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

General Information of Drug (ID: DR1709)
Drug Name
Voriconazole
Synonyms
Voriconazol; Voriconazole; Voriconazole [USAN:INN:BAN]; Voriconazolum; JFU09I87TR; UK 109496; UK-109,496; UK-109496; (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol; (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; (alphaR,betaS)-alpha-(2,4-Difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol; 137234-62-9; C16H14F3N5O; CHEBI:10023; CHEMBL638; CPD000466350; DRG-0301; UNII-JFU09I87TR; VCZ; VRC; Vfend
Indication Candidiasis [ICD11: 1F23] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 349.31 Topological Polar Surface Area 76.7
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
71616
PubChem SID
9824 ; 618929 ; 7847644 ; 8194731 ; 12014673 ; 14754154 ; 14900759 ; 26719857 ; 43127923 ; 46386721 ; 46506421 ; 49681678 ; 49830865 ; 50065685 ; 53790739 ; 57318277 ; 58107314 ; 79258320 ; 92308499 ; 92712543 ; 93165418 ; 99437153 ; 103042056 ; 103188976 ; 104350892 ; 109692905 ; 117510444 ; 118048601 ; 121361066 ; 124658937 ; 124757251 ; 124766492 ; 125083219 ; 125164055 ; 126592905 ; 126625471 ; 126656629 ; 126670609 ; 127494461 ; 134338507 ; 135029377 ; 136340251 ; 136367733 ; 137006421 ; 140298163 ; 144076218 ; 144205794 ; 152164501 ; 160870955 ; 160963927
ChEBI ID
CHEBI:10023
CAS Number
137234-62-9
TTD Drug ID
D0N3VR
Formula
C16H14F3N5O
Canonical SMILES
CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
InChI
1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1
InChIKey
BCEHBSKCWLPMDN-MGPLVRAMSA-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
4-Hydroxyvoriconazole DM005293
125264509
Oxidation - Hydrolyzationn 1 [4] , [3]
Voriconazole N-Oxide Metabolite DM005288
10044355
Oxidation - Oxidationn 1 [4] , [3]
4-Hydroxyvoriconazole 4-O-glucuronide metabolite DM005294 N. A. Conjugation - O-glucuronidation 2 [4] , [3]
UK-51,060 DM005289
588080
Unclear 2 [4] , [3]
UK-215,364 DM005290
6426669
Unclear 3 [4] , [3]
Voriconazole O-glucuronide derivative (1) DM005291 N. A. Conjugation - Glucuronidation 4 [4] , [3]
Voriconazole O-glucuronide derivative (2) DM005292 N. A. Conjugation - Glucuronidation 4 [4] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013245 Voriconazole Voriconazole N-Oxide Metabolite Oxidation - Oxidationn CYP2C9 ... [4], [3]
MR013250 Voriconazole 4-Hydroxyvoriconazole Oxidation - Hydrolyzationn CYP3A4 ... [4], [3]
MR013251 4-Hydroxyvoriconazole 4-Hydroxyvoriconazole 4-O-glucuronide metabolite Conjugation - O-glucuronidation Unclear [4], [3]
MR013246 Voriconazole N-Oxide Metabolite UK-51,060 Unclear Unclear [4], [3]
MR013247 UK-51,060 UK-215,364 Unclear Unclear [4], [3]
MR013248 UK-215,364 Voriconazole O-glucuronide derivative (1) Conjugation - Glucuronidation Unclear [4], [3]
MR013249 UK-215,364 Voriconazole O-glucuronide derivative (2) Conjugation - Glucuronidation Unclear [4], [3]
⏷ Show the Full List of 7 MR(s)
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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4] , [3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [6]
⏷ Show the Full List of 13  DME(s)
References
1 Voriconazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of voriconazole on the pharmacokinetics of diclofenac. Fundam Clin Pharmacol. 2007 Dec;21(6):651-6.
3 Roles of CYP3A4 and CYP2C19 in methyl hydroxylated and N-oxidized metabolite formation from voriconazole, a new anti-fungal agent, in human liver microsomes. Biochem Pharmacol. 2007 Jun 15;73(12):2020-6.
4 The disposition of voriconazole in mouse, rat, rabbit, guinea pig, dog, and human
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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