635728-49-3

Basic information

• Product Name: Unii-33o78xf0bw
• Synonyms: Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)-, (3R,3as,6ar)-hexahydrofuro(2,3-B)furan-3-yl ester, compd. with ethanol (1:1);Darunavir ethanolate;Unii-33o78xf0bw;N-[(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester compd. with ethanol;Darunavir Ethanolate(Prezista);Darunavir(TMC-114,UIC 94017) Ethanolate;N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl carbamic acid ester, compd. with ethanol (1:1);(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate compound with ethanol (1:1)
• CAS NO: 635728-49-3
• Molecular Formula: C₂H₆O*C₂₇H₃₇N₃O₇S
• Molecular Weight: 593.73202
• Product Categories: Inhibitor;Prezista, TMC114;Other APIs;Inhibitors
• Mol File: 635728-49-3.mol
• Article Data: 3

Chemical Properties

• Appearance: White Solid
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Unii-33o78xf0bw(CAS DataBase Reference)
• NIST Chemistry Reference: Unii-33o78xf0bw(635728-49-3)
• EPA Substance Registry System: Unii-33o78xf0bw(635728-49-3)

Safety Data

• Hazardous Substances Data: 635728-49-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 635728-49-3 differently. You can refer to the following data:
1. Darunavir Ethanolate(Prezista) is an inhibitor of HIV protease. [1] Darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including strains from treatment-experienced patients with multiple resistance mutati
2. Darunavir Ethanolate (Prezista) is an HIV protease inhibitor. Derivative of Darunavir (D193500), a second generation HIV-1-protease inhibitor; structurally similar to amprenavir. Antiviral. It is a COVID19-related research product.

Biological Activity

darunavir ethanolate is a nonpeptidic hiv protease inhibitor approved for the treatment of hiv infection[1].transepithelial transport of darunavir in caco-2 cell monolayers is 2-fold greater in the basal-to-apical direction compared to that in the opposite direction. in l-mdr1 cell, darunavir (121 mm) inhibits p-glycoprotein-mediated efflux of calcein-acetoxymethyl ester[1].darunavir is effective against wild-type and pi-resistant hiv, and has a low oral bioavailability (37%). when used in combination with ritonavir, bioavailability can be increased to 82%[2].[1]. fujimoto h, higuchi m, watanabe h, et al. p-glycoprotein mediates efflux transport of darunavir in human intestinal caco-2 and abcb1 gene-transfected renal llc-pk1 cell lines. biological & pharmaceutical bulletin, 2009, 32(9): 1588-1593.[2]. bhalekar mr, et al. in-vivo bioavailability and lymphatic uptake evaluation of lipid nanoparticulates of darunavir. drug deliv, 2016, 23(7): 2581-2586.

Upstream product

• 64-17-5 ethanol 
• 206361-99-1 darunavir 
• 192725-55-6 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid 
• 169280-56-2 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 183004-94-6 3-S-(N-tert-butyloxyformamido)-[2R-hydroxy-1-[(4-aminophenylsulfonyl)(2-methylpropyl)]amino]-4-phenylbutane 
• 191226-98-9 [(1S,2R)-3-[(4-nitrophenylsulfonyl)(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester 
• 160232-08-6 (2R,3S)-3-tert-butoxycarbonylamino-1-isobutylamino-4-phenyl-2-butanol 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 

Downstream Products

• 206361-99-1 darunavir 

Relevant articles and documents

An improved and robust scale-up process aided with identification and control of critical process impurities in darunavir ethanolate

A robust and safe industrial process, including five isolations and drying steps for widely prescribed anti-HIV (protease inhibitor) drug darunavir ethanolate 2, has been developed. A salient feature of this process is the development of procedures enabling the efficient synthesis of multi-kilogram quantity of darunavir ethanolate, and process demonstrations through plant scale preparation are offered where darunavir molecule has been prepared with overall > 70% chemical yield and > 99.8% purity without involving any purification procedure(s), with all possible process impurities below than the desired limit (not more than 0.08%) were isolated, synthesized and characterized. The developed process is entirely robust, very efficient and demonstrated up to kilograms scale.

A NOVEL PROCESS FOR PREPARATION OF DARUNAVIR AND DARUNAVIR ETHANOLATE OF FINE PARTICLE SIZE

The present invention provides a novel process for preparation of darunavir that involves reduction of [(1S,2R)-3-[[(4-nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy -1-(phenylmethyl) propyl] carbamic acid (3R,3aS,6aR)-hexahydrofuro [2,3-b]furan-3-yl ester, of formula (5). The present invention also provides darunavir ethanolate of particle size wherein d0.9 is less than 130 μm, d0.5 is less than 30 μm, d0.1 is less than 10 μm and process for its preparation.