Prodrug Information
| Prodrug General Information | Top | |||||
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| Prodrug ID |
DPL6T5
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| Prodrug Name |
Isavuconazonium sulfate
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| Synonyms |
Cresemba; Isavuconazonium (sulfate); BAL-8557-002; Isavuconazonium sulfate [USAN]; CHEBI:85977; 946075-13-4 (sulfate); Isavuconazonium sulfate (USAN); UNII-31Q44514JV; 31Q44514JV; CHEMBL3137333; EX-A1786; AK1820; AKOS030527357; AK-1820; SB16704; BAL8557-002; AC-31126; AS-35043; SC-12899; HY-100373; CS-0018702; D10643; Q27158829
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| Indication | Invasive aspergillosis [ICD-11: 1F20.0; ICD-10: B44.0, B44.8] | Approved | [1] | |||
| Mucormycosis [ICD-11: 1F2C] | Approved | [1] | ||||
| Activation |
Prodrug 
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Parent Drug 
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| 2D MOL | 2D MOL 3D MOL | |||||
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(1) Bioconversion Enzyme:
Esterase (mainly butyrylcholinesterase)
(EC 3.1)
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[1] | |||||
| Prodrug Strategy |
Classical prodrug strategy
[Carrier linked prodrug]
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| Improved property |
Increase solubility
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[3] | ||||
| Description |
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.Oral administration of isavuconazonium shows 98% oral bioavailability.
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[2] | ||||
| Formula |
C35H36F2N8O9S2
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| Canonical SMILES |
C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@](CN3C=[N+](C=N3)C(C)OC(=O)N(C)C4=C(C=CC=N4)COC(=O)CNC)(C5=C(C=CC(=C5)F)F)O.OS(=O)(=O)[O-]
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| 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
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| InChIKey |
LWXUIUUOMSMZKJ-KLFWAVJMSA-M
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| CAS Number |
CAS 946075-13-4
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| PubChem Compound ID | ||||||
| ChEBI ID |
CHEBI:85977
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| Parent Drug General Information | Top | |||||
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| Parent Drug ID |
DW4YJ0
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| Parent Drug Name |
Isavuconazole
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| Synonyms |
Isavuconazol; BAL 4815; BAL-4815; UNII-60UTO373KE; Isavuconazole [INN]; 60UTO373KE; Isavuconazole(BAL-4815; RO-0094815); CHEBI:85979; Isavuconazole (INN); 1286730-05-9; RO-0094815; Bal4815; isavuconazolum; RO 0094815; BAL-8557(pro-drug); SCHEMBL939038; CHEMBL409153; DTXSID2058251; ASP9766; BCP07587; EX-A1785; KS-00000T6L; ZINC1485935; 3748AH; MFCD06407745; s3722; AKOS027250772; CCG-269093; CS-3492; DB11633; SB16703; NCGC00390646-01; NCGC00390646-02; AC-31076; AS-30128; HY-14273; SC-98350; BAL-4815;RO-0094815; Isavuconazole; BAL-4815; RO-0094815; D10750; J-015363; Q6079042; BAL-4815;BAL4815;BAL 4815;RO-0094815; RO0094815; RO 0094815
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| Formula |
C22H17F2N5OS
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| Canonical 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
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| 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
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| InChIKey |
DDFOUSQFMYRUQK-RCDICMHDSA-N
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| CAS Number |
CAS 241479-67-4
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| PubChem Compound ID | ||||||
| ChEBI ID |
CHEBI:85979
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| References | Top | |||||
|---|---|---|---|---|---|---|
| REF 1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | |||||
| REF 2 | Isavuconazonium. | |||||
| REF 3 | The prodrug approach in the era of drug design. Expert Opin Drug Deliv. 2019 Jan;16(1):1-5. | |||||
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