A triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4.
Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.
triazole antifungalARO:3007499
CHEBI:26878CHEBI:38582CHEBI:39447CHEBI:87071CHEBI:87101ARO:3007499| Molecular formula | C16H14F3N5O |
|---|---|
| Charge | 0 |
| Average mass | 349.316 Da |
| Monoisotopic mass | 349.11504 Da |
| Source | ChEBI |
| InChIKey | BCEHBSKCWLPMDN-MGPLVRAMSA-N |
C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
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
CHEBI:35718CHEBI:86327| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:3007512 |
voriconazole | antibioticmech:aro-7c51b80ef5 |
2026-08-30 |
| CHEBI | CHEBI:10023 |
voriconazole | antibioticmech:chebi-35a61b95ae |
2026-08-30 |
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Aspergillus flavus Cyp51B with mutations conferring resistance to voriconazole | ARO:3009485 | — | ||
| Aspergillus flavus Cyp51a with mutations conferring resistance to voriconazole | ARO:3009498 | — | ||
| Aspergillus flavus Cyp51c with mutations conferring resistance to voriconazole | ARO:3009283 | — | ||
| Aspergillus fumigatus Cyp51B with mutations conferring resistance to voriconazole | ARO:3009483 | — | ||
| Aspergillus fumigatus Cyp51a with mutations conferring resistance to voriconazole | ARO:3009503 | — | ||
| Aspergillus fumigatus Hmg1 with mutations conferring resistance to voriconazole | ARO:3009235 | — | ||
| Aspergillus fumigatus Hmg2 with mutations conferring resistance to voriconazole | ARO:3009369 | — | ||
| Aspergillus fumigatus ase1 with mutations conferring resistance to voriconazole | ARO:3009274 | — | ||
| Aspergillus fumigatus cyp51a with mutations conferring resistance to voriconazole | ARO:3009201 | — | ||
| Aspergillus niger Cyp51a with mutations conferring resistance to voriconazole | ARO:3009508 | — | ||
| Aspergillus spp. Hmg1 with mutations conferring resistance to triazoles antibiotics | ARO:3007670 | — | ||
| Aspergillus spp. cyp51A with mutations conferring resistance to triazoles antibiotics | ARO:3007565 | — | ||
| Aspergillus terreus cyp51a with mutations conferring resistance to voriconazole | ARO:3009205 | — | ||
| Candida albicans Cyp51 with mutations conferring resistance to voriconazole | ARO:3009526 | — | ||
| Candida albicans Erg11 with mutations conferring resistance to voriconazole | ARO:3009415 | — | ||
| Candida auris Erg11 lanosterol 14-alpha-demethylase with mutations associated with resistance to voriconazole | ARO:3009221 | — | ||
| Candida auris FKS1 beta-1,3-glucan synthase with mutations conferring resistance to voriconazole | ARO:3009613 | — | ||
| Candida orthopsilosis ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to voriconazole | ARO:3009581 | — | ||
| Candida parapsilosis Erg11 lanosterol 14-alpha-demethylase with mutations associated with resistance to voriconazole | ARO:3009582 | — | ||
| Candida parapsilosis Erg3 C-5 sterol desaturase with mutations conferring resistance to itraconazole | ARO:3009243 | — | ||
| Candida parapsilosis Erg3 C-5 sterol desaturase with mutations conferring resistance to voriconazole | ARO:3009245 | — | ||
| Candida spp. ERG11 with mutations conferring resistance to azole antibiotics | ARO:3007524 | — | ||
| Candida tropicalis Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to voriconazole | ARO:3009227 | — | ||
| Colletotrichum truncatum cyp51a with mutations associated with resistance to voriconazole | ARO:3009218 | — | ||
| Cryptococcus neoformans Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to voriconazole | ARO:3009229 | — | ||
| Histoplasma capsulatum Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to voriconazole | ARO:3009223 | — | ||
| Nakaseomyces glabratus FKS1 beta-1,3-glucan synthase with mutations associated with resistance to voriconazole | ARO:3009616 | — | ||
| Nakaseomyces glabratus FKS2 beta-1,3-glucan synthase with mutations associated with resistance to voriconazole | ARO:3009620 | — | ||
| Pichia kudriavzevii ERG11 with mutations conferring resistance to voriconazole | ARO:3009399 | — | ||
