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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:itraconazole
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Accession:CHEBI:6076 term browser browse the term
Definition:An N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhibitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, and sporotrichosis.
Synonyms:exact_synonym: 2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
 related_synonym: Formula=C35H38Cl2N8O4;   InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1;   InChIKey=VHVPQPYKVGDNFY-ZPGVKDDISA-N;   Itrizole (TN);   Oriconazole;   SMILES=CCC(C)n1ncn(-c2ccc(cc2)N2CCN(CC2)c2ccc(OC[C@H]3CO[C@@](Cn4cncn4)(O3)c3ccc(Cl)cc3Cl)cc2)c1=O;   Sporanox (TN)
 xref: CAS:84625-61-6;   DrugBank:DB01167;   KEGG:D00350
 xref_mesh: MESH:D017964
 xref: PMID:11219548;   PMID:11403818;   PMID:11422002;   PMID:15521894;   PMID:19025521;   PMID:20400651;   PMID:25326091;   Patent:EP6711;   Patent:US4267179;   VSDB:1853;   Wikipedia:Itraconazole


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itraconazole term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb11 ATP binding cassette subfamily B member 11 decreases activity ISO Itraconazole results in decreased activity of ABCB11 protein CTD PMID:20829430, PMID:23956101 NCBI chr 3:55,480,024...55,587,946
Ensembl chr 3:55,480,024...55,587,946
JBrowse link
G Abcb1a ATP binding cassette subfamily B member 1A affects activity
decreases activity
multiple interactions
affects transport
ISO Itraconazole affects the activity of ABCB1 protein
Itraconazole results in decreased activity of ABCB1 protein
Itraconazole inhibits the reaction [ABCB1 protein affects the transport of Digoxin]; Itraconazole promotes the reaction [ABCB1 gene SNP affects the susceptibility to fexofenadine]
ABCB1 protein affects the transport of Itraconazole
CTD PMID:15905803, PMID:15964336, PMID:15969931, PMID:16084853 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Ahr aryl hydrocarbon receptor multiple interactions ISO AHR promotes the reaction [Itraconazole results in increased expression of NQO1 mRNA]; AHR promotes the reaction [Itraconazole results in increased expression of NQO1 protein] CTD PMID:17923278 NCBI chr 6:54,963,990...55,001,806
Ensembl chr 6:54,963,990...55,001,464
JBrowse link
G Ar androgen receptor multiple interactions ISO Itraconazole binds to and results in decreased activity of AR protein CTD PMID:25752796 NCBI chr  X:67,656,253...67,828,998
Ensembl chr  X:67,656,253...67,829,026
JBrowse link
G Ccl5 C-C motif chemokine ligand 5 multiple interactions ISO Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of CCL5 mRNA] CTD PMID:23688403 NCBI chr10:70,739,764...70,744,303
Ensembl chr10:70,739,800...70,744,315
JBrowse link
G Cxcl10 C-X-C motif chemokine ligand 10 multiple interactions ISO Itraconazole inhibits the reaction [Biological Products results in increased expression of CXCL10 mRNA]; Itraconazole inhibits the reaction [Biological Products results in increased expression of CXCL10 protein] CTD PMID:24471457 NCBI chr14:17,210,733...17,212,930
Ensembl chr14:17,210,733...17,212,930
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions
increases expression
decreases activity
ISO Dactinomycin inhibits the reaction [Itraconazole results in increased expression of CYP1A1 mRNA]; Itraconazole results in increased expression of and results in increased activity of CYP1A1 protein
Itraconazole results in increased expression of CYP1A1 mRNA; Itraconazole results in increased expression of CYP1A1 protein
Itraconazole results in decreased activity of CYP1A1 protein
CTD PMID:17283379, PMID:28390928 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp24a1 cytochrome P450, family 24, subfamily a, polypeptide 1 decreases activity ISO
EXP
Itraconazole results in decreased activity of CYP24A1 protein CTD PMID:15328084 NCBI chr 3:168,097,484...168,111,920
Ensembl chr 3:168,097,485...168,111,920
JBrowse link
G Cyp51 cytochrome P450, family 51 decreases activity
decreases response to substance
multiple interactions
ISO Itraconazole results in decreased activity of CYP51A1 protein
CYP51A1 gene results in decreased susceptibility to Itraconazole
CYP51A1 gene inhibits the reaction [Itraconazole results in decreased chemical synthesis of Ergosterol]; CYP51A1 gene inhibits the reaction [Itraconazole 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 [Itraconazole results in decreased metabolism of and results in increased abundance of Lanosterol]
CTD PMID:16989930, PMID:18694951 NCBI chr 4:27,175,564...27,194,018
Ensembl chr 4:27,175,243...27,194,018
JBrowse link
G Gli1 GLI family zinc finger 1 decreases expression ISO Itraconazole analog results in decreased expression of GLI1 mRNA CTD PMID:21936514 NCBI chr 7:70,620,794...70,633,171
Ensembl chr 7:70,620,766...70,630,338
JBrowse link
G Gstp1 glutathione S-transferase pi 1 multiple interactions ISO Itraconazole inhibits the reaction [GSTP1 protein results in increased metabolism of 1-chloro-2,4-dinitrobenzene-glutathione conjugate] CTD PMID:23769903 NCBI chr 1:219,291,679...219,294,147
Ensembl chr 1:219,291,679...219,294,147
JBrowse link
G Il4 interleukin 4 multiple interactions
decreases expression
decreases secretion
ISO 1-Methyl-3-isobutylxanthine inhibits the reaction [Itraconazole results in decreased expression of IL4 mRNA]; 1-Methyl-3-isobutylxanthine inhibits the reaction [Itraconazole results in decreased secretion of IL4 protein]; 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-(4-(2H-tetrazol-5-yl)butyl)piperidine inhibits the reaction [Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in decreased secretion of 15-deoxy-delta(12,14)-prostaglandin J2]]; 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-(4-(2H-tetrazol-5-yl)butyl)piperidine inhibits the reaction [Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in decreased secretion of Prostaglandin D2]]; 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-(4-(2H-tetrazol-5-yl)butyl)piperidine inhibits the reaction [Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP mRNA]]; 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-(4-(2H-tetrazol-5-yl)butyl)piperidine inhibits the reaction [Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP protein]]; Bucladesine inhibits the reaction [Itraconazole results in decreased expression of IL4 mRNA]; Bucladesine inhibits the reaction [Itraconazole results in decreased secretion of IL4 protein]; Colforsin inhibits the reaction [Itraconazole results in decreased expression of IL4 mRNA]; Colforsin inhibits the reaction [Itraconazole results in decreased secretion of IL4 protein]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in decreased secretion of 15-deoxy-delta(12,14)-prostaglandin J2]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in decreased secretion of Prostaglandin D2]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased degradation of NFKBIA protein]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of CCL5 mRNA]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of CXCL8 mRNA]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP mRNA]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP protein]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased secretion of Thromboxane B2]; Itraconazole promotes the reaction [[Poly I-C co-treated with IL4 protein] results in increased secretion of Dinoprostone] CTD PMID:11886533, PMID:15284827, PMID:23688403 NCBI chr10:38,963,979...38,969,531
Ensembl chr10:38,963,979...38,969,531
JBrowse link
G Il5 interleukin 5 multiple interactions
decreases secretion
decreases expression
ISO 1-Methyl-3-isobutylxanthine inhibits the reaction [Itraconazole results in decreased expression of IL5 mRNA]; 1-Methyl-3-isobutylxanthine inhibits the reaction [Itraconazole results in decreased secretion of IL5 protein]; Bucladesine inhibits the reaction [Itraconazole results in decreased expression of IL5 mRNA]; Bucladesine inhibits the reaction [Itraconazole results in decreased secretion of IL5 protein]; Colforsin inhibits the reaction [Itraconazole results in decreased expression of IL5 mRNA]; Colforsin inhibits the reaction [Itraconazole results in decreased secretion of IL5 protein] CTD PMID:11886533, PMID:15284827 NCBI chr10:39,066,716...39,069,587
Ensembl chr10:39,066,716...39,069,587
JBrowse link
