159989-65-8

Basic information

• Product Name: Nelfinavir mesylate
• Synonyms: 8a-beta))-a-betmonomethanesulfonate(salt);droxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-,(3s-(2(2,s*,3s*),3-alpha,4;viracept;NELFINAVIR MESYLATE;AG-1343;(3s,4as,8as)-n-(1,1-dimethylethyl)decahydro-2-[(2r,3r)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide mesylate;Nelfinavir1;NELFINAVIRMESYLATE(SUBJECTTOPATENTFREE)
• CAS NO: 159989-65-8
• Molecular Formula: CH₄O₃S*C₃₂H₄₅N₃O₄S
• Molecular Weight: 663.89
• Product Categories: Active Pharmaceutical Ingredients;Anti-viral Compounds;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals;Nelfinavir;Pfizer compounds;peptides
• Mol File: 159989-65-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 131-135°C
• Boiling Point: 786.8 °C at 760 mmHg
• Flash Point: 429.7 °C
• Appearance: white to off-white/
• Storage Temp.: Store at +4°C
• Solubility: DMSO: ≥2mg/mL
• PKA: pKa -1.20(at 25℃)
• Water Solubility: 4.5g/L(temperature not stated)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• Merck: 14,6443
• CAS DataBase Reference: Nelfinavir mesylate(CAS DataBase Reference)
• NIST Chemistry Reference: Nelfinavir mesylate(159989-65-8)
• EPA Substance Registry System: Nelfinavir mesylate(159989-65-8)

Safety Data

• WGK Germany: 3
• RTECS: NW6995333
• Hazardous Substances Data: 159989-65-8(Hazardous Substances Data)

Usage

Description

Viracept was launched in the US as an orally-available, non-peptidic HIV protease inhibitor. It is prepared in an eight step synthesis beginning with N- (benzyloxycarbonyl)-L-serine β-lactone. The HIV protease inhibitory activity blocks the processing of gag and gagpol polyproteins that are required for viral maturation. It was discovered based on an experimentally derived 3D-structure of HIV-1 protease. Viracept has a high oral bioavailability, lacks toxicity, and has a resistance profile different from other protease inhibitors. Viracept with ziduvudine and larnivudine generated a 98% mean reduction from baseline in viral load after 24 weeks compared to ziduvudine and larnivudine alone. Viracept also had better CD4 counts and is available in adult and pediatric formulations.

Chemical Properties

White Powder

Originator

Agouron (US)

Uses

Different sources of media describe the Uses of 159989-65-8 differently. You can refer to the following data:
1. Nelfinavir Mesylate is an antiviral. HIV protease inhibitor. It is a COVID19-related research product.
2. An antiviral. HIV protease inhibitor.

Definition

ChEBI: A methanesulfonate (mesylate) salt prepared from equimolar amounts of nelfinavir and methanesulfonic acid. It is used for treatment of HIV and also exhibits some anticancer properties.

Biological Activity

Orally active human immunodeficiency virus protease inhibitor. Potently inhibits HIV-1 protease (K i = 2 nM) in vitro .

Biochem/physiol Actions

Nelfinavir mesylate hydrate, also known as AG1343, is used as a therapeutic agent for acquired immunodeficiency syndrome (AIDS). It acts as an antifibrotic agent and is used to treat pulmonary fibrosis in patients with systemic sclerosis (SSc). In addition, nelfinavir mesylate hydrate reduces inflammation by activating protein phosphatase 2 (PP-2) and blocking mitogen-activated protein kinases (MAPK) signaling in macrophages. It also stimulate autophagy and exhibit anti-cancer property.

References

1) Olmo?et al.?(2006),?A review of nelfinavir for the treatment of HIV infection; Expert Opin. Drug Metab. Toxicol.,?2?285 2) Bruning?et al.?(2010),?New prospects for nelfinavir in non-HIV-related diseases; Curr. Mol. Pharmacol.,?3?91 3) Gills?et al.?(2007),?Nelfinavir, A lead HIV protease inhibitor, is a broad-spectrum, anticancer agent that induces endoplasmic reticulum stress, autophagy, and apoptosis in vitro and in vivo; Clin. Cancer Res,?13?5183 4) Shim?et al. (2012),?Selective inhibition of HER2-positive breast cancer cells by the HIV protease inhibitor nelfinavir; J. Natl. Cancer Inst,,?104?1576

InChI:InChI=1/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

Upstream product

• 201402-97-3 2-{(S)-4-[(R)-2-((3S,4aS,8aS)-3-tert-Butylcarbamoyl-octahydro-isoquinolin-2-yl)-1-hydroxy-ethyl]-4,5-dihydro-oxazol-2-yl}-benzoic acid methyl ester 
• 201402-98-4 (2R,3R)-4-((3S,4aS,8aS)-3-(tertbutylcarbamoyl)octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate 
• 67000-01-5 methyltertbutyl ether 
• 159989-64-7 nelfinavir 
• 75-75-2 methanesulfonic acid 

Relevant articles and documents

Optimization of an electrolyte system for the simultaneous separation of nelfinavir mesylate and two impurities by micellar electrokinetic chromatography

A methodology for the simultaneous determination of nelfinavir mesylate and the impurities 3-hydroxy-2-methylbenzoic acid and (2R,3R)-4-((3S,4aS,8aS)-3-(tert-butylcarbamoyl) octahydroisoquinolin-2(1H)-yl)-3-hydroxy-1-(phenylthio)butan-2-aminium benzoate by micellar electrokinetic chromatography, with an analysis time of 25 min, was proposed. An electrolyte composed of sodium tetraborate buffer (pH 9.24; 25 mmol L-1), sodium dodecyl sulphate (9 mmol L-1) and methanol (10percent, v/v) was optimized using a mixed-level factorial design, with direct detection at 200 nm. After evaluating some figures of merit, such as selectivity, linearity, precision, limit of detection, limit of quantification, accuracy and robustness (using Youden's test), the method was successfully applied to the analysis of nelfinavir mesylate and its impurities in a pharmaceutical formulation. The optimized methodology is demonstrated to be useful in the determination of these analytes in a synthesis monitoring process, in raw materials and in pharmaceutical formulations, while offering low solvent consumption, requiring a small sample and using non-specific columns as advantages.

NOVEL CRYSTALLINE FORMS OF NELFINAVIR MESYLATE

The present invention provides novel crystalline forms of Nelfinavir mesylate, Form-A, Form-B, Form-C, Form-D and the process for their preparation without the use of any special equipment such as a spray drier, avoiding the use of highly flammable solven

Production of amide derivatives and intermediate compounds therefor

A method for producing an amide derivative of the formula ?XV! STR1 wherein each symbol is as defined in the specification, and an enantiomer thereof, a novel intermediate useful for producing said compound and a production method thereof. The production method of the present invention is extremely easy and simple as compared to the conventional methods, and enables effective production of compound ?XV! at high yields, which includes compound ?XVI! having an HIV protease inhibitory action. In addition, the novel intermediates of the present invention are extremely useful as intermediates for producing not only the aforementioned compound ?XVI! but also compounds useful as X-ray contrast media.