Isavuconazole

Base Information

• Chemical Name: Isavuconazole
• CAS No.: 241479-67-4
• Deprecated CAS: 672948-06-0
• Molecular Formula: C22H17F2N5OS
• Molecular Weight: 437.473
• European Community (EC) Number: 889-355-8
• UNII: 60UTO373KE
• DSSTox Substance ID: DTXSID2058251
• Nikkaji Number: J1.733.414J
• Wikidata: Q6079042
• NCI Thesaurus Code: C64543
• RXCUI: 1720882
• Metabolomics Workbench ID: 152758
• ChEMBL ID: CHEMBL409153
• Mol file: 241479-67-4.mol

Synonyms:1-((2R,3R)-3-(4-(4-cyanophenyl)-1,3-thiazol-2-yl)-2-(2,5-difluorophenyl)-2-hydroxybutyl)-4-((1RS)-1-((methyl(3-((((methylamino)acetyl)oxy)methyl)pyridin-2-yl)carbamoyl)oxy)ethyl)-1H-1,2,4-triazol-4-ium monosulfate;4-(2-((2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)-1,3-thiazol-4-yl)benzonitrile;AK-1820;AK1820;BAL 4815;BAL 8557;BAL-4815;BAL-8557;BAL-8557-002;BAL4815;BAL8557;BAL8557-002;Cresemba;isavuconazole;isavuconazonium sulfate

Chemical Property of Isavuconazole

Chemical Property:

• Boiling Point: 678 °C at 760 mmHg
• PKA: 11.42±0.29(Predicted)
• Flash Point: 363.8 °C
• PSA: 115.86000
• Density: 1.38 g/cm³
• LogP: 4.24298
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 437.11218768
• Heavy Atom Count: 31
• Complexity: 657

Purity/Quality:

99% ^*data from raw suppliers

Isavuconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=NC(=CS1)C2=CC=C(C=C2)C#N)C(CN3C=NC=N3)(C4=C(C=CC(=C4)F)F)O
• Isomeric SMILES: C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@](CN3C=NC=N3)(C4=C(C=CC(=C4)F)F)O
• Recent ClinicalTrials: Phase 1 Study of Ibrutinib and Immuno-Chemotherapy Using Temozolomide, Etoposide, Doxil, Dexamethasone, Ibrutinib,Rituximab (TEDDI-R) in Primary CNS Lymphoma
• Recent EU Clinical Trials: Phase IV, unicentric, multiple dose, clinical trial, with a single treatment arm to evaluate bronchopulmonary penetration of isavuconazole in pulmonary transplant recipients (PBISA01)
• Description: BAL-8557 (isavuconazonium) is the water-soluble pro-drug of BAL-4815 (isavuconazole). The conversion to isavuconazole is rapid and complete with very little cleavage product detectable – thus this chapter will focus entirely on isavuconazole. Isavuconazole is produced and developed by Basilea Pharmaceutica and, in common with the other azoles, works by inhibition of ergosterol synthesis. Isavuconazole is a water-soluble compound (the only broad-spectrum water soluble triazole) with oral and intravenous formulations and excellent bioavailability. Its long elimination half-life allows up to once-weekly dosing.
• Uses: Isavuconazole is a new triazole currently undergoing phase III clinical trials. Isavuconazole has shown in vitro activity against a large number of clinical important yeasts and molds including Asperg illus spp., Fusarium spp., Scedosporium spp., Candida spp., the Zygomycetes and Cryptococcus spp. Isavuconazole is a new triazole currently undergoing phase III clinical trials. Isavuconazole has shown in vitro activity against a large number of clinical important yeasts and molds including Aspergillus spp., Fusarium spp., Scedosporium spp., Candida spp., the Zygomycetes and Cryptococcus spp.
• Clinical Use: Three regimens of isavuconazonium (BAL 8557) – single 200 mg dose followed by 50 mg daily, single 400 mg followed by 100 mg daily and single 400 mg followed by 400 mg weekly –were demonstrated to be as efficacious as fluconazole in a phase II study conducted on patients with uncomplicated esophageal candidiasis. The results of a phase II open-label dose-escalating trial of intravenous isavuconazonium as prophylaxis in AML (NCT00413439) are pending (NIH, 2008). Two phase III randomized double-blind studies to evaluate the safety and efficacy of isavuconazole are currently under way, versus caspofungin followed by voriconazole in the treatment of candidaemia and invasive candidiasis and versus voriconazole in primary treatment of invasive filamentous fungal infection . A phase III open-label study using isavuconazole in patients with aspergillosis and renal impairment and those with rare fungi is being planned NCT00634049.
• Drug interactions: Rifampicin, a potent CYP3A4 inducer, decreases the Cmax and AUC of isavuconazole . Ketoconazole increases exposure to isavuconazole. Neither ciclosporin nor warfarin is affected by isavuconazole co-administration. Isavuconazole increases tacrolimus levels.

Technology Process of Isavuconazole

There total 25 articles about Isavuconazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.6%

isavuconazole hydrobromide → Isavuconazole (241479-67-4)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate;

Reference yield: 86.0%

(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide + 4-Cyanophenacyl bromide (20099-89-2) → Isavuconazole (241479-67-4)

Guidance literature:

With sodium hydrogencarbonate; In ethanol;

Reference yield: 70.0%

4-Cyanophenacyl bromide (20099-89-2) + C13H19FN4OS → Isavuconazole (241479-67-4)

Guidance literature:

In ethanol; at 60 ℃; for 2h;

upstream raw materials:

4-Cyanophenacyl bromide

(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile

(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate

4-(2-chloroacetyl)benzenecarbonitrile

Downstream raw materials:

1-[[N-methyl-N-2-(t-butoxycarbonyl-isopropylaminomethyl)phenyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

1-[(2R,3R)-3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-2-(2,5-difluorophenyl)-2-hydroxybutyl]-4-[1-({methyl[3-({[2-(methylamino)acetyl]oxy}methyl)pyridin-2-yl]carbamoyl}oxy)ethyl]-1H-1,2,4-triazol-4-ium hydrogensulfate

Refernces

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

10.1021/acs.orglett.1c02588

The research focuses on the development of an efficient and enantioselective catalytic asymmetric epoxidation reaction of α-substituted vinyl ketones, which are key intermediates for the synthesis of various triazole antifungal agents. The purpose of this study was to create a concise and efficient method for constructing optically active epoxides with consecutive chiral carbon centers, a challenging task in the field of antifungal drug synthesis. The researchers successfully employed a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aqueous hydrogen peroxide as the oxidant, achieving high yields and good enantioselectivities. This method not only provided a highly efficient and enantioselective route for the synthesis of antifungal agents such as isavuconazole and efinaconazole but also demonstrated the potential for synthesizing other potential antifungal agents. The study concluded that the chiral N,N′-dioxide/Sc(OTf)3 catalytic system was effective in the asymmetric epoxidation process, offering a wide range of α,α-disubstituted epoxides in good yields with high enantioselectivities.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 241479-67-4 Isavuconazole

Send

Send

Metric Ton KG G Pound L ML

Send

Send