Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:35 UTC
HMDB IDHMDB0014342
Secondary Accession Numbers
  • HMDB14342
Metabolite Identification
Common NameFluconazole
DescriptionFluconazole is only found in individuals that have used or taken this drug. It is a triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. [PubChem]Fluconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Fluconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Structure
Data?1582753167
Synonyms
ValueSource
2,4-Difluoro-alpha,alpha-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcoholChEBI
2-(2,4-DIFLUOROPHENYL)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-olChEBI
BiozoleChEBI
DiflucanChEBI
ElazorChEBI
FluconazolChEBI
FluconazolumChEBI
TriflucanChEBI
2,4-Difluoro-a,a-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcoholGenerator
2,4-Difluoro-α,α-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcoholGenerator
Alpharma brand OF fluconazoleHMDB
Armstrong brand OF fluconazoleHMDB
Effik brand OF fluconazoleHMDB
FlucobetaHMDB
FungataHMDB
LavisaHMDB
Lichtenstein brand OF fluconazoleHMDB
Mack brand OF fluconazoleHMDB
OxifungolHMDB
Silanes brand OF fluconazoleHMDB
Betapharm brand OF fluconazoleHMDB
CT Arzneimittel brand OF fluconazoleHMDB
CT-Arzneimittel brand OF fluconazoleHMDB
BéagyneHMDB
Chemia brand OF fluconazoleHMDB
Fluc hexalHMDB
Fluconazol alHMDB
Fluconazol abzHMDB
Fluconazol ratiopharmHMDB
Fluconazol von CTHMDB
Fluconazol-isisHMDB
Fluconazol-ratiopharmHMDB
NeofomiralHMDB
Pfleger brand OF fluconazoleHMDB
SAT brand OF fluconazoleHMDB
SolacapHMDB
Ratiopharm brand OF fluconazoleHMDB
Fluconazol isisHMDB
Fluconazol stadaHMDB
FlunazulHMDB
Hexal brand OF fluconazoleHMDB
LoitinHMDB
Pfizer brand OF fluconazoleHMDB
Vita brand OF fluconazoleHMDB
ZonalHMDB
AbZ brand OF fluconazoleHMDB
Aliud brand OF fluconazoleHMDB
Apo fluconazoleHMDB
Apo-fluconazoleHMDB
Apotex brand OF fluconazoleHMDB
FlucoLichHMDB
Lesvi brand OF fluconazoleHMDB
Stada brand OF fluconazoleHMDB
Fluconazole capsulesHMDB
Chemical FormulaC13H12F2N6O
Average Molecular Weight306.2708
Monoisotopic Molecular Weight306.104065446
IUPAC Name2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
Traditional Namefluconazole
CAS Registry Number86386-73-4
SMILES
OC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1
InChI Identifier
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
InChI KeyRFHAOTPXVQNOHP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fluorobenzenes. Fluorobenzenes are compounds containing one or more fluorine atoms attached to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentFluorobenzenes
Alternative Parents
Substituents
  • Fluorobenzene
  • Aryl fluoride
  • Aryl halide
  • Azole
  • Tertiary alcohol
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Aromatic alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point138 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.39 g/LNot Available
LogP0.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM163.930932474
[M+H]+Not Available163.378http://allccs.zhulab.cn/database/detail?ID=AllCCS00000733
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.39 g/LALOGPS
logP0.58ALOGPS
logP0.56ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)2.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.65 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.2 m³·mol⁻¹ChemAxon
Polarizability26.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+166.88130932474
DeepCCS[M-H]-164.52330932474
DeepCCS[M-2H]-197.57430932474
DeepCCS[M+Na]+172.97430932474
AllCCS[M+H]+168.832859911
AllCCS[M+H-H2O]+165.332859911
AllCCS[M+NH4]+172.132859911
AllCCS[M+Na]+173.032859911
AllCCS[M-H]-167.232859911
AllCCS[M+Na-2H]-166.632859911
AllCCS[M+HCOO]-166.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FluconazoleOC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C13140.7Standard polar33892256
FluconazoleOC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C12279.9Standard non polar33892256
FluconazoleOC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C12114.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluconazole,1TMS,isomer #1C[Si](C)(C)OC(CN1C=NC=N1)(CN1C=NC=N1)C1=CC=C(F)C=C1F2439.3Semi standard non polar33892256
Fluconazole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CN1C=NC=N1)(CN1C=NC=N1)C1=CC=C(F)C=C1F2668.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fluconazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-7950000000-e40a22ece3de9aec63412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluconazole GC-MS (1 TMS) - 70eV, Positivesplash10-003s-7190000000-b0fd755fce78f1747bdd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluconazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-qTof , Positive-QTOFsplash10-0g70-2920000000-a8a6188f5a32495c6efa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-339ec0708a6a6299e4d12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-ea278fc262275613a1fe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-bbdadb624a7360b26fa32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-00kf-6900000000-0316b801589bae74a3f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-014i-9100000000-d7b76913f55978a00d102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-014i-9000000000-45cd8f87d45358745d5b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-014i-9000000000-2f3230e2968762340fb02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-ea0bdd0dd4905f7ca2a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-643df112c60eecdd6f262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-00kf-6900000000-636d53fe2393f25b4cc42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-014i-9100000000-2d05579f16a7ce194afb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-014i-9000000000-bb834fc848ba7398b2782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-014i-9000000000-e3f46745a82b72dc28b02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , negative-QTOFsplash10-0006-0900000000-565636d9f9e684b114292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-QFT , negative-QTOFsplash10-0006-0900000000-224c620bb2943c3558aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , positive-QTOFsplash10-000i-0090000000-d00a2d66aa1d041452792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , positive-QTOFsplash10-0a4i-0019000000-9ddd55ba2decdc6d30072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluconazole LC-ESI-ITFT , positive-QTOFsplash10-0079-0091000000-5501d6ab39e3fb2e36762017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluconazole 10V, Positive-QTOFsplash10-0a4i-0019000000-476f05b29d87ff4033492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluconazole 20V, Positive-QTOFsplash10-0r09-0093000000-61a1882c6efca9aa9bdb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluconazole 40V, Positive-QTOFsplash10-00di-7690000000-8c3dcc7b7469b99a5ee82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluconazole 10V, Negative-QTOFsplash10-052f-0905000000-e49e8ab1264fe8c942322016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluconazole 20V, Negative-QTOFsplash10-0a4i-2469000000-a1df61d9dd20cf349f792016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluconazole 40V, Negative-QTOFsplash10-014i-9340000000-a2819b76c4147ab6396d2016-08-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00196 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00196 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00196
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3248
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluconazole
METLIN IDNot Available
PubChem Compound3365
PDB IDTPF
ChEBI ID46081
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567 ]
  2. Kunze KL, Wienkers LC, Thummel KE, Trager WF: Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos. 1996 Apr;24(4):414-21. [PubMed:8801056 ]
  3. Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [PubMed:15969931 ]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567 ]
  2. Kunze KL, Wienkers LC, Thummel KE, Trager WF: Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos. 1996 Apr;24(4):414-21. [PubMed:8801056 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Wang EJ, Lew K, Casciano CN, Clement RP, Johnson WW: Interaction of common azole antifungals with P glycoprotein. Antimicrob Agents Chemother. 2002 Jan;46(1):160-5. [PubMed:11751127 ]
  2. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
  3. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]