| Saccharomyces cerevisiae ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to voriconazole | ARO:3009591 | — | ||
| antifungal resistance-associated MSH | ARO:3009134 | — |
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| CYP51A transformant(CM2627-CYP51Apromoter(2x34bp tandem repeat) and CM2627-CYP51A(L98H)) (transformant) [Overexpression] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:330879UniProtKB:Q4WNT5 PHIPO:0000590 |
— | |
| Candida albicans TAC1 with mutations conferring resistance to voriconazole | ARO:3009429 | — | ||
| ERG11 transformant(JEY162-ERG11(824-955bpdelta + D275V) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Candida tropicalis NCBITaxon:5482UniProtKB:P14263 PHIPO:0000590 |
— | |
| ERG11 transformant(MRL862-ERG11(Y145F)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Cryptococcus neoformans NCBITaxon:5207UniProtKB:Q870D1PHIPO:0000590 |
— | |
| ERG11(Y132F F145L) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Candida albicans NCBITaxon:5476NCBITaxon:237561UniProtKB:P10613 PHIPO:0000590 |
— | |
| ERG11(Y132F K143R) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Candida albicans NCBITaxon:5476NCBITaxon:237561UniProtKB:P10613 PHIPO:0000590 |
— | |
| ERG3 transformant(JEY162-ERG3(S258F)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Candida tropicalis NCBITaxon:5482UniProtKB:N0A5G3PHIPO:0000590 |
— | |
| ERG3delta (deletion) associated with resistance to voriconazole |
— | Candida albicans NCBITaxon:5476NCBITaxon:237561UniProtKB:Q59VG6 PHIPO:0000590 |
— | |
| ERG3delta (deletion) associated with resistance to voriconazole |
— | Candida parapsilosis NCBITaxon:5480NCBITaxon:578454UniProtKB:G8B7T4PHIPO:0000590 |
— | |
| HapE transformant(Isolate3-HapE(P88L)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:330879UniProtKB:Q4WDM9PHIPO:0000590 |
— | |
| cox10 transformant(W004-cox10(R243Q)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:451804UniProtKB:B0Y628PHIPO:0000590 |
— | |
| cyp51A transformant(F33-cyp51A (G448S)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:330879UniProtKB:Q4WNT5 PHIPO:0000590 |
— | |
| cyp51A(G448S) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:330879UniProtKB:Q4WNT5 PHIPO:0000590 |
— | |
| cyp51A(G448S) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:330879UniProtKB:Q4WNT5 PHIPO:0000590 |
— | |
| cyp51A(G448S) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128NCBITaxon:330879UniProtKB:Q4WNT5 PHIPO:0000590 |
— | |
| cyp51A(K197N) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8N2C8 PHIPO:0000590 |
— | |
| cyp51A(K197N, D282E, M288L) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8N2C8 PHIPO:0000590 |
— | |
| cyp51A(Y132N, T469S) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8N2C8 PHIPO:0000590 |
— | |
| cyp51A+ (wild type) [Overexpression] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8N2C8 PHIPO:0000590 |
— | |
| cyp51B(H399P, D411N) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8NFL5 PHIPO:0000590 |
— | |
| cyp51B(T454P, T486P) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8NFL5 PHIPO:0000590 |
— | |
| cyp51B+ (wild type) [Overexpression] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8NFL5 PHIPO:0000590 |
— | |
| cyp51C-T788G(S240A) (amino acid mutation) [Wild type product level] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059NCBITaxon:332952UniProtKB:B8NUK6 PHIPO:0000590 |
— |
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Aspergillus flavus MFS1 with mutations conferring resistance to voriconazole | ARO:3009458 | — | ||
| Aspergillus flavus Mdr2 with mutations conferring resistance to voriconazole | ARO:3009451 | — | ||
| Trychophyton rubrum Mdr1 with mutations associated with resistance to voriconazole | ARO:3009252 | — | ||
| Trychophyton rubrum Mdr3 with mutations associated with resistance to voriconazole | ARO:3009257 | — | ||
| Trychophyton rubrum Mfs1 with mutations associated with resistance to voriconazole | ARO:3009265 | — | ||
| Trychophyton rubrum Mfs2 with mutations associated with resistance to voriconazole | ARO:3009267 | — | ||
| fungal MDR | ARO:3009425 | — |
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