Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0704)
Drug Name
Fluconazole
Synonyms
Flucazol; Fluconazol; Fluconazol [Spanish]; Fluconazolum; Fluconazolum [Latin]; Flucostat; Flukezol; Flunizol; Flusol; Forcan; Fungata; Alflucoz; Biocanol; Biozolene; Canzol; Cryptal; DIFLUCAN IN SODIUM CHLORIDE 0.9%; Diflucan; Dimycon; Elazor; Oxifugol; Pritenzol; Syscan; Triflucan; UK 49858; UK-49858; Zoltec; fluconazole; 2-(2,4-DIFLUOROPHENYL)-1,3-DI(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL; 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol; 86386-73-4; Baten; C13H12F2N6O; CCRIS 7211; DRG-0005; Mutum; UNII-8VZV102JFY; Zemyc; Zonal
Indication Candidiasis [ICD11: 1F23] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 306.27 Topological Polar Surface Area 81.6
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
3365
PubChem SID
596175 ; 604503 ; 649080 ; 842010 ; 5329899 ; 7847388 ; 7890846 ; 7979232 ; 8150102 ; 8152140 ; 11336205 ; 11361444 ; 11364548 ; 11367110 ; 11369672 ; 11373103 ; 11373499 ; 11377834 ; 11462416 ; 11485349 ; 11489423 ; 11491727 ; 11491905 ; 11495468 ; 12013592 ; 14849790 ; 24724485 ; 25819912 ; 26612568 ; 26680134 ; 26697093 ; 26748877 ; 26748878 ; 26753743 ; 29222500 ; 46499870 ; 46505735 ; 47193701 ; 47216862 ; 47810843 ; 48035227 ; 48413782 ; 49665806 ; 49666152 ; 49815674 ; 49835432 ; 49855965 ; 50086001 ; 50107476 ; 53788618
ChEBI ID
ChEBI:46081
CAS Number
86386-73-4
TTD Drug ID
D09LNI
Formula
C13H12F2N6O
Canonical SMILES
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
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
InChIKey
RFHAOTPXVQNOHP-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Fluconazole N-oxide DM000195 N. A. Oxidation - Oxidation 1 [3]
Fluconazole O-Glucuronidated metabolite DM000194 N. A. Conjugation - Glucuronidation 1 [3] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001059 Fluconazole Fluconazole O-Glucuronidated metabolite Conjugation - Glucuronidation UGT2B7 [3], [5]
MR001060 Fluconazole Fluconazole N-oxide Oxidation - Oxidation CYP3A4 [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
⏷ Show the Full List of 13  DME(s)
References
1 Fluconazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of fluconazole on plasma fluvastatin and pravastatin concentrations. Eur J Clin Pharmacol. 2000 Jun;56(3):225-9.
3 The disposition and metabolism of [14C]fluconazole in humans Drug Metab Dispos. 1991 Jul-Aug;19(4):764-7.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Investigation into UDP-glucuronosyltransferase (UGT) enzyme kinetics of imidazole- and triazole-containing antifungal drugs in human liver microsomes and recombinant UGT enzymes. Drug Metab Dispos. 2010 Jun;38(6):923-9.

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