voriconazole
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.
Classification
triazole antifungalARO:3007499
-
CHEBI:26878 -
CHEBI:38582 -
CHEBI:39447 - conazole antifungal drug
CHEBI:87071 - triazole antifungal drug
CHEBI:87101 - triazole antifungal
ARO:3007499
Chemical structure
| 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
Also called
- Vfend
- voriconazol
- voriconazolum
- (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
- (R-(R*,S*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
- (αR,βS)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
- VCZ
Cross-references
- voriconazole
ARO:3007512 - beilstein:7694998
- cas:137234-62-9
- kegg.compound:C07622
- lincs.smallmolecule:LSM-5244
- chembl:CHEMBL638
- pubchem.compound:71616
Drug registries
Patents and articles
Activity roles
- antifungal agent
CHEBI:35718 - antifungal drug
CHEBI:86327
Source concepts
| 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 |
Mechanism summary
- Mode of action
- ERGOSTEROL_PATHWAY_INHIBITION host shared target
- Clinical status
- APPROVED
Activity spectrum
| Organism | Activity | MIC | Disk diffusion | Assay | Strain | Sample/genome | Evidence |
|---|---|---|---|---|---|---|---|
| Aspergillus flavus NCBITaxon:5059 | RESISTANT | 8.0 mg/L | — | CLSI M38-A2 broth microdilution | BMU29791 | — | EvidencePage data (JSON.gz) |
| Candida albicans NCBITaxon:5476 | — | <0.0078 mg/L | — | EUCAST broth microdilution, source RPMI 1640 condition | JEY355 | — | EvidencePage data (JSON.gz) |
| Candida tropicalis NCBITaxon:5482 | RESISTANT | >16.0 mg/L | — | EUCAST broth microdilution, source RPMI 1640 condition | JEY162 | — | EvidencePage data (JSON.gz) |
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 31
| 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 | — |
UNKNOWN 24
| 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:746128PHIPO:0000590 |
— | |
| Candida albicans TAC1 with mutations conferring resistance to voriconazole | ARO:3009429 | — | ||
| Clinical ERG3 association with voriconazole resistance |
— | Candida tropicalis NCBITaxon:5482UniProtKB:N0A5G3 |
ERG3 | |
| ERG11 transformant(JEY162-ERG11(824-955bpdelta + D275V) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Candida tropicalis NCBITaxon:5482PHIPO:0000590 |
— | |
| ERG11 transformant(MRL862-ERG11(Y145F)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Cryptococcus neoformans NCBITaxon:5207PHIPO:0000590 |
— | |
| ERG11(Y132F F145L) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Candida albicans NCBITaxon:5476PHIPO:0000590 |
— | |
| ERG11(Y132F K143R) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Candida albicans NCBITaxon:5476PHIPO:0000590 |
— | |
| ERG3 transformant(JEY162-ERG3(S258F)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Candida tropicalis NCBITaxon:5482PHIPO:0000590 |
— | |
| ERG3delta (deletion) associated with resistance to voriconazole |
— | Candida albicans NCBITaxon:5476PHIPO:0000590 |
— | |
| ERG3delta (deletion) associated with resistance to voriconazole |
— | Candida parapsilosis NCBITaxon:5480PHIPO:0000590 |
— | |
| HapE transformant(Isolate3-HapE(P88L)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO:0000590 |
— | |
| cox10 transformant(W004-cox10(R243Q)) (transformant) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus fumigatus NCBITaxon:746128PHIPO: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:5059PHIPO:0000590 |
— | |
| cyp51A(K197N, D282E, M288L) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— | |
| cyp51A(Y132N, T469S) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— | |
| cyp51A+ (wild type) [Overexpression] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— | |
| cyp51B(H399P, D411N) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— | |
| cyp51B(T454P, T486P) (amino acid mutation) [Not assayed] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— | |
| cyp51B+ (wild type) [Overexpression] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— | |
| cyp51C-T788G(S240A) (amino acid mutation) [Wild type product level] associated with resistance to voriconazole |
— | Aspergillus flavus NCBITaxon:5059PHIPO:0000590 |
— |
ANTIBIOTIC_EFFLUX 7
| 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 | — |
Curation history
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SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO, CHEBI)
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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REVIEWED_RESISTANCE_IDENTIFIER_SCOPE
Applied pinned PHI-base identifier-scope review to five associations; withheld reference-only protein and strain identifiers without replacing source claims.
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REVIEWED_RESISTANCE_IDENTIFIER_SCOPE
Refreshed the whole-file PHI-base review checksum after an additional review; all biological fields and previous identifier-scope decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Resolved three PHI-base tested-derivative labels, retained reference-only UniProt grounding, withheld parent strain/protein identity, and added one independently reported clinical-isolate MIC with its historical source interpretation. Refreshed review checksums without changing prior decisions.
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REVIEWED_RESISTANCE_IDENTIFIER_SCOPE
Refreshed the whole-file PHI-base review checksum after the FKS1 review; all biological fields and previous identifier-scope decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Applied 2 pinned subject-context reviews, retaining reference-locus grounding while withholding unverified experimental protein/strain identifiers. Source alterations, phenotypes, species, genes, and existing activities unchanged. Refreshed provenance checksums on any previously reviewed claims. ERG11 parent, replicate and clinical-donor contexts remain separate.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped 2 imported associations without conflating reference, donor and unresolved tested-subject identities. Preserved source alterations and phenotypes; refreshed older review checksums without biological changes. Added two independently reported clinical MICs in mg/L, preserving qualifiers and historical interpretation, and one deposit-grounded ERG3 same-isolate association without independent component causality.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped two imported ERG3 associations: reference proteins and strain TaxIDs are not experimental-subject identifiers. Retained source species, background labels, alterations and phenotypes; clinical isolates remain separate. Existing activities and curator claims unchanged; refreshed older review checksums.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after carboxin reference-context reviews; all biological fields, activities and previous decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after two additional carboxin identifier-scope corrections; all biological fields, activities and previous decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after eleven additional identifier-scope corrections; biological fields, activities and decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped imported associations to the reported parent background: Af293 reference protein and strain TaxID are not tested-subject identities. Source alterations, phenotypes, assays and clinical activities unchanged; no exact allele or genome inferred.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the whole-file PHI-base review checksum after one yeast identity-scope correction; biological fields, activities and prior decisions unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped imported reference protein and strain TaxID to provenance, not tested-subject identity. Source parent labels, alterations, phenotypes and assays preserved; no experimental allele, genome or activity measurement inferred.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Scoped source protein and reference-strain identifiers to provenance, not exact experimental subjects, after primary-paper review. Parent labels and source biological fields preserved; no new allele, measurement or genome inferred.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after six identifier-scope corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Darlington subject correction; prior review decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Nakayama reference-scope review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Duan reference-scope review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Piotrowska parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Xu subject and species corrections; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the HDF1 subject-reference review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed shared PHI-base review checksum after the Fouche parent-cohort review; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_REFERENCE_CONTEXT
Refreshed shared PHI-base review checksum after the SDH8 reference-alias correction; prior decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after the Posteraro subject-context review; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_REFERENCE_CONTEXT
Refreshed the shared PHI-base review checksum after four reference-identifier scope corrections; previous decisions, biological fields and activities unchanged.
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT
Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.