Nelfinavir mesylate CAS 159989-65-8
Introduction：Basic information about Nelfinavir mesylate CAS 159989-65-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Nelfinavir mesylate Basic informationBackground
| 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 Chemical Properties
| Melting point | 131-135°C |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | DMSO: ≥2mg/mL |
| pka | pKa -1.20(at 25℃) |
| form | powder |
| color | white to off-white |
| Water Solubility | 4.5g/L(temperature not stated) |
| 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) |
Safety Information
| WGK Germany | 3 |
| RTECS | NW6995333 |
| HS Code | 29334900 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 159989-65-8(Hazardous Substances Data) |
| Description | Viracept was launched in the US as an orally-available, non-peptidic HIVprotease inhibitor. It is prepared in an eight step synthesis beginning with N-(benzyloxycarbonyl)-L-serine β-lactone. The HIV protease inhibitory activity blocks theprocessing of gag and gagpol polyproteins that are required for viral maturation. Itwas discovered based on an experimentally derived 3D-structure of HIV-1 protease.Viracept has a high oral bioavailability, lacks toxicity, and has a resistance profiledifferent from other protease inhibitors. Viracept with ziduvudine and larnivudinegenerated a 98% mean reduction from baseline in viral load after 24 weeks comparedto ziduvudine and larnivudine alone. Viracept also had better CD4 counts and isavailable in adult and pediatric formulations. |
| Chemical Properties | White Powder |
| Originator | Agouron (US) |
| 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 | 75-75-2 159989-64-7 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). |
| storage | Store at +4°C |
| Background | Nelfinavir 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 materials | Methanesulfonic acid-->Butane, 2,2'-oxybis[2-methyl--->NELFINAVIR |