G Madcam1 mucosal vascular addressin cell adhesion molecule 1 multiple interactions ISO Itraconazole inhibits the reaction [TNF protein results in increased expression of MADCAM1 protein] CTD PMID:12388057 NCBI chr 7:12,918,352...12,922,509
Ensembl chr 7:12,918,710...12,922,112
JBrowse link
G Ncoa1 nuclear receptor coactivator 1 multiple interactions ISO Itraconazole promotes the reaction [Rifampin promotes the reaction [NR1I2 protein binds to NCOA1 protein]] CTD PMID:17998298 NCBI chr 6:28,677,563...28,931,844
Ensembl chr 6:28,677,540...28,931,843
JBrowse link
G Nfkbia NFKB inhibitor alpha multiple interactions ISO Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased degradation of NFKBIA protein] CTD PMID:23688403 NCBI chr 6:76,267,227...76,270,457
Ensembl chr 6:76,267,228...76,270,457
JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
increases expression
ISO AHR promotes the reaction [Itraconazole results in increased expression of NQO1 mRNA]; AHR promotes the reaction [Itraconazole results in increased expression of NQO1 protein]; Dactinomycin inhibits the reaction [Itraconazole results in increased expression of NQO1 mRNA]
Itraconazole results in increased expression of NQO1 mRNA; Itraconazole results in increased expression of NQO1 protein
CTD PMID:17923278 NCBI chr19:38,422,210...38,437,103
Ensembl chr19:38,422,164...38,437,180
JBrowse link
G Nr1i2 nuclear receptor subfamily 1, group I, member 2 multiple interactions
increases expression
ISO Itraconazole promotes the reaction [Rifampin promotes the reaction [NR1I2 protein binds to NCOA1 protein]]; Itraconazole promotes the reaction [Rifampin results in increased expression of NR1I2 mRNA]
Itraconazole results in increased expression of NR1I2 mRNA
CTD PMID:17998298 NCBI chr11:65,022,100...65,058,546
Ensembl chr11:65,022,100...65,058,545
JBrowse link
G Stat1 signal transducer and activator of transcription 1 multiple interactions ISO Itraconazole inhibits the reaction [Biological Products results in increased phosphorylation of and results in increased activity of STAT1 protein] CTD PMID:24471457 NCBI chr 9:54,287,540...54,327,958
Ensembl chr 9:54,287,541...54,484,533
JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO Itraconazole inhibits the reaction [TNF protein results in increased expression of MADCAM1 protein] CTD PMID:12388057 NCBI chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
JBrowse link
G Tslp thymic stromal lymphopoietin multiple interactions ISO 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-(4-(2H-tetrazol-5-yl)butyl)piperidine inhibits the reaction [Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP mRNA]]; 4-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-1-(4-(2H-tetrazol-5-yl)butyl)piperidine inhibits the reaction [Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP protein]]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP mRNA]; Itraconazole inhibits the reaction [[Poly I-C co-treated with IL4 protein] results in increased expression of TSLP protein] CTD PMID:23688403 NCBI chr18:25,613,601...25,618,066
Ensembl chr18:25,613,831...25,617,361
JBrowse link

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  CHEBI ontology 19816
    role 19764
      biological role 19764
        inhibitor 18247
          enzyme inhibitor 18173
            pathway inhibitor 8896
              Hedgehog signaling pathway inhibitor 41
                itraconazole 21
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  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      carbon group element atom 19608
                        carbon atom 19597
                          organic molecular entity 19597
                            organic molecule 19522
                              organic cyclic compound 19320
                                organic heterocyclic compound 18432
                                  heteroarene 16467
                                    monocyclic heteroarene 13313
                                      azole 12480
                                        triazoles 3641
                                          triazole antifungal agent 2363
                                            triazole antifungal drug 61
                                              itraconazole 21
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.