ChemicalBook > CAS DataBase List > Darunavir ethanolate

Darunavir ethanolate

Product Name: Darunavir ethanolate
CAS No.: 635728-49-3
Chemical Name: Darunavir ethanolate
Synonyms: Darunavir ethanolate;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);To the drug;Unii-33o78xf0bw;[14C]-Darunavir ethanolate;Darunavir Ethanolate (100 mg);Darunavir ethanolate- Bio-X ?;Darunavir Ethanolate(Prezista);Darunavir Ethanolate, 10 mM in DMSO;Darunavir Ethanolate (DRV, Prezista)
CBNumber: CB32496602
Molecular Formula: C29H43N3O8S
Formula Weight: 593.74
MOL File: 635728-49-3.mol

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Darunavir ethanolate Property

Melting point:: 98-100°C
storage temp.: Refrigerator
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Solid
color: White
InChIKey: QWSHKNICRJHQCY-MVUAUMSNNA-N
SMILES: C(O)C.O([C@H]1CO[C@@]2([H])OCC[C@@]12[H])C(=O)N[C@@H](CC1C=CC=CC=1)[C@H](O)CN(CC(C)C)S(C1C=CC(N)=CC=1)(=O)=O |&1:4,7,12,17,25,r|

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Safety

HS Code: 29334900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: D193520
Product name: DarunavirEthanolate
Packaging: 5mg
Price: $150
Updated: 2021/12/16

Usbiological

Product number: 163597
Product name: Darunavir Ethanolate
Packaging: 5mg
Price: $460
Updated: 2021/12/16

TRC

Product number: D193520
Product name: DarunavirEthanolate
Packaging: 50mg
Price: $770
Updated: 2021/12/16

Ark Pharm

Product number: P000132501
Product name: Darunavir Ethanolate
Purity: 98+%
Packaging: 1mg
Price: $43
Updated: 2021/12/16

ChemScene

Product number: CS-0750
Product name: DarunavirEthanolate
Purity: 99.92%
Packaging: 5mg
Price: $50
Updated: 2021/12/16

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Darunavir ethanolate Chemical Properties,Usage,Production

Uses

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

Uses

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.

Synthesis

64-17-5

192725-55-6

169280-56-2

635728-49-3

GENERAL STEPS: A solution of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (4-nitrophenyl) carbonate (75.4 g) was prepared by dissolving it in N-methyl-2-pyrrolidone (300 mL). This solution was slowly added to a pre-cooled solution of 4-amino-N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-isobutylbenzenesulfonamide (100 g) in N-methyl-2-pyrrolidinone (200 mL) at -4 to 0 °C, maintaining the temperature at 2±2 °C for 2 hours. Subsequently, the temperature of the reaction mixture was slowly increased to 25-30 °C and kept at this temperature for 8 hours. The reaction process was monitored by TLC. Upon completion of the reaction, ethyl acetate (1000 mL) and purified water (500 mL) were added to the reaction mixture and layered. The organic layer was washed sequentially with sodium carbonate solution (2 x 500 mL) and sodium chloride solution. After concentrating the organic layer, ethanol (300 mL) was added and heated to 45-50 °C and kept for 1 h. Then it was filtered and washed with ethanol. The wet compound was added to a mixture of ethyl acetate-ethanol (7:93, 600mL), heated to reflux, activated carbon added and filtered. The filtrate was cooled to 0-5 °C, the separated solid was filtered and washed with ethanol. Finally, the wet compound was dried at 45 °C to give 124.3 g of the target product, i.e., the ethanol salt of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylbenzenesulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate, which had an HPLC area purity of 99.79%. The area of difuranyl impurity determined by HPLC was 0.08%, and the yield was 82.5%.

in vivo

Darunavir is effective against wild-type and PI-resistant HIV, and has an oral bioavailability of 37%. It needs to be combined with ritonavir, which increases the bioavailability to 82%^[3].

IC 50

HIV-1

References

[1] Patent: US2012/251826, 2012, A1. Location in patent: Page/Page column 10

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Preparation Products

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View Lastest Price from Darunavir ethanolate manufacturers

Anhuyan (Hainan) Biotechnology Co., LTD

Product: Darunavir ethanolate 635728-49-3
Price: US $0.00/G/KG
Min. Order: 1G/KG
Purity: 99%
Supply Ability: 100MT
Release date: 2025-04-22

Sinoway Industrial co., ltd.

Product: Darunavir ethanolate 635728-49-3
Price: US $0.00/Kg/Bag
Min. Order: 2Kg/Bag
Purity: 0.0099
Supply Ability: 20 tons
Release date: 2021-08-05

Baoji Guokang Healthchem Co., Ltd.

Product: Unii-33o78xf0bw 635728-49-3
Price: US $63.00/g
Min. Order: 1g
Purity: 98%
Supply Ability: 100kg
Release date: 2021-06-04

635728-49-3, Darunavir ethanolateRelated Search:

1-epi-Darunavir (3aS,4R,6aR)-Tetrahydro-4-Methoxyfuro[3,4-b]furan-2(3H)-one BIS THF Nitro Derivative 2 Darunavir O-β-D-Glucuronide BIS THF HNS Derivative 3 Repaglinide Pazopanib Hydrochloride 4-Hydroxy Darunavir [(3R,3aS,6aR)-Hydroxyhexahydrofuro[2,3-β]furanyl Succinimidyl Carbonate tert-Butyl [(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl[(4-nitrophenyl)sulfonyl]amino]propyl]carbamate Darunavir (3R,3αS,6αR)-Hexahydrofuro[2,3-β]furan-3-yl-4-nitrophenyl carbonate 4-AMINO-N-[(2R,3S)-3-AMINO-2-HYDROXY-4-PHENYLBUTYL]-N-ISOBUTYLBENZENE-1-SULFONAMIDE 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile GSK1349572 Raltegravir Etravirine Atazanavir sulfate

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)

[14C]-Darunavir ethanolate

DARUNAVIR ETHANOLATE (TMC114 ETHANOLATE)

Darunavir Ethanolate (DRV, Prezista)

Darunavir EthanolateQ: What is Darunavir Ethanolate Q: What is the CAS Number of Darunavir Ethanolate Q: What is the storage condition of Darunavir Ethanolate Q: What are the applications of Darunavir Ethanolate

To the drug

(3R,3AS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate Ethanolate

Darunavir Ethanolate (100 mg)

Darunavir Ethanolate, 10 mM in DMSO

Darunavir ethanolate- Bio-X ?

635728-49-3

20661-99-1

C29H43N3O8S

C27H37N3O7SC2H6O

C27H37N3O7SC2H5OH

API

Inhibitor

Prezista, TMC114

Other APIs

Inhibitors