001 Apr	11306154
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	11317086
Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology.	2001 Apr 15	11401294
Lack of association between pregnancy and selected gastrointestinal adverse events among women prescribed nelfinavir.	2001 Apr 15	11391176
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.	2001 Apr 15	11391173
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir.	2001 Apr 15	11391165
Antiviral drugs: current state of the art.	2001 Aug	11418355
Antiapoptotic mechanism of HIV protease inhibitors: preventing mitochondrial transmembrane potential loss.	2001 Aug 15	11493454
Antiretroviral therapy for previously treated patients.	2001 Aug 9	11496858
Nelfinavir, efavirenz, or both after the failure of nucleoside treatment of HIV infection.	2001 Aug 9	11496850
An argument for routine therapeutic drug monitoring of HIV-1 protease inhibitors during pregnancy.	2001 Feb 16	11273224
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	11491417
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.	2001 Jun	11397623
The effect of nevirapine in combination with nelfinavir in heavily pretreated HIV-1-infected patients: a prospective, open-label, controlled, randomized study.	2001 Jun 1	11404533
Design and synthesis of a conformationally restricted trans peptide isostere based on the bioactive conformations of saquinavir and nelfinavir.	2001 Jun 1	11374993
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
The binding energetics of first- and second-generation HIV-1 protease inhibitors: implications for drug design.	2001 Jun 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 Jun 15	11372025
Predictors of virological response in HIV-infected patients to salvage antiretroviral therapy that includes nelfinavir.	2001 Mar	11417761
Phase III trials for new PI.	2001 Mar	11313031
Severe bleeding complications in HIV-positive haemophiliac patients treated with protease inhibitors.	2001 Mar 26	11309224
Sequencing of protease inhibitor therapy: insights from an analysis of HIV phenotypic resistance in patients failing protease inhibitors.	2001 Mar 30	11316998
Ergotism related to interaction between nelfinavir and ergotamine.	2001 May	11347624
Tolerability of postexposure prophylaxis with zidovudine, lamivudine, and nelfinavir for human immunodeficiency virus infection.	2001 May 15	11317252
Low incidence of genotypic and phenotypic resistance in paediatric HIV-infected patients on long-term first-line antiretroviral triple therapy.	2001 May 25	11399999
Editorial comment on Analysis of variation in plasma concentrations of nelfinavir and its active metabolite M8 in HIV-positive patients.	2001 May 25	11399989
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment.	2001 May 25	11399984
Analysis of variation in plasma concentrations of nelfinavir and its active metabolite M8 in HIV-positive patients.	2001 May 25	11399981
Simultaneous determination of the HIV protease inhibitors indinavir, amprenavir, saquinavir, ritonavir and nelfinavir in human plasma by high-performance liquid chromatography.	2001 May 5	11393736
Novel low molecular weight spirodiketopiperazine derivatives potently inhibit R5 HIV-1 infection through their antagonistic effects on CCR5.	2001 Sep 14	11454872

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 `Mon Mar 31 18:12:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:39 GMT 2025`
Record UNII	98D603VP8V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NELFINAVIR MESYLATE

Official Name

English

NELFINAVIR MESILATE

Preferred Name

English

AG1343

Code

English

NELFINAVIR MESYLATE [VANDF]

Common Name

English

NELFINAVIR MESILATE [JAN]

Common Name

English

(3S,4aS,8aS)-N-tert-Butyl-2-[(2R,3R)-3-(3,2-cresotamido)-2-hydroxy-4-(phenylthio)butyl]decahydro-3-isoquinolinecarboxamide monomethanesulfonate (salt)

Common Name

English

VIRACEPT

Brand Name

English

AG-1343

Code

English

NELFINAVIRI MESILAS [WHO-IP LATIN]

Common Name

English

NELFINAVIR MESYLATE [ORANGE BOOK]

Common Name

English

NELFINAVIR MESYLATE [USAN]

Common Name

English

NELFINAVIR METHANESULFONATE [MI]

Common Name

English

NELFINAVIR METHANESULFONATE

Common Name

English

NELFINAVIR MESYLATE [HSDB]

Common Name

English

Nelfinavir mesilate [WHO-DD]

Common Name

English

NELFINAVIR MESILATE [MART.]

Common Name

English

NELFINAVIR MESILATE [WHO-IP]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97366