| Identification | More | [Name]
Nelfinavir mesylate | [CAS]
159989-65-8 | [Synonyms]
(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
AG-1343
NELFINAVIR MESYLATE
8a-beta))-a-betmonomethanesulfonate(salt)
droxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-,(3s-(2(2,s*,3s*),3-alpha,4
viracept
Nelfinavir1
(3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide
NELFINAVIRMESYLATE(SUBJECTTOPATENTFREE)
Nelfinavir nesylate
(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
(3S,4aS,8aS)-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methyl-benzoyl)amino]-4-phenylsulfanyl-butyl]-N-tert-butyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide | [Molecular Formula]
C33H49N3O7S2 | [MDL Number]
MFCD00931436 | [Molecular Weight]
663.89 | [MOL File]
159989-65-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [Melting point ]
131-135°C | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
DMSO: ≥2mg/mL | [form ]
powder | [pka]
pKa -1.20(at 25℃) | [color ]
white to off-white | [Water Solubility ]
4.5g/L(temperature not stated) | [Usage]
An antiviral | [Merck ]
14,6443 | [BCS Class]
2,4 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. | [InChIKey]
NQHXCOAXSHGTIA-SKXNDZRYSA-N | [SMILES]
CC1=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 Reference]
159989-65-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [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]
An antiviral. HIV protease inhibitor. | [Uses]
Nelfinavir Mesylate is an antiviral. HIV protease inhibitor. It is a COVID19-related research product. | [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. | [Brand name]
Viracept (Agouron). | [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. | [Synthesis]
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). | [storage]
Store at +4°C | [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 |
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
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https://www.jkchemical.com |
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T&W GROUP
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021-61551611 13296011611 |
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www.trustwe.com/ |
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