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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.

Term:fluconazole
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Accession:CHEBI:46081 term browser browse the term
Definition:A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.
Synonyms:exact_synonym: 2-(2,4-difluorophenyl)-1,3-bis-(1H-1,2,4-triazol-1-yl)propan-2-ol
 related_synonym: 2,4-difluoro-alpha,alpha-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol;   2-(2,4-DIFLUOROPHENYL)-1,3-DI(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL;   Biozole;   Diflucan;   Elazor;   Formula=C13H12F2N6O;   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;   SMILES=OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F;   Triflucan;   fluconazol;   fluconazolum
 alt_id: CHEBI:46079;   CHEBI:5099
 xref: Beilstein:4269710;   CAS:86386-73-4;   DrugBank:DB00196;   Drug_Central:1187;   HMDB:HMDB0014342;   KEGG:D00322;   LINCS:LSM-2106
 xref_mesh: MESH:D015725
 xref: PDBeChem:TPF;   PMID:11366931;   PMID:16822276;   PMID:23171950;   PMID:23793863;   Patent:GB2099818;   Patent:US4404216;   Reaxys:7311650;   Wikipedia:Fluconazole



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fluconazole term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb9 ATP binding cassette subfamily B member 9 decreases expression EXP Fluconazole results in decreased expression of ABCB9 mRNA CTD PMID:16643972 NCBI chr12:32,499,225...32,531,932
Ensembl chr12:32,499,225...32,531,931
JBrowse link
G Adh1 alcohol dehydrogenase 1C (class I), gamma polypeptide decreases expression EXP Fluconazole results in decreased expression of ADH1 mRNA CTD PMID:16643972 NCBI chr 2:226,797,303...226,808,892
Ensembl chr 2:226,797,303...226,808,892
JBrowse link
G Akr7a3 aldo-keto reductase family 7 member A3 increases expression EXP Fluconazole results in increased expression of AKR7A3 mRNA CTD PMID:16643972 NCBI chr 5:151,590,968...151,601,394
Ensembl chr 5:151,584,479...151,601,394
JBrowse link
G Apoa4 apolipoprotein A4 decreases expression EXP Fluconazole results in decreased expression of APOA4 mRNA CTD PMID:16643972 NCBI chr 8:46,539,083...46,541,464
Ensembl chr 8:46,539,082...46,541,469
JBrowse link
G Ces2h carboxylesterase 2H increases expression EXP Fluconazole results in increased expression of CES2 mRNA CTD PMID:16643972 NCBI chr19:32,974,242...32,988,842
Ensembl chr19:32,974,242...32,988,830
JBrowse link
G Cyp17a1 cytochrome P450, family 17, subfamily a, polypeptide 1 affects activity ISO Fluconazole affects the activity of CYP17A1 protein CTD PMID:31330226 NCBI chr 1:245,535,462...245,543,148
Ensembl chr 1:245,535,462...245,541,573
JBrowse link
G Cyp19a1 cytochrome P450, family 19, subfamily a, polypeptide 1 multiple interactions
decreases activity
ISO [Fluconazole results in decreased activity of CYP19A1 protein] which results in decreased chemical synthesis of Estrone; [Fluconazole results in decreased activity of CYP19A1 protein] which results in decreased metabolism of Androstenedione CTD PMID:31330226 NCBI chr 8:54,553,165...54,580,758
Ensembl chr 8:54,553,165...54,580,758
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 increases expression ISO Fluconazole results in increased expression of CYP1A2 mRNA CTD PMID:16730040 NCBI chr 8:58,075,367...58,082,255
Ensembl chr 8:58,075,367...58,082,312
JBrowse link
G Cyp26a1 cytochrome P450, family 26, subfamily a, polypeptide 1 increases expression ISO Fluconazole results in increased expression of CYP26A1 mRNA CTD PMID:19429397 NCBI chr 1:235,471,368...235,475,204
Ensembl chr 1:235,471,298...235,475,204
JBrowse link
G Cyp26b1 cytochrome P450, family 26, subfamily b, polypeptide 1 increases expression ISO Fluconazole results in increased expression of CYP26B1 mRNA CTD PMID:19429397 NCBI chr 4:117,041,808...117,058,628
Ensembl chr 4:117,041,808...117,058,628
JBrowse link
G Cyp2b1 cytochrome P450, family 2, subfamily b, polypeptide 1 multiple interactions
increases expression
ISO NR1I3 promotes the reaction [Fluconazole results in increased expression of CYP2B10 mRNA] CTD PMID:16730040 PMID:25656644 NCBI chr 1:81,518,387...81,544,999
Ensembl chr 1:81,518,408...81,542,052
JBrowse link
G Cyp2c11 cytochrome P450, subfamily 2, polypeptide 11 decreases expression EXP Fluconazole results in decreased expression of CYP2C mRNA CTD PMID:16643972 NCBI chr 1:236,762,719...236,799,069
Ensembl chr 1:236,762,842...236,799,066
JBrowse link
