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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
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Targets

Primary TargetPharmacologyConditionPotency
5.1 µM [IC50]
100.0 µM [IC50]
7.3 µM [IC50]
12.0 nM [IC50]
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
International Congress on Chemotherapy.
1995 Sep
Viracept and irregular heartbeat warning.
1999 Oct
Saquinavir soft gelatin capsule: a comparative safety review.
2001
Virologic outcome and predictors of virologic failure of highly active antiretroviral therapy containing protease inhibitors.
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
Differences in the intracellular accumulation of HIV protease inhibitors in vitro and the effect of active transport.
2001 Apr 13
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
Determination of interaction kinetic constants for HIV-1 protease inhibitors using optical biosensor technology.
2001 Apr 15
Lack of association between pregnancy and selected gastrointestinal adverse events among women prescribed nelfinavir.
2001 Apr 15
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.
2001 Apr 15
A phase II trial of dual protease inhibitor therapy: amprenavir in combination with indinavir, nelfinavir, or saquinavir.
2001 Apr 15
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
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
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
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
New developments in anti-HIV chemotherapy.
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
Limits of deep salvage antiretroviral therapy with nelfinavir plus either efavirenz or nevirapine, in highly pre-treated patients with HIV disease.
2001 Jun
The HIV protease inhibitor nelfinavir induces insulin resistance and increases basal lipolysis in 3T3-L1 adipocytes.
2001 Jun
Severe lactic acidosis and thiamine administration in an HIV-infected patient on HAART.
2001 Jun
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
Design and synthesis of a conformationally restricted trans peptide isostere based on the bioactive conformations of saquinavir and nelfinavir.
2001 Jun 1
Hypercholesterolemia in a health care worker receiving thyroxine after postexposure prophylaxis for human immunodeficiency virus infection.
2001 Jun 1
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
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
Structure-activity studies of FIV and HIV protease inhibitors containing allophenylnorstatine.
2001 May
Ergotism related to interaction between nelfinavir and ergotamine.
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
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
Sexual dysfunction associated with protease inhibitor containing highly active antiretroviral treatment.
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
Peptide mimetic HIV protease inhibitors are ligands for the orphan receptor SXR.
2001 Sep 7
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 Oct 21 19:48:07 UTC 2019
Edited
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on Mon Oct 21 19:48:07 UTC 2019
Record UNII
HO3OGH5D7I
Record Status Validated (UNII)
Record Version
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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
NELFINAVIR [WHO-DD]
Common Name English
NELFINAVIR [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175889
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
WHO-ATC J05AE04
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
NCI_THESAURUS C97366
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
WHO-VATC QJ05AE04
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
FDA ORPHAN DRUG 554316
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
LIVERTOX 675
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
NDF-RT N0000000246
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
Code System Code Type Description
EVMPD
SUB09186MIG
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
PUBCHEM
64143
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
CAS
159989-64-7
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
MERCK INDEX
M7798
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY Merck Index
MESH
D019888
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
WIKIPEDIA
NELFINAVIR
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
NCI_THESAURUS
C29285
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
RXCUI
134527
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL584
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
DRUG BANK
DB00220
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
EPA CompTox
159989-64-7
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
LactMed
159989-64-7
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
INN
7494
Created by admin on Mon Oct 21 19:48:07 UTC 2019 , Edited by admin on Mon Oct 21 19:48:07 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC