posaconazole

CHEBI:64355 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An N-arylpiperazine that consists of piperazine carrying two 4-substituted phenyl groups at positions 1 and 4. A triazole antifungal drug. — ChEBI

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

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:26912
Label unavailable CHEBI:35618
Label unavailable CHEBI:35727
Label unavailable CHEBI:37143
Label unavailable CHEBI:46848
conazole antifungal drug CHEBI:87071
triazole antifungal drug CHEBI:87101
triazole antifungal ARO:3007499

Chemical structure

Computed structure properties
Molecular formula	C37H42F2N8O4
Charge	0
Average mass	700.791 Da
Monoisotopic mass	700.32971 Da
Source	ChEBI
InChIKey	RAGOYPUPXAKGKH-XAKZXMRKSA-N

SMILES

CC[C@@H]([C@H](C)O)n1ncn(-c2ccc(N3CCN(c4ccc(OC[C@@H]5CO[C@@](Cn6cncn6)(c6ccc(F)cc6F)C5)cc4)CC3)cc2)c1=O

InChI

InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1

Also called

Noxafil (BRAND_NAME)— chebi
2,5-anhydro-1,3,4-trideoxy-2-(2,4-difluorophenyl)-4-({4-[4-(4-{1-[(2S,3S)-2-hydroxypentan-3-yl]-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl}phenyl)piperazin-1-yl]phenoxy}methyl)-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol (EXACT_SYNONYM)— chebi
SCH56592 (EXACT_SYNONYM)— chebi
Sch 56592 (EXACT_SYNONYM)— chebi
Schering 56592 (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antifungal agent CHEBI:35718
trypanocidal drug CHEBI:36335
antifungal drug CHEBI:86327

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3007513`	posaconazole	`antibioticmech:aro-10b0bd302a`	2026-08-30
CHEBI	`CHEBI:64355`	posaconazole	`antibioticmech:chebi-5ebcb88ca0`	2026-08-30

Mechanism summary

Mode of action: ERGOSTEROL_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:75282 (ergosterol biosynthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

Resistance mechanisms

28 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 20

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Aspergillus flavus Cyp51A with mutations associated with resistance to posaconazole	ARO:3009496	not organism-specific	—	ARO:3009496 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus flavus Cyp51c with mutations conferring resistance to posaconazole	ARO:3009492	not organism-specific	—	ARO:3009492 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus fumigatus Cyp51B with mutations conferring resistance to posaconazole	ARO:3009484	not organism-specific	—	ARO:3009484 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus fumigatus Hmg1 with mutations conferring resistance to posaconazole	ARO:3009230	not organism-specific	—	ARO:3009230 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus fumigatus Hmg2 with mutations conferring resistance to posaconazole	ARO:3009366	not organism-specific	—	ARO:3009366 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus fumigatus ase1 with mutations conferring resistance to posaconazole	ARO:3009272	not organism-specific	—	ARO:3009272 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus fumigatus cyp51a with mutations conferring resistance to posaconazole	ARO:3009203	not organism-specific	—	ARO:3009203 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus spp. Hmg1 with mutations conferring resistance to triazoles antibiotics	ARO:3007670	not organism-specific	—	ARO:3007670 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus spp. cyp51A with mutations conferring resistance to triazoles antibiotics	ARO:3007565	not organism-specific	—	ARO:3007565 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Aspergillus tubingensis Cyp51a with mutations conferring resistance to posaconazole	ARO:3009510	not organism-specific	—	ARO:3009510 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida albicans ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to posaconazole	ARO:3009575	not organism-specific	—	ARO:3009575 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida albicans cyp51 with mutations conferring resistance to posaconazole	ARO:3009525	not organism-specific	—	ARO:3009525 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida auris Erg11 lanosterol 14-alpha-demethylase with mutations associated with resistance to posaconazole	ARO:3009220	not organism-specific	—	ARO:3009220 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida glabrata ERG11 with mutations conferring resistance to posaconazole	ARO:3009398	not organism-specific	—	ARO:3009398 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida parapsilosis Erg3 C-5 sterol desaturase with mutations conferring resistance to posaconazole	ARO:3009244	not organism-specific	—	ARO:3009244 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida tropicalis Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to posaconazole	ARO:3009585	not organism-specific	—	ARO:3009585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Cryptococcus neoformans Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to posaconazole	ARO:3009587	not organism-specific	—	ARO:3009587 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Nakaseomyces glabratus FKS2 beta-1,3-glucan synthase with mutations associated with resistance to posaconazole	ARO:3009619	not organism-specific	—	ARO:3009619 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Nakaseomyces glabratus FSK1 beta-1,3-glucan synthase with mutations associated with resistance to posaconazole	ARO:3009615	not organism-specific	—	ARO:3009615 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Saccharomyces cerevisiae ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance to posaconazole	ARO:3009590	not organism-specific	—	ARO:3009590 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)

UNKNOWN 6

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Candida albicans TAC1 with mutations conferring resistance to posaconazole	ARO:3009430	not organism-specific	—	ARO:3009430 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
HapE transformant(Isolate3-HapE(P88L)) (transformant) [Not assayed] associated with resistance to posaconazole This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review camps-2012-fumigatus-reference-context: The strain label denotes a parent background, not either later tested replicate or the native clinical isolate. UniProtKB:Q4WDM9 / AFUA_6G05300 and TaxID 330879 denote Af293 reference context. Reference-guided sequence analysis does not identify a clinical or experimental subject as Af293. Source alterations and phenotypes are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:Q4WDM9.	—	Aspergillus fumigatus `NCBITaxon:746128` strain akuBKU80 `PHIPO:0000625`	—	PMID:23226235 (PHI-base primary-literature antimicrobial interaction PHIG:8691; joined to this record by exact ChEBI identifier.) DOI:10.1371/journal.pone.0050034 (Identifier-scope review: Results sections s3a-s3b: clinical series and reference genomes, Results section s3d and Table 7: later experimental groups, UniProtKB release 2026_03: Q4WDM9 entry 125, sequence version 1; AFUA_6G05300 reference crosswalk and taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.) Cell growth assay
cyp51A transformant(MS6-cyp51A(G54R)) (transformant) [Ectopic] associated with resistance to posaconazole This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review mann-2003-fumigatus-reference-context: The strain label denotes a parent background, not a uniquely resolved tested derivative or clinical isolate. The later recipient background is distinct from the original parent. UniProtKB:Q4WNT5 and the retained gene_id denote the Af293 reference locus; TaxID 330879 is reference-only. Source alterations and phenotypes are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:Q4WNT5.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) DOI:10.1128/aac.47.2.577-581.2003 (Identifier-scope review: Strains and plasmids: background identity, Results and Tables 1-2: distinct subject groups, UniProtKB release 2026_03: Q4WNT5 entry 146, sequence version 1; EnsemblFungi cross-reference and reference taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.) Cell growth assay
cyp51A transformant(R7-1-cyp51A(G54W)) (transformant) [Ectopic] associated with resistance to posaconazole This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review mann-2003-fumigatus-reference-context: The strain label denotes a parent background, not a uniquely resolved tested derivative or clinical isolate. The later recipient background is distinct from the original parent. UniProtKB:Q4WNT5 and the retained gene_id denote the Af293 reference locus; TaxID 330879 is reference-only. Source alterations and phenotypes are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:Q4WNT5.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) DOI:10.1128/aac.47.2.577-581.2003 (Identifier-scope review: Strains and plasmids: background identity, Results and Tables 1-2: distinct subject groups, UniProtKB release 2026_03: Q4WNT5 entry 146, sequence version 1; EnsemblFungi cross-reference and reference taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.) Cell growth assay
cyp51A(G54R) (amino acid mutation) [Not assayed] associated with resistance to posaconazole This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review mann-2003-fumigatus-reference-context: The strain label denotes a parent background, not a uniquely resolved tested derivative or clinical isolate. The later recipient background is distinct from the original parent. UniProtKB:Q4WNT5 and the retained gene_id denote the Af293 reference locus; TaxID 330879 is reference-only. Source alterations and phenotypes are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:Q4WNT5.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) DOI:10.1128/aac.47.2.577-581.2003 (Identifier-scope review: Strains and plasmids: background identity, Results and Tables 1-2: distinct subject groups, UniProtKB release 2026_03: Q4WNT5 entry 146, sequence version 1; EnsemblFungi cross-reference and reference taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.) Cell growth assay
cyp51A(G54W) (amino acid mutation) [Not assayed] associated with resistance to posaconazole This is a curated gene-alteration/chemical resistance association, not evidence for a specific biochemical resistance mechanism. Grounding review mann-2003-fumigatus-reference-context: The strain label denotes a parent background, not a uniquely resolved tested derivative or clinical isolate. The later recipient background is distinct from the original parent. UniProtKB:Q4WNT5 and the retained gene_id denote the Af293 reference locus; TaxID 330879 is reference-only. Source alterations and phenotypes are unchanged; exact subject protein, strain TaxID and genome remain unresolved. Reference-only source identifiers: strain_taxon_id=NCBITaxon:330879; protein_accession=UniProtKB:Q4WNT5.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) DOI:10.1128/aac.47.2.577-581.2003 (Identifier-scope review: Strains and plasmids: background identity, Results and Tables 1-2: distinct subject groups, UniProtKB release 2026_03: Q4WNT5 entry 146, sequence version 1; EnsemblFungi cross-reference and reference taxonomy. Reviewed 2026-10-08 by codex; curation/phibase_grounding_reviews.json SHA-256 1f5d50346b2916fce10969afa8d6409ea836dd15e8cf7fe3cfa3a78d6289b4ed.) Cell growth assay

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Candida glabrata CDR1 with mutations conferring resistance to posaconazole	ARO:3009439	not organism-specific	—	ARO:3009439 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)
Candida glabrata Yor1 with mutations conferring resistance to posaconazole	ARO:3009466	not organism-specific	—	ARO:3009466 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007513 (posaconazole); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
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RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
Refreshed the whole-file PHI-base review checksum after one yeast identity-scope correction; biological fields, activities and prior decisions unchanged.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
Refreshed the shared PHI-base review checksum after six identifier-scope corrections; previous decisions, biological fields and activities unchanged.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
Refreshed the shared PHI-base review checksum after eight subject-identity corrections; previous decisions, biological fields and activities unchanged.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
Refreshed shared PHI-base review checksum after the Shima parent-reference review; prior decisions, biological fields and activities unchanged.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
Refreshed shared PHI-base review checksum after the Mehrabi parent-reference review; prior decisions, biological fields and activities unchanged.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-08 · codex · LLM-assisted
Refreshed shared PHI-base review checksum after the Huang parent-reference review; prior decisions, biological fields and activities unchanged.
REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted
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REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-09 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-09 · codex · LLM-assisted
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REVIEWED_RESISTANCE_REFERENCE_CONTEXT 2026-10-12 · codex · LLM-assisted
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REVIEWED_RESISTANCE_SUBJECT_CONTEXT 2026-10-13 · codex · LLM-assisted
Refreshed the shared PHI-base review checksum after one Neurospora subject-context correction; previous decisions, biological fields and activities unchanged.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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