G Cyp2c24 cytochrome P450, family 2, subfamily c, polypeptide 24 increases expression ISO Fluconazole results in increased expression of CYP2C55 mRNA CTD PMID:16730040 NCBI chr 1:236,873,967...236,936,238
Ensembl chr 1:236,873,967...236,936,238
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 decreases activity
increases metabolic processing
multiple interactions
ISO Fluconazole results in decreased activity of CYP2C19 protein
CYP2C19 protein results in increased metabolism of Fluconazole
[Fluconazole results in decreased activity of CYP2C19 protein] which results in decreased metabolism of Omeprazole
CTD PMID:12464242 PMID:15843491 PMID:17702393 PMID:19328226 PMID:26599973 NCBI chr 1:237,938,521...237,976,238
Ensembl chr 1:237,693,094...238,057,596
JBrowse link
G Cyp2c79 cytochrome P450, family 2, subfamily c, polypeptide 79 increases expression ISO Fluconazole results in increased expression of CYP2C29 mRNA CTD PMID:16730040
G Cyp2g1 cytochrome P450, family 2, subfamily g, polypeptide 1 decreases expression EXP Fluconazole results in decreased expression of CYP2G1 mRNA CTD PMID:16643972 NCBI chr 1:82,145,635...82,156,862
Ensembl chr 1:82,145,073...82,156,828
JBrowse link
G Cyp2j4 cytochrome P450, family 2, subfamily j, polypeptide 4 decreases expression ISO Fluconazole results in decreased expression of CYP2J9 mRNA CTD PMID:16730040 NCBI chr 5:111,179,981...111,207,490
Ensembl chr 5:111,178,703...111,244,794
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 decreases activity ISO Fluconazole results in decreased activity of CYP3A4 protein CTD PMID:15784650 PMID:15843491 NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
JBrowse link
G Cyp3a23-3a1 cytochrome P450, family 3, subfamily a, polypeptide 23-polypeptide 1 increases expression
affects expression
EXP Fluconazole results in increased expression of CYP3A23-3A1 mRNA
Fluconazole affects the expression of CYP3A23-3A1 mRNA
CTD PMID:16643972 PMID:20623750 NCBI chr12:9,256,159...9,285,020
Ensembl chr12:9,254,475...9,285,030
JBrowse link
G Cyp3a9 cytochrome P450, family 3, subfamily a, polypeptide 9 increases expression EXP Fluconazole results in increased expression of CYP3A13 mRNA CTD PMID:16643972 NCBI chr12:16,806,222...16,846,428
Ensembl chr12:16,806,207...16,846,422
JBrowse link
G Cyp51 cytochrome P450, family 51 decreases activity
multiple interactions
decreases response to substance
ISO Fluconazole results in decreased activity of CYP51A1 protein
CYP51A1 gene inhibits the reaction [Fluconazole results in decreased chemical synthesis of Ergosterol]; CYP51A1 gene inhibits the reaction [Fluconazole results in decreased metabolism of and results in increased abundance of 14-methylergosta-8,24(28)-dien-3,6-diol]; CYP51A1 gene inhibits the reaction [Fluconazole results in decreased metabolism of and results in increased abundance of Lanosterol]
CYP51A1 gene results in decreased susceptibility to Fluconazole
CTD PMID:16989930 PMID:18694951 NCBI chr 4:30,036,956...30,055,410
Ensembl chr 4:30,036,865...30,055,410
JBrowse link
G Gstm1 glutathione S-transferase mu 1 increases expression ISO Fluconazole results in increased expression of GSTM1 mRNA CTD PMID:16730040 NCBI chr 2:195,649,845...195,655,402
Ensembl chr 2:195,649,845...195,655,411
JBrowse link
G Jund JunD proto-oncogene, AP-1 transcription factor subunit decreases expression EXP Fluconazole results in decreased expression of JUND mRNA CTD PMID:16643972 NCBI chr16:18,734,121...18,735,799
Ensembl chr16:18,734,122...18,735,799
JBrowse link
G Lcn2 lipocalin 2 increases expression EXP Fluconazole results in increased expression of LCN2 mRNA CTD PMID:20623750 NCBI chr 3:15,680,688...15,684,033
Ensembl chr 3:15,680,687...15,684,095
JBrowse link
G Mark2 microtubule affinity regulating kinase 2 increases expression ISO Fluconazole results in increased expression of MARK2 mRNA CTD PMID:16730040 NCBI chr 1:204,461,029...204,526,247
Ensembl chr 1:204,461,030...204,525,652
JBrowse link
G Mpo myeloperoxidase increases expression EXP Fluconazole results in increased expression of MPO mRNA CTD PMID:20623750 NCBI chr10:72,594,458...72,608,862
Ensembl chr10:72,594,661...72,604,819
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions ISO Fluconazole inhibits the reaction [Rifampin results in increased activity of NR1I2 protein] CTD PMID:17438109 NCBI chr11:62,460,213...62,496,665
Ensembl chr11:62,460,213...62,496,658
JBrowse link
G Nr1i3 nuclear receptor subfamily 1, group I, member 3 affects response to substance
multiple interactions
increases response to substance
ISO NR1I3 protein affects the susceptibility to Fluconazole
NR1I3 promotes the reaction [Fluconazole results in increased expression of CYP2B10 mRNA]; NR1I3 promotes the reaction [Fluconazole results in increased expression of CYP3A11 mRNA]; NR1I3 promotes the reaction [Fluconazole results in increased expression of POR mRNA]
NR1I3 results in increased susceptibility to Fluconazole
CTD PMID:23721867 PMID:25656644 NCBI chr13:83,632,940...83,638,193
Ensembl chr13:83,632,899...83,637,906
JBrowse link
G Por cytochrome p450 oxidoreductase decreases expression
increases expression
multiple interactions
EXP
ISO
Fluconazole results in decreased expression of POR mRNA
Fluconazole results in increased expression of POR mRNA
NR1I3 promotes the reaction [Fluconazole results in increased expression of POR mRNA]
CTD PMID:16643972 PMID:16730040 PMID:25656644 NCBI chr12:20,951,058...20,999,198
Ensembl chr12:20,951,058...20,999,245
JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma increases expression EXP Fluconazole results in increased expression of PPARG mRNA CTD PMID:20623750 NCBI chr 4:148,423,102...148,548,471
Ensembl chr 4:148,423,194...148,548,468
JBrowse link
G Slc13a2 solute carrier family 13 member 2 decreases expression ISO Fluconazole results in decreased expression of SLC13A2 mRNA CTD PMID:16730040 NCBI chr10:63,291,813...63,319,127
Ensembl chr10:63,291,815...63,319,127
JBrowse link
G Slc6a13 solute carrier family 6 member 13 decreases expression EXP Fluconazole results in decreased expression of SLC6A13 mRNA CTD PMID:16643972 NCBI chr 4:154,539,246...154,577,784
Ensembl chr 4:154,540,468...154,576,152
JBrowse link
G Slco1a4 solute carrier organic anion transporter family, member 1a4 increases expression ISO Fluconazole results in increased expression of SLCO1A4 mRNA CTD PMID:16730040 NCBI chr 4:174,710,004...174,764,810
Ensembl chr 4:174,710,004...175,254,573
JBrowse link
G Srd5a1 steroid 5 alpha-reductase 1 decreases expression EXP Fluconazole results in decreased expression of SRD5A1 mRNA CTD PMID:16643972 NCBI chr 1:33,686,069...33,720,468
Ensembl chr 1:33,686,391...33,720,461
JBrowse link
G Star steroidogenic acute regulatory protein increases expression ISO Fluconazole results in increased expression of STAR mRNA CTD PMID:23038793 NCBI chr16:66,267,094...66,274,368
Ensembl chr16:66,264,807...66,271,672
JBrowse link
G Ugt1a9 UDP glucuronosyltransferase family 1 member A9 affects expression EXP Fluconazole affects the expression of UGT1A9 mRNA CTD PMID:20623750 NCBI chr 9:88,696,981...88,808,465
Ensembl chr 9:88,713,184...88,808,465
JBrowse link
G Ugt2b17 UDP glucuronosyltransferase family 2 member B17 increases expression EXP Fluconazole results in increased expression of UGT2B1 mRNA CTD PMID:16643972 NCBI chr14:21,024,035...21,035,784
Ensembl chr14:21,024,006...21,035,986
JBrowse link
G Ugt2b7 UDP glucuronosyltransferase family 2 member B7 multiple interactions ISO Fluconazole inhibits the reaction [[Uridine Diphosphate Glucuronic Acid co-treated with UGT2B7 protein] results in increased glucuronidation of Labetalol] CTD PMID:18098064 NCBI chr14:20,896,682...20,919,604
Ensembl chr14:20,896,682...20,919,604
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 20057
    role 20023
      biological role 20010
        xenobiotic 18687
          fluconazole 38
            Fosfluconazole 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 20057
    subatomic particle 20056
      composite particle 20068
        hadron 20056
          baryon 20056
            nucleon 20056
              atomic nucleus 20056
                atom 20056
                  main group element atom 19971
                    p-block element atom 19971
                      carbon group element atom 19889
                        carbon atom 19894
                          organic molecular entity 19882
                            organic molecule 19830
                              organic cyclic compound 19603
                                organic heterocyclic compound 18888
                                  heteroarene 16612
                                    monocyclic heteroarene 13619
                                      azole 12840
                                        triazoles 3710
                                          triazole 44
                                            1,2,4-triazole 44
                                              1H-1,2,4-triazole 44
                                                fluconazole 38
                                                  Fosfluconazole 0
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