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Isavuconazole

Product Name
Isavuconazole
CAS No.
241479-67-4
Chemical Name
Isavuconazole
Synonyms
Isavuconazonium;4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile;4-[2-[(1R,2R)-2-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile;4-(2-((2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)thiazol-4-yl)benzonitrile;Isaconazole;BAL 4815;RO 0094815;Isavucozole;Esaconazole;Isavuconazole
CBNumber
CB32498813
Molecular Formula
C22H17F2N5OS
Formula Weight
437.47
MOL File
241479-67-4.mol
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Isavuconazole Property

Melting point:
89 - 91oC
Boiling point:
678.0±65.0 °C(Predicted)
Density 
1.38
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
11.42±0.29(Predicted)
color 
Off-White to Beige
InChI
InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-8-17(23)6-7-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
InChIKey
DDFOUSQFMYRUQK-RCDICMHDSA-N
SMILES
C(#N)C1=CC=C(C2=CSC([C@H](C)[C@](C3=CC(F)=CC=C3F)(O)CN3C=NC=N3)=N2)C=C1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML2357
Product name
Isavuconazole
Purity
≥98% (HPLC)
Packaging
5MG
Price
$94.2
Updated
2024/03/01
Sigma-Aldrich
Product number
SML2357
Product name
Isavuconazole
Purity
≥98% (HPLC)
Packaging
25MG
Price
$381
Updated
2024/03/01
Cayman Chemical
Product number
26211
Product name
Isavuconazole
Packaging
5mg
Price
$111
Updated
2024/03/01
Cayman Chemical
Product number
26211
Product name
Isavuconazole
Packaging
100mg
Price
$765
Updated
2024/03/01
Cayman Chemical
Product number
26211
Product name
Isavuconazole
Packaging
10mg
Price
$177
Updated
2024/03/01
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Isavuconazole Chemical Properties,Usage,Production

Description

Isavuconazonium, the water-soluble pro-drug of isavuconazole, is developed by Basilea Pharmaceutica. Isavuconazole, like other azoles, inhibits ergosterol synthesis and is a water-soluble compound with both oral and intravenous formulations. It has excellent bioavailability and a long elimination half-life, allowing for once-weekly dosing. It is the only broad-spectrum water-soluble triazole available.

Uses

Isavuconazole is a new triazole currently undergoing phase III clinical trials. This compound 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.

Definition

ChEBI: Isavuconazole is a 1,3-thiazole that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,5-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively. It is an antifungal drug used for the treatment of invasive aspergillosis and invasive mucormycosis. It has a role as an ergosterol biosynthesis inhibitor, an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an orphan drug. It is a member of 1,3-thiazoles, a nitrile, a difluorobenzene, a tertiary alcohol, a triazole antifungal drug and a conazole antifungal drug.

Antimicrobial activity

Isavuconazole is a new broad-spectrum triazole with activity against Candida, Cryptococcus, Aspergillus, Zygomycetes, Rhizopus, and Rhizomucor spp. and dimorphic fungi including Histoplasma capsulatum and Blastomyces dermatitidis and a range of dermatophytes. In animal models, isavuconazole is highly effective against systemic candidiasis and disseminated Aspergillus fumigatus and flavus infections.

Biochem/physiol Actions

Maximum plasma concentrations of BAL 4815 are observed 1.5–3 hours after oral doses or at the end of the 1-hour intravenous infusion. Mean elimination half-lives are remarkably long more than 50 and 70 hours after oral and intravenous doses, respectively, allowing for once-daily (or less frequent) dosing. The volume of distribution is large and systemic clearance low. The protein binding is 98%. Escalation in multiple dosing regimens results in a proportional increase in maximum plasma drug concentration.

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.

Toxicology

In animals, isavuconazole has revealed no mutagenic, allergenic, phototoxic, or irritant potential. In 15 healthy volunteers, single doses of isavuconazole (up to 200 mg) were well tolerated, and no severe or serious adverse events occurred. In a multiple-dose pharmacokinetic study, 24 healthy males received isavuconazole for 21 days of oral or 14 days of intravenous dosing. The most frequent adverse events were headache, nasopharyngitis, and rhinitis, and all were mild or moderate; however one subject on oral high-dose BAL 8557 had mild transient abnormal liver function on day 14 of therapy, which resolved despite continuing the drug. No clinically relevant changes in vital signs or electrocardiogram were observed. In a double-blind randomized phase II trial for the treatment of esophageal candidiasis, BAL 8557 was safe and well tolerated, with an adverse event profile similar to that of fluconazole, the comparator drug.

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.

Mode of action

Isavuconzaole inhibits cytochrome P450-dependent lanosterol 14α-demethylase, which is essential for the synthesis of ergosterol, a component of the fungal membrane. This disruption leads to alterations in the structure and function of the fungal membrane leading to cell death. The isavuconazole structure includes a side arm that orients the molecule to engage the triazole ring to the binding pocket of the fungal CYP51 protein. This confers broader antifungal activity in comparison to other azoles.
PMC7712939

Isavuconazole Preparation Products And Raw materials

Raw materials

Preparation Products

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Isavuconazole Suppliers

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View Lastest Price from Isavuconazole manufacturers

Sinoway Industrial co., ltd.
Product
Isavuconazole 241479-67-4
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
0.99
Supply Ability
20 tons
Release date
2023-05-11
Sinoway Industrial co., ltd.
Product
Isavuconazole 241479-67-4
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
0.99
Supply Ability
20 tons
Release date
2023-05-11
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Isavuconazole 241479-67-4
Price
US $0.00-0.00/Kg/Bag
Min. Order
1g
Purity
99.5%min HPLC
Supply Ability
1000G
Release date
2021-07-13

241479-67-4, IsavuconazoleRelated Search:

Fluconazole TICAGRELOR Fluorocytosine Tauroursodeoxycholic acid VT-1161 ecteinascidin 743 Caspofungin Cariprazine Tafluprost Ketoconazole Micafungin Voriconazole Posaconazole

  • Isaconazole
  • 4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile
  • Isavucozole
  • 4-(2-((2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butan-2-yl)thiazol-4-yl)benzonitrile
  • Isavuconazonium
  • Isavuconazole(BAL-4815
  • Isavuconazole
  • 4-[2-[(1R,2R)-2-(2,5-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]benzonitrile
  • NaMe:Isavuconazole
  • 2R,3R)-3-[4-(4-Cyanophenyl)thiazol-2-yl]-2-(2,5- difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
  • BAL 4815
  • RO 0094815
  • Benzonitrile, 4-[2-[(1R,2R)-2-(2,5-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-thiazolyl]-
  • YiShaKang azole
  • 4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile Create Date: 2006-07-28
  • 4-(2-((1R,2R)-1-(2,5-Difluorophenyl)-1-hydroxy-1-(1H-1,2,4-triazol-1-yl)propan-2-yl)thiazol-4-yl)benzonitrile (Isavuconazole Impurity)
  • Ilsavuconazole
  • Esaconazole
  • 241479-67-4
  • Inhibitors
  • Aromatics
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • Isavuconazonium sulfate
  • API