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.

CHEBI:26912 CHEBI:26912
CHEBI:35618 CHEBI:35618
CHEBI:35727 CHEBI:35727
CHEBI:37143 CHEBI:37143
CHEBI:46848 CHEBI:46848
CHEBI:87071 CHEBI:87071
CHEBI:87101 CHEBI:87101
ARO:3007499 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

Equivalent identifiers for this same structure in other resources.

ARO:3007513
cas:171228-49-2
drugbank:DB01263
drugcentral:3483
kegg.drug:D02555
patent:US5661151
patent:WO9517407
reaxys:8379448
wikipedia.en:Posaconazole
chembl:CHEMBL1397
pubchem.compound:468595

Activity roles

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

CHEBI:35718 CHEBI:35718
CHEBI:36335 CHEBI:36335
CHEBI:86327 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 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

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.	—	Aspergillus fumigatus `NCBITaxon:746128` strain akuBKU80 `NCBITaxon:330879` `UniProtKB:Q4WDM9` `PHIPO:0000625`	—	PMID:23226235 (PHI-base primary-literature antimicrobial interaction PHIG:8691; joined to this record by exact ChEBI identifier.) 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.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 `NCBITaxon:330879` `UniProtKB:Q4WNT5` Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) 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.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 `NCBITaxon:330879` `UniProtKB:Q4WNT5` Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) 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.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 `NCBITaxon:330879` `UniProtKB:Q4WNT5` Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) 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.	—	Aspergillus fumigatus `NCBITaxon:746128` strain ND158 `NCBITaxon:330879` `UniProtKB:Q4WNT5` Afu4g06890-T `PHIPO:0000625`	—	PMID:12543662 (PHI-base primary-literature antimicrobial interaction PHIG:1837; joined to this record by exact ChEBI identifier.) 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
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-03 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

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