Isavuconazonium sulfateProduct ingredient for Isavuconazonium
- Name
- Isavuconazonium sulfate
- Drug Entry
- Isavuconazonium
Isavuconazonium is a second-generation triazole antifungal approved on March 6, 2015 by the FDA and July 2015 by the EMA for the treatment of adults with invasive aspergillosis and invasive mucormycosis, marketed by Astellas under the brand Cresemba.4 It is the prodrug form of isavuconazole, the active moiety, and it is available in oral and parenteral formulations. Due to low solubility in water of isavuconazole on its own, the isovuconazonium formulation is favorable as it has high solubility in water and allows for intravenous administration. This formulation also avoids the use of a cyclodextrin vehicle for solubilization required for intravenous administration of other antifungals such as voriconazole and posaconazole, eliminating concerns of nephrotoxicity associated with cyclodextrin. Isovuconazonium has excellent oral bioavailability, predictable pharmacokinetics, and a good safety profile, making it a reasonable alternative to its few other competitors on the market.1,2,3
On December 08, 2023, the FDA approved the expanded use of isovuconazonium in pediatric patients for the same indications.7
- Accession Number
- DBSALT001102
- Structure
Structure for Isavuconazonium sulfate (DBSALT001102)
- Synonyms
- Not Available
- External IDs
- BAL-8557-002
- UNII
- 31Q44514JV
- CAS Number
- 946075-13-4
- Weight
- Average: 814.84
Monoisotopic: 814.201473445 - Chemical Formula
- C35H36F2N8O9S2
- InChI Key
- LWXUIUUOMSMZKJ-KLFWAVJMSA-M
- InChI
- InChI=1S/C35H35F2N8O5S.H2O4S/c1-22(33-42-30(18-51-33)25-9-7-24(15-38)8-10-25)35(48,28-14-27(36)11-12-29(28)37)19-45-21-44(20-41-45)23(2)50-34(47)43(4)32-26(6-5-13-40-32)17-49-31(46)16-39-3;1-5(2,3)4/h5-14,18,20-23,39,48H,16-17,19H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1/t22-,23?,35+;/m0./s1
- IUPAC Name
- 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 hydrogen sulfate
- SMILES
- OS([O-])(=O)=O.[H]C(C)(OC(=O)N(C)C1=C(COC(=O)CNC)C=CC=N1)[N+]1=CN(C[C@](O)(C2=C(F)C=CC(F)=C2)[C@@]([H])(C)C2=NC(=CS2)C2=CC=C(C=C2)C#N)N=C1
- External Links
- ChemSpider
- 32701987
- ChEBI
- 85977
- ChEMBL
- CHEMBL3137333
- Wikipedia
- Isavuconazonium
- Predicted Properties
Property Value Source Water Solubility 0.00731 mg/mL ALOGPS logP 3.11 ALOGPS logP 0.52 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 12.57 Chemaxon pKa (Strongest Basic) 6.45 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 159.37 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 193.86 m3·mol-1 Chemaxon Polarizability 71.63 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon