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Nelfinavir mesylate

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CAS:159989-65-8
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  • 2020-01-03
  • CAS:159989-65-8
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Nelfinavir mesylate Basic information
Background
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;3-Isoquinolinecarboxamide, N-(1,1-dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-, (3S,4aS,8aS)-, methanesulfonate (1:1);(3S,4AS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl;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
CAS:159989-65-8
MF:C33H49N3O7S2
MW:663.89
EINECS:
Product Categories:Pfizer compounds;peptides;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals;Nelfinavir;Active Pharmaceutical Ingredients;Anti-viral Compounds;Coronavirus
Mol File:159989-65-8.mol
Nelfinavir mesylate Structure
Nelfinavir mesylate Chemical Properties
Melting point 131-135°C
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility DMSO: ≥2mg/mL
pkapKa -1.20(at 25℃)
form powder
color white to off-white
Water Solubility 4.5g/L(temperature not stated)
Merck 14,6443
BCS Class2,4
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChIKeyNQHXCOAXSHGTIA-SKXNDZRYSA-N
SMILESCC1=C(O)C=CC=C1C(N[C@@H](CSC2=CC=CC=C2)[C@H](O)CN3[C@H](C(NC(C)(C)C)=O)C[C@@]4([H])[C@@](CCCC4)([H])C3)=O.[CH2]S(O)(=O)=O
CAS DataBase Reference159989-65-8(CAS DataBase Reference)
Safety Information
WGK Germany 3
RTECS NW6995333
HS Code 29334900
Storage Class11 - Combustible Solids
Hazardous Substances Data159989-65-8(Hazardous Substances Data)
MSDS Information
Nelfinavir mesylate Usage And Synthesis
DescriptionViracept 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 PropertiesWhite Powder
OriginatorAgouron (US)
UsesNelfinavir Mesylate is an antiviral. HIV protease inhibitor. It is a COVID19-related research product.
DefinitionChEBI: 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.
Brand nameViracept (Agouron).
Biological ActivityOrally active human immunodeficiency virus protease inhibitor. Potently inhibits HIV-1 protease (K i = 2 nM) in vitro .
Biochem/physiol ActionsNelfinavir 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.
Synthesis
Methanesulfonic acid

75-75-2

NELFINAVIR

159989-64-7

Nelfinavir mesylate

159989-65-8

Methanesulfonic acid (8.46 g, 88 mmol) was slowly added to (3S,4aS,8aS)-N-(tert-butyl)-2-((2R,3R)-2-hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-(phenylthio)butyl)decahydroisoquinoline-3-carboxamide (50 g, 88 mmol) in acetone ( 400 ml) suspension with continuous stirring until a clarified solution was formed. The reaction mixture was continued to be stirred at 20-25 °C for 2 h. The precipitated product was subsequently collected by filtration and washed with acetone (100 ml). The resulting solid was dried under reduced pressure at 70-75 °C until the weight loss (LOD) reached -8% w/w, resulting in 57.5 g (98% yield) of (3S,4aS,8aS)-N-(tert-butyl)-2-((2R,3R)-2-hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-(phenylthio)butyl)decahydroisoquinoline-3- formamide methanesulfonate, the purity of which was analyzed by high performance liquid chromatography (HPLC) to be greater than 99.5%, and its crystalline form was confirmed by X-ray diffraction (XRD).

storageStore at +4°C
BackgroundNelfinavir Mesylate, also known as AG-1343, is a potent antiviral inhibitor of HIV-1 protease with a Ki value of 2 nM, in vitro. This small molecule is an effective antitumor agent, known to induce endoplasmic reticulum stress, autophagy, and apoptosis in vitro and in vivo. Nelfinavir Mesylate has anti-microbial effects on malaria, tuberculosis, and SARS. It has also been used in therapies as an antifibrotic agent against pulmonary fibrosis in patients with systemic sclerosis. Nelfinavir Mesylate is known to reduce inflammation by activating protein phosphatase 2 and blocking MAPK signaling in macrophages. Through a novel mechanism of heat shock protein 90 inhibition, Nelfinavir Mesylate selectively inhibits the growth of HER2-positive breast cancer cells in vitro.
References[1] MONTSERRAT OLMO  Daniel P. A review of nelfinavir for the treatment of HIV infection.[J]. Expert Opinion on Drug Metabolism & Toxicology, 2006, 2 2: 285-300. DOI:10.1517/17425255.2.2.285
[2] ANSGAR BRÜNING. New prospects for nelfinavir in non-HIV-related diseases.[J]. Current molecular pharmacology, 2010, 3 2: 91-97. DOI:10.2174/1874467211003020091
[3] JOELL J GILLS. 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.[J]. Clinical Cancer Research, 2007, 13 17: 5183-5194. DOI:10.1158/1078-0432.ccr-07-0161
[4] JOONG SUP SHIM. Selective inhibition of HER2-positive breast cancer cells by the HIV protease inhibitor nelfinavir.[J]. JNCI Journal of the National Cancer Institute, 2012, 104 20: 1576-1590. DOI:10.1093/jnci/djs396
Nelfinavir mesylate Preparation Products And Raw materials
Raw materialsMethanesulfonic acid-->Butane, 2,2'-oxybis[2-methyl--->NELFINAVIR
Tag:Nelfinavir mesylate(159989-65-8) Related Product Information
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