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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 3:54,016,854...54,112,797
Ensembl chr 3:54,017,127...54,112,730
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 4:25,357,467...25,529,941
Ensembl chr 4:25,158,362...25,442,709
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 6:52,234,089...52,271,568
Ensembl chr 6:52,234,089...52,271,568
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:63,104,771...63,273,934
Ensembl chr  X:63,104,771...63,273,925
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 chr10:68,322,826...68,327,365
Ensembl chr10:68,322,829...68,327,377
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 chr14:15,704,772...15,706,969
Ensembl chr14:15,704,758...15,706,975
JBrowse link
G Cyp11b2 cytochrome P450, family 11, subfamily b, polypeptide 2 multiple interactions ISO Itraconazole binds to and results in decreased activity of CYP11B1 protein CTD PMID:31982514 NCBI chr 7:106,838,590...106,845,004
Ensembl chr 7:106,838,590...106,845,004
JBrowse link
G Cyp11b3 cytochrome P450, family 11, subfamily b, polypeptide 3 multiple interactions ISO Itraconazole binds to and results in decreased activity of CYP11B2 protein CTD PMID:31982514 NCBI chr 7:106,808,559...106,814,048
Ensembl chr 7:106,808,559...106,814,048
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 8:58,096,021...58,102,130
Ensembl chr 8:58,096,077...58,102,125
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 3:159,275,947...159,290,383
Ensembl chr 3:159,275,947...159,290,383
JBrowse link
G Cyp3a2 cytochrome P450, family 3, subfamily a, polypeptide 2 multiple interactions
increases hydroxylation
affects activity
decreases activity
affects metabolic processing
increases metabolic processing
decreases expression
ISO Itraconazole binds to and results in decreased activity of CYP3A4 protein
CYP3A4 protein results in increased hydroxylation of Itraconazole
Itraconazole affects the activity of CYP3A4 protein
Itraconazole results in decreased activity of CYP3A4 protein
CYP3A4 protein affects the metabolism of Itraconazole
CYP3A4 protein results in increased metabolism of Itraconazole
Itraconazole results in decreased expression of CYP3A4 mRNA; Itraconazole results in decreased expression of CYP3A4 protein
CTD PMID:15328084 PMID:15383492 PMID:15447735 PMID:15684493 PMID:15784650 More... NCBI chr12:9,207,986...9,230,038
Ensembl chr12:9,015,383...9,285,008
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 4:30,036,956...30,055,410
Ensembl chr 4:30,036,865...30,055,410
JBrowse link
G Gli1 GLI family zinc finger 1 decreases expression ISO
EXP
Itraconazole analog results in decreased expression of GLI1 mRNA; Itraconazole results in decreased expression of GLI1 mRNA CTD PMID:21936514 PMID:33905526 NCBI chr 7:63,156,926...63,169,579
Ensembl chr 7:63,156,926...63,169,251
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 1:201,337,762...201,340,230
Ensembl chr 1:201,321,672...201,340,226
JBrowse link
G Hsd11b2 hydroxysteroid 11-beta dehydrogenase 2 decreases activity ISO Itraconazole results in decreased activity of HSD11B2 protein CTD PMID:28131847 PMID:29385285 PMID:33387577 NCBI chr19:33,397,656...33,402,899
Ensembl chr19:33,397,656...33,402,899
JBrowse link
G Ihh Indian hedgehog signaling molecule decreases expression EXP Itraconazole results in decreased expression of IHH mRNA CTD PMID:33905526 NCBI chr 9:76,504,315...76,510,532
Ensembl chr 9:76,504,315...76,510,532
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 chr10:37,771,203...37,776,750
Ensembl chr10:37,771,203...37,776,750
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 chr10:37,874,342...37,877,213
Ensembl chr10:37,874,342...37,877,213
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 7:10,036,301...10,039,703
Ensembl chr 7:10,036,301...10,039,703
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 6:27,232,609...27,507,992
Ensembl chr 6:27,232,611...27,475,664
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 6:72,858,713...72,861,941
Ensembl chr 6:72,858,712...72,861,941
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 chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557
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 chr11:62,460,213...62,496,665
Ensembl chr11:62,460,213...62,496,658
JBrowse link
G Ptch1 patched 1 decreases expression EXP Itraconazole results in decreased expression of PTCH1 mRNA CTD PMID:33905526 NCBI chr17:1,542,705...1,607,730
Ensembl chr17:1,542,877...1,607,333
JBrowse link
G Smo smoothened, frizzled class receptor decreases expression EXP Itraconazole results in decreased expression of SMO mRNA CTD PMID:33905526 NCBI chr 4:58,344,101...58,372,828
Ensembl chr 4:58,343,529...58,373,829
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 9:49,419,561...49,459,969
Ensembl chr 9:49,419,340...49,588,540
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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629
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 chr18:24,447,409...24,454,244
Ensembl chr18:24,449,844...24,453,548
JBrowse link

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  CHEBI ontology 19659
    role 19634
      biological role 19633
        inhibitor 18659
          enzyme inhibitor 18436
            pathway inhibitor 9737
              Hedgehog signaling pathway inhibitor 51
                itraconazole 28
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  CHEBI ontology 19659
    subatomic particle 19658
      composite particle 19658
        hadron 19658
          baryon 19658
            nucleon 19658
              atomic nucleus 19700
                atom 19658
                  main group element atom 19607
                    p-block element atom 19607
                      carbon group element atom 19550
                        carbon atom 19547
                          organic molecular entity 19588
                            organic molecule 19506
                              organic cyclic compound 19324
                                organic heterocyclic compound 18682
                                  heteroarene 16681
                                    monocyclic heteroarene 14210
                                      azole 13579
                                        triazoles 6049
                                          triazole antifungal agent 5064
                                            triazole antifungal drug 69
                                              itraconazole 28
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