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

CAS DataBase Reference

159989-65-8(CAS DataBase Reference)

Safety Information

WGK Germany 

3

RTECS 

NW6995333

HS Code 

29334900

Hazardous Substances Data

159989-65-8(Hazardous Substances Data)

Nelfinavir mesylate Usage And Synthesis

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

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] 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

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