ketoconazole

antibioticmech:aro-4655b07df9 ·ANTIFUNGAL ·MINTED SEEDED

Ketoconazole is a type of imidazole antibiotic, particularly antifungal. It was one of the first available oral broad-spectrum antifungals for the treatment of systemic and superficial mycoses. — PMID:707893

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

imidazole antibioticARO:3007500

Strictly broader compounds or drug classes this molecule belongs to.

ARO:3007500 ARO:3007500

Chemical structure

Computed structure properties
Molecular formula	C26H28Cl2N4O4
Charge	0
Average mass	531.4 Da
Monoisotopic mass	530.1487608 Da
Source	PubChem · retrieved 2026-08-29
InChIKey	XMAYWYJOQHXEEK-OZXSUGGESA-N

SMILES

CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl

InChI

InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1

Cross-references

Equivalent identifiers for this same structure in other resources.

Activity roles

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

CHEBI:35718 CHEBI:35718
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:3007517`	ketoconazole	`antibioticmech:aro-4655b07df9`	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.

Resistance mechanisms

8 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 5

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Aspergillus fumigatus Cyp51a with mutations conferring resistance to ketoconazole	ARO:3009500	not organism-specific	—	ARO:3009500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)
Candida albicans Cyp51a with mutations conferring resistance to ketoconazole	ARO:3009506	not organism-specific	—	ARO:3009506 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)
Candida albicans ERG11 with mutations conferring resistance to ketoconazole	ARO:3009426	not organism-specific	—	ARO:3009426 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)
Candida spp. cyp51A1 with mutations conferring resistance to triazoles and imidazole antibiotics	ARO:3007666	not organism-specific	—	ARO:3007666 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)
Candida tropicalis Erg11 lanosterol 14-alpha-demethylase with mutations conferring resistance to ketoconazole	ARO:3009584	not organism-specific	—	ARO:3009584 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 3

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Cryptococcus neoformans AFR1 with mutations conferring resistance against ketoconazole	ARO:3009435	not organism-specific	—	ARO:3009435 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)
Trychophyton rubrum Mdr3 with mutations associated with resistance to ketoconazole	ARO:3009256	not organism-specific	—	ARO:3009256 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)
Trychophyton rubrum Mfs1 with mutations associated with resistance to ketoconazole	ARO:3009263	not organism-specific	—	ARO:3009263 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007517 (ketoconazole); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO)
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
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · 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.