Prodrug Information
Prodrug General Information | Top | |||||
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Prodrug ID |
D8R7FM
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Prodrug Name |
Fosfluconazole
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Synonyms |
Fosfluconazole [INN:BAN]; Phosfluconazole; Fosfluconazole(INN); Prodif (TN); UNII-3JIJ299EWH; 3JIJ299EWH; UK-292,663; CHEBI:31634; NCGC00182029-01; Procif; UK 292663; Fosfluconazole (JAN/INN); DSSTox_CID_28527; DSSTox_RID_82799; DSSTox_GSID_48601; SCHEMBL378428; CHEMBL1908301; DTXSID3048601; CTK7B9037; BCP09246; ZINC3609266; Tox21_112934; MFCD28978011; s6467; CS-6032; HY-100666; CAS-194798-83-9; A13990; D01429; Q1439361
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Indication | Fungal infection [ICD-11: 1F29-1F2F; ICD-10: B35-B49; ICD-9: 110-118] | Approved in Japan | [1] | |||
Activation |
Prodrug |
Parent Drug |
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2D MOL 3D MOL | 2D MOL 3D MOL | |||||
(1) Bioconversion Enzyme:
Alkaline phosphatase
(EC 3.1)
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[2] | |||||
Prodrug Strategy |
Classical prodrug strategy
[Carrier linked prodrug]
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Improved property |
Increase solubility
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Description |
The aqueous solubility of fosfluconazole is increased compared with parent drug (over 300 mg/ml).
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Formula |
C13H13F2N6O4P
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Canonical SMILES |
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)OP(=O)(O)O
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InChI |
1S/C13H13F2N6O4P/c14-10-1-2-11(12(15)3-10)13(25-26(22,23)24,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9H,4-5H2,(H2,22,23,24)
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InChIKey |
GHJWNRRCRIGGIO-UHFFFAOYSA-N
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CAS Number |
CAS 194798-83-9
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PubChem Compound ID | ||||||
ChEBI ID |
CHEBI:31634
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Parent Drug General Information | Top | |||||
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Parent Drug ID |
DFNU71
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Parent Drug Name |
Fluconazole
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Synonyms |
Diflucan; Triflucan; Biozolene; Elazor; Biocanol; Fluconazol; Fungata; Fluconazolum; Flucazol; Flucostat; Flukezol; Flunizol; Pritenzol; Zonal; UK 49858; Alflucoz; Oxifugol; Canzol; Cryptal; Dimycon; Flusol; Forcan; Syscan; Zoltec; Baten; Mutum; Zemyc; Fluconazol [Spanish]; Fluconazolum [Latin]; UK-49858; Fluconazole, 98%; Flunazol; Fluzone; Loitin; Diflazon; Fuconal; Triconal; Diflucan (TN); Fluconazole [USAN:INN:BAN:JAN]; Fluconazole [USAN]
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Formula |
C13H12F2N6O
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Canonical SMILES |
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
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InChI |
1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2
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InChIKey |
RFHAOTPXVQNOHP-UHFFFAOYSA-N
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CAS Number |
CAS 86386-73-4
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PubChem Compound ID | ||||||
ChEBI ID |
CHEBI:46081
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Target and Pathway | Top | |||||
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Target(s) | Candida Cytochrome P450 51 (Candi ERG11) | Target Info | Inhibitor | [4] |
References | Top | |||||
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REF 1 | The expanding role of prodrugs in contemporary drug design and development. Nat Rev Drug Discov. 2018 Aug;17(8):559-587. | |||||
REF 2 | Population pharmacokinetics of fluconazole after administration of fosfluconazole and fluconazole in critically ill patients. J Clin Pharm Ther. 2012 Jun;37(3):356-63. | |||||
REF 3 | Prodrugs: design and clinical applications. Nat Rev Drug Discov. 2008 Mar;7(3):255-70. | |||||
REF 4 | Pharmacokinetics of fosfluconazole and fluconazole following multiple intravenous administration of fosfluconazole in healthy male volunteers. Br J Clin Pharmacol. 2004 Jul;58(1):20-5. |